Anna Maria News

All the latest stories from the Island of Anna Maria.

How to Get to Anna Maria Island

Anna Maria Island is a wondrous vacation getaway, and one of the top gulf coast destinations in Florida.

But the big questions may still remain: where is it? How do you get here?

We cover the best routes to the island, what airport to use, and how you can find this majestic beachside nook for your upcoming vacation escape.

directions to anna maria

Where is Anna Maria Island on the Map?

First, we start by zooming out wide. Anna Maria Island is located right along the Gulf of Mexico in Florida. Look about halfway down Florida’s boot, just below Tampa, and you are sure to settle somewhere along Anna Maria Island’s seven-mile stretch. It is snug tight between Sarasota and Tampa.

What Airport Do You Fly Into?

There are three main airports near the island. Which airport you use depends on your travel itinerary and the city you choose to fly into. The three closest major airports are Tampa International Airport (TPA), Sarasota-Bradenton International Airport (SRQ), and Orlando International Airport (MCO).

The closest is SRQ, though flights are expectedly limited. The furthest airport is in Orlando, but it is one of the largest airports in the state and a perfectly reasonable flight-in if you end up spending any time at Disney World.

main ami roads

What’s the Most Direct Route to the Island from the Cities?

Which major road you take to the island will depend on which city you start at. If you wind up in Orlando, you are certainly going to take I4 west to the island. This is the major route across the state of Florida, and one you will likely utilize if you head to the eastern side as well. There is no toll road on I4. The drive from Orlando to Anna Maria Island takes about two hours.

If you are coming in from Tampa, 75 South will be your main road to the island. It carries southwest, but you will want to jump off near Bradenton to get to Anna Maria Island. This drive will take at least an hour.

Lastly, visitors from Sarasota will have a nice non-highway ride to their destination. The most direct route is along 301 as it carries directly east of the island. You will eventually want to hit a left at 64 or 684 in Bradenton proper or South Bradenton to reach the island. This drive will take, on a good day, about 40 minutes.

How do You Get to the Island?

After zooming in a bit, you will eventually see the local streets in and around Anna Maria Island. There are three total main roads onto the island. The first is at the northern point. This is by 64, locally called Manatee Ave. This will take you close to Anna Maria city.

The second main entrance is near the middle of the island by Cortez Beach. This is called Cortez Rd and it will land you right at the heart of Bradenton Beach.

How About the Scenic Route?

Finally, we also recommend the southernmost bridge access point by way of Longboat Key. It is likely the longest ride in, and only viable for visitors coming from the south, but it is a stunning run along the breadth of Anna Maria Island’s coastline. This route is useful for anyone coming in from Sarasota. It is a wonderful drive as you can see the water in many spots from the road. To utilize this path, you have to escape west in the Sarasota area and drive through St. Armand’s Circle and then up to Longboat Key.

anna maria island vacations

Where is the Best Anna Maria Island Lodging?

The best lodging is by the beach, of course! We want you to have an absolutely thrilling time when you finally make your way to the island. Contact us about all our Anna Maria Island houses for rent. We can connect you with the perfect home for you and your whole crew. We have beach views, furnished kitchens, pool access, and more.

Stay right by the water. Relax by the pool. Admire the view from the balcony. We have fallen in love with Anna Maria Island, and we are sure you will too.

What is Anna Maria Island Like Today?

Anna Maria Island has undergone a pretty dramatic evolution. If you happened to last see the island back before 2000, a lot has changed.

What is the island like now? What are some of the most revolutionary changes you can expect? We cover how far Anna Maria Island- and what it is like today.

Anna Maria Island has undergone a pretty dramatic change, but the island vibe is still flourishing.

Growth Came- and Quickly

If you spend any amount of time researching Anna Maria Island and how it has changed, you will certainly come across one big reality- it has grown tremendously. The growth has been at an accelerated rate, and this has created some seismic shifts in the community.

There have been some political disagreements over where and how fast developers can build new homes and businesses. There is a pushback to development, with detractors arguing that the island can only develop so far and so fast. They argue that the island is losing some of its identity. Supporters are arguing that they are bringing finances, tourists, and a strong community backbone to Anna Maria Island.

Various building subcontracts have led to new structures, but many of these projects have stalled due to government blockage and other local concerns.

The Island Vibes

With that said, Anna Maria Island still retains its Old Florida charms and island energy. While some development has occurred, it could have been more if it wasn’t for strong local support against it.

The island vibe is still flourishing. There are wide assortments of local businesses which are local mainstays. Three Island Monkeys is a colorful and exuberant local boutique shop, Beach Bums still as many beach rental offerings, the Olive Oil Outpost has local treats and delicacies, and Island Gallery West keeps the torch hanging high for local art and artisans.

As long as visitors continue to aspire towards local places, and residents support the island’s individuality by buying locally, there will be a vibrant and healthy community.

Anna Maria Island things to do

Three Distinct Parts

There are incredible Anna Maria Island houses for rent on all three parts of the island. Each one has developed its own peculiar identity. These are Bradenton Beach, Holmes Beach, and Anna Maria city.

Bradenton Beach has a very colorful Old Florida vibe. It is home to a number of antique and boutique shops, including One Stop Shell Shop, Back Alley Treasures, and Bridge Street Jewelers. There is a very eccentric vibe in Bradenton Beach, with colorful pink shops lining the beach and small casual eateries at every turn.

Holmes Beach is most well-known for its major beach access points. The most notable (and main beach access) on the whole island is Manatee Public Beach. It features the most amenities, accessible parking, and many activities for all ages.

Finally, Anna Maria Island has a very culturally-rich downtown area. The northern part of the island is soaked in small side streets, unique shops, and old city history. Anna Maria city is the top place to go for shopping and dining. Its top feature is Pine Ave, where you can find acclaimed ice cream shops, massage spas, and more.

Anna Maria Island is defined by its three main sections, and each one is worth exploring and seeing.


Transportation has been a very important piece to keeping traffic flowing gracefully on the island. The free Anna Maria Island shuttle service is an invaluable resource for locals and visitors. The option offers a nice trolley-going experience through the smaller inner streets of downtown Anna Maria Island. See some of the best attractions and get easy transportation to and from the sights. You can use the trolley as a useful transportation tool or even a tour guide!

So what is Anna Maria Island like today? Public transportation is widely available. Each major part of the island has its own unique character. The beach access points are well-developed enough to accommodate the traffic flow without losing its charming beach vibes. The entire island is a tropical paradise, developed but still stunning, popular but still quiet in many areas.

Contact us to find Anna Maria Island lodging for your upcoming island escape. There are many reasons why the island is such an acclaimed and popular destination. The locals love it, the visitors crave more of it, and the beaches remain as vibrant as ever.

Distance from Sarasota to Anna Maria Island

Anna Maria Island is home to some of the most beautiful Florida weather nature you can find. From luxurious beaches to stunning and diverse wildlife, there’s something for everyone to see and enjoy outside. Whether you’d rather be running on the beach, trying to spot a dolphin, or discovering new beautiful sites, there’s no shortage of outdoor fun on Anna Maria Island.

So how do you get to the fun shores of Anna Maria Island from its nearby neighbor of Sarasota? Many visitors pass through Sarasota to get to Anna Maria. But navigating to the island may not always be so easy, especially for visitors unfamiliar with the gulf side of Florida.

how to get to anna maria from sarasota

Locating Sarasota on the Map

Overall, Sarasota is southeast of Anna Maria Island. Sarasota has a few small neighborhoods, including Sarasota Springs and North Sarasota. Sarasota is against the Sarasota Bay, while Lido Key is directly west, and against the Gulf of Mexico.

Sarasota is a pivotal gateway to the region. Visitors to Lido Key, Siesta Key, and, in many instances, Anna Maria Island, often pass through Sarasota on their island vacation adventure.

Many flying travelers will use SRQ Airport, or Sarasota-Bradenton International Airport. It is undoubtedly Sarasota’s largest airport, and one of the largest in the region for international travel. For travel purposes, you may want to mark the airport’s address of 6000 Airport Cir., Sarasota, FL 34243.

Locating Anna Maria Island on the Map

Anna Maria Island is an elongated island that spans about seven miles. You can almost see the water on each side because it is such a thin vacation escape. It averages about two miles wide, and spans from the city proper on the northern end to Bradenton Beach towards the south.

Anna Maria Island is directly west of Bradenton and just south of St. Petersburg across a massive body of water called Tampa Bay.

How Long is the Trip From Sarasota to Anna Maria Island?

So how far is it to the island and the many Anna Maria Island houses for rent? Travelling from Sarasota to Anna Maria Island is straightforward if you follow the major arteries.

