Pool Retreats
389 properties available
Sunset View by Siesta Key Luxury Rental Properties Welcome to Sunset View, an eight bedroom, five and a half bath Siesta Key luxury rental just four houses from Siesta Key Beach. This four story coastal retreat blends spacious living, modern coastal design, multiple balconies, and a private heated pool and spa. Designed for large families and group
Calypso Current by Exclusive VacationsVacation Rental License #VR25-000049Welcome to Calypso Current by Exclusive Vacations, a newly constructed luxury beach-block home in the heart of Anna Maria Island. This four-bedroom, four-and-a-half-bath retreat features a resort-style lazy river pool, rooftop deck with fire pit and Gulf views, private puttin
Sunset Splash by Siesta Key Luxury Rental Properties Welcome to Sunset Splash, a legendary eight bedroom, seven and a half bathroom ground-level vacation home. Just a 2-minute walk to Siesta Key Beach and steps from Siesta Key Village, this private pool home is designed for unforgettable group getaways. The true WOW factor is the resort style back
Total Package by AMI Locals Welcome to Total Package by AMI Locals, a brand-new luxury beach home on the North End of Anna Maria Island, just a one-minute walk from the Gulf beaches. This five-bedroom, four-bath retreat combines modern sophistication and coastal charm, featuring a multi level rooftop deck with Gulf views, a private pool and spa, a
Sunset Gulf by Siesta Key Luxury Rental Properties Welcome to Sunset Gulf, an eight bedroom, five and a half bath Siesta Key luxury rental just three houses from the nearest Siesta Key Beach access. This four story coastal retreat features a private heated pool and spa, sweeping Gulf views, multiple balconies, and an elevator connecting every floor
Sunset Cove by Siesta Key Luxury Rental Properties Welcome to Sunset Cove, a stunning four-bedroom, three and a half-bath oasis overlooking the tranquil Heron Lagoon! This luxurious retreat features a private dock for exploring the lagoon, a spacious screened-in patio with a private pool, and direct access to nature’s beauty. Perfectly situated ju
Montego Bay by AMI Locals Vacation Rental License #VPR16-000472Escape to Montego Bay, an Anna Maria Island vacation home with a private pool, rooftop deck with Gulf views, and multiple balconies designed to give you the ultimate experience! This spacious five-bedroom, four-bath home is just one and a half blocks from the north end of the beaches an
Villa La Concha by Anna Maria Island AccommodationsVR16-000446Welcome 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 room, and multiple outdoor entertaining a
Salty Dog by Siesta Key Luxury Rental Properties Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!Welcome to Salty Dog, an exceptional six-bedroom, four-bathroom canal-front townhome located just a short two-minute stroll from the world-famous Siesta Key Beach and only a seven-minute walk or a qui
Welcome to Bay View Beauty, part of our Exclusive Collection. This luxurious seven-bedroom, seven and a half bath waterfront home with unobstructed bay views. Ideally located along Anna Maria’s North Shore Drive, this luxury retreat places you steps from the white-sand Bay beaches, minutes from the Gulf beaches and Bean Point, and within walking di
Siesta Dreamin’ by Tropical Sands AccommodationsWelcome to Siesta Dreamin’, a stylish and inviting 4-bedroom, 2.5-bath canal front home with a private dock, perfect for extended stays on Siesta Key. Located just a 12-minute walk to Siesta Key Beach, this comfortable retreat offers a peaceful waterfront setting while still being close to local shops
Tahiti Bay by AMI Locals Vacation Rental License #VR16-000466Welcome to Tahiti Bay, a luxury beach vacation home just a short walk from Anna Maria Island’s dazzling beach! This five-bedroom, four-bath retreat offers multiple outdoor decks, a rooftop balcony, a private pool, hot tub, putting green, games, and amenities, all designed for fun, relaxat
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