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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GONE COASTAL at FOUNTAINHEAD CONDOMINIUMS - Accommodating up to four guests for a fun laid back beach vacation, Fountainhead Unit 2 offers the perfect two bedroom, two bathroom getaway for you and your family. Centrally located on Anna Maria Island, Fountainhead Unit 2 is near everything for an entertaining stay including gulf beaches, free trolley
Fountainhead 2 - Gone Coastal
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 10 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
- 33 Views
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“115 South Beach Village” is the perfect Anna Maria Island vacation home to make a fun and memorable beach vacation destination! This pastel pink 3 bedroom, 2.5 bathroom, town house style vacation rental rooms up to 6 guests with 1 king bed, 1 queen bed and 2 twin beds. <br /><br />Stroll across the street to enjoy the best white sandy beaches the
South Beach Village 115
Condominium- 3
- 2 Full Baths , 1 Half Baths
- Pool
- Dogs Allowed
- Sleeps 6
- 11 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
- 17 Views
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“EverLasting Sunsets B” is the perfect Anna Maria Island beach rental for a relaxed Florida getaway. When you arrive at this unit you’ll be greeted with a lush tropical landscaping letting you know your vacation has begun!<br /><br /> During your visit you’ll be less than a block from the Gulf of Mexico beaches and endless Florida sunshine! This du
EverLasting SunSets B
Multi-Family- 2
- 2
- Pool
- No Pets
- Sleeps 5
- 17 Views
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Experience the magic of Anna Maria Island with our stunning vacation rental, "Sans Souci - North Beach Village 40." This beautiful townhouse-style property is designed to make you fall in love with island life. With 3 bedrooms and 2.5 bathrooms, it comfortably accommodates up to 6 guests, offering 2 Queen beds and 2 Twin beds in a charming coastal
North Beach Village 40 - Sans Souci
Condominium- 3
- 2 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 14 Views
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When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Piece of Paradise”. This fun four bedroom, three bathroom Holmes Beach vacation rental spaciously sleeps up to 8 guests in comfort and style. After spending a week at this fabulous Holmes Beach vacation rental home within walking di
Tinas Piece of Paradise
Home- 4
- 3
- Pool
- No Pets
- Sleeps 8
- 10 Views
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“Appletini” is just a few blocks away from pristine gulf beaches! Not only will you be able to walk to the beach, but you’ll find nearby free trolley stops on Marina Drive and Gulf Drive. Hop on the free trolley and you’ll find restaurants and shops just minutes away. While you visit you’ll have access to a propane barbecue grill great for a Flor
Appletini
Multi-Family- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 47 Views
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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
- 18 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
- 12 Views
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This recently built single-family home is situated on a serene and picturesque street, just 6 houses away (ONLY STEPS) from the beach access path!On the ground floor, the home features a 1 car garage and provides access to the stunning pool and patio areas within the beautifully landscaped backyard. The residence boasts a dazzling, spacious heated
Sea Glass on Park
Home- 4
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 17 Views
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For a laid back beach vacation you won’t soon forget, visit “EverLasting Sunsets A” in the city of Holmes Beach! <br /><br />“EverLasting Sunsets A” offers accommodations for three guests in a premium beach bound location. This cozy duplex is just a short block walk from some of Anna Maria Island’s most coveted beaches in Holmes Beach. These beach
EverLasting SunSets A
Multi-Family- 1
- 1
- Pool
- No Pets
- Sleeps 3
- 8 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.