Pool Retreats
332 properties available
The Big Yellow House on Pine by Anna Maria Vacations Home in Anna Maria, FL Welcome to The Big Yellow House on Pine by Anna Maria Vacations, a beachfront five-bedroom, four-bath home that captures the relaxed spirit of Anna Maria Island. Perfectly positioned along the Gulf, this charming coastal retreat offers spectacular beach views, a private poo
Ilha Bela by Anna Maria VacationsHome in Holmes Beach, Florida Welcome to Ilha Bela, a timeless three-bedroom, two and a half bath vacation home tucked away in the heart of Holmes Beach on beautiful Anna Maria Island. Blending classic Old Florida charm with modern comfort, this inviting getaway features a lush backyard oasis with tropical landscapi
Sea The Light by Lido Key Vacations #VR22-00131 Minimum stay duration of 7 nights Welcome to Sea The Light, a luxurious seven bedroom, seven and a half bathroom coastal home perfectly situated for unforgettable Lido Key vacation rentals. Just a three-minute walk to Lido Beach and a pleasant stroll to St. Armands Circle, this upscale retreat offers
Covey Cottage by Anna Maria Island Accommodations Home in Anna Maria, FloridaVR16-000292 Welcome to Covey Cottage by Anna Maria Island Accommodations, a three bedroom, three and a half bathroom vacation home with a private pool and an unbeatable location. Just a seven-minute walk to the white-sand Gulf beaches and one minute to Pine Avenue’s shops
Bayshores by Anna Maria Island Accommodations VRC18-000040 Welcome to Bayshores by Anna Maria Island Accommodations, a charming three-bedroom, three-bathroom canal front home in Holmes Beach that captures the nostalgic charm of Old Florida while offering all the comforts of modern coastal living. Perfectly situated along serene waterways and just a
Magnolia Shores by Anna Maria Island Accommodations Welcome to Magnolia Shores, a renovated two-bedroom, one-bath coastal retreat just a five-minute walk from the beach. Perfect for small families or couples, this ground-level home offers a private heated pool, screened-in lanai, and putting green, along with easy access to Anna Maria Island’s belo
Pineapple Palms by Anna Maria Island Accommodations VRC17-000041Welcome to Pineapple Palms, the ultimate ocean-loving getaway just two-and-a-half blocks from the stunning beaches of Holmes Beach! Perfect for a small family or friends, this charming two-bedroom, two-bathroom home offers a private heated pool, lush, landscaped backyard, and a breezy
Siesta Dreamin’ by Tropical Sands AccommodationsWelcome to Siesta Dreamin’, a stylish and inviting 4-bedroom, 3-bath canal front home with a private dock, perfect for extended stays on Siesta Key. Located just a 12-minute walk to Siesta Key Beach, this comfortable retreat offers a peaceful waterfront setting while still being close to local shops,
Beach Views by Lido Key Vacations #VR22-00034 Minimum Stay Duration 7 days/nights Welcome to Beach Views, an exceptional three-level coastal retreat located just steps from Lido Beach. Designed for upscale group getaways and unforgettable family vacations, this seven bedroom, seven and a half bath home offers refined comfort, expansive gathe
Calypso Cottage by Anna Maria Vacations Home in Holmes Beach, Florida VRC16-000622Your island vacation starts at Calypso Cottage, a Mediterranean-inspired escape just a short stroll from Holmes Beach’s white sandy beaches on Anna Maria Island! This three-bedroom, three-bath home offers a private pool with a spa, a ping pong table, and tropical outd
Island Hopping by Lido Key Vacations Minimum stay duration of 7 days/nights #VR23-00009 Island Hopping by Lido Key Vacations is a one of a kind coastal retreat featuring two separate cottages and a private pool, just a 3-minute walk to Lido Key Beach. Recently remodeled with a chic beach design, this five bedroom, four bath property is ideal for fa
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