The drive will take anywhere from 30 minutes on the short end to 50 minutes on the longer end, depending on seasonal traffic. There is no immediate and clear fastest route, as there are three viable options in total.

The two most direct routes to take are US-41 N and US-301 N. Both of these northern routes from Sarasota will take you directly into Bradenton, where you will cut west into Anna Maria Island by either route 64 or route 684. 64 is the northern entrance to the island while 684 will take you closer to the southern side. Both utilize one of two main bridge entrances from the east. If you do take 64, you will hug the water and eventually turn left onto Conquistador Parkway. You will follow this up to one of the two bridge accesses. Take the left at either 684 (44th Ave/Cortez Rd) or 64 (Manatee Ave). Keep an eye out for a left turn which will take you over to the island.

There is another bridge entrance on the very southern tip of Anna Maria Island, and this makes for the most interesting ride. When you leave Sarasota, you can choose to cross directly west into Lido Key. Here, you can follow the only route north all the way into Bradenton Beach and to Anna Maria. The majority of the time this route will be named Gulf of Mexico Drive (or Gulf Drive as you enter Anna Maria Island).

It is a sensational and scenic drive. While usually a few minutes longer than the inland driving of 301 or 41, it is far more satisfying. Beach views can be caught between the small coastal homes, and you can get an idea of the Anna Maria Island lodging as you span the Gulf of Mexico.

We love the island life, and we want to share Anna Maria Island with anyone and everyone. Sarasota is a great entry-point, but the real island life is up in Anna Maria.

Beaches Near Anna Maria Island

If you need a break from winter weather and choose to spend a long weekend or week on Anna Maria Island, an island off the Gulf Coast of Florida, you’re certainly in for a treat.

There’s nothing like sun, sand and lots of outdoor activities to make you forget about subzero temperatures and nor’easters. You’ll enjoy your time sunbathing, paddleboarding, snorkeling and, of course, eating all right on the island.

Of course, all of these activities are made even better by not just being next to the beach, but right on it. Anna Maria Island, and the surrounding communities are coated with hidden nooks, big escapes, and activity-filled beaches to see. Below we take a look at most, if not all, of the local beaches. Whether they are right on the island or within a short drive, there’s an amazing beach at every turn.

beaches to visit near Anna Maria

Beaches on the Island

For obvious convenience, you may want beaches closest to the Anna Maria Island houses for rent. Fortunately, don’t even need to get behind the wheel to get to some of the best beaches on the Gulf Coast.

  • Coquina Beach: Coquina Beach is one of the most popular beach escapes on the island, famous for its idyllic beachside expanse, its bright-white sand, and views of the nearby marine life.
  • Bayfront Park: Bayfront Park has a small beach area, but it is actually more known for its expansive picnic area, public grills, convenient amenities, playground, and close proximity to the local pier.
  • Palmetto Ave Beach: On the west side of the island, facing the gulf, is this popular escape. We have a number of Anna Maria Island houses for rent right in this popular area.
    Manatee Public Beach: Manatee is the defining public beach on the island. With many annual events, an array of boutique shops, bike trails, and rentals, and playground area, the majority of visitors wind up settling here for the day.
  • Bean Point: Bean Point is on the northern point of the island, and is only moderately well-known. It’s a reclusive and isolated beach escape, even enough to where there’s no clear signage and no available public parking!

Anna Maria is filled with beaches, and they all offer something a little different. Our Anna Maria lodging is located right by some of these top destinations. Whether you are looking for a big beach to socialize or a quiet escape, the island has it.

Beaches About 20 Minutes from the Island

You may want to venture off the island for a bit, and that’s perfectly okay! There are some lovely day trips or afternoon getaways you can make from your Anna Maria Island lodging to see a little more of the Gulf Coast of Florida. Below are some of the best beaches you can find within a short drive.

  • Beer Can Island: Beer Can Island is usually only accessible by boat. Snug between Anna Maria Island and Longboat Key, the name hardly does this powdery white sand beach justice.
  • Cortez Beach: Cortez Beach is technically in Bradenton Beach and is still on the island, but it is quite far south compared to other beach stops. It boasts its own unique and charming identity compared to the center and northern parts of Anna Maria.
  • Longboat Key: Longboat Key has about 12 small beach access points, all of them subtly tucked between private homes and rentals. Head south past the island about 10 minutes and keep your eye out for some of this quiet enclaves amidst some of the best sandy points in the whole gulf coast.

While some beaches are highly-trafficked, others lack even the most basic of amenities. What are you looking for on a vacation escape? What does your dream beach locale look like?

Top Resorts and Hotels on Anna Maria Island

As you would expect from a prime vacation spot like Anna Maria Island, there’s no shortage of top resorts and hotels to choose from when you book a stay on this beautiful barrier island.

Need accommodations for a large family? Or will a simple one-bedroom do? Looking for two baths? Fully equipped kitchens? Beachfront views?

Staying on Anna Maria Island

Anna Maria Island has it all when it comes to things to do and fine restaurants, but you’ll also find that the island offers a wide range of houses, condos and cottages for rent.

Here are a few of the top resorts and hotels you can consider when it’s time to book your long-awaited trip to Anna Maria Island. The below is an overview of our best places to stay for small groups.

Gulf View Rooms

It’s easy to use words like “perfect” and “superb” to describe our assortment of Gulf view rooms in Holmes Beach. These accommodations feature full kitchens or kitchenettes, large beds, dishwashers, community pool access and patios or balconies.

You’ll be able to enjoy the glowing gulf sunset every evening from this home away from home.

Deluxe King Resort View Rentals

Our fully-equipped Deluxe King Resort View rentals give you everything you need to spend a comfortable and memorable vacation on Anna Maria Island.

The rentals are idyllic romantic escapes. Their one-bedroom one-bath accommodations can help you relax right into the vacation experience.

You are within a short walk to the beach, and you can always lounge out quietly by the pool. Enjoy high-speed WiFi, oversized armchairs, and more.

Anna Maria Island Luxury Suite

As one of the finest hotels not only on the island but on the entire Florida Gulf Coast, our Anna Maria Luxury Suite offers a truly magical place to stay. It has everything you could ask for. A double vanity, two sofas, a shower and tub, high-speed internet, accessible parking accommodations, stocked kitchen cabinets, nightstands, lovely beach décor, and a lot more. You can always wander right down to the water or to the large turquoise pool.

Beachside hammocks. Tropical gardens. Perfect gulf views. You can prepare entire meals in fully-equipped kitchens and enjoy them outside. It has everything you need to make a great vacation better.

anna maria island lodging

Gulf Front Suites

What can be lovelier than spending a Florida vacation in a Gulf front suite? Achieve an old Florida feel with a mix of modern amenities with our selection of suites facing right out into the gulf.

We fit our suites with some top accommodations. Relax on a pillowtop mattress with convenient and comfortable duvet. Enjoy the fully-stocked kitchen, so you can easily prepare any meals you need without having to fully rely on dining out.

Rollaway beds can accommodate additional guests and a spacious dining and separate living room area can give you all places to lounge around.

At this location, you are very close to the warm Gulf of Mexico. The water is just a few steps away. If you don’t want to head to the beach, you can always stay in and enjoy the courtyard grills, swimming pools, and cabana areas.

Our gulf front rentals are also close to Bridge Street, with its many attractions and among the best restaurants on Anna Maria Island.

Explore Our Many Rentals

Anna Maria Beach Resort has plenty of Anna Maria Island houses for rent.

We offer 31 suites and deluxe and standard rooms, many with pools and views of the ocean. Our homes have multiple bathrooms, sleeping accommodations for 10 or more, fully stocked kitchens, decks, patios, balconies. The rentals offer so many outdoor spaces, you won’t know where to sit to enjoy the breathtaking vistas Anna Maria has to offer.

Review our full list of Anna Maria Island lodging to see and experience Florida’s premiere island destination. With our available Anna Maria Island houses for rent, you are never short of possibilities for the perfect vacation getaway in southern Florida.

Where to Eat – Anna Maria Island

When it comes to food you’ll find that Anna Maria Island boasts many top-rated eateries and five-star restaurants that are favorites of both locals and tourists. From breakfast to brunch and dinner to cocktails, there’s a place for everyone when it comes to Anna Maria Island dining.

Anna Maria Places to Eat

Restaurant Choices on Anna Maria Island

Let’s take a closer look at five restaurants that’ll answer the question: Where to eat on Anna Maria Island?

