Search Holiday Rentals in Siesta Key

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Siesta Key holiday rentals

Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5164)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is 3.332.795 ₫
4.360.777 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Tropical Beach Resorts
Beach nearby, white sand, beach umbrellas, beach towels
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is 7.488.986 ₫
9.919.615 ₫ total
includes taxes & fees
23 Dec - 24 Dec
The Inn On Siesta Key
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services
Siesta Heron Suites & Villas

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is 4.895.379 ₫
10.824.778 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas
Front of property – evening/night
Captiva Beach Resort

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1176)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort
447 Avenida De Mayo, Siesta Key, FL W/Pool | Private kitchen
Siesta Key Island Rentals

Holiday Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (54)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
Siesta Key Island Rentals
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2216)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services
Tiny House Siesta

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is 2.999.910 ₫
6.587.171 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Tiny House Siesta
Property grounds
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (301)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is 10.420.740 ₫
13.113.554 ₫ total
includes taxes & fees
21 Jan - 22 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (79)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
The price is 8.131.335 ₫
9.188.409 ₫ total
includes taxes & fees
23 Dec - 24 Dec
SeaSpray 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.
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Top Siesta Key Hotel Reviews

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"Room was clean. The heated pool and Back patio was spacious with great amenities for sunbathing. 75” Samsung Smart TV was huge and was able to stream from my I-Phone to TV via Apple play."
Michael 3-night trip
Posted 3 days ago
Tropical Breeze Resort

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.

How many holiday rentals are there in Siesta Key?

With 390 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, Siesta Key Marina and Point of Rocks 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.