Monthly Rentals Siesta Key
Make one of our monthly rentals, Siesta Key, part of the vacation experience. More than just a place where you spend your evenings, our luxurious homes and amenities will create lasting memories for your entire group. Feel at home during extended stays while lounging along your private heated pool in your rental’s backyard. Or take a stroll along the nearby beach. We’ve thought of everything to ensure you have the time of your life with our monthly rentals in Siesta Key! From birthday party planning to grocery deliveries and helping arrange surprise engagements, we can do it all. So relax and take it easy when you book one of our luxurious homes. We truly have it handled!
6 properties available
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
Sundown Sanctuary by Siesta Key Luxury Rental Properties Welcome to Sundown Sanctuary, a refined four-bedroom, three and a half bath Siesta Key luxury rental that blends iconic mid century modern design with effortless coastal living. Set along Midnight Pass Road in a tranquil North Siesta Key neighborhood, this architecturally significant estate o
Penthouse Paradise by Siesta Key Luxury Rental Properties Penthouse Paradise is a spacious three-bedroom, three-and-a-half-bathroom penthouse condo perched on the 6th floor of a premier building in the heart of Siesta Key. Located just a short walk from the world-renowned white sands of Siesta Key Beach, this upscale residence offers panoramic balc
Sunset Cove by Siesta Key Luxury Rental Properties Welcome to Sunset Cove, a stunning four-bedroom, three and a half-bath oasis overlooking the tranquil Heron Lagoon! This luxurious retreat features a private dock for exploring the lagoon, a spacious screened-in patio with a private pool, and direct access to nature’s beauty. Perfectly situated ju
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,
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
