Siesta Key Holiday Rentals

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Our top choices for Siesta Key holiday rentals

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5182)
"Great location, value, clean, friendly staff. Will definitely stay there again. "
United States
JