October Sale
Autumn Tides & Siesta Vibes:
Book a Stay between Now and Dec. 21st 2026 and save yourself 15% off your nightly rate on select properties!
23 properties available
Step into tranquility at this charming private home, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Featuring a private kitchen, living room, and an onsite private pool, this cottage is perfect for winding down after a day in
Step into tranquility at this charming 1-bedroom cottage, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Complete with a private kitchen, living room, and an onsite shared pool and hot tub, this cottage is perfect for winding
Step into tranquility at this charming 1-bedroom cottage, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Featuring a king size bed, private kitchen, living room, and an onsite shared pool and hot tub, this cottage is perfect f
Browse Bianco Sands Siesta Key vacation rentals for a dreamy Gulf Coast getaway! Bianco Sands features 9 casitas (villas), ranging from 1 to 3 bedrooms, each with a full kitchen, a spacious living room, and dining space. These Siesta Key rentals are perfect for small groups or large groups who want to spend their vacation together, but be able
Welcome to the Sand Dollar; a charming condo in the heart of Siesta Key. This cozy one-bed, one-bath getaway offers the perfect blend of comfort, style, and convenience for a relaxing beach vacation with family or friends. The home offers a fully equipped kitchen and a spacious back patio within a short walking distance to the world-famous Siesta K
Spend your vacation at The Sandcastle; a charming second-floor condo in the heart of Siesta Key. This spacious two-bedroom, two-bathroom getaway offers the perfect blend of comfort, style, and convenience for a relaxing beach vacation with family or friends. The home offers a fully equipped kitchen, private balcony, and a spacious back patio all wi
Welcome to the Seagull Suite; a charming condo in the heart of Siesta Key. This cozy one-bed, one-bath getaway offers the perfect blend of comfort, style, and convenience for a relaxing beach vacation with family or friends. The home offers a fully equipped kitchen and a spacious back patio within a short walking distance to the world-famous Siesta
Experience unforgettable Siesta Key sunsets just steps from the Gulf. Located only 300 feet from Crescent Beach’s powder-soft sand and turquoise waters, this inviting 2-bedroom, 2-bath condo features a spacious, open-concept kitchen, comfortable living areas, and a large private balcony for relaxing outdoors. Guests enjoy access to two heated pools
Stay in paradise with stunning views of the Gulf! This 2-bed, 2-bath condo located in the Crystal Sands tower features a spacious, chef’s kitchen, comfortable living areas, and a large private balcony for relaxing outdoors Guests have direct access to Crescent Beach, a quieter stretch of Siesta Key known for its soft white sand and clear blue water
Experience breathtaking Siesta Key sunsets just steps from the Gulf! Located only 300 feet from Crescent Beach’s powder-soft sand and turquoise waters, this inviting 2-bedroom, 2-bath condo features a spacious, chefs kitchen, comfortable living areas, and a large private balcony for relaxing outdoors. Guests enjoy access to two heated pools, and a
Welcome to the enchanting Crystal Sands - Sea La Vie, your perfect beach side retreat in the heart of Siesta Key. This charming two-bedroom villa offers a cozy and inviting space for up to 5 guests and features a full kitchen and spacious living room accompanied by a cozy nook. Guests enjoy access to two heated pools, and a private beach area. Expe
Experience Siesta Key in this lovely island condo! Conveniently located above one of our island’s grocery stores, this condo is directly in the heart of the vibrant South Siesta Key Village. With great food, shopping, and plenty of activities, Siesta Key promises amazing experiences for everyone who visits. Take advantage of the tranquil waters, so
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