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!
29 properties available
Sunset Gulf by Siesta Key Luxury Rental Properties Welcome to Sunset Gulf, an eight bedroom, five and a half bath Siesta Key luxury rental just three houses from the nearest Siesta Key Beach access. This four story coastal retreat features a private heated pool and spa, sweeping Gulf views, multiple balconies, and an elevator connecting every floor
Manatee Cove by Lido Key Vacations VR24-00003 Minimum Stay Duration 7 days/nights Welcome to Manatee Cove, your ultimate Lido Key beach getaway! This stunning canal front home features four spacious bedrooms and five luxurious bathrooms, providing the perfect space for relaxation after a sun-soaked day at the beach. Ideally located just around the
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
The Big Dipper by Siesta Key Luxury Rental Properties Vacation Rental License #VR24-00291 Minimum stay duration of 7 days/nights Welcome to The Big Dipper, your ultimate Siesta Key vacation rental. This stunning canal front home offers four spacious bedrooms, a private bonus room with a queen bed and Jack-and-Jill bathroom, and three and a half bat
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
Ocean Overlook by Siesta Key Luxury Rental Properties Ocean Overlook by Siesta Key Luxury Rental Properties is an exceptional eight bedroom, eight bathroom coastal retreat with two additional half baths, thoughtfully designed for large families and large group getaways seeking luxury coastal living. Located just a three-minute walk to Siesta Key B
Knot A Basic Beach House by Lido Key Vacations #VR23-00003 Minimum stay duration of 7 days/nights Welcome to Knot A Basic Beach House, an elevated coastal retreat where modern design meets effortless island living. This beautifully appointed six-bedroom, six-bathroom home with two additional half baths is just a short walk from Lido Beach and withi
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
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
Treasure on the Canal by Siesta Luxury Rental Properties Welcome to Treasure on the Canal, a luxurious waterfront, Tuscan contemporary retreat with three bedrooms and two full baths, plus two half baths. Featuring a private pool and spa with stunning canal vistas, this home offers seamless indoor-outdoor living just moments from Siesta Key Beach a
The Hideaway by Siesta Key Luxury Rental Properties Welcome to The Hideaway, a luxurious private gated retreat featuring four bedrooms and five bathrooms, located less than a 5-minute walk to Siesta Key Beach. This beautifully designed home offers the perfect blend of upscale comfort and relaxed island living, complete with a screened in pool, spac
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
