Siesta Key Beach House Rentals

Compare 9 vacation rentals.
Home > 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.

Top Siesta Key property types

housing_type_condo.jpg

Condo rentals

View 4 Condo rentals
housing_type_studio.jpg

Studios

View 2 Studios
housing_type_apartment.jpg

Apartments

View 1 Apartments

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

$224 avg / night
(excludes fees and taxes)
4.25 (96)
Parrot Beach Cottages Suite #1
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

$199 avg / night
(excludes fees and taxes)
4.53 (89)
Parrot Beach Cottages Suite #4
1 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #4 - Siesta Key, FL

$234 avg / night
(excludes fees and taxes)
4.36 (83)
Parrot Beach Cottages Suite #2
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #2 - Siesta Key, FL

$193 avg / night
(excludes fees and taxes)
4.61 (103)
Midnight Cove II 823
2 Bedroom | 1.5 Bath | Sleeps 6

Midnight Cove II 823 - Siesta Key, FL

$188 avg / night
(excludes fees and taxes)
4.39 (28)

View 4 more homes

Recent Siesta Key guest reviews

If you’re looking for a place to spend most of your time at the beach and The Village this is the rental for you! It is designed for 2 adults but the pull out couch is connected in one singular piece, making it extremely convenient to open and close. It’s also much more comfortable for a 30 year old adult than we anticipated, previous reviews say they felt springs, we did not. Though it was a small space for 2 adults I could see a 3rd being just fine on the living room pull out. A 20 second walk from the front door to the edge of the sand was exactly what we wanted and got out of this location! (Note this area of the beach is considered a state park and you can not hang out on the beach at night.) Also only a 7 min (or less) walk to The Village for restaurants, bars, and a gas station. It is a 4 unit space with thin walls so be prepared to hear neighbors if that bothers you, I travel with ear plugs and it doesn’t bother me! You can see the ocean from the kitchen and bathroom windows. We loved this place and will be recommending to friends and family.
Carissa M. | Apr 2026
The house was perfect & Vacasa was very responsive.
Adrienne B. | Apr 2026
Everything was as lovely as the first time- place was immaculate, loads of towels, and kitchen well appointed. I forgot how close it was to beach, restaurants, breakfast and how easy to get on the free bus up to the shops and pubs. Fantastic! Pool a big plus too. We will be back - 15 out of 10.
Sue U. | Apr 2026
Siesta Key vacation rental FAQ

Yes. 75 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.