Sandbar Restaurant

According to TripAdvisor, nearly 80% of patrons rate this restaurant as “Excellent” and “Very Good”. Many reviews note the restaurant’s atmosphere, beach views and, of course, favorite dishes, such as blackened grouper and the shrimp sandwich.

The Sandbar Restaurant has lunch and dinner specials, a nice list of red and white wines, appetizers and, of course, premium seafood fare.

Classics include the Sandbar Steak, fried shrimp platter, stuffed shrimp and crab cake. You can also choose non-seafood dishes such as a gourmet burger, chicken n’ waffles, ribs, steak burger and sausage hoagie.

Waterfront Restaurant

“Amazing food.” “Delicious food.” “Great food and atmosphere.” “Perfect”, “wonderful” and “delightful.” These are the descriptions you’ll see in the many positive reviews written about the Waterfront Restaurant.

With mouth-watering main dinner dishes such as maple mustard salmon, mahi salsa de langosta (made with fresh Gulf Coast fillet), frutti di mare (Key West shrimp, mussels, clams and scallops) and apricot-glazed pork tenderloin, you can’t go wrong at the Waterfront.

The lunch menu features the Waterfront Chicken Sandwich, a fresh catch fish sandwich, the Waterfront signature burger and so much more. There’s even a vegan quinoa bake! Check out the kids’ menu, too.

Outdoor dining, specialty drinks, daily specials and a list of draft and craft beers make the Waterfront a must-visit if you’re looking for a relaxed dinner, a family meal or maybe a date night with your partner.

Beach House Restaurant

Beach House Restaurant in Bradenton Beach gets top ratings for food, service and atmosphere.

Covering 650 feet of beach, this restaurant was renovated in 2017 and has been an island favorite since 1993. Those renovations boast environmentally-conscious lighting and stunning landscaping.

From seafood gumbo and fish platter to burgers and short rib tacos, there’s something for everyone on the menu. There are fresh catch dishes, specialties (such as pork, snapper and even wild boar!) and house-made desserts.

Bridge Street Bistro

Referred to as “Anna Maria’s Hot Spot”, it’d be remiss not to mention at least one restaurant on Bridge Street. One place you can try is Bridge Street Bistro. It’s fairly new in town, but people are talking.

Highlights include Potato-crusted Grouper, Seafood risotto, Veal and chicken dishes, and an expansive list of wines from around the world. Nearly 90% of reviews on TripAdvisor rate this restaurant as “Excellent” or “Very Good”–if you’re shopping and need to stop for a bite, check out Bridge Street Bistro.

Harry’s Grill

If you’re on Gulf Drive, check out Harry’s Grill. Voted Best Burger on Anna Maria Island!

Tacos, quesadillas, chicken strips, fish sandwiches–this is a place the whole family will love.

It features a pet-friendly patio, live music, karaoke, and even cornhole! Stay, eat, play, and relax. You can make a whole afternoon or early evening when you happen by Harry’s Grill.

Every Friday from 3-5 is Harry Hour, with live entertainment and discounts on food and drinks.

Anna Maria Places to Stay

Where to Stay?

So whether you’re looking for formal, relaxed, fun–Anna Maria Island has a food establishment that will cater to your current mood.

In addition, there are lots of Anna Maria Island lodging options close to these and other restaurants and eateries. From beachfront houses to 1-bedroom cottages, you’ll find accommodations that comfortably sleep up the whole family, with two or more baths, private patios, pools and more.
Anna Maria Beach Resort has everything you’re looking for, book your stay today!

New Years Events on Anna Maria Island

Vacationing during the holidays can really provide for a memorable experience. You’ll be able to plan some fun activities to celebrate some of your favorite traditions.

And if you love to celebrate the New Year watching a ball drop or enjoying a big island event, you are in the right place. There is plenty to do on Anna Maria Island to kick it off right. New Year’s Eve is just around the corner and there are many ways to celebrate.

Anna Maria New Years Eve

Where to Watch the Fireworks

One of the most popular Anna Maria Island New Years things to do is, of course, watch the fireworks. You can do it from the comforts of your vacation rental or you can check out one of the fun spots on the island.

A local favorite is The Beach House on Gulf Drive North. Grab something to eat from their special dinner menu up until 10 p.m. and kick back with a few drinks until the fireworks go off.

This fireworks show is one of the most highly anticipated events all year long on Anna Maria Island. You can watch the incredible light show right from the beach as you say goodbye to the old year.

Other great spots to ring in the New Year on Anna Maria Island include Bortell’s Lounge on Gulf Drive and D Coy Ducks Bar and Grille on Marina Drive. Both bars are open past midnight and provide unique atmospheres to watch the ball drop on television and get ready for a brand new year in front of us.

Explore the Island

You can always check out some of the attractions that might be busier at other times of the year. Take this off-season time to check out some spots that will be much less crowded than usual. Explore the historic City Pier, Bean Point, and Coquina Beach. These areas may be remarkably quiet in the days leading up to the New Year.

You’ll still be able to spot some dolphins, birds, and other wildlife. If you’re feeling adventurous, you can rent a kayak or go on a boat tour to see some incredible views. Holiday hours may vary by boat availability, but there’s almost always a group heading out into the Gulf for a sunset or dolphin cruise.

Anna Maria New Years Eve

Nearby Celebrations

Anna Maria Island lights up with lovely New Year’s Eve events. Below are a few more that you can check out in and around the island.

Main Street Live is a big block party on Old Main Street in downtown Bradenton. The whole thing kicks off in the late afternoon with live music, food trucks, vendors, and more. Of course, as the clock ticks closer and closer to midnight you’ll want to find the best spot to watch the ball drop.

Additionally, you could head to Main Street in Sarasota for the downtown New Year’s Eve Party. Festivities start in the afternoon with music and dancing. The night highlights local musicians and performers, as well as a delicious collection of food and drinks from local-only vendors. The most unique thing about this party is that as the old year leaves and we ring in the new one—a “Pineapple Ball Drop” counts us down to midnight. This event is definitely one to add to the bucket list.

No matter how you choose to enjoy New Year’s Eve on Anna Maria Island, we’re sure you will have a fantastic time. It’s a holiday you won’t soon forget.

Celebrate it surrounded by friends and family during your holiday vacation to Anna Maria Island.

Anna Maria Island Weather

For many, spending some time away from home is what makes a good vacation. But, what can make for an even better vacation is heading somewhere with some more comfortable weather. That’s where a trip away to Anna Maria Island can be the perfect option for a winter getaway.

The weather in Anna Maria Island is balmy and beautiful nearly the entire year. This makes it a wonderful option if you’re looking to get away from some of the more frigid temperatures up north.

Weather Anna Maria

Average Temperatures

Anna Maria Island Florida weather holds a year-round average of about 75 degrees. In the summer, temperatures are a little higher, averaging around 80 degrees. And even though the winter weather on Anna Maria Island can sometimes be a bit cooler, it’s still warm enough generally to enjoy all the outdoor activities the area has to offer. You’ll still be able to take a walk along the shoreline, kayak, and explore many of the beautiful natural attractions of the island.

On, and In, the Water

The beachside wind chill shouldn’t scare you away. AMI can provide perfect weather for catching some rays. You’ll likely be able to enjoy a day sitting by the pool or even on the beach as the weather in December can be anywhere between 60 to 70 degrees, with lower dips in the 50’s. Bright a light jacket to prepare and enjoy- the sun will probably still be out in the heart of the winter.

However, if you’re looking to actually get in the water, you might want to hold off. The Gulf of Mexico can cool down dramatically as the winter months approach. It’s better to stick to a heated pool if you’re looking to get in some swimming time.

Winter Anna Maria

Winter Things to Do

One of the best things about the sensational temperatures on Anna Maria Island in the wintertime is the opportunity to experience your favorite holiday activities without the fear or frostbite or a snowstorm. Imagine singing Christmas carols or looking at light displays without shivering and bundling up in layers.

You can even cozily enjoy New Years Eve outside. On Anna Maria Island, you’ll be able to wear your favorite summertime outfit to watch the ball drop without chattering teeth the entire time. The balmy weather in Anna Maria Island can definitely provide some unique opportunities to make your vacation even more special and exciting than you may have thought before.

Although there are some hiccups in the winter months, sometimes the summer months on Anna Maria Island can be just as unpredictable. Just like anywhere else, Anna Maria Island Florida weather can change quickly.

The biggest hurdle in the summer months is the rainfall. Some months have seen upwards of 7 inches of rain, and it can vary from month to month or even week to week. When a rain shower comes through, it can cool things down considerably. So, you may want to pack a rain jacket or a light sweatshirt just in case you get caught in one of those famous Anna Maria Island sun showers.

