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!
40 properties available
Siesta Sunset Sanctuary by Siesta Key Luxury Rental Properties Welcome to Siesta Sunset Sanctuary, an architecturally stunning waterfront retreat designed by award-winning Sarasota architect Guy Peterson. This elevated four bedroom, five and a half bath luxury home blends modern coastal elegance with serene water views, offering the perfect escape
Vitamin Sea by Lido Key Vacations Vacation Rental License #VR22-00137 Welcome to Vitamin Sea, an elegant 8 bedroom, 8 full and 2 half baths Lido Key vacation rental located just a 5-minute walk from Lido Beach and a pleasant stroll to the boutiques and restaurants of St. Armands Circle. Perfect for upscale group getaways, this stunning home featur
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
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
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 Shore House by Lido Key Vacations Vacation Rental License #VR22-00033 Minimum stay duration of 7 days/nights The Shore House by Lido Key Vacations is a refined seven bedroom, four and a half bath private retreat designed for families and groups seeking elegant beach living near Sarasota’s most desirable destinations. Located in the heart of
Talk To The Sand by Siesta Key Luxury Rental Properties Talk To The Sand by Siesta Key Luxury Rental Properties is a seven bedroom, seven and a half bath Siesta Key luxury rental designed for families and group getaways seeking elevated coastal living. Just a short four-minute walk to Siesta Key Beach and a quick three-minute walk to Siesta Key Vi
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
Knot A Basic Beach House by Lido Key VacationsVacation Rental License #VR23-00003Minimum stay duration of 7 days/nightsHighlights • 2 minute walk to Lido Beach • 5 minute walk to St. Armands Circle • 1/2 mile to Nature Park Kayak Launch • Pool w/ Spa • Rooftop Wet Bar and GrillWelcome to Knot a Basic Beach House, an exquisite 6 bedrooms, 6 bathroom
Lido Luxe Estate by Lido Key Vacations Vacation Rental License #VR25-00081 Minimum stay duration of 7 days/nights Experience unmatched luxury at Lido Luxe Estate, Sarasota's finest island retreat located in the prestigious Lido Key! This beautifully appointed six-bedroom, six and a half bath home offers a perfect combination of elegance, privacy,
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
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
