Anna Maria Island Vacation Rentals With a Pool

Properties Available 105 properties available
Breakaway by Anna Maria Vacations Home in Anna Maria, FL VPR16-000458Escape to Breakaway, a beautiful ground-level bayfront home with stunning views of the bay on Anna Maria Island! This stunning vacation home includes four bedrooms and two bathrooms, a private heated pool, outdoor lounge areas, and a cozy yet chic interior. This rental is perfect
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Breakaway
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 5 (67)
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Key Lime Beach House by Anna Maria Vacations Home in Holmes Beach, Florida VRC000324 Welcome to Key Lime Beach House, a stunning beach retreat just a seven-minute walk from Holmes Beach! This four-bedroom, three-bath home offers a new private pool, outdoor games, a game room, and multiple dining options, perfect for families, friends, or large gro
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Key Lime Beach House
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (13)
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Buttonwood Cottage by AMI Locals Welcome to Buttonwood Cottage, a recently restored three bedroom, two bathrooms home full of Florida charm. Perfectly located on iconic Pine Avenue in Anna Maria and 10-minute walk to the Gulf. With a private heated pool, a pet-friendly policy, and easy access to island boutiques, restaurants, and attractions, this
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Buttonwood Cottage
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (21)
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Aqua Cove by Anna Maria Vacations Home in Anna Maria, FL VR16-000429 Welcome to Aqua Cove by Anna Maria Vacations, a beautiful canal-front vacation rental featuring 4 bedrooms and 3.5 bathrooms in the heart of Anna Maria Island, Florida. Perfect for families who love boating and beach adventures, this home offers a private pool with spa, boat dock,
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Aqua Cove
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
HalfBathrooms 1 Half baths
Guests 10 guests
Rating 4.8 (29)
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Salty Margarita by AMI LocalsWelcome to Salty Margarita, a stunning three-level coastal retreat just two houses from the white-sand shores of Holmes Beach! This luxury Anna Maria Island vacation rental features four king suites, a private heated pool and spa, elevator access, and a rooftop deck with breathtaking Gulf and sunset views. With vibrant
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Salty Margarita
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 8 guests
Rating 5 (6)
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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 Home in 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 experience. Wi
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Aqua Bay
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (16)
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Sugar Plum Beach by Anna Maria Vacations Home in Anna Maria, FL VRC18-000058 Welcome to Sugar Plum Beach, your perfect family and friends retreat just five houses from the sugar-white sands of Anna Maria Island’s Gulf beaches. This colorful 6-bedroom, 4-bathroom vacation duplex offers two fully furnished living spaces, making it ideal for large gro
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Sugar Plum Beach
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.8 (5)
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Mango Breeze by Anna Maria Vacations Home in Holmes Beach, Florida VRC17-000130 Welcome to Mango Breeze, a charming four-bedroom, three-and-a-half-bath waterfront home just moments from the crystal-clear Gulf waters of Anna Maria Island! This tropical retreat features a private heated pool, a lush backyard with a tiki bar, and vibrant island decor
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Mango Breeze
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Rating 5 (52)
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Sand Dollar by Anna Maria Vacations Home in Holmes Beach, Florida VR16-000501 Escape to Sand Dollar, a blissful island retreat nestled in Holmes Beach, featuring four bedrooms and three bathrooms, and a private backyard oasis with a pool, BBQ grill, and ample outdoor seating! Located less than five minutes from pristine Gulf beaches, this family
Sand Dollar (AMV)
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House
Bedrooms 4 bedrooms
Bathrooms 3 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Rating 5 (12)
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Welcome to Antigua Bay, a stunning five-bedroom, four-bath luxury vacation home located on the prestigious north end of Anna Maria Island, just steps from the Gulf. Perfect for large families and groups, this dog-friendly retreat offers premium amenities including a rooftop deck with panoramic island views, a private pool and in-ground spa, and fun
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Antigua Bay
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 4.9 (41)
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Salty Dog by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC17-000089 Escape to Salty Dog, a cozy and cheerful two-bedroom, one-bath duplex just a two-minute walk from Holmes Beach! This inviting retreat offers a private heated saltwater pool, dog-friendly policy, and all the essentials for a relaxing beach getaway. Perfect for small fa
Salty Dog (AMV)
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Duplex Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.9 (18)
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Welcome to A Wave From It All, a luxurious five-bedroom, six-and-a-half-bath vacation rental in the heart of Anna Maria Island. Just a short seven-minute walk to the island’s white-sand beaches and steps from the boutiques and eateries along Pine Avenue, this family-friendly retreat is ideal for large families and groups seeking comfort, fun, and r
A Wave From It All
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A Wave From It All
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 6 baths
HalfBathrooms 1 Half baths
Guests 14 guests
Rating 5 (34)
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