Regardless of what season you plan your vacation for, the weather is sure to give you a handful of lovely days to explore everything from your Anna Maria vacation rental. You’ll almost always be able to take a stroll on the beach, enjoy a cocktail on an outdoor patio, or sit by the pool. This is the magic of Florida island living. You get the winter without the winter. You get a family getaway for the season that only requires a light jacket and a smile.

Two Bedroom Houses for Rent on Anna Maria island

Anna Maria Island is an elegant and quiet vacation destination tucked away along the Gulf coast of Florida. You can see the breathtaking views for yourself and a loved one by enjoying our many 2 bedroom houses for rent on Anna Maria Island.

Below are 10 incredible 2 bedroom houses for rent today.

Two Bedroom Houses for Rent on Anna Maria Island

Magnolia Breeze

Magnolia Breezes infuses a little bit of that key West flavor into a quaint little canal front cottage. The bright open floor plan is a delight. You are within walking distance of the acclaimed Historic Anna Maria City Pier.

Two Bedroom Houses for Rent on Anna Maria Island

Tropical Breeze

This beach cottage provides you a virtually uninterrupted view of the gorgeous gulf front. Take advantage of some convenient amenities, including a private washer and dryer, linen program, three televisions, and eight big beach chairs. The open air deck is your place to lounge out and see the gulf over a coffee, a beer, or a book.

Two Bedroom Houses for Rent on Anna Maria Island

Blue Oasis

The ground floor Blue Oasis is a nice secret alcove with a private heated pool, a fully stocked kitchen, and a beautiful back patio space with chairs, umbrellas carts, and bikes.

The Blue Oasis is titled appropriately. Stroll about two minutes down through the backyard for a gorgeous and expansive stop on the gulf front beaches of Anna Maria Island. Dip on back and enter the private pool. You can’t go wrong with this cozy island escape.

Two Bedroom Houses for Rent on Anna Maria Island

The Gulf Front

The Gulf Front has some of the most spectacular views on the island. The undisturbed view is in a quiet part of the beach line, where local wildlife plays, naps, and strolls around. There’s a TV in every room, a private walkway to the water, and an elevator to the front door. The Gulf Front is designed to maximize convenience and relaxation.

Two Bedroom Houses for Rent on Anna Maria Island

Beach Isle

The beach Isle is defined by its bountiful upstairs deck. Watch the private heated pool and spa from above and appreciate the intimate privacy offered from the bold property gate. You are in your own little nook of the world, with flat screen televisions, a stand-in shower, professional linen service, and close proximity to some of the island’s most alluring and romantic restaurants.

Two Bedroom Houses for Rent on Anna Maria Island

Beach Bliss

This blissful beach bungalow is just what you need. Stay inside and enjoy the tropical landscaping, the stand-in shower, and the fully-furnished and wonderfully-decorated beach décor. Of course, you can always make your way outside for an afternoon in the private heated pool and spa or an evening walking the beaches- only two minutes away by foot.

Two Bedroom Houses for Rent on Anna Maria Island

Beach Life at the Pointe

Beach Life at the Pointe is filled with romantic energy. Spend the days of your vacation lounging out in this classic-styled Old Florida beach cottage. Make a nice meal in the newly upgraded kitchen. Afterwards, take a nice walk over to the water. You don’t even have to go anywhere. Enjoy a direct gulf front view from your screened in wrap around deck.

Two Bedroom Houses for Rent on Anna Maria island

Redfish Cottage

This one-bedroom one-bath retreat is the perfect fit for a romantic getaway. The adorable cottage is charming and rustic, with a bold Old Florida kitchen design and a community grill for an evening cook-out. Take a walk on over to the pier for a luxurious view of the bay. Redfish Cottage is an idyllic beachside bungalow for two.

Two Bedroom Houses for Rent on Anna Maria Island

Aqua Reef

The open kitchen concept really brings everything to life in this unabashed beach-themed home. Aqua Reef offers a five-minute walk to the gulf, a solar heated pool, a luxurious waterfall, a washer and dryer unit, a gas grill, and much more. The furniture is even special. Feel the wonder of a bamboo memory foam sleeper sofa. When not lounging around inside, take it outside and chill out by the water by six beach chairs and a private boat dock.

Two Bedroom Houses for Rent on Anna Maria Island

Shell Haven

Shell Haven’s grandest feature is its instant access to the beach. You can hear the morning waves settle on the coast as it sits just outside your condo. The porch overlooks the beach and a walking path to get you right to it. The fully stocked kitchen acts as a nice lunch break area.

These wonderful vacation getaways are some of the best places for you to stay on the island. You won’t get better beach access and proximity to the local hotspots anywhere else.

Christmas Things to do on Anna Maria island

When the snowy season is creeping around the corner and the air stays consistently cool during noon, escape on over to Anna Maria Island.

This welcoming Florida destination glows bright and beautiful in December. So what can you do to really absorb that holiday spirit? Below is an overview of just a few of the top things to do on Anna Maria Island during the holiday season.

Annual Privateers Parade

Annual Privateers Parade

It’s another year, another boat-filled and pirate-themed Christmas romp through the gulf coast. Anna Maria Island has many holiday events, but few are as eventful and charming as the AMI Privateer’s Boat parade. From Bayfront Park to Bradenton Beach and up along Coquina Beach, a slew of pirate-adorned ships cruise rambunctiously along the coast.

The ships will come coated with festive decorations. The show will feature the firing of black powder. These are pirates after all.

Santa will also give away Christmas gifts when the parade ends in Bradenton. The event is completely free, as you can come along the beaches of Anna Maria Island, select a seat in the sand, and soak in the sights all day long.

The parade is expected to begin at 10 a.m.

Anna Maria Island Christmas Tree

The huge Bridge St Christmas Tree is a community staple and a sight to behold. For decades, the community has erected and lit up a massive Christmas tree for all to see. It then sits for the month of December as a spectacle for visitors and locals, and a reminder of the spirited magic of Florida’s coastlines during the winter season.

The tree lights up at 6:45 p.m. The event is at the end of Bridge St. Once the Christmas tree lights up, the family-friendly fun begins. The city hosts a special screening of How the Grinch Stole Christmas. The original animated classic features the Grinch, the citizens of Whoville, and an adorable and hesitant puppy as they all learn to get along.

The movie begins at 7 p.m. on Nov 26th in the same location. The entire event, from the Christmas tree light-up to the film screening, is entirely free. Popcorn and a concession stand will be available on-site. Bring a blanket once the sun settles down. Utilize local transportation as needed.

Christmas on Bridge Street

Bridge Street is a community haven- the center of the action for Anna Maria Island locals. It is not just the home for one major Christmas event, but two.

The Christmas on Bridge Street festival is December 17th. The crux of the event is the Kids’ Craft & Cookie Bazaar, with local handmade ornaments and baked fresh cookies.

Visitors can make their own hot cocoa at the cocoa-making station or join a raffle in support of the Turning Points of Manatee. A performance by the Dickens Carolers helps deliver that big and unrestrained holiday energy.

The event is expected to begin around 4:30 p.m. and end at 8:30 p.m.

Anna Maria Island Cocktail Tour

Anna Maria Island Cocktail Tour

Looking for something to do on Anna Maria Island that captures that wild and fun spirit? Go on a cocktail tour to some of the best drinking stops on the Island. There are high-class stops by Bridge Street and some casual and laid-back sports bars. Slim’s Place is a Philadelphia-styled sports bar in the northern side of the Island.

The Doctors Office on Holmes Beach is known for its memorable cocktail concoctions. Anchor Inn, right nearby, is a cozy little dive bar that captures a very relaxed Old Florida ambiance.

You can even settle with the Sandbar Restaurant – a riveting and gorgeous getaway on the northern tip of the island with some of the best views anywhere in the area- maybe even the whole of Florida. The Sandbar Restaurant closes early, but be sure to escape on over to it at some point for your trip.

There’s so much more to explore during Christmas on Anna Maria Island, a time of year when the weather is nice compared to colder areas up north, the beach views are incredible and the events, restaurants and attractions draw people from all over the nation.

These are just a few fun ways to soak in your Anna Maria Island vacation. Have an amazing Christmas away from home and on the majestic island beaches.

Visit Anna Maria Island’s Famous Piers

Anna Maria Island is known for its piers. It has three main piers that stretch out over the Gulf of Mexico waters, and each has something different to offer. Anna Maria Island piers are perfect places to enjoy a cold dessert, watch the sun go down, eat tasty seafood, or even do some pier fishing.

Here is a brief introduction to the three Anna Maria Island piers to visit while on vacation.

