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.
166 properties available
Blue Marlin by AMI Locals Vacation Rental License #VR18-000106 Welcome to Blue Marlin by AMI Locals, a stunning four bedroom, four and a half bath Anna Maria Island vacation home featuring a private pool, hot tub, and putting green. This luxury beach retreat is perfectly located just a 10-minute walk to the Gulf beaches and two blocks from Pine Ave
Casa Del Mar by AMI Locals Vacation Rental License #TPL22-000060, DWE5105473Welcome to Casa Del Mar, a stunning three-level coastal home offering five spacious bedrooms and five bathrooms, perfect for family vacations, group getaways, or reunions by the sea. Located just a two-minute walk to Bradenton Beach, this vacation oasis boasts a private po
Freckled Fin by AMI Locals Vacation Rental License #VR19-000006 Welcome to Freckled Fin, a vibrant and luxurious four-bedroom, four-and-a-half-bathroom vacation home located just a short walk from the beautiful beaches of Anna Maria Island and the charming boutiques and cafes of Pine Avenue. Designed for comfort and connection, this retreat feature
Sea Swept by Exclusive Vacations TPL22-000035, DWE5105473 Welcome to Sea Swept, part of our Exclusive Collection. This beachfront luxury home boasts ten-bedrooms, eight-and-a-half-baths with breathtaking Gulf views, private beach access, and resort-style amenities. Located just steps from the pristine beaches, this home offers a private pool and ho
Fine and Sandy by AMI Locals Vacation Rental License #VR22-000094 Welcome to Fine and Sandy, a grand seven-bedroom, seven-bath luxury beach home perfectly located on the north end of Anna Maria Island. This newly constructed coastal retreat combines modern design, high-end finishes, and resort-style amenities for the ultimate island escape. Just a
Walking on Sunshine by AMI Locals VRC19-000232 Welcome to Walking on Sunshine by AMI Locals, a stylish three-bedroom, three-bath coastal getaway located just one block from the pristine sands of Holmes Beach. Perfect for families and pet owners, this Anna Maria Island vacation rental features a private pool, a fenced-in tropical backyard, and invit
A Pirate’s Dream by AMI Locals Welcome to A Pirate’s Dream by AMI Locals, a grand waterfront retreat that perfectly blends coastal elegance with island adventure on beautiful Anna Maria Island. This four bedroom, three and a half bath vacation home plus loft is designed for families and groups seeking both relaxation and excitement. Located just a
Beach View Retreat by AMI Locals Vacation Rental License #VRC19-000046 Welcome to Beach View Retreat, a five bedroom, four bath home in Holmes Beach, just one block from Manatee Public Beach. With a private heated pool and spa, rooftop deck with panoramic views, and a prime location where you can walk everywhere. This vacation rental offers the per
Heavenly Sunset by AMI LocalsVacation Rental License #TPL24-000103, DWE5105909Welcome to Heavenly Sunset, an upscale three-bedroom vacation home located directly across the street from the sugar white sands of Bradenton Beach. Designed for families and relaxed group getaways, this coastal retreat offers Gulf views, a private pool, a putting green,
Highlights• Beachfront • Outdoor kitchen area• Pool and hot tub• Private beach access• ElevatorTarpon Lookout by Anna Maria Island AccommodationsTPL18-000468, DWE5105266The ultimate beachfront vacation awaits you at Tarpon Lookout, a luxury five-bedroom and five-and-a-half bathroom getaway with private beach access, a gulf-side pool, hot tub, and b
Oceanfront Paradise by AMI Locals TPL25-000069, DWE5105909Welcome to Oceanfront Paradise by AMI Locals, a spectacular five bedroom, five full and two half bath beachfront home perfectly positioned along the white sands of Bradenton Beach on Anna Maria Island. Designed for ultimate relaxation and entertainment, this luxury getaway offers direct beac
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
Tell us what you're looking for and someone will contact you with available options.