Waterfront Rentals


Properties Available 15 properties available
Tortuga Unit 406 by Tropical Sands Accommodations 30-night Minimum stay Welcome to Tortuga Unit 406, a bright and comfortable two-bedroom, two-bathroom condo located along the tranquil Midnight Pass Road on beautiful Siesta Key. Enjoy stunning beach views from your private balcony and effortless access to the island’s pristine private beach, situ
Tortuga Unit 406
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
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,
Siesta Dreamin'
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (3)
Peppertree Penthouse #803 by Tropical Sands Accommodations Welcome to Peppertree Penthouse #803, a spacious 2-bedroom, 2-bath Siesta Key condo with breathtaking Gulf views, private beach access, and a spacious enclosed lanai perfect for sunset dining. Located within the highly desirable Peppertree community on Siesta Key Beach, this home provides u
Peppertree Penthouse #803
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
Sea Club II Unit 7E by Tropical Sands Accommodations Step into your laid back Siesta Key escape at Sea Club II Unit 7E by Tropical Sands Accommodations, a relaxed and welcoming 2-bedroom, 1-bath bayfront condo that’s perfect for couples, small families, or friends seeking affordable Siesta Key vacation rentals. Nestled right on the Intracoastal Wa
Sea Club II Unit 7E
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (5)
Harbor Towers 420 by Tropical Sands Accommodations Experience the perfect Gulf Coast getaway at Harbor Towers 420, a charming bayfront condo ideally located just a short walk from Siesta Key Beach. This bright and inviting two-bedroom, two-bathroom residence offers stunning views of Siesta Key Beach and the Intracoastal Waterway. With access to two
Harbor Towers 420
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4 (1)
Sea Club II Unit 2A by Tropical Sands Accommodations Welcome to Sea Club II Unit 2A, a spacious bayfront retreat featuring 3 bedrooms and 3 and a half bathrooms. This Siesta Key vacation rental is perfect for extended families or groups looking for comfort, convenience, and the laid back charm of island living. Located directly on the Intracoastal
Sea Club II Unit 2A
Condo
Bedrooms 3 bedrooms
Bathrooms 3 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Rating 5 (20)
Coastal Charm by Tropical Sands Accommodations Welcome to Coastal Charm, a refreshed 3-bedroom, 2-bath Siesta Key home located just a 10-minute walk to Siesta Key Beach and close to the shops and restaurants of Siesta Key Village. This peaceful canal front property features a private pool, outdoor dining, and dog friendly options. Perfect for famil
Coastal Charm
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (3)
Just across the street from the acclaimed #1 Beach in the US. This beautiful 2 bedroom/2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities include a hea
Our House at the Beach W-601
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (11)
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
Leona Breeze
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Rating 4 (1)
Fisherman’s Cove – A207 by Tropical Sands Accommodations Welcome to Fisherman’s Cove – A207, a beautifully remodeled one-bedroom, one-bathroom beachfront condo located directly on Turtle Beach in Siesta Key. Situated on the second floor, this inviting retreat offers full Gulf views, allowing you to relax to the sound of the waves and enjoy unforget
Fisherman's Cove -A207
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (5)
Bay Oaks E-93 by Tropical Sands Accommodations Discover your perfect escape at Bay Oaks E-93, a coastal-inspired Siesta Key condo for rent, nestled just a short walk from the soft sands of Siesta Beach! This charming two-bedroom, two-bathroom retreat in Sarasota offers a relaxing oasis ideal for families or groups. Enjoy days sunbathing and swimmin
Bay Oaks E-93
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (3)
Sea Club II Unit 2B by Tropical Sands Accommodations Welcome to Sea Club II Unit 2B by Tropical Sands Accommodations, a relaxing bayfront one bedroom, one bathroom condo perfect for a couple’s Siesta Key getaway. Located directly on the Intracoastal Waterway and just a 10 minute walk to Siesta Key Beach, this ground level retreat offers peaceful wa
Sea Club II Unit 2B
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (12)

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