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Anna Maria Rentals with Pools

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430 rentals in Anna Maria.
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A bird's view of Dragonfly from the north
Dragonfly in the Evening
Enjoying an Evening on the Beaches of Bean Point
Dragonfly - Southern charm on the North end of Anna Maria Island
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Spectacular Beachfront House with Pool
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
Rental Home
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
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!
Rental Home
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Serendipity - Beach Front Home on Bean Point , Anna Maria
Rental Home
4 bedrooms
8 bathrooms
Sleeps 8
Match: Sleeps, All pools
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North Island Beach Escape
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, All pools
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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Anna Maria, Prive Heated Pool, Lanai
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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$200 towards a private fishing charter with Captain Josh with 2020 reservation
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
Rental Home
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
Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Spacious canal front home with private heated pool on Anna Maria Island
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Island Living, refreshing outdoor shower and pool , pet friendly if approved
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St.
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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NEW!! Amie’s House Modern Coastal Getaway
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Tucked Away in Anna Maria
Rental Home
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
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beautiful 4-BR, Very Close to Gulf Beach, Large Heated Pool
Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Grab your swimsuit!! Private heated pool is now open!!!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Diamond Surf, AMI North End Private Heated Saltwater Pool
Rental Home
2 bedrooms
2 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
Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Charming cottage located close to beach - private heated pool
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Turtle Cottage - Anna Maria Island
Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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BON AMI: 3BR Family-Friendly Pool Home Less than Block from Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Bay -Canal Waterfront! Tiki Bar 5 BR 2 King Sleeprs,5 BA Heated Pool, 2 Kitchen
Rental Home
7 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Seahorse Cottage - 1820659
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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New Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point & Pine Ave
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Close to beach, gorgeous 5 bd luxury home! Private Pool, Spa, and Putting Green!
Rental Home
5 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location
Rental Home
3 bedrooms
2 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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AMI North End Pool Home with Gulf Views & Tiki Hut
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Cloud 9 - Beach Front/Hot Tub/Golf Cart/SUP/Kayak/Bikes/heated pool/BBQ/Elevator
Rental Home
5 bedrooms
12 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Bridgeview in Anna Maria
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Beautiful home, private pool with water VIEWS! Enjoy Anna Maria Island in Luxury
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Cancel upto 48hrs Before Check-In, Huge Outdoor Kitchen,Roof Top Deck with Amazi
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, All pools
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