Anna Maria Island Vacation Rentals With a Pool
Looking for a refreshing vacation? Explore these fantastic Anna Maria Island rentals with pools! After a day at the beach, a relaxing swim in your pool is the perfect way to unwind.
A vacation rental with a pool adds significant value to your getaway. A private pool offers a relaxing escape from crowded beaches, providing a convenient way to cool off with a refreshing swim whenever desired. It also creates a safe and enjoyable space for family fun, especially for children. It grants you a personal area to unwind and soak up the Florida sunshine in complete privacy.
174 properties available
Beach Escape by AMI Locals Vacation Rental License #VR18-000090 Welcome to Beach Escape, a stunning five-bedroom, four-bath luxury home just one street from the powdery white sands of Anna Maria Island. Ideally located on the peaceful north end near Bean Point Beach, this coastal retreat combines upscale comfort with endless outdoor fun. Spend your
Welcome to 81A by Exclusive Vacations, a design-forward luxury retreat inspired by the iconic architecture of Florida’s 30A and thoughtfully reimagined for Anna Maria Island. Located just two blocks from the beach and Pine Avenue, this five-bedroom, five-and-a-half-bath home offers a seamless blend of refined Mediterranean style, resort-level ameni
Set in Sand by AMI Locals TPL24-000009, DWE5105449Welcome to Set in Sand by AMI Locals, a spectacular seven bedroom, six and a half bath luxury home located just a four-minute walk from the pristine beaches of Anna Maria Island. This coastal masterpiece combines modern design, resort-style amenities, and spacious comfort, perfect for families and l
Avalon by AMI Locals Vacation Rental License #VRC18-000082 Welcome to Avalon by AMI Locals, a luxury 4-bedroom, 3.5-bathroom coastal home just steps from the white sands of Holmes Beach on Anna Maria Island. Perfect for families or groups seeking a refined retreat, Avalon offers breathtaking Gulf views, high end finishes, and elegant details throug
Avalon by AMI Locals Vacation Rental License #VRC18-000082 Welcome to Avalon by AMI Locals, a luxury 4-bedroom, 3.5-bathroom coastal home just steps from the white sands of Holmes Beach on Anna Maria Island. Perfect for families or groups seeking a refined retreat, Avalon offers breathtaking Gulf views, high end finishes, and elegant details throug
The Renata at Hunter’s Point by AMI Locals Experience the perfect blend of eco-luxury and modern comfort at The Renata, a brand-new home nestled in the heart of Hunter’s Point! This stunning three bedroom, two and half bath retreat features a private pool, elevated balcony with water views, and an elevator for effortless access. Surrounded by natu
Native Sun by AMI Locals VR22-000055 Welcome to Native Sun, a beautifully updated coastal home featuring four bedrooms and three bathrooms one block from Holmes Beach! This island retreat boasts a private pool, lush backyard lounge area, and convenient outdoor dining and BBQ area, ideal for relaxing family vacations or gatherings with friends. Pe
A Change in Latitude by AMI Locals Welcome to A Change in Latitude, a beautiful three bedroom, three bath elevated vacation home perfectly located on the north end of Anna Maria Island. This modern coastal retreat features a private pool with an in-ground spa, outdoor living area, and putting green, offering the ideal mix of comfort and fun. Just a
Peachy Keen by AMI Locals VPR22-000026 Escape to Peachy Keen, a luxurious family vacation rental on Anna Maria Island! This spacious three-bedroom, plus loft, home is just 200 steps from the Gulf, offering stunning water views and easy access to the island’s best amenities. Wake up to breathtaking sunsets, splash in your private saltwater pool, or
Beachfront Paradise by Exclusive Vacations TPL19-000058, DWE5105473 Escape to Beachfront Paradise, part of our Exclusive Collection. Offering an exquisite eight bedroom, six-and-a-half bath waterfront estate with spectacular ocean views and private beach access! This boutique luxury home boasts a heated pool and spa, perfect for large family gather
Sea Gal by AMI Locals Vacation Rental License #TPL23-000008, DWE5105473Welcome to Sea Gal by AMI Locals, a seven bedroom, seven and a half bath luxury beach home perfectly positioned between the Gulf beaches and the Intracoastal Bay. This stunning retreat pairs modern coastal elegance with breathtaking 360° rooftop views and an unbeatable location,
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
Casa Flamingo by AMI Locals Escape to Casa Flamingo, a beautifully refreshed luxury beach home in Bradenton, Florida! This inviting three-bedroom, three and a half-bath home offers a private saltwater pool, ample outdoor space, and stunning water views, perfect for creating lifelong memories. Located just 6.5 miles from the white sandy beaches of A
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