Vacation Rentals
Siesta Key Vacation Rentals
Tropical Sands Accommodations offers a premium selection of Siesta Key beach vacation rentals for weekly, monthly, or even shorter stays. Browse our full availability below!
414 properties available
Harbor Towers 515 by Tropical Sands AccommodationsWelcome to Harbor Towers 515, a beautiful two-bedroom, two-bath Siesta Key vacation rental featuring scenic Intracoastal Waterway views. Located within the gated Harbor Towers Yacht and Racquet Club, this inviting condo combines a peaceful waterfront setting with convenient access to Siesta Key Vill
Midnight Cove II – 137 by Tropical Sands Accommodations Welcome to Midnight Cove II – 137, a comfortable two-bedroom, one and a half bath third floor condo overlooking the Intracoastal Waterway in Siesta Key. Just a 4-minute walk to Crescent Beach and a quick 2-minute walk to the trolley stop, this Siesta Key condo rental is perfect for family beac
Jamaica Royale 085 by Tropical Sands AccommodationsWelcome to Jamaica Royale 085, a newly renovated two-bedroom, two-bath garden-view villa in the popular Jamaica Royale beachfront complex on Siesta Key. Featuring a bright, open layout and fresh coastal design, this modern retreat offers updated finishes, stylish furnishings, and all the comforts o
Harbor Towers 417 by Tropical Sands Accommodations Welcome to the perfect Gulf Coast retreat at Harbor Towers 417, a beautifully updated Bayfront condominium nestled directly on the Gulf Coast Intracoastal Waterway. This charming fourth-floor residence offers stunning bay views, near Siesta Key’s powdery sands and warm Gulf waters. With two bedroo
Welcome to the ultimate Florida retreat at the newly renovated Midnight Cove II 311F! This 1st floor, 2 bed - 2 full bath condo with la washer and dryer is perfectly situated in the heart of Crescent Beach on Siesta Key, America’s #1 beach destination. Enjoy easy access with no stairs- just a short distance to a covered parking space and private he
Jamaica Royale 064 by Tropical Sands AccommodationsWelcome to Jamaica Royale 064, a beautifully updated one-bedroom, one-bath garden view villa located in the desirable Jamaica Royale community on Siesta Key. This inviting coastal retreat combines stylish modern updates with a comfortable open layout, all just a short stroll from the powdery white
Midnight Cove II – Unit 513 - Pool View!1500 Cove II Place 513 Siesta Key FL 34242Welcome to Midnight Cove II 513F, a relaxing two-bedroom, two-bath Siesta Key vacation rental near the world famous quartz-white sands and turquoise Gulf waters of Crescent Beach. Located within the peaceful Midnight Cove II community, this comfortable condo offers a
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,
Midnight Cove II – Unit 912 Midnight Oasis!1100 Cove II Place 912 Siesta Key FL 34242Welcome to Midnight Cove II 912C! Situated in the heart of Crescent Beach on Siesta Key, our community offers a delightful mix of shopping, dining, art, and culture that is sure to entertain you. Enjoy the complimentary Siesta Key Breeze Trolley, which takes the wo
A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true 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 wait
Second Floor Townhouse, steps to access unit, no elevator. **King in guest bedroom can be separated into two twins**Welcome to Our House at the Beach C-205! This spacious two-bedroom, two-bath condo is perfect for families seeking a comfortable and flexible accommodation option, whether for a beach getaway, a weekend retreat, or a longer stay. With
Our House at the Beach C-114 by Tropical Sands AccommodationsWelcome to Our House at the Beach C-114, a comfortable two bedroom, two bathroom townhouse style vacation rental located directly across from the world famous Crescent Beach on Siesta Key. Situated within the well loved Our House at the Beach community, this inviting condo offers a relaxe
