Vacation Rentals with Private Pools on Anna Maria Island

Homes with Private Pools on Anna Maria Island...

The Beaches on Anna Maria Island are absolutely amazing. So is having a private heated pool right in the backyard of your vacation rental. Being able to cool off in a pool is one of the most requested items during an Anna Maria Island vacation rental search. It is definitely a must have item for your next vacation. Anna Maria Island Accommodations has a robust inventory of pool homes with a variety of distances to the beach and even some gulffront. Let us help you find your perfect pool home rental.


Properties Available 197 properties available
Anna Maria Wave by Anna Maria Island Accommodations 2806 Avenue E, Holmes Beach, FL 34217 Welcome to Anna Maria Wave by Anna Maria Island Accommodations, a spectacular four-bedroom, four-bathroom beachfront home that captures the essence of coastal luxury on beautiful Anna Maria Island. Perfect for families and groups, this contemporary retreat com
Hot HOT 34
Anna Maria Wave
Holmes Beach Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Guests 8 guests
Rating 5 (2)
Anna Maria Guest House 317 by Anna Maria Island Accommodations 317 Pine Avenue, Anna Maria, FL 34216 Welcome to Anna Maria Guest House 317, a charming three-bedroom, two-bath beach cottage located right on Pine Avenue, just two and a half short blocks from the soft white sands of the Gulf beaches. With multiple balconies, cozy living spaces, and a
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Anna Maria Guest House 317
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (43)
Coco Cottage by Anna Maria Island Accommodations 113 Los Cedros Dr, Anna Maria, FL, 34216 Welcome to Coco Cottage, a welcoming 3 bedroom, 3 bath canal-front home designed for easy island living. Located just a 4-minute walk to Anna Maria Beach and moments from the shops and restaurants along Pine Avenue, this relaxing getaway blends coastal comfort
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Coco Cottage
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (4)
Another Paradise by Anna Maria Island Accommodations 115 Willow Ave, Anna Maria, FL 34216 VR16-000382 Welcome to Another Paradise, a beautifully designed three-bedroom, three-bath coastal retreat located just a two-minute walk from the white sands of Anna Maria Beach. Perfect for families or small groups, this Anna Maria Island accommodation offers
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Another Paradise
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (39)
Orange Crush by Anna Maria Island Accommodations 312 61st St Unit B, Holmes Beach, FL 34217Welcome to Orange Crush, a beautifully updated and thoughtfully decorated three bedrooms, two bath home just two blocks from the gorgeous beaches of Anna Maria Island! This vibrant retreat offers a perfect blend of relaxation and fun, featuring a game room w
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Orange Crush
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (14)
Covey Cottage by Anna Maria Island Accommodations 418 Spring Ave, Anna Maria, FL 34216 VR16-000292 Welcome to Covey Cottage by Anna Maria Island Accommodations, a three bedroom, three and a half bathroom vacation home with a private pool and an unbeatable location. Just a seven-minute walk to the white-sand Gulf beaches and one minute to Pine Avenu
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Covey Cottage
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Bathrooms 1 Half Bath
Guests 7 guests
Rating 5 (68)
Pelican Paradise by Anna Maria Island Accommodations 214 Elm Ave, Anna Maria, FL 34216 VR19-000001 Welcome to Pelican Paradise, your dream getaway just one block from the white sands of Anna Maria beach and steps from the boutique shops and dining along Pine Avenue. These four bedrooms, four and a half-bathroom luxury retreat offers a private pool
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Pelican Paradise
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Rating 5 (28)
Water Colors by Anna Maria Island Accommodations 109 Palm Avenue, Anna Maria, FL, 34216 VR18-000060 Welcome to Water Colors, a stunning four-bedroom, four-bath Anna Maria Island accommodation just a one-minute walk from the powdery white sands of Anna Maria Beach. Perfect for family getaways or group vacations, this coastal retreat combines luxury
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Water Colors
Anna Maria Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Guests 10 guests
Rating 5 (35)
Queen Palm by Anna Maria Island Accommodations 5701 Holmes Blvd, Unit B (North), Holmes Beach, FL 34217 VRC19-000042 Welcome to Queen Palm by Anna Maria Island Accommodations, a cozy two-bedroom, one-bath ground-level retreat located less than a five-minute walk from the white-sand shores of Holmes Beach. Perfect for couples, small families, or fri
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Queen Palm
Holmes Beach
Bedrooms 2 BR
Bathrooms 1 BA
Guests 6 guests
Rating 5 (41)
Villa La Concha by Anna Maria Island Accommodations113 Maple Avenue, Anna Maria, FL, 34216VR16-000446Welcome to Villa La Concha, a luxurious six-bedroom, four-and-a-half-bath vacation rental just a one minute from the white sands of Anna Maria beach! Perfect for large families or groups, this coastal retreat features a private pool and spa, game ro
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Villa La Concha
Anna Maria
Bedrooms 6 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 12 guests
Rating 5 (38)
Majestic Summer by Anna Maria Island Accommodations 2213 Avenue C, Bradenton Beach, FL 34217Experience the ultimate luxury vacation at Majestic Summer, a seven-bedroom, seven and a half bath estate nestled just minutes from the pristine beaches of Anna Maria Island! Boasting a private pool with an in-ground spa, a spacious rooftop deck with Gulf vi
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Majestic Summer
Bradenton Beach Pet Friendly
Bedrooms 7 BR
Bathrooms 7 BA
Bathrooms 1 Half Bath
Guests 14 guests
Rating 5 (6)
Highlights • Canal front • 5-minute walk to the beach • Rooftop deck • Private pool with in-ground spa • Outdoor living space Aqua Bay by Anna Maria Vacations 217 North Harbor Drive Holmes Beach, Florida Welcome to Aqua Bay! This luxurious canal-front home has four bedrooms and three bathrooms, providing guests with a relaxing and top-notch getaway
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Aqua Bay
Holmes Beach
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (16)

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