The Rod and Reel Pier Anna Maria Island

Anna Maria City Pier

The island’s historic City Pier is the longest on the island at 700 feet, a long finger dipping into the turquoise gulf waters.

The City Pier has been victim to many tropical storms over the years, and was badly damaged by Irma in 2017. The pier is currently being rebuilt from the last major onslaught of weather, and is close to pedestrians for a period of time.

When it reopens, expect a lively hub of activity, especially during high season. Both visitors and locals love to visit the City Pier to watch the sky burst with color over the bay – on clear days, you can even see the Sunshine Skyway Bridge that connects St. Petersburg to the north with Bradenton and Sarasota to the south.

You’ll find the Anna Maria City Pier at 100 S. Bay Blvd., just south of Bayfront Park.

The Rod and Reel Pier

Head a few blocks north on the same side of the island and you’ll find the Rod and Reel Pier, a 350-foot wharf where you can eat great seafood and go pier fishing.

The Rod and Reel Pier is also the name of the restaurant that sits at the end of the pier on top of the blue water. This two-story restaurant is newly renovated, but still retains the charm and flavors of Old Florida. This eatery serves only the finest local fish and seafood – a mix of traditional dishes, local favorites, and famous Rod and Reel specials. The fried grouper, seafood omelette, and crispy fries are just a few of the menu favorites.

Pier fishing is popular activity on this wharf, particularly among young kids. Rent a rod or bring your own, and drop the line into the blue waters below. Keep your eyes peeled for playful dolphins and slow-moving manatees in the water below. They are curious, social animals that often pay pier-goers a visit.

The Rod and Reel Pier is located in the city of Anna Maria at the northern tip of the island at 875 N. Shore Dr.

Bridge Street Pier

Historic Bridge Street is Anna Maria Island’s bustling shopping and dining area – all at the foot of the Bridge Street Pier.

The pier was once part of the original – and only – bridge onto Anna Maria Island before the island was developed and other access roads were built. The pier is located south of the Cortez Bridge which offers a southern access to the island from the mainland village of Cortez. It is an historic pier on the bay side of the island, with white-painted railings, a clock tower, and a covered area with benches.

Grab a cone and watch the sailboats bob in the harbor beside the Bridge Street Pier. Keep an eye out for dolphins, manatees, and pelicans catching their next meal, while the kids enjoy some catch-and-release pier fishing. Then, head to one of Bridge Street’s restaurants for a scrumptious meal.

Find the pier at 200 Bridge St., in Bradenton Beach, a quick trolley ride from many local vacation rentals.

The perfect place to take an evening stroll, the Anna Maria Island piers have become gathering spots for vacationers and locals. You can read more about AMI’s activities and attractions on our website. While you’re at it, browse our list of luxury rental properties to find your next vacation paradise.

4-bedroom Houses for Rent on Anna Maria Island

Anna Maria Island is the perfect place for a beach vacation with family, friends, or both. Our four-bedroom houses for rent on Anna Maria Island offer perfect hotel alternatives for multi-generational families, groups of friends, or couples with grandkids.

Here are a few rental properties to consider for your next Anna Maria Island vacation.


Aqua Bay Anna Maria Island

Aqua Bay

Aqua Bay is unique because it has a pool and spa on one side of deck and the canal on the other. A five- to seven-minute walk to the beach, this beautiful Holmes Beach property sleeps eight people comfortably, and has a rooftop firepit overlooking the canal.


AMI Beach Home Anna Maria Island

AMI Beach Home

AMI Beach House is a sprawling four-bedroom bungalow with a spacious interior in Holmes Beach.

It features a private, heated pool and covered spa for rainy days, as well as giant chess, a swing, a hammock, and a foot shower. It has a large living room for relaxing with family and friends, and is steps – about 30 seconds – to the beach.


Pineapple Key Anna Maria Island

Pineapple Key

Pineapple Key is the perfect place to host a family with older kids.

The property features two sets of bunks, a private heated pool, a covered living area, and plenty of entertainment: Wii, board games, and multiple TVs. Located in Holmes Beach, this home is located just two houses from a free trolley that offers quick access to the rest of the island.


Avenue E By the Sea Anna Maria Island

Avenue E by the Sea

Avenue E features a large outdoor deck on the roof dotted with colored deck chairs. From here, you can see the beautiful waters of the Gulf of Mexico, whose beaches are a short, two-minute walk away.

It has a small pool that sparkles in the sun surrounded plenty of colorful deck chairs, as well as a covered patio with comfortable furniture, a two-car garage, and an elevator.


Hawaiian Hideaway Anna Maria Island

Hawaiian Hideaway

This bright, yellow four-bedroom is a great place for families who want to bring their pup along, as it is dog-friendly. It’s also perfect for young children, as it has a pool with a large shallow end – and submerged barstools for adults – and quick access to the beach.


Seahorse Beach House Anna Maria Island

Sea Horse Beach House

Our Seahorse Beach House is located at the south end of the island in Bradenton Beach, and is one of the best four-bedroom houses for rent on Anna Maria Island for people who like to shop and dine. The property is just around the corner from bustling Bridge Street, and is a 30-second walk to the warm waters of the Gulf of Mexico.


Gulf Front Paradise Anna Maria Island

Gulf Front Paradise

This brand-new Anna Maria rental is one-of-a-kind, featuring a number of decks overlooking the ocean. It’s right on the beach, with a large, resort-style saltwater pool in the backyard. It sleeps 10 people, thanks to a bedroom with two bunk beds – perfect for large families and groups. An elevator makes this property accessible.


Sunset Point Anna Maria Island

Sunset Point

As the name suggests, this AMI rental offers spectacular views of the sun setting over the Gulf of Mexico. Watch it while soaking in the pool, on a lounge chair with a glass of wine, or through the large dining room windows.

Located on the island’s quiet north end, this four-bedroom is chock-full of amenities and right on the sand.


Sunchase Villa Anna Maria Island

Sunchase Villa

Also on the north end of the island is Sunchase Villa, a ground-level beach cottage that exudes Old Florida living. From the screened in front porch overlooking the Gulf of Mexico, to the wooden interior, to the cozy rooms, you’ll feel right at home in this luxury cabin.


Reef Romance Anna Maria Island

Reef Romance

For those who want to spend their whole vacation on the beach, this vacation rental might be your best bet.

Located just a few houses from the beach, Reef Romance offers quick, easy access to the beach on a quiet street. At the foot of the outdoor spiral staircase is a rectangular pool surrounded by tropical foliage and cushioned lounge chairs.

With so many incredible four-bedroom houses for rent on Anna Maria Island, you’ll have no trouble finding the perfect vacation rental for you and your family. Check out any one of these property listings on our website for more information or to check availability.

Weddings on Anna Maria Island

Powdery white sand, swaying palm trees, crystal-clear turquoise waters – what could be a better backdrop for saying “I Do”?
There are plenty of reasons to get married on Anna Maria Island. If you’re looking for a relaxed beach environment with high-quality food and a touch of elegance, this island might be the right place for you and your partner.

Below is a guide to Florida destination weddings on beautiful Anna Maria Island.

Why Get Married on AMI?

Florida destination weddings are a popular choice for many who want to get married with their toes in the sand. There are lots of benefits to hosting this special day on Anna Maria Island. Here are just a few of them:

They’re cheaper. First off, destination weddings tend to be cheaper than local ones. With a number of Anna Maria Island vacation rentals for weddings to choose from, you can have your wedding and honeymoon in the same place.

Most wedding venues offer packages that include everything, reducing the cost (and hassle) of individually hiring caterers, decorators, dish rentals, and a DJ. Florida destination weddings are typically more intimate – usually, only family and close friends and family will fly across the country for the celebration. This means you can go with quality over quantity when it comes to the dinner, spending less overall on food and drink.

They’re easier. Let’s face it: we have enough stresses in day-to-day life. Why should wedding be another one? Florida destination weddings tend to be less work. While you’d think it would be simpler to do a wedding in your hometown, destination wedding accommodations and venues are set up to make your job easy. Rather than coordinating everything yourself, let experts at Anna Maria wedding venues do the work for you.

They’re more laid-back. There’s something about a palm-tree dotted beach and a tropical cocktail that says relaxed. And since your wedding will likely have both of those, it should be relaxed, too.

Invite your guests to come in sundresses and linen shirts. You can even walk down the aisle barefoot if you get married on the beach. Leave the hairspray at home, and opt for a loose beachy ‘do. You can even opt for a buffet seafood grill instead of a plated meal. Take advantage of the island setting with a low-pressure event. Sometimes a more casual wedding can be more fun!

