Pool Rentals
377 properties available
Gulf and Bay Club- E308 Welcome to Gulf and Bay Club E308, a beautifully renovated two bedroom, two bath condo in the only true resort community on Siesta Key. Ideal for families or friends seeking Siesta Key vacation rentals that combine comfort, convenience, and island charm. This unique unit is just steps from Siesta Key Beach and offers sweepi
Beautifully updated and furnished property with everything you would expect from a resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses, and if you like, Americas #1 beach is w
Gulf and Bay Club Unit A704 Tropical Sands AccommodationsWelcome to Gulf and Bay Club Unit A704, a bright and inviting two bedroom, two bathroom condo located in one of Siesta Key’s most sought-after beachfront communities. Perfect for extended stays, this 28-night minimum retreat places guests just a 5-minute walk from world-famous Siesta Beach, k
Jamaica Royale Unit 065 by Tropical Sands AccommodationsWelcome to Jamaica Royale Unit 065, a beautifully updated one-bedroom, one-bath garden villa nestled in the heart of Siesta Key. Perfect for couples or small families, this bright and beachy retreat offers easy access to the community’s three heated pools and a private stretch of Siesta Key’s
Completed renovated unit as of July 2025! ABSOLUTELY STUNNING UNIT 59! Completely remodeled in 2025! This sun-filled garden unit is steps to world renowned #1 Siesta Key Beach. One of the QUIETEST units at JR with all Hurricane safe windows and doors, including a separate key for the front and rear patio doors. Designer kitchen with stainless steel
Jamaica Royale 083 by Tropical Sands AccommodationsWelcome to Jamaica Royale 083, a beautifully refreshed two-bedroom, two-bath garden view villa located directly on the Gulf at the highly sought after Jamaica Royale resort on Siesta Key. Recently updated with new paint, flooring, and furnishings in June 2025, this inviting vacation rental offers a
Welcome to Midnight Cove II Unit 933! This spacious 2-bedroom, 2-bathroom condo is your ideal Crescent Beach getaway. Located on the third floor, this 1,400 sq. ft. retreat offers stunning views of the Intracoastal Waterway and the pool, just steps from the beach access. Perfect for families or friends, this condo comfortably accommodates up to 6 g
Jamaica Royale 025 by Tropical Sands AccommodationsWelcome to Jamaica Royale 025, a beautifully updated 1-bedroom, 1-bathroom condo located in the heart of Siesta Key. This charming garden-view retreat offers a bright and modern interior, private patio, and easy access to three sparkling community pools and the world-famous quartz sands of Siesta B
Welcome to Midnight Cove II 710F! This beautifully renovated 1st-floor condo offers 2 bedrooms and 1.5 bathrooms, making it the perfect getaway for families, friends, or couples seeking a memorable vacation on Crescent Beach on Siesta Key. Located just steps from the sparkling waters of Crescent Beach and our dedicated private beach access, this ch
Jamaica Royale 014 by Tropical Sands AccommodationsWelcome to Jamaica Royale 014, a beautifully renovated studio villa located in the desirable garden and poolside area of the Jamaica Royale community on Siesta Key. Updated in 2025 with a fresh coastal design, this thoughtfully upgraded retreat offers modern finishes, a private lanai, and close pro
Jamaica Royale Unit 061 by Tropical Sands AccommodationsWelcome to Jamaica Royale Unit 061, a newly refreshed one-bedroom retreat featuring two queen beds, a queen sleeper sofa, and stylish upgrades completed in June 2025. Located in the peaceful garden and pool area of the Jamaica Royale community, this spacious ground level condo offers a bright,
Jamaica Royale 076 by Tropical Sands AccommodationsWelcome to Jamaica Royale 076, a newly renovated two-bedroom, two-bath garden villa located just steps from Siesta Key Beach, consistently ranked the #1 beach in the USA. Nestled beside Pool #2 within the beautifully landscaped Jamaica Royale complex, this modern coastal retreat features a complete
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