Siesta Key, Florida
187 properties available
🌞 Casita Sol | Walk to Siesta Key's Crescent Beach, HOA Pool, Easy Island Living💖 Why You'll Love This HomeCasita Sol delivers relaxed island comfort with a location that makes beach days effortless and dining walkable. Everything you love about Siesta Key is right outside your door.👨👩👧 Perfect ForCouples, small families, snowbirds, and pet
🌴 Silver Shore | Modern Escape, Rooftop Deck, Pool & Across from Siesta Key Beach💖 Why You'll Love This HomeFrom morning coffee on the rooftop to sunset dips in your private heated pool, Silver Shore invites you to unwind in total comfort. Spacious enough for large families or groups, this upscale retreat offers elevator access, beach proximity,
🌴 Avanti Villa | Rooftop Deck, Walk to Siesta Key Beach & Village, Canal Access💖 Why You'll Love This HomeAvanti Villa is a well-located Siesta Key retreat just a short walk to both Siesta Key Beach and Siesta Key Village. This three-bedroom duplex unit is designed for easy island living, combining walkability with comfortable indoor and outdoor
🌴 Coconut House | Siesta Key Retreat with Shared Heated Pool💖 Why You'll Love This HomeStep into a bright, spacious haven perfect for your Siesta Key getaway. Coconut House features three inviting bedrooms, a fully equipped kitchen for group meals, and access to a screened-in heated pool shared with Palm Shade Cottage. Just 0.1 miles from the whi
Aloha Kai #63 A Siesta Key Beachside Bliss Awaits! Escape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #63. This charming one-bedroom beach cottage offers the perfect blend of comfort and coastal charm, where the gentle breeze from the Gulf and the lively atmosphere of Crescent Beach set the stage
Gulf and Bay Club Bayside stands out as one of the most attractive condominium complexes on Siesta Key. Professionally managed by Gulf Coast Vacation Rentals, this beautifully remodeled unit offers luxurious accommodations at a reasonable cost, making it the perfect getaway destination. With a stunning lake view and just steps away from the resort-
🌴 Crescent Cottage | Private Pool + Walk to Crescent Beach💖 Why You'll Love This HomeJust 0.2 miles from world-famous Crescent Beach, this freshly renovated island villa blends beachy charm with upscale finishes—plus a private heated pool and pet-friendly perks. Whether you're gathering with family or escaping with friends, the home's thoughtful
The Anchorage Resort on Siesta Key - includes resort amenity access!Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.* Anchorage Resort Condo* 2 bedrooms / 2 bathrooms* Spacious Balcony overlooking Southern Siesta Key* Top Floor Condo with amazin
🌴 Tropical Retreat | Heated Pool + 1 Block to Siesta Key Beach💖 Why You'll Love This HomeTwo charming cottages, one unforgettable escape—Tropical Retreat brings together private indoor space and outdoor serenity just one block from Siesta Key Beach. With a screened-in heated pool, BBQ area, and alfresco dining, your group can unwind in complete e
🌴 Casita Morning Star | A Coastal Charm with Private Pool, Walk to Crescent Beach + Village💖 Why You'll Love This HomeWelcome to Casita Morning Star, a cheerful Siesta Key hideaway with its own private heated pool, tropical outdoor space, and a 3-minute walk to Crescent Beach and Point of Rocks. One half of a charming duplex, this home gives you
Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. Professionally managed by Gulf Coast Vacation Rentals, with breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat.
Aloha Kai #17A Siesta Key Beachside Bliss Awaits!Escape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #17. This is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. With it's retro charm and casual elegan
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