Siesta Key Vacation Rentals
53 properties available
Blue Paradise by Siesta Key Luxury Rental Properties Experience the epitome of Siesta Key luxury at Blue Paradise, a stunning six-bedroom, six and a half-bath retreat perfectly situated just half a block from Siesta Key Beach and across the street from Siesta Key Village. With breathtaking tropical views, this resort-style home is designed to prov
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
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
Summer Nights by Lido Key Vacations Vacation Rental License #VR23-00017 Minimum stay duration of 7 days/nights Summer Nights by Lido Key Vacations is a charming two-bedroom, two-bathroom coastal retreat ideally located just three homes from Lido Key Beach. Designed for couples or small families, this Lido Key vacation rental offers relaxed island l
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
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
Three Sandy Sisters by Siesta Key Luxury Rental Properties is a charming two bedroom, two bath villa offering the perfect balance of relaxed coastal living and resort style amenities. Located along scenic Midnight Pass Road, this Siesta Key vacation rental provides easy access to Siesta Key Beach entry through the Aloha Kai community, along with ba
Sunshine on Siesta – by Siesta Key Luxury Rental PropertiesWelcome to Sunshine on Siesta, a recently refreshed four-bedroom, two-bath Super Unit designed for families and groups who want to vacation together while enjoying space, comfort, and an unbeatable Siesta Key location. By combining both the Sunrise and Sunset residences, this home offers a
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
Island Time West by Siesta Key Luxury Rental Properties Discover the perfect Gulf Coast escape at Island Time West, a beautiful three-bedroom, three-and a half-bath luxury home located just minutes from the stunning Siesta Key Beach and vibrant Siesta Key Village, your gateway to great dining, shopping, and island adventures. This bright and airy
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,