Anna Maria Wedding Venues

There are some incredible Anna Maria wedding venues to choose from.

The Sandbar Restaurant is an excellent Gulf-front restaurant on the beach – the perfect venue for couples who want to get married with their toes in the sand. The venue is at the north end of Anna Maria Island right on the beach. They prepare incredibly tasty seafood and have an outdoor wedding pavilion that can seat up to 160 guests.

The Beach House is another waterfront restaurant that offers wedding packages for both ceremony and reception. Like the Sandbar, this restaurant boasts a white-sand beach and stunning sunset views. It features a covered, outdoor event space for weddings of up to 100 guests. They take care of everything: rentals, setup, centerpieces, and, of course, a scrumptious meal. They also have a bridal suite for wedding parties that want to get ready on-site.

For a wedding with a nautical feel, tie the knot at the Waterline Marina Resort & Beach Club. They boast Old Florida hospitality, beautiful water views, and elegant facilities for your event. Waterline offers event planning, full set-up and tear-down services, and in-house catering from their restaurant, Eliza Ann’s Coastal Kitchen. They have a number of multi-bedroom suites that can sleep families and groups of friends. This 50-slip marina offers a classic and elegant backdrop for wedding photos.

Consider Anna Maria vacation rentals for weddings to combine your big day with a beach holiday. With Anna Maria wedding venues dotting the island, there’s no shortage of places to walk down the aisle – er, beach.

Give us a call today at 941.778.4178 for more information on our island vacation homes and condos. Or, check our website for photos and availability.

Girls’ Getaway to Anna Maria Island

If you’re planning a girls’ getaway to Anna Maria Island, you’re in luck: there are tons of great things to do on Anna Maria Island with your BFFs. Visit Anna Maria Island spas, relax body and mind at a rejuvenating yoga class, and eat, eat, eat.

Here are a few of the AMI must-dos when traveling with a girl-only group:

Get Pampered at the Spa

Anna Maria Island spas are a real treat for the body, mind, and soul. What better way to start the day than a relaxing massage, rejuvenating facial, or mani-pedi with the girls? Book a post-breakfast treatment at one of these great spas before hitting the beach.

Bradenton Beach’s Aluna Wellness Center & Spa (2219 Gulf Dr. N.) is a five-star spa known for its top-notch massages and pain-relieving acupuncture. This is one of the best Anna Maria Island spas for a post-beach backrub.

Body & Sol Spa and Wellness, located at the north end of the island, offers therapeutic massages, nails, and facials in a relaxing environment. You and the girls will feel like a million bucks after an hour or two at Body & Sol.

Salon Salon on Pine (313 Pine Ave.) is another north end Anna Maria Island spa that is known for its quality service and friendly staff. Its hip turquoise interior complete with a chalkboard in the shape of a surfboard makes it a little less stuffy than other spas. From wedding hair to a mean mani-pedi, this salon offers all you need to feel beautiful on your girls’ getaway to Anna Maria Island.

Stretch it Out at a Yoga Class

You’ve heard it before: true beauty means feeling great inside as well as out. Take a yoga class to stretch your muscles, align your body, and clear your mind while on a getaway with your girlfriends.

Island Yoga Space (9805 Gulf Dr.) is a great place to start. They are located in the city of Anna Maria on the north end of the island. They offer a variety of classes, from vinyasa flow to gentle yin, as well as workshops and events.

The studio is conveniently located right upstairs from Body & Sol Spa, overlooking the blue gulf waters. Take an energizing yoga class, then unwind with calming massage.

If you’re looking for a bit of diversity in your vacation exercise regime, grab the girls and head to Island Fitness (407 Magnolia Av.) in Holmes Beach. Take a yoga class, or opt for something a little different, such as yoga/pilates mix or “guts & butts” to give your abdominals and glutes a workout.

Dine at One of the Island’s Many Restaurants

Now that you’ve got a solid workout, indulge in some Florida delicacies. Eating is one of the best things to do on Anna Maria Island. There are a number of fabulous restaurants for a perfect girls’ night out.

The Sandbar Restaurant (100 Spring Av.) is an excellent choice for any occasion. It’s the only restaurant that allows you to dine with your toes in the sand, with tables right on the beach. Elegant and casual at the same time, The Sandbar has scrumptious menu of seafood creations, including stuffed grouper, stone crab, and coconut shrimp.

For something a little more casual but with incredible flavor, head to eat here AMI, a cozy restaurant with a creative, eclectic menu. Pair your meal – try the bruschetta, lime-butter mahi mahi, or swordfish – with a flavorful craft beer or a glass of wine from the long drink menu.

Even if you have your own kitchen at Anna Maria vacation rentals, it’s nice to go for a big breakfast at least once. Grab breakfast or brunch at Anna Maria Island Beach Café, located right on beautiful Holmes Beach. They have lots of great breakfasts, but the all-you-can-eat pancakes is a definite winner.

Consider Anna Maria vacation rentals for your next girls’ getaway. We have plenty of accommodations to choose from, including multi-bedroom homes so your group can stay together. With so many group-oriented things to do on Anna Maria Island, there’s something everyone in your party will enjoy.

Biking Rules & Rentals on Anna Maria Island

If you’re looking for a bike-friendly beach vacation, Anna Maria Island is for you. This island is perfect for couples and families who like to keep their transportation “green” by using bike paths instead of motorized vehicles.

Stop off at one of the many Anna Maria Island bike rentals shops, and cruise around the island, stopping at your favorite beaches, restaurants, and attractions along the way.

anna maria island bike rentals

Bike trails & paths

Walking and cycling are the norm for transportation around the island, which is only about two miles long and seven miles wide.

The beach is a stone’s throw away from pretty well anywhere, and many Anna Maria Island vacation rentals are located right along the waterfront. With lots of lights, stops, and pedestrian crossings, speed limits between 15 and 25 miles per hour, and heavy traffic depending on the season, biking can be just as fast – if not faster – than getting around by car.

Fortunately, Anna Maria Island is set up for cyclists, with bike trails, paths, and lanes throughout the island. Ride up and down Gulf Drive, the main north-south street that runs the length of the island, using its wide bike paths. Many of the attractions, beaches, and restaurants on the island have free bike racks in order to lock up your ride while exploring the island.

If you’re looking to explore the opposite end of the island by bike but aren’t up to the seven-mile ride, hop on the free island trolley that runs all day long. Each trolley can hold two bikes.

Check out the City of Anna Maria’s online “Bike Route Guide” for more information on official bike routes on the island. Nearby Longboat Key and Lido Key also both offer bike paths with beautiful views, if you’re up for a longer ride. Or, alternatively, head across the southern bridge to the mainland village of Cortez for some dockside, Gulf-to-table fish and seafood.

Rules & Regulations

Cyclists on Anna Maria Island should obey traffic laws and signs at all times while riding on both roads and bike paths. Here are some road safety tips to adhere to:

  • Cycle single file with the flow of traffic
  • Ride in the right lane unless passing or making a left turn
  • Use an outstretched arm to signal left and right turns
  • Stop for pedestrians or anyone moving slower than you
  • Watch out for opening car doors
  • Use lights and reflectors at night
  • Use your bike bell when passing parked cars, as well as pedestrians, cyclists, and roller-bladers on bike trails

For additional safety, don’t forget the “ABC” bike check: air in your tires, brakes working properly, and a chain that’s taught, clean, and oiled.

Bike Rentals

Anna Maria Island has a variety of rental shops that offer everything from bikes to kayaks to beach equipment. Check out AMI Adventure Rentals with so many adventure excursion options in additional to bike rentals.

On the north end of the island, try Beach Bums Rentals & Gift Shop (427 Pine Ave.) or Island Scouter Rentals (9908 Gulf Dr.). These shops are located within a few blocks from each other, and offer beach cruisers, tandem bikes, geared bikes, and even tricycles. Prices range from $5 an hour to $100 a month, depending on the size and type of bike.

Midway down the island, you’ll find even more Anna Maria Island bike rentals. Try Fun and More Rentals (5347 Gulf Dr.) or Island Scooter Store (5321 Gulf Dr.), both in Holmes Beach. At the southern end of Anna Maria Island, check out AMI Beach Fun Rentals (3228 E. Bay Dr.) for all your vacation gear.

Many of these shops also rent motorized scooters, golf carts, and paddlecrafts, as well as beach equipment like umbrellas, lounge chairs, baby gear, and water toys.

Main Streets on Anna Maria Island

Fortunately for newcomers, getting around Anna Maria Island is a breeze – literally.

