Siesta Key Vacation Home Rentals

Explore our Siesta Key vacation home rentals for your Gulf Coast vacation! A vacation home provides guests with more space and freedom than a traditional hotel stay. Our inventory includes private homes and cottages perfect for those traveling with children or for group stays. These Siesta Key vacation rentals feature amenities like beach views, close to the ocean, private hot tubs, and more. 

Spend your vacation swimming in crystal-clear waters, snorkeling at Point of Rocks, and enjoying the live entertainment, shopping, and restaurants at Siesta Village and Crescent Village! Whether you prefer a low-key vacation or prefer to spend your days adventuring, our Siesta Key vacation home rentals provide a dreamy island escape.

Browse our Siesta Key home and cottage rentals below, or search our full collection of Siesta Key condos and homes. Book directly on our website and save!

Properties Available 6 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
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A Charming Beach Cottage
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A Charming Beach Cottage
House
$409 - $1,299 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (15)
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
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A Charming Beach Cottage - Unit A
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A Charming Beach Cottage - Unit A
Cottage
$199 - $449 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (8)
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
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A Charming Beach Cottage - Unit B
A Charming Beach Cottage - Unit B 2
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A Charming Beach Cottage - Unit B
Cottage
$199 - $449 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (6)
Welcome to Las Palmas! This gorgeous new home on Siesta Key offers luxury around every turn. Stay with up to 16 guests in this 7-bedroom, 7.5-bathroom home, complete with a private pool and spa area, fenced in yard, large full kitchen, dining room, two living spaces with a game room, and much more! Spend time outside by the pool, featuring a kid’s
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A Las Palmas
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A Las Palmas
House Pet Friendly
$1,249 - $4,499 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half baths
Guests 16 guests
Rating 5 (22)
Experience modern luxury in this stunning Siesta Key retreat with floor-to-ceiling glass showcasing breathtaking Gulf and beach views. Enjoy quartz countertops, premium appliances, a heated private lap pool, and a rooftop deck with an electric grill and spectacular sunsets. Just 0.1 miles from beach access and minutes from Siesta Key Village, you'l
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House
$549 - $2,199 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 2 half baths
Guests 10 guests
Rating 5 (32)
The property features a heated community pool, shuffleboard courts right outside your door, and on-site coin-operated laundry. Just south of Siesta Key Public Beach and a short distance from Siesta's Crescent Village, you'll be close to popular restaurants, unique shops, and lively entertainment.
Siesta Beach House
Siesta Beach House - 2 Units
$199 - $499 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (4)

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