BEST Anna Maria Vacation Rentals
Book a stay at one of our stunning Anna Maria Island vacation rentals. Known around the world for its pristine turquoise waters and white, sandy beaches, Anna Maria Island is the BEST destination for your island vacation. Island Real has 80+ Anna Maria Island vacation rentals in Anna Maria City, Holmes Beach, and Bradenton Beach.
Our Anna Maria Island vacation rentals feature a wide range of amenities, including hot tubs, pools, updated designs, outdoor lounge areas, multiple bedrooms, and more!
Popular Anna Maria Island Rental Searches
Everyone has specific needs and desires when it comes to choosing the perfect Anna Maria Island vacation rental property. Check out some of our most popular searches and get the best rate on your Anna Maria Island rental! From pet-friendly homes to oceanfront rentals with private pools, we have an Anna Maria Island vacation rental perfect to suit everyone's needs at Island Real Estate.
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Find the perfect Anna Maria Island vacation spot at “Sugaree”! This renovated duplex is comfortable, stylish and close to the beach too! When you visit “Sugaree” you’ll find everything you’ll need for up to six guests.<br /><br />Inside this Holmes Beach rental you’ll find a spacious main living area and well-appointed bedrooms. <br /><br />In the
Sugaree
Multi-Family- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 129 Views
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Luxury Anna Maria vacation rental "Sunset at 714" is a casually sophisticated four-bedroom three-bathroom home nestled a short walk away from Anna Maria’s best gulf beaches with one small road to cross. Accommodating up to 8 guests, "Sunset at 714" offers three king beds and set of twinsThe North Shore beach access for Bean Point is a favorite amon
Sunset at 714
Home- 4
- 3
- Pool
- No Pets
- Sleeps 8
- 15 Views
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Enjoy a week in tropical island luxury when you visit the beautiful “Gulfview Townhomes Unit 4"! The perfect Anna Maria Island vacation rental condominium, “Gulfview Townhomes Unit 4" is a refreshing departure from the ordinary Florida holiday. Sleeping up to six guests just a short walk to pristine gulf beaches, this Holmes Beach vacation rental i
Gulfview Townhomes 4
Condominium- 2
- 2 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 28 Views
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Relax and unwind in the luxurious Anna Maria Island vacation rental home “Beach Pearl”. This five star rental has everything experienced vacationers look for in a home from the perfect location to well-appointed amenities. Just a block and a half from the powder sand beaches of Anna Maria City, “Beach Pearl” is the quintessential Anna Maria Island
Beach Pearl
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 26 Views
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“Summer Breeze” is one of the premier homes on the island. The perfect home for an Anna Maria Island getaway. With tropical landscaping, updated inside and out, and this rental home is stunning on all fronts. Elevated, high-end tropical décor, and pristine floors, “Summer Breeze” is love at first sight. Five large bedrooms, a spacious layout, this
Summer Breeze
Home- 5
- 4
- Pool
- Dogs Allowed
- Sleeps 14
- 26 Views
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Inside this Holmes Beach vacation rental you’ll find a well-appointed condominium to kick your feet up in island style. The living room offers a flat screen television, comfortable furniture and the dining area seating four. In the kitchen you’ll find all the basics including a dishwasher. Off the kitchen there is a private balcony.Accommodating up
Casa Sierra 205B
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 19 Views
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Anna Maria Island vacation rental home “EverLasting Sunsets A and B” is a fabulous ground level duplex perfect for any family getaway. Enjoy 3 bedrooms and 2 bathrooms with 2 king beds and 1 queen bed providing everyone space for a comfortable vacation.<br /><br />With separate units “EverLasting Sunsets A&B” is a great way to vacation with fam
EverLasting Sunsets AB
Home- 3
- 3
- Pool
- No Pets
- Sleeps 8
- 16 Views
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DISCLOSURE!!: There is currently an ongoing disagreement regarding the beach access path on 78th Street. In the meantime, we ask that you use the beach access trail that is located on 77th street, directly behind the home you will be staying in.You can access it by walking through the side yard of this home. There is no need to walk all the way up
Flirty Flamingo
Home- 2
- 2
- No Pets
- Sleeps 4
- 14 Views
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Holmes Beach is a quaint and salty beach town with tons of character. From perfect beaches to great dining and nightlife, this destination is sure to please. “The Villas 3B” is a few blocks north from Holmes Beach city center. Here is where you’ll find many things to do within a short walk. The complex offers a shared free dryer and coin-op washer.
