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.
164 properties available
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
Sea Grape Escape by AMI Locals VRC18-000063 Welcome to Sea Grape Escape by AMI Locals, a beautifully appointed two-bedroom, two-bathroom elevated home in the heart of Holmes Beach on Anna Maria Island. Perfect for small families or couples seeking a stylish and peaceful retreat, this coastal chic getaway combines modern comfort with relaxed island
Day Break Bungalow by AMI Locals VRC19-000140Experience the ultimate beachside escape at Day Break Bungalow, a beautifully remodeled three bedroom, three and a half bath home, just an eight-minute walk to stunning Holmes Beach! This elegant vacation retreat is perfectly situated in the heart of Anna Maria Island, offering panoramic balcony views,
Love Me Blue by Exclusive Vacations Vacation Rental License #VR24-000043 Welcome to Love Me Blue, part of our Exclusive Collection. This luxury beach home offers four bedrooms, four and a half baths, located on the north end of Anna Maria Island! Just a three-minute walk to the serene Bean Point beach and one mile to the shops and restaurants of Pi
Welcome to Midnight Breeze by Exclusive Vacations, a modern coastal luxury home located just one block from the Gulf in Holmes Beach. This four-bedroom, four and a half-bath retreat features a rooftop deck with outdoor kitchen and putting green, theater room, game room, resort style pool and spa, and elevator, all within a short walk or bike ride t
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
Bleuphoria by AMI Locals Welcome to Bleuphoria, a four-bedroom, four-bath luxury beach home on the peaceful North End of Anna Maria Island. Just three houses away from the sugar white sands of the Gulf and steps from Pine Avenue’s boutique shops and restaurants, this designer retreat delivers modern coastal elegance and resort-style amenities. With
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,
Pure Beach by AMI Locals VRC21-000101 Welcome to Pure Beach by AMI Locals, a luxurious three-bedroom, three-bath vacation home designed for relaxation, style, and island living at its finest. Nestled in the heart of Holmes Beach on Anna Maria Island, this stunning retreat is just a two-minute walk to the Gulf beaches and features a private saltwate
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
Blue Bay by Anna Maria Island Accommodations Home in Anna Maria, FloridaVPR16-000138Experience the ultimate coastal retreat at Blue Bay, a luxurious and expansive vacation estate offering eight bedrooms and six bathrooms! Located just across the street from the pristine Tampa Bay, this home embodies beachside elegance with breathtaking water views,
Escape to Island Hideaway, a charming one-bedroom, one-bath home perfectly situated just a four-minute walk from Anna Maria Island’s stunning white sand beaches! This ground-level, fully accessible retreat boasts a private heated pool surrounded by lush tropical landscaping, making it an ideal romantic, small family, or solo escape. Enjoy a seclude
