Siesta Key Beach House Rentals

Compare 9 vacation rentals.
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Make Siesta Key your next getaway

You deserve nothing but the best for your next Florida getaway. In 2020, the barrier island of Siesta Key was voted TripAdvisor’s No. 1 beach in the U.S., and No. 11 in the world. With sandy shores and a fun, laid-back vibe, our Siesta Key beach rentals are the perfect place to go for some much needed relaxation.

Top Siesta Key property types

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Condo rentals

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Studios

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Apartments

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Popular amenities for Siesta Key vacation rentals

Popular
Internet Pool Electric vehicle charger
Parrot Beach Cottages Suite #3
1 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #3 - Siesta Key, FL

$212 avg / night
(excludes fees and taxes)
4.26 (97)
Parrot Beach Cottages Suite #1
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

$188 avg / night
(excludes fees and taxes)
4.52 (91)
Parrot Beach Cottages Suite #4
1 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #4 - Siesta Key, FL

$222 avg / night
(excludes fees and taxes)
4.37 (84)
Parrot Beach Cottages Suite #2
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #2 - Siesta Key, FL

$185 avg / night
(excludes fees and taxes)
4.62 (104)
Midnight Cove II 823
2 Bedroom | 1.5 Bath | Sleeps 6

Midnight Cove II 823 - Siesta Key, FL

$189 avg / night
(excludes fees and taxes)
4.38 (29)

View 4 more homes

Recent Siesta Key guest reviews

This cottage was perfect for two adults for a few nights (for our 17th anniversary). It sleeps an additional two on the pullout couch, but you would want to put kids there. This was easily walkable to the beach and to the shops and restaurants in Siesta Key Village. Very little traffic in this area as it is tucked away a bit. It was also very quiet area, but did hear a group of males walking/yelling in the street below two nights in a row. 30 minute drive from Sarasota airport and 30 minutes to Lido Key for kayaking. We would stay here again and would recommend to friends.
Cassie D. | Jun 2026
Great location and proximity to the beach. The room was clean and I have very high standards for cleanliness. There was some sand in the pool from people not rinsing before getting in. And you can occasionally hear neighbors next and above you. But didn’t bug us any. Will def stay here again our next travel to siesta
Miranda G. | Jun 2026
The cottage is small and cute. It is only big enough for a couple at most. Good for a few days but it maybe too small for a week or longer. Beautiful decor though! Loved it for our short stay!
Brent B. | May 2026
Siesta Key vacation rental FAQ

Yes. 71 of our Siesta Key vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Siesta Key vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Siesta Key team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Siesta Key, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Get into the spirit of this fun town with a visit to the Sunday evening drum circles. These events take place right on the sandy beach, where locals and tourists alike gather for a night of dancing, music, and not to mention beautiful ocean sunsets. Or you can head to the cute shops and eateries at Siesta Key Village. Roam the artfully landscaped streets or hop aboard the trolley as you explore the clothing boutiques, beauty supply stores, spas, eateries, and more.

A trip to nearby Marie Selby Botanical Gardens’ Historic Spanish Point is a must. You’ll find this 30-acre museum just minutes from our Siesta Key vacation rentals, on Little Sarasota Bay. Whether you’re enjoying the grounds and exhibits via guided tour or meandering solo, it's sure to delight history buffs, gardeners, and architecture fans alike.

And, of course, there are the pristine beaches that make this little corner of Florida so special. Our Siesta Key condos are near multiple beaches where you can splash, stand-up paddleboard, explore, or just lounge in the warm sun. If you’re looking to spend a day offshore, you can launch your boat or kayak from the ramps at Turtle Beach (many local companies are ready to help outfit you for your perfect day on the water.) Siesta Beach is beloved for its shallow waters, while Crescent Beach boasts incredible snorkeling amid coral reefs and tidal pools.

There’s so much to see and do and explore on Florida’s Gulf Coast. Experience the best of it with our Siesta Key beach rentals. Choose your favorite from our collection and start planning your next beach vacation today.