The Villas 3B
Condominium- 2
- 1
- No Pets
- Sleeps 6
- 21 Views
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Welcome to Spacious Oasis! Spacious Oasis is a Mediterranean style 3-bedroom, 3-bathroom pool home located just blocks away which is a short stroll from the gorgeous beach of Anna Maria Island! This home has everything you need to feel like you are on vacation every day. This home also has an elevator for your convenience. Spacious Oasis is located
Spacious Oasis
Home- 3
- 3
- Pool
- Dogs Allowed
- Sleeps 6
- 25 Views
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After you stay at the "Sea Pirate 2" you’ll want to make it your vacation destination year after year! This two bedroom one bathroom Holmes Beach vacation rental home sleeps six guests with one queen bed, two twin beds and queen sleeper sofa. "Sea Pirate 2" offers a fun and fresh island feel with exciting colors and endless style. Find everything f
Sea Pirate 2
Condominium- 2
- 1
- Pool
- No Pets
- Sleeps 6
- 30 Views
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Stylishly decorated and spaciously accommodating, you’ll fall in love with Florida living when you stay at the gorgeous vacation rental 1107 Edgewater Circle in Perico Bay Club. Come for the sun, but stay for the view from this beautiful two bedroom, two bathroom condominium sleeping up to four guests!Perico Bay Club is a prestigious gated communit
Perico Bay Club 1107 Edgewater
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 31 Views
Where can I find your BEST Anna Maria Island Vacation Rentals?
Our Anna Maria rental properties are spread across the island, giving our guests the power to choose where they want to stay on the island. For those traveling with their dogs, we offer pet-friendly vacation rentals that are perfect for the whole family. To be as close to the ocean as possible, be sure to check out our beachfront rentals.
My parents need help up and down the stairs - are any of your units one story or elevator accessible?
We have a number of Anna Maria Island elevator-equipped vacation rentals available - we also have some single story homes and ground-floor condos to make access easier for anyone who needs it. You can also haul luggage to bedrooms, groceries to the kitchen level, or just access rooms much more easily in these homes.
What are some fun things to do on Anna Maria Island?
While staying in an Anna Maria rental there are tons of activities available to you. The island is best known for its soft, sandy beaches and stunning turquoise water. With seven miles of beach to explore, there's plenty to keep the kids and parents entertained. If you want to shake things up on your stay in one of our Anna Maria Island Vacation Rentals, check out what the locals say are the best things to do on Anna Maria Island.
Where is Anna Maria Island located?
Anna Maria Island is 109 miles west of Florida as the crow flies, but it's just over 117 miles by car. It's about an hour and a half southwest of Tampa International Airport and 30 minutes northwest of the Sarasora-Bradenton International Airport. Anna Maria Island is also about 2 hours southwest of Orlando and Disney World.
What is the difference between Anna Maria and Anna Maria Island?
For sure this can be confusing. Anna Maria Island is made up of three cities. Bradenton Beach, the southernmost city. Holmes Beach is in the middle of the Island and the northernmost city is Anna Maria City. So when someone refers to Anna Maria it could be short for Anna Maria Island or it could be short for Anna Maria City. Most of the time when a local references Anna Maria means Anna Maria City.
Are there supermarkets on Anna Maria Island?
Yes, Publix located on Anna Maria Island is a major grocery store. It has a deli, bakery, and seafood along with all the normal amenities. The grocery store does get very busy Saturday afternoon as well as Sunday due to the high amount of vacation rental check-ins on Saturdays.
What sort of restaurants are on Anna Maria Island?
The island has a vast collection of unique eateries to choose from, offering everything from gourmet donuts to delectable sushi to mouthwatering seafood. The island is proud to offer a wide selection of restaurants that are not chain restaurants and are unique to the island. To see more of our restaurant selection check out the dining and nightlife page of our site.