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.
171 properties available
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
SeaLuxe by Anna Maria Island Accommodations VR19-000031 Welcome to SeaLuxe, a luxury four-bedroom, four full bath, and two half bath vacation home located just a block and a half from the Gulf beaches at the end of Willow Avenue. Designed for families and groups who love both comfort and fun, this coastal retreat features a private heated pool, hot
Mojito Splash by AMI Locals VRC18-000068 Welcome to Mojito Splash, a stunning five-bedroom, three and a half bath waterfront retreat located just a short stroll from Holmes Beach’s white sandy beaches on Anna Maria Island! This beautifully designed home boasts a sparkling pool, dual waterfalls, a stone-edged spa, and a large, covered lanai with a
Florida Fling by AMI Locals Vacation Rental License #DWE5105449Welcome to Florida Fling by AMI Locals, a breathtaking seven bedroom, seven and a half bath luxury home just a 1-minute walk to the pristine beaches of Anna Maria Island. Newly built and elegantly designed, this stunning retreat features a resort-style pool with in-ground spa, a rooftop
Feelin' Beachy by AMI Locals VRC20-000140Prepare for endless enjoyment at Feelin’ Beachy, a luxurious four-bedroom, four and a half bath home just around the corner from the soft sands and warm waters of Holmes Beach! This thoughtfully designed coastal retreat features a lavish backyard oasis with a private pool, in-ground spa, and multiple outdoo
Under The Sea by AMI Locals Vacation Rental License #VR17-000055 Welcome to Under the Sea, a luxurious four bedroom, four and a half bath home just a two-minute walk to the Gulf white sand beaches. With private balconies, a resort-style pool and spa, and lush tropical landscaping, this elegant coastal retreat offers the perfect setting for families
North End Escape by AMI Locals Welcome to North End Escape, a stylish three-bedroom, two-bath custom built home in one of Anna Maria Island’s most desirable neighborhoods. Just a two minute walk from Bean Point Beach and steps to Pine Avenue’s shops and dining, this upscale retreat features designer interiors, a private heated pool, and a rooftop d
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
Welcome to Aqua Paradise, a stunning seven bedroom, six full bath, and two half bath luxury retreat just a two-minute walk to Bradenton Beach. Perfectly designed for large groups and multi-family getaways, this home features a rooftop terrace with panoramic Gulf and Bay views, a private heated pool and spa, and endless entertainment amenities inclu
Gulf Breeze by AMI Locals VRC21-000001Welcome to Gulf Breeze, a charming three bedroom, two bath home just a short five-minute walk from Holmes Beach! This tropical oasis offers a private pool, lush, landscaped backyard, and easy access to local parks, shops, and restaurants, all within walking or biking distance. Perfect for families or groups se
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
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
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