Siesta Key Beach House Rentals

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USA > Florida > Siesta Key

Make Siesta Key your next getaway—choose from 17 great vacation rentals

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 #3
1 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #3 - Siesta Key, FL

$252 avg / night
Parrot Beach Cottages Suite #1
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

$211 avg / night
Bay Oaks 75
1 Bedroom | 1 Bath | Sleeps 4

Bay Oaks 75 - Siesta Key, FL

$190 avg / night
Parrot Beach Cottages Suite #2
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #2 - Siesta Key, FL

$227 avg / night
Parrot Beach Cottages Suite #4
1 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #4 - Siesta Key, FL

$245 avg / night

View 12 more homes

Recent Siesta Key vacation rental reviews

The cottage was so close to the beach! well kept great location had beach items And bbq private pool! Great value!! Personable.
Michelle P. | Apr 2023
I loved the bright decor and functionality of the condo. The shower was spacious for the condo’s size. We did not try the futon but the leather couch was a smart choice for its proximity to the beach. The bed was comfortable, as was the couch. The huge draw is feeling as if you had an almost Beach front property. The walking distance from condo to shore was probably closer than regular parking at the public siesta key beach. The beach was nowhere near as crowded as the public one, but there are no lifeguards on duty. We loved being able to walk into town for a bite to eat or a quick shopping trip. The stairs are extremely steep and narrow leading into the condo, so this may not be suited to older people. The pool was extremely small, but very nice. It was exceptionally clean when we arrived, and we were pleased with our stay.
Joanna B. | Apr 2023
The cottage was super clean and smelled fresh. The location cannot be beat! The space is small, but plenty for 2 people. Would definitely book again!
Tammy S. | Mar 2023
Siesta Key vacation rental FAQ

Yes, 23 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. 72 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.