Featured Properties

Beautiful Rentals for your Beach Vacation

Get away from the everyday routine and book a stay at one of these Siesta Key homes! Wake up to Florida Gulf Coast sunshine and stroll to the award-winning Siesta Key Beach. 


Properties Available 12 properties available
Peppertree Paradise #507 by Tropical Sands Accommodations Minimum stay duration 30 nights Welcome to Peppertree Paradise #507, a bright and stylish two-bedroom, two-bath condo located in the sought after Peppertree Bay community on beautiful Siesta Key. This charming home is infused with vibrant artwork, colorful accents, and coastal charm, offer
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Peppertree Paradise #507
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Siesta Beach House #201 by Tropical Sands Accommodations Welcome to Siesta Beach House #201, a comfortable and family friendly two bedroom, one and a half bathroom condo located on the quiet south end of Siesta Key. Tucked away on a private lane with gated beach access, this inviting retreat places you just a short walk from the powdery white sands
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Siesta Beach House #201
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
HalfBathrooms 1 Half baths
Guests 4 guests
Rating 5 (2)
The Coastal Nest by Tropical Sands AccommodationsWelcome to The Coastal Nest, an upscale three-bedroom, two-bath vacation home tucked away in a quiet residential neighborhood of Sarasota. Designed for comfort and longer stays, this inviting retreat offers a relaxed coastal atmosphere, thoughtful amenities, and a convenient island location ideal for
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The Coastal Nest
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4 (1)
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,
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Siesta Dreamin'
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)
Leona Breeze by Tropical Sands AccommodationsWelcome to Leona Breeze, the perfect home for long-term renters seeking a relaxed, comfortable stay on Siesta Key. Designed for extended stays, this two-story residence offers four bedrooms and two and a half bathrooms, providing the ideal backdrop for families, professionals, or groups looking to settle
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Leona Breeze
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Rating 4 (1)
Off The Hook – A by Tropical Sands Accommodations Welcome to Off The Hook – A, your cheerful vacation duplex just steps away from the world famous Siesta Key Beach! This delightful two-bedroom, one-bath home is perfectly suited for couples or families with young children, providing a fun and sunny atmosphere for your next getaway. Highlights • 5-m
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Off The Hook - A
Duplex Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 (20)
Casa Siesta 2 by Tropical Sands Accommodations Welcome to Casa Siesta 2, your ideal romantic beach getaway located just a 6-minute walk from Crescent Beach in beautiful Siesta Key. This cozy one-bedroom, one-bath ground level condo is perfect for couples seeking a relaxing coastal escape, offering comfort, convenience, and easy access to the islan
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Casa Siesta 2
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.5 (2)
Oceanside Retreat by Tropical Sands AccommodationsOceanside Retreat is a recently refreshed three-bedroom, three-bath ground floor vacation rental on Siesta Key, ideal for families and small groups who want a comfortable home base close to the island’s famous beaches, dining, and laid back coastal vibe. After a day on the sand, come home to bright,
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Oceanside Retreat
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 5 (2)
Siesta Beach House #312 by Tropical Sands Accommodations Welcome to Siesta Beach House #312, a comfortable two-bedroom, two-bathroom condo located just steps from the white sands of Siesta Key Beach. Set within a quiet complex on a private lane, this inviting condo offers gated beach access, making it easy to enjoy stress free beach days. With shar
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Siesta Beach House #312
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.8 (9)
Gulf Holiday Unit 8 by Tropical Sands Accommodations Welcome to Gulf Holiday Unit 8, a recently refreshed one bedroom, one bathroom condo perfectly located in the heart of Siesta Key Village and just a two-minute walk to Siesta Key Beach. Ideal for couples or small families, this cozy and budget friendly Siesta Key vacation rental offers updated in
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Gulf Holiday Unit 8
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 (20)
Off The Hook - B by Tropical Sands Accommodations Welcome to Off The Hook – B, your ideal sunny vacation getaway just a 5-minute walk from the world famous Siesta Key Beach. This charming two-bedroom, one-bath duplex offers a delightful blend of comfort and convenience, just minutes from the beach and Siesta Key Village. Perfect for couples and sma
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Off The Hook - B
Duplex Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (26)
Casa Mango by Tropical Sands Accommodations Welcome to Casa Mango, a bright and inviting 3-bedroom, 2-bath Sarasota home offering a private screened-in pool, outdoor living spaces, and access to a shared dock just down the street for kayaking and paddleboarding. Perfect for families and groups seeking comfortable Sarasota and Siesta Key vacation re
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Casa Mango
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 4.6 (6)