Siesta Key Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Siesta Key

The Residences at Siesta Key Beach by Hyatt Vacation Club
Sports facility

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (211)
"Facility was great … would certainly stay here again in the future "
The price is S$629
includes taxes & fees
3 Dec - 4 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club
Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
Tropical Beach Resorts
The Ringling Beach House
Aerial view

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (285)
"This was a lovely place. Just loved it. Will be back. "
The Ringling Beach House
Captiva Beach Resort
Private kitchen

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1057)
"Nice and quiet place, close to the beach and dining places."
The price is S$383
includes taxes & fees
27 Dec - 28 Dec
Captiva Beach Resort
The Inn On Siesta Key
Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (164)
"Such a beautiful week maintained property with every thing you could possibly need or want to enjoy the area. ♥️"
The Inn On Siesta Key
Siesta Key Island Rentals
Room amenity

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals
Siesta Palms By the Beach
Beach nearby, white sand, sun-loungers, beach umbrellas

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (108)
"Everything was as expected no surprise's. Not right on the beach but a few blocks walk. "
Siesta Palms By the Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Siesta Key
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Siesta Key you may be interested in

Siesta Key Beach Resort and Suites
Outdoor pool, open 9 AM to 9 PM, pool loungers

Siesta Key Beach Resort and Suites

2.5 star property
8.6 out of 10, Excellent, (1097)
"Our room was just newly renovated. It was beautiful And very clean. All the staff were very professional friendly and helpful"
The price is S$276
includes taxes & fees
1 Dec - 2 Dec
Siesta Key Beach Resort and Suites
Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
Tropical Beach Resorts
Tropical Breeze Resort
Lobby sitting area

Tropical Breeze Resort

3.0 star property
9.0 out of 10, Wonderful, (1090)
"A very quaint quiet place to stay. We loved our stay and hope they recover quickly from the Hurricanes they experienced. We loved the main pool and had it to ourselves every evening. One important and unusual fact, the mattress was as comfortable as ours at home. We are looking forward to our next visit."
The price is S$599
includes taxes & fees
26 Dec - 27 Dec
Tropical Breeze Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

Can I find a holiday rental in Siesta Key?

Yes, there are holiday rentals in Siesta Key close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Siesta Key like the popular beaches and live music. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that Siesta Key has to offer?

Siesta Key Island Rentals: This highly rated holiday home rental in Siesta Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Siesta Key?

With 760 Expedia holiday rentals, you're guaranteed to find just the right place for your Siesta Key stay.

What can I see and do in Siesta Key?

Siesta Key Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. While here, Point of Rocks and Turtle Beach are other places worth a visit.

What are holiday rentals like in Siesta Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Siesta Key. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.