Many of the island’s main roads run parallel to the ocean or bay, allowing you to easily locate yourself without turning on the GPS or opening Google Maps. Below are a few of the most important main streets to know on Anna Maria Island.

main streets on anna maria island

Gulf Drive

Gulf Drive runs from the southern tip of the island through the city of Holmes Beach and along Manatee Beach, continuing north through the middle of the island, and eventually winding its way to the gulf side of the island.

Gulf Drive is a happening place, with great Anna Maria Island shopping, restaurants, accommodations, and more along it. Though a main thoroughfare, it’s largely a quiet residential street with beautiful foliage and ocean views. Gulf Drive is the most westerly north-south street on the island, ending at the north end close to where it intersects with Pine Avenue.

Gulf Drive North and South on the southern end of the island, connects the cities of Anna Maria, Holmes Beach and Bradenton Beach, and, eventually, AMI to Longboat Key. In southern Bradenton Beach, the street is home to a number of restaurants, including Gulf Drive Café, a Mexican cantina, and a beachside café.

Pine Avenue

Historic Pine Avenue is a bustling street of eateries and attractions – the perfect walkable place to grab a bite to eat, go shopping, and absorb some of the island’s local history.

Pine Avenue is full of cafes and restaurants, including a tasty Mexican taqueria, a pizzeria, an ice cream parlor, and a dress-your-own donut shop. Here, you’ll find a couple of different surf shops for all your beach gear, souvenirs, and paddlecraft rentals. Some of the best Anna Maria Island shopping can be found here.

Pine Avenue is also the heart of the island’s history. The Anna Maria Island Historical Society and the Roser Community Church are both located on Pine, and Bean Point, the island’s first settlement and homestead, is just a few blocks away.

The road runs from gulf to bay sides of the island, ending at Anna Maria City Pier on the east end. Bayfront Park is just north of the City Pier.

Conveniently, the free local trolley stops at the City Pier, so it’s very easy to get to Pine Avenue for shopping, eating and outdoor fun no matter where your vacation rental is located.

Bay Boulevard

Turn north at the eastern end of Pine Avenue, and you’ll be on Bay Boulevard. Head just a few blocks north to Bayfront Park, a popular family spot for swimming, picnicking, and playing outside. This spot is known for its incredible views of Egmont Key, the Sunshine Skyway Bridge and Tampa Bay.

Continue north on North Bay Boulevard to historic Bean Point for more amazing ocean views, more wildlife and the perfect sunset. Or, head south on Bay Boulevard to a point overlooking Bimini Bay that’s home to a few sailing companies and the Island Ocean Star restaurant.

Manatee Avenue

While Manatee Avenue isn’t the best road for an afternoon stroll, it is an important one to know, as it’s the main access point onto the island from mainland Bradenton.

The road includes large sections of bridge, crossing Palma Sola Bay, passing by the Robinson Preserve to the north and the Neal Preserve to the south – both worthwhile visits for the nature-loving vacationer.

The stretch of Manatee Avenue closest to Anna Maria Island looks out over the open Gulf waters, crossing Anna Maria Sound, with the Sunshine Skyway Bridge in the far distance north. A couple blocks after passing the “Welcome to Anna Maria Island” sign, Manatee Avenue turns into Gulf Drive.

Anna Maria is a small, quaint island with a few main streets that you’ll soon get to know well. Getting around Anna Maria Island by car, bike, or foot is easy – after a day or two on vacation, the island will start to feel like a home away from home.

For more information on things to do, transportation, and vacation rentals on Anna Maria Island, give us a call today. Our team can help answer all your pre-departure questions – by the time you’ll get to AMI, you’ll already to know the island like the back of your hand.

Best Beachfront Vacation Rentals on Anna Maria Island

Summer has finally arrived, and everyone wants to spend it on the beach.

For the months of July and August, Anna Maria beachfront vacation rentals are a hot commodity. Though some are booked through until fall, a number of fantastic properties have availability over the summer months.

Choose to stay in the quiet north end of Anna Maria or the bustling south end in Holmes Beach or Bradenton Beach. But, wherever you stay, be sure to secure a rental with beach access and a Gulf view to get the most out of your holiday.

Below is a list of a few of our favorite vacation rentals right on the beach – all with vacancy at some point during the warm, summer season.

anna maria island beach front rentals

The Group Rental: Gulf Front Paradise

If you’re planning a group or multi-family trip this summer, this incredible private residence is worth checking out.

This luxury beachfront home has four bedrooms and almost as many bathrooms. It has a professional chef’s kitchen with modern appliances to help make your family vacation even more enjoyable.

The house has a private saltwater pool with a hot tub, and a number of balconies at different levels. Enjoy private, white-sand beach access, beach chairs, cooler, and umbrella.

With a big pool and even bigger one out front, this house offers the best of both worlds.

beachfront anna maria island cottages

The Old Florida Cottage: Low Tide

This intimate two-bedroom, one-bathroom cottage takes you back to simpler times.

Brown wood flooring, white paneled wood walls, and a small deck with chairs makes this the perfect private getaway for a couple or small family. The cottage has a queen bed and two twins, and sleeps up to four people in rooms with large windows.

The cottage has a minimal, but fully equipped kitchen. The cottage features wireless internet, a television, and a DVD player, as well as a washer and a dryer.

This elevated cottage is right on the beach, offering quick access to the north end’s secluded beaches, as well as the shops and restaurants of Pine Avenue.

pine avenue anna maria rentals

The Beach and City in One: White Sands

The white sands right outside the front door is just one of the benefits of this bright yellow seaside cottage.

It has a big screened-in porch with comfortable furniture looking over the Gulf of Mexico – the perfect place for a morning coffee, an afternoon snooze, or an evening chardonnay. The cottage has two bedrooms and two bathrooms, sleeping up to four people.

White Sands is located just south of bustling Holmes Beach, halfway down the island this means easy access to both north and south ends, as well as close to the amenities of the city of Holmes Beach. Hop on the free Anna Maria Island trolley that runs up and down the island from morning to evening – it stops right outside this cottage.

beach front condo anna maira island rentals

The Beachfront Condo: Island Paradise 6

This low-rise condo has a panoramic Gulf view from the open concept living room and kitchen.

The condominium has three bedrooms and two bathrooms, with a modern Italian-tiled kitchen with a bar. The unit comes with wireless internet and a flat-screen TV, and is walking distance to shops and restaurants in Holmes Beach.

The unit has a spacious balcony and a large, shared heated pool with a railing and wide steps leading down into the water. The unit is located right on the waterfront, connected to beautiful Coquina Beach by a short path through the grasses.

For more information on summer availability for these incredible Anna Maria Island beachfront vacation rentals, give us a call today at 941-778-4178. From palatial beach homes to seaside cottage to modern condos, we have a variety of rentals available to help you spend the upcoming summer season on the beach.

Best Beachfront Restaurants on Anna Maria Island

There’s no such thing as too much time spent on the beach on an Anna Maria Island vacation. So, why not finish off your beach day right by dining with your feet in the sand?

Anna Maria has plenty of great restaurants, from casual pub food to world-class dining experiences. While you may enjoy cooking at Anna Maria vacation rentals on occasion, vacation is about treating yourself. What better way to do this than eat with an ocean view at the best Anna Maria Island restaurants on the beach?

Here are our top picks for waterfront dining on the island:

The Sandbar Restaurant

The Waterfront Restaurant

This restaurant has a long Old Florida-style wrap-around patio under a striped awning – the perfect setting for a beach front restaurant on the quiet northern tip of Anna Maria Island.

Here, beautiful views are paired with an innovative menu – in fact, a page of the menu is dedicated to unusual specials in order to allow their skilled chefs to use their creativity.

The Waterfront Restaurant serves lunch and dinner daily. For lunch, tropical-inspired salads topped with beef, chicken, or seafood seem to take the cake. Dinner menu includes appetizers like lobster bisque and grouper tacos, and mains ranging from the classic chicken parmesan to moqueca, a traditional Brazilian stew made with local seafood.

Beach Bistro

Halfway down the island is Beach Bistro, an upscale beachfront restaurant in the city of Holmes Beach.

This restaurant features white-tablecloth dining in a romantic atmosphere. Floor-to-ceiling windows bring the indoor dining room closer to nature. A large outdoor patio offers incredible views overlooking white sands and the blue waters of the Gulf of Mexico. Beach service is weather dependent.

The foie gras, lamb, and varied tasting menu are popular choices, along with a number of seafood dishes, such as maple shrimp and “lobstercargots,” imitation escargot made with juicy lobster meat.

beachfront restaurants anna maria island

Gulf Drive Café

This Bradenton Beach joint is a casual beachside café during the day, and a party spot at night.

