Siesta Key Rentals with a Pool
There’s no more relaxing place to spend your next vacation than one of our Siesta Key rentals with a pool! Siesta Key has tons of fun things to do throughout the day, but when it’s time to unwind in the evening, you’ll love having your own pool. You could even spend the afternoon hanging out in your rental and enjoying the sunshine or resting while your kids take a dip. Besides the incredible pool, you’ll also have access to these other amenities in our Siesta Key rentals including high-speed internet, fully stocked kitchens, beautiful outdoor space, cozy living areas, flat-screen TVs, and convenient parking. Book today!
36 properties available
High Tide by Siesta Key Luxury Rental Properties Welcome to High Tide, a stunning six bedroom, six and a half bath luxury retreat designed for unforgettable coastal living just a two-minute walk to Siesta Key Beach. Ideally located near Siesta Key Village, this expansive home is perfect for large families or group getaways seeking elevated comfort
Village Time by Siesta Key Luxury Rental PropertiesWelcome to Village Time, a terrific choice for multi-family groups booking accommodation together, as each can enjoy their own separate space while staying close. Offering a total of six bedrooms, six full baths, and two half baths in two unique living areas, this home is a quick walk to Florida's
The Big Top by Lido Key Vacations #VR22-00043 Minimum stay duration of 7 days/nights Welcome to The Big Top, an impressive three-level coastal retreat offering refined comfort, generous gathering spaces, and elevator access to all floors. Located just a short walk from St. Armands Circle and within easy reach of Lido Beach, this six bedroom, fi
Stone’s Throw by Lido Key Vacations Vacation Rental License #VR22-00037 Minimum stay duration of 7 days/nights Welcome to Stone’s Throw, a beautiful Lido Key cottage just moments from the Gulf of Mexico beaches! Gather your loved ones for an unforgettable getaway at this three-bedroom, two-bathroom retreat. Relax in the private backyard oasis, comp
Casa Playa by Siesta Key Luxury Rental Properties Vacation Rental License #VR23-00001 Welcome to Casa Playa, a Mediterranean inspired coastal retreat featuring five beautifully designed bedrooms and three bathrooms, located 1.5 miles from Siesta Key Beach. Surrounded by lush tropical landscaping and offering a private pool, tiki style outdoor kitch
The Midnight Turtle by Siesta Key Luxury Rental PropertiesWelcome to The Midnight Turtle, a beautifully refreshed four-bedroom, three-bath vacation rental tucked inside the exclusive Tortoise Estates community on South Siesta Key. This spacious coastal retreat offers private deeded beach access, a sparkling private pool, screened balconies, and ple
Casa Siesta by Siesta Key Luxury Rental Properties is a beautifully designed three-bedroom, three-bathroom private pool home, ideal for families and friends seeking a refined Siesta Key vacation rental just steps from the beach. Located approximately a 1-minute walk to Siesta Key Beach, this retreat offers an exceptional blend of walkable beach acc
Mainsail by Siesta Key Luxury Rental Properties Mainsail by Siesta Key Luxury Rental Properties is a breathtaking 4 bedroom, 3 and a half bath waterfront luxury home with a bonus room, private dock, and spectacular Intracoastal Waterway views. Nestled at the end of a quiet street and just a 10-minute walk to Crescent Beach, this upscale retreat off
Surf View by Siesta Key Luxury Rental PropertiesSurf View is a spacious eight bedroom, eight and a half bath Siesta Key luxury rental designed for large families and group gatherings seeking relaxed coastal living. Ideally located just a three-minute walk to Siesta Key Beach and steps from Siesta Key Village, this inviting retreat places guests nea
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
Sunset Splash by Siesta Key Luxury Rental Properties Welcome to Sunset Splash, a legendary eight bedroom, seven and a half bathroom ground-level vacation home. Just a 2-minute walk to Siesta Key Beach and steps from Siesta Key Village, this private pool home is designed for unforgettable group getaways. The true WOW factor is the resort style back
The Pink Flamingo by Lido Key VacationsVacation Rental License #VR24-00001 The Pink Flamingo by Lido Key Vacations is a charming two-bedroom, two-bathroom private pool home that blends classic Old Florida character with relaxed coastal comfort. Located just a 4-minute walk to Lido Key Beach, this Lido Key vacation rental is ideal for couples or sma
