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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This elevated villa boasts a private heated pool and a fenced yard. Step into the ultimate home away from home, nestled in the heart of Anna Maria city, directly along historic Pine Ave. During the updates the aim was to both preserve the charming village atmosphere of the street and create a versatile environment for boutique shopping, dining, and
AMI Outpost
Multi-Family- 3
- 2
- Pool
- Dogs Allowed
- Sleeps 8
- 153 Views
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**Please Note Pool Closure the Week of August 19th 2024 - rates reduce for that week to compensate for not having use of the pool**With stunning direct gulf front views, the stylish “Gulf Place 23” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 6 guests this 2 bedroom 2 bathroom Holmes Beach vacation rental condomi
Gulf Place #23
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 28 Views
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The perfect spot for a memorable island vacation! This ground level vacation rental offers a gorgeous heated pool with a fabulous outdoor common area including gazebo, tropical landscaping, dining areas and plenty of lounge chairs for relaxing. There is also a putting green, custom cornhole and a bocce ball pitch. If you want to enjoy the outdoors,
Casa Sierra 205A
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 10 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
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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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"Flip Flop Oasis" Two Single Family Homes with Adjoining Yards and TWO Heated PoolsFirst Home 201 57th Street "Flip Flop Inn" If you are searching for luxury on your Island vacation, this home is your dream come true. Tucked away on a quiet street on Anna Maria Island, this Mediterranean-style Townhouse is your perfect family vacation destination.T
Flip Flop Oasis
Multi-Family- 6
- 6
- Pool
- No Pets
- Sleeps 12
- 11 Views
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Discover unparalleled comfort on Anna Maria Island with "Mambo Italiano." This Mediterranean-style retreat caters to your every need, accommodating up to 8 guests across its 4 bedrooms and 4 bathrooms. From the moment you arrive, the striking white facade and elegant black gates welcome you.Step inside to find a haven of solitude, where every detai
Mambo Italiano
Home- 4
- 4
- Pool
- Dogs Allowed
- Sleeps 8
- 90 Views
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Spend your Anna Maria Island vacation in five star luxury when you visit “Fernweh”. This new Holmes Beach vacation rental offers both a stylish and relaxing destination for up to eight guests. If you experience wanderlust “Fernweh” is truly the place for you with a fabulous location, gorgeous floor plan, beautiful aesthetic and sophisticated island
Fernweh
Home- 4
- 4
- Pool
- No Pets
- Sleeps 8
- 12 Views
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Welcome to your newly updated tropical retreat at “Jacaranda Beach House” located just steps away from the serene beaches of Anna Maria Island's Northend. This exquisite 3-bedroom, 3-bath home promises a deluxe island living experience, suited perfectly for family vacations or a peaceful getaway.Step inside “Jacaranda Beach House” to discover a spa
Jacaranda Beach House
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 21 Views
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“Hideaway” is a fantastic Anna Maria Island vacation rental in Holmes Beach offering space for up to six guests just a few blocks from the beach! <br /><br />During your stay you’ll find everything you need for a laid back island getaway. Inside this Holmes Beach rental you’ll enjoy updated decor with a coastal flair. <br /><br />The main living sp
Hideaway
Multi-Family- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 26 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
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.