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.
153 properties available
The Oasis at Palmetto by AMI LocalsWelcome to The Oasis at Palmetto, an upscale four-bedroom retreat with a private pool, bright coastal interiors, and an unbeatable location just a 2-minute walk to the Gulf of Mexico. Nestled on the quiet north end of Anna Maria and steps from Pine Avenue’s boutique shops and cafes, this home is perfect for famili
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
Sweet Caroline by Exclusive Vacations Vacation Rental License #VR23-000009 Welcome to Sweet Caroline, part of our Exclusive Collection. This luxury four bedroom, four and a half bath Anna Maria Island vacation home just one small block from the Gulf beaches. This coastal retreat blends refined design, resort-style amenities, and a relaxed island vi
Blue Tide (Formerly Island Sol) by Anna Maria Vacations Home in Bradenton Beach, FL TPL20-000004 / RBT20-000002 / DWE5105831Welcome to Blue Tide by Anna Maria Vacations, a luxury five-bedroom, four-bathroom custom home designed for the ultimate Anna Maria Island vacation. Perfectly located in Bradenton Beach, just two blocks from the Gulf beaches,
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
Lay'By, Too by AMI Locals VPR16-000175 Welcome to Lay'By, Too, a vibrant ground-level vacation home just four houses from the stunning beaches of Anna Maria Island, with no streets to cross! This spacious four-bedroom, three-bath retreat offers a private pool, lush backyard, outdoor dining and grilling area, and cheerful coastal decor, perfect fo
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
Serenity Beach by AMI Locals Vacation Rental License #VR16-000464 Welcome to Serenity Beach by AMI Locals, a stunning five-bedroom, four-and-a-half-bath luxury vacation home located on the exclusive north end of Anna Maria Island, just a seven-minute walk to the Gulf beaches. This elegant canal-front retreat combines modern design, high-end ameniti
Rising Tide by AMI Locals Vacation Rental License #TPL22-000006, DWE5105473Welcome to Rising Tide by AMI Locals, a stunning five-bedroom, four-bathroom beach-view vacation home just 75 steps from the sands of Bradenton Beach. This spacious multi-level retreat offers a private heated pool and spa, family-friendly game areas, and an unbeatable locati
Gypsy Sol by Anna Maria Island Accommodations VR18-000034 Welcome to Gypsy Sol, your ultimate Anna Maria Island escape! This four bedroom, two bath canal front vacation home is packed with fun and relaxation, featuring a private pool, hot tub, and ping pong table for endless entertainment. Just a short stroll from Pine Avenue’s charming boutiques,
Beachfront Bungalow by AMI Locals Vacation Rental License #VRC19-000270 Welcome to Beachfront Bungalow, a rare four-bedroom, three and a half bath coastal cottage located directly on the sandy shores of Holmes Beach on Anna Maria Island! With nothing but your private pool and spa between you and the Gulf, this beachfront escape is designed for trav
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,
