Siesta Key Beach House Rentals

Compare 616 vacation rentals with savings up to 30% off this summer.
USA > Florida > Siesta Key

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.

Explore Siesta Key condo rentals, studios, townhouses, and more


Condo rentals

View 10 Condo rentals


View 3 Studios


View 2 Townhouses

Siesta Key vacation rentals for every getaway

Dog-friendly Hot tub Internet
Parrot Beach Cottages Suite #1
0 Bed | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

$251 avg / night
Parrot Beach Cottages Suite #4
1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #4 - Siesta Key, FL

$287 avg / night
Parrot Beach Cottages Suite #2
0 Bed | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #2 - Siesta Key, FL

$267 avg / night
Parrot Beach Cottages Suite #3
1 Bed | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #3 - Siesta Key, FL

$298 avg / night
Midnight Cove II 823
2 Bed | 1.5 Bath | Sleeps 6

Midnight Cove II 823 - Siesta Key, FL

$204 avg / night

View 12 more homes

Recent Siesta Key vacation rental reviews

Excellent location with ample security and security measures. Private beach with real lounge chairs provided - umbrellas for rental. Two pools - one built out on the bay. We had everything we wanted and needed!
Suzan S. | Jun 2023
My husband and I came to Siesta Key for a few days of vacation while we were down here for a wedding, and it could NOT have been a more perfect location! You can see the beach from your windows; it’s just steps away from the beach in one direction, and only a few blocks from the heart of the village in the other direction. Aside from the location, it was a nice little cottage for us 2 and had everything we needed, including beach chairs/umbrellas/wagons/towels. Thanks so much for allowing us to stay! We will book this anytime we come back to Siesta!
McKayla W. | May 2023
Great location, close to everything. No frills, but you have everything you need.
Joshua W. | May 2023
Siesta Key Frequently Asked Questions

Yes, 46 of our Siesta Key homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 125 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 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 worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Siesta Key, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional 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.