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Anna Maria Island Vacation Rentals: Homes

There’s nothing quite like staying in one of these Anna Maria Island vacation rentals. These island homes offer luxurious amenities, privacy, and plenty of space for a family or group. Take in Anna Maria Island off the beaten path. Each lodging experience has its own identity and character, creating a unique experience you’ll cherish for a lifetime.

With your own backyard oasis and private pool, you can relax knowing that your neighbor’s kids won’t barge in on your relaxing pool time. We’ll even supply you with fun beach equipment like umbrellas, snorkeling gear, towels, and toys.

Select the home that speaks to you and book online today.

Paradise Village
From $158 - $280/night
Bed/Bath: 3/2 Sleeps: 6 Pets: dog Address: 241 64th Street City: Holmes Beach  
Isle Haven A
From $208 - $293/night
5.0
Bed/Bath: 3/2.5 Sleeps: 6 Pets: dog Address: 119 52nd Street, Unit A City: Holmes Beach  
Coastal Cottage
From $185 - $286/night
4.9
Bed/Bath: 3/2 Sleeps: 6 Pets: dog Address: 215 Palm Avenue City: Anna Maria  
Aquaville B
From $158 - $243/night
4.9
Bed/Bath: 3/1 Sleeps: 4 Pets: dog Address: 305 Magnolia, Unit B City: Anna Maria  
Coconut Bayou
From $236 - $458/night
5.0
Bed/Bath: 3/3.5 Sleeps: 6 Pets: dog Address: 310 Coconut Avenue City: Anna Maria  
Sea Pearl
From $240 - $480/night
5.0
Bed/Bath: 3/2.5 Sleeps: 8 Pets: dog Address: 317 Hardin Avenue City: Anna Maria  
North Beach Village 50
From $158 - $270/night
4.7
Bed/Bath: 3/2.5 Sleeps: 6 Pets: none Address: 6250 Holmes Blvd. City: Holmes Beach  
Gulf Winds
From $110 - $222/night
4.3
Bed/Bath: 2/2 Sleeps: 4 Pets: dog Address: 305 62nd Street, Unit A City: Holmes Beach  
Sandy Toes
From $129 - $229/night
4.5
Bed/Bath: 2/1 Sleeps: 4 Pets: dog Address: 132 48th Street City: Holmes Beach  
Sandcastle
From $172 - $258/night
4.6
Bed/Bath: 2/2 Sleeps: 4 Pets: dog Address: 309 B 66th Street City: Holmes Beach  
Beach Dream B (upstairs)
From $100 - $165/night
4.8
Bed/Bath: 1/1 Sleeps: 2 Pets: none Address: 111 78th Street City: Holmes Beach  
Gertie's East
From $100 - $200/night
4.7
Bed/Bath: 1/1 Sleeps: 2 Pets: none Address: 206 35th Street, Unit A, East City: Holmes Beach  
Mykonos
From $172 - $300/night
4.8
Bed/Bath: 3/2 Sleeps: 6 Pets: dog Address: 211A 69th Street City: Holmes Beach  
The Idle House
From $179 - $329/night
Bed/Bath: 4/4 Sleeps: 8 Pets: none Address: 668 Key Royale Drive City: Holmes Beach  
It's My Dream
From $213 - $346/night
5.0
Bed/Bath: 3/2 Sleeps: 6 Pets: dog Address: 5607 Carissa Street City: Holmes Beach  
Tropical Terrace
From $115 - $236/night
4.7
Bed/Bath: 2/2 Sleeps: 4 Pets: dog Address: 3100 Gulf Drive, Unit 5 City: Holmes Beach  
Mermaid Cove
From $200 - $343/night
4.8
Bed/Bath: 3/2.5 Sleeps: 6 Pets: none Address: 309 66th Street, Unit A City: Holmes Beach  
Sunshine Dream
From $160 - $220/night
5.0
Bed/Bath: 3/2 Sleeps: 6 Pets: dog Address: 5311 18th Ave Dr West City: Bradenton  
Isle Haven B
From $143 - $215/night
4.8
Bed/Bath: 2/2 Sleeps: 4 Pets: dog Address: 119 52nd Street, Unit #B City: Holmes Beach  
Tropical Oasis
From $179 - $260/night
5.0
Bed/Bath: 3/2 Sleeps: 6 Pets: none Address: 5208 9th Ave Dr W City: Bradenton  
Spoonbill
From $79 - $143/night
5.0
Bed/Bath: 2/2 Sleeps: 4 Pets: none Address: 505 Sanderling Circle City: Bradenton  
Beach Dream A (downstairs)
From $125 - $186/night
4.7
Bed/Bath: 2/1.5 Sleeps: 4 Pets: none Address: 111 78th Street City: Holmes Beach  
Coral Breeze (B)
From $172 - $286/night
4.9
Bed/Bath: 2/2 Sleeps: 4 Pets: dog Address: 207 70th Street Unit B City: Holmes Beach  
Sunbreeze
From $200 - $343/night
5.0
Bed/Bath: 3/2.5 Sleeps: 6 Pets: none Address: 310 57TH STREET City: Holmes Beach  
Egret's Landing
From $185 - $330/night
4.8
Bed/Bath: 3/2 Sleeps: 6 Pets: none Address: 303 74th Street, #A City: Holmes Beach  
Aquaville A
From $143 - $229/night
4.9
Bed/Bath: 2/1 Sleeps: 4 Pets: dog Address: 305 Magnolia, Unit A City: Anna Maria  
Jacaranda Beach House
From $210 - $360/night
Bed/Bath: 3/3 Sleeps: 6 Pets: none Address: 744 Jacaranda Rd City: Anna Maria  
Palm Villa
From $222 - $386/night
4.9
Bed/Bath: 3/3 Sleeps: 6 Pets: none Address: 307 A 63rd Street City: Holmes Beach  
Beach Daisy
From $258 - $520/night
4.6
Bed/Bath: 3/2 Sleeps: 6 Pets: none Address: 111 75th Street City: Holmes Beach  
Beautiful Villa by the Sea
From $222 - $390/night
5.0
Bed/Bath: 3/3 Sleeps: 6 Pets: cat, dog Address: 7007 Holmes Boulevard City: Holmes Beach  
Island Delight
From $143 - $243/night
5.0
Bed/Bath: 2/1 Sleeps: 4 Pets: cat, dog Address: 424 62nd Street City: Holmes Beach  
Sailors Dream
From $165 - $236/night
4.9
Bed/Bath: 3/3 Sleeps: 6 Pets: dog Address: 3904 Royal Palm Drive City: Bradenton  
Coral Breeze (A)
From $172 - $286/night
4.8
Bed/Bath: 2/2 Sleeps: 4 Pets: dog Address: 207 70th Street Unit A City: Holmes Beach  
Lemon Tree by the beach
From $100 - $200/night
5.0
Bed/Bath: 1/1 Sleeps: 2 Pets: dog Address: 208 69th Street, Unit B City: Holmes Beach  
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Florida Dreams Realty