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Holiday Rentals with Pools in Anna Maria

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355 rentals in Anna Maria.
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Charming cottage with heated pool, tropical landscaping in prime location!
2 bedrooms
2 bathrooms
Sleeps 6
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Bay Breeze Cottages #1 (The Mahi-Mahi)
1 bedroom
1 bathroom
Sleeps 4
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New listing! Pet-friendly home with private pool, short walk to the beach
2 bedrooms
3 bathrooms
Sleeps 6
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Cherryfish, a spectacular spacious 4-bed home!
4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful, Beach-Front Home on Bean Point--Halcyon House
4 bedrooms
4 bathrooms
Sleeps 8
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Dragonfly - Southern charm on the North end of Anna Maria Island
5 bedrooms
4 bathrooms
Sleeps 10
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Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
2 bedrooms
2 bathrooms
Sleeps 6
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$200 towards a private fishing charter with Captain Josh with 2020 reservation
3 bedrooms
2 bathrooms
Sleeps 8
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Luxury Spacious Waterfront Pool, Spa, Bar, Dock, Near Beaches, Fall $380/n
4 bedrooms
3 bathrooms
Sleeps 8
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Anna Maria, Prive Heated Pool, Lanai
2 bedrooms
2 bathrooms
Sleeps 6
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Ocean View 3 bedroom, pool, North Shore Drive
3 bedrooms
2 bathrooms
Sleeps 6
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41 other travellers have booked this property
Charming Cottage! Quiet North- End Oasis, Steps To Bay And Gulf. Heated Pool.
2 bedrooms
3 bathrooms
Sleeps 6
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North Island Beach Escape
3 bedrooms
2 bathrooms
Sleeps 6
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Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool
2 bedrooms
2 bathrooms
Sleeps 6
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Spoonbill Hideaway-NOW FULLY OPEN!/Huge Pool/Spa/Across from Gulf Beach
3 bedrooms
2 bathrooms
Sleeps 6
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
2 bedrooms
1 bathroom
Sleeps 6
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Gulf front, charming home right on the beach - stunning views & dogs welcome!
2 bedrooms
1 bathroom
Sleeps 6
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Stunning luxury beachfront house with pool and spa
4 bedrooms
5 bathrooms
Sleeps 8
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Anna Maria Island Rentals - Beach Front - 'Angels Envy'
2 bedrooms
2 bathrooms
Sleeps 4
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Full refund or reschedule during Carona. 200 foot walk to beach or pier or beach
2 bedrooms
1 bathroom
Sleeps 5
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Beautiful cottage w/ private pool - walk to the beach, dining, and Bayfront Park
3 bedrooms
2 bathrooms
Sleeps 8
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Bungalow On The Bayou (Best Location on the Island)
2 bedrooms
1 bathroom
Sleeps 5
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Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach
4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful AMIBeachClub north end elevated pool home. Minutes walk to the Gulf.
3 bedrooms
2 bathrooms
Sleeps 6
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Tucked Away in Anna Maria
3 bedrooms
2 bathrooms
Sleeps 6
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Waterfront Luxury North End w/ Dock, Pool, Spa and No Steps!
3 bedrooms
2 bathrooms
Sleeps 8
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Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location
3 bedrooms
2 bathrooms
Sleeps 8
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Bay Breeze Cottages #3
2 bedrooms
2 bathrooms
Sleeps 7
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Dog-friendly house w/ private pool & entertainment - walk to the beach!
5 bedrooms
3 bathrooms
Sleeps 8
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Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island
2 bedrooms
3 bathrooms
Sleeps 6
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North End of AMI- Ground Level Family Friendly updated home
3 bedrooms
2 bathrooms
Sleeps 6
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Cute, Beachy, Canal-Front w/Dock on Historic Pine Ave! Steps to Beach and Pier!
2 bedrooms
1 bathroom
Sleeps 4
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise
3 bedrooms
3 bathrooms
Sleeps 6
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THANKSGIVING SPECIAL!! Waterfront Island Escape w Full Service Guest House
5 bedrooms
5 bathrooms
Sleeps 10
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Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier
3 bedrooms
2 bathrooms
Sleeps 8
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Luxury canal-front home with stunning pool - minutes to beach and Pine Avenue!
4 bedrooms
4 bathrooms
Sleeps 8
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Gorgeous views,spectacular home!
5 bedrooms
3 bathrooms
Sleeps 12
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90 other travellers have booked this property
Naut 2 Shabby Bungalow In the Heart of Anna Maria Village
1 bedroom
1 bathroom
Sleeps 4
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Spacious 5 bedroom, canal front luxury home with private Pool and Spa!
5 bedrooms
5 bathrooms
Sleeps 13
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Luxury Butterfly Garden, Steps to Pine Ave, Pool/Spa, Bikes, 4 Houses to Beach
4 bedrooms
5 bathrooms
Sleeps 8
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Blue Heron Cottage - Anna Maria Island
1 bedroom
2 bathrooms
Sleeps 4
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Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine
4 bedrooms
6 bathrooms
Sleeps 8
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Beautiful home, private pool with water VIEWS! Enjoy Anna Maria Island in Luxury
4 bedrooms
3 bathrooms
Sleeps 12
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Charming house with private heated pool, patio, and grill - steps from beach
3 bedrooms
2 bathrooms
Sleeps 6
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BEACHFRONT Beauty! Luxury home with amazing beachfront views, private Pool!
3 bedrooms
3 bathrooms
Sleeps 10
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Grab your swimsuit!! Private heated pool is now open!!!
2 bedrooms
2 bathrooms
Sleeps 6
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BEACHFRONT Luxury home with 7 bedrooms, Pool and Spa, views of Rod 'n Reel Pier!
7 bedrooms
8 bathrooms
Sleeps 16
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Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!
3 bedrooms
2 bathrooms
Sleeps 6
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Cancel upto 48hrs Before Check-In, Huge Outdoor Kitchen,Roof Top Deck with Amazi
4 bedrooms
4 bathrooms
Sleeps 12
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2-3 Minute Walk to the Gulf Beaches - Private Heated Pool
3 bedrooms
2 bathrooms
Sleeps 8
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