It features a large deck overlooking the beach – perfect for families with young kids who want to play in the sand while waiting for the food.

Gulf Drive Café serves classic American pub food, with a focus on fried seafood plates. Breakfast is available in the mornings, too (try the French toast), and there is often live music in the evening.

With its panoramic view of the beach, this has got to be one of the best places to watch the sunset fill the sky.

The Beach House Restaurant

Watch the sun go down from the patio of The Beach House Restaurant as colorful cocktails float by on a platter, begging you to order another.

This restaurant a casual-fine dining restaurant located in Bradenton Beach, on the south end of Anna Maria Island – yet another beachfront gem among the array of Anna Maria Island restaurants.

The Beach House is a seafood restaurant with an eco-friendly bent. Mains include a seafood capellini, crab cakes, and stuffed red grouper. They use turtle-friendly lighting and native landscaping in the design of the restaurant, buy locally sourced seafood and produce, recycle, and serve drinks without straws.

Coquina Beach Cafe

Coquina Beach Café is a great little Bradenton Beach patio dotted with thatched umbrellas and outdoor furniture. It’s a casual daytime cafe right on beautiful Coquina Beach, typically open from 8 a.m. to 4 p.m. (5 p.m. on weekends).

They make a mean breakfast, which includes waffles, French toast, and all the staple bacon-and-egg fishes. Not a bad place to have your morning coffee, if you ask us.

Lunch includes a long list of sandwiches, salads, and, of course, fish tacos. Stop by for a cold beer on a hot, sunny afternoon while the kids continue to play on the beach.

Best Anna Maria Island Rental Company

Forget something back at home during your beach vacation on Anna Maria Island? Curious to give a new outdoor sport a shot?

Anna Maria Island has quite a few rental companies on its small shores. You can’t go wrong checking out some of the rental providers and seeing what they have in store. Below is a look at what the best rental companies offer, and not always just in item rentals.

AMI Adventure Rentals

With AMI Adventure Rentals, you can go on many different adventures all in one place. They deliver directly to your vacation rental for your convenience.

Go solo or go with a guide. Equip yourself with everything you need and just explore or go on a specific and scheduled journey. It is all available.

AMI Adventure Rentals is an amazingly varied rental provider. You can rent a Segway one day or take to the waters the next with a jet ski, kayak, or boat. You will find beach gear, miscellaneous equipment, grills, and baby equipment available for rent. Rates for these items are by the day or the week.

But, AMI Adventure Rentals has an ace in the hole. If you are eager for a totally unique and fresh experience, try flyboarding. This family-friendly activity is the closest you can get to a jet pack flight in the 21st century (so far).

You stand on a platform connected by a long hose to a watercraft. Water provides thrust to let you soar through the air. Hold your hands high and fly in this reinvigorating and one-of-a-kind adventure.

With the variety that’s offered AMI Adventure Rentals is certainly one of the best rental companies on Anna Maria Island.

The place is an excellent resource to stock up with the rental items you need. Give the group a call at (941)-254-2311 to confirm availability and get the things you need delivered to you on time.

Of course, there are a few other specialized rental providers on the island to choose from that might have more of what you are seeking.

Fun and More Rentals

Location: 5347 Gulf Dr, Holmes Beach, FL 34217

This rental provider caters specifically to families. You can find arguably the widest selection of baby gear on the island here, including cribs for your Anna Maria Island vacation rentals, all sorts of stroller types, and more. You can also find tandem kayaks and other family-friendly beach equipment.

Delivery is available on all equipment and beach gear. Grab a golf cart or a few bicycles for the week to increase your mobility. The prices are affordable and the equipment is more than solid.

ABC Baby Rentals

Location: 5352 Gulf Dr, Holmes Beach, FL 34217

ABC also places emphasis on baby gear and equipment. This provider has a storefront, where you can purchase outfits, snorkeling gear, and all sorts of other objects to improve your vacation experience.

Items vary, from safety gear, beach towels, sleeping items, strollers, bags, and a lot more. There are many rentals here to help you manage the day in and day out of your family vacation with your young ones.

All items have a one-week minimum charge, but you will find the prices very fair even if you are only staying for a few days.

Island Scooter Rentals

Location: 9908 Gulf Dr B, Anna Maria, FL 34216

We had to mention Island Scooter Rentals for their excellent prices on some fancy and fun one or two passenger scooters.

Navigating the island by car can be frustrating, which is why scooter rentals are so popular. You can jump around the island with ease, taking your ride to the nooks and crannies of Anna Maria without being burdened by parking limitations.

You can also find bicycles for rent and golf carts for hitting the beaches and other nearby attractions without needing a car. This rental provider is open from 9:30 a.m. to 5 p.m. (10:30 a.m. to 5 p.m. on weekends).

Contact us at (941)-778-4178 for more details about rental providers and beachfront places to stay on Anna Maria Island.

Top 5 Ways to Spend Your Day on Anna Maria Island

Anna Maria Island is always something special and a unique experience for visitors to cherish. You can spend a lifetime here and soak in the acclaimed sights and the long list of ocean activities, but let’s just start at a day.

Whether you are looking for an exciting adventure on the beach or water or a relaxing getaway with your family and loved ones, you’ll find the perfect experience that you’ll remember for years to come

Below are 5 top ways to spend a day on Anna Maria Island to help you plan your schedule.

anna maria island beach vacation rentals

Stay on the Beach

If you don’t have a schedule and you don’t have a place to be, you may as well stay on the beach for a day.

There’s Manatee Public Beach in Holmes Beach for a centrally located main island beach with lifeguards and facilities, while you can head north to visit the beautiful Bayfront Park – a popular spot for picnics and the sights.

Coquina Beach on the southern end of the island is another top option with its famous paved trail, amazing scenery and full facilities for groups and families.

Anna Maria Island is filled with other more private beach access points that are never too far by trolley, bike, car or just your two legs.

Visit a Performing Arts Hall and See a Show

Due to the passion of local leaders, artists and institutions, Anna Maria Island and the surrounding communities have fostered an excellent performing arts culture.

The Island Players (10009 Gulf Dr, Anna Maria, FL 34216) is a community theater on the island where can see repertory theatre shows, brand new plays written by locals, or touring classics.

The Manatee Performing Arts Center (502 3rd Ave W, Bradenton, FL) isn’t too far from Anna Maria Island and features a variety of exciting Broadway musicals and long-time fan favorite plays on two stages.

Or you can head over to Sarasota for a banquet-styled show in the massive Van Wezel Performing Arts Hall (777 N Tamiami Trail, Sarasota, FL 34236).

Get Out on the Water

The beach is one thing, but the surrounding mangrove forests, marshes and manatees, dolphins and sea turtles and more are all found on the water.

Whether you rent a boat charter that takes you deep in the Gulf of Mexico or hop on a guided kayak tour through the nearby preserves, you really should get out on the water.

Paradise Boat Tours (200 Bridge St at the Bridge Street Pier, Bradenton Beach, FL 34217) will get you on the water in style. AMI Charters (424 Pine Ave, Anna Maria, FL 34216) offers a wide assortment of adventure packages.

Visit the Nearby Nature Preserves

The Anna Maria Island and Bradenton government cherishes local nature. Hundreds of acres of the island and surrounding areas are protected preserve land.

The Robinson Preserve (1704 99th St NW, Bradenton, FL 34209) is a fantastic place to visit, with biking trails and large shaded picnic areas. You can really get lost within the foliage of Neal Preserve (12301 Manatee Ave W, Bradenton, FL 34209).

Spend a day kayaking or paddleboarding at either preserve – a very popular option for a day out with the family. Also available are hiking and bird watching trails at Neal Preserve, and picnic spots, hiking paths, and a 53-foot tall viewing tower at Robinson Preserve.

Visit the Historic Sites, Learn the Modern Culture

It’s always fun to learn a bit about Anna Maria Island history and some of the attractions that still stand.

Visit one of the island’s iconic piers, such as the Bridge Street Pier in Bradenton Beach or the Rod and Reel Pier on the north end of the island. The Historic Green Village and Roser Church on Pine Avenue give you the chance to see several restored historic buildings.

These sites all have a fascinating history tied to the roots of the island that you can learn more about at the Anna Maria Historical Society. It is a free museum that holds the city’s first jail. It’s an informative flash back in time and a nice way to spend a rainy afternoon.

As you plan your adventure, choose from our many beautiful vacation rentals on Anna Maria Island. Soak in the sunset views on your outdoor patio. Take day trips and find plenty of rewarding things to do, knowing you have a cozy home-away-from-home to always come back to. Contact us at (941)-778-4178 for more.