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Holiday Rentals with Pools in Anna Maria

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430 rentals in Anna Maria.
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Close to beach, gorgeous 5 bd luxury home! Private Pool, Spa, and Putting Green!
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Dragonfly - Southern charm on the North end of Anna Maria Island
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
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Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Serendipity - Beach Front Home on Bean Point , Anna Maria
Holiday Rental House
4 bedrooms
8 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Anna Maria, Prive Heated Pool, Lanai
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps, All pools
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$200 towards a private fishing charter with Captain Josh with 2020 reservation
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Save time - get the best Anna Maria rentals sent straight to your email!
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Spectacular Beachfront House with Pool
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Tucked Away in Anna Maria
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St.
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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NEW!! Amie’s House Modern Coastal Getaway
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Island Living, refreshing outdoor shower and pool , pet friendly if approved
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, All pools
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Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Charming cottage located close to beach - private heated pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Grab your swimsuit!! Private heated pool is now open!!!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Charming cottage with heated pool, tropical landscaping in prime location!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Spacious canal front home with private heated pool on Anna Maria Island
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Seahorse Cottage - 1820659
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Bayside condo w/ a shared pool - close to the beach & restaurants
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
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Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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New Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point & Pine Ave
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Sea Vous Play ! Great for Families! 3 Block Walk to Beach, 2 Blocks to Pine St
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Beautiful 4-BR, Very Close to Gulf Beach, Large Heated Pool
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Dog-friendly beach bungalow with private, heated pool, balcony, and lanai
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Beautiful home, private pool with water VIEWS! Enjoy Anna Maria Island in Luxury
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Premium Cleaned | Bay-facing condo w/amazing view, shared pool & beach across st
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Private Salt Water Pool & Spa, WALK TO BEACH, near Bean Point, GROUND LEVEL.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Diamond Surf, AMI North End Private Heated Saltwater Pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Canal-front home with private dock, covered lanai with heated pool and grill
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Breezy canalfront home w/ heated pool & dock - 3 blocks to Bean Point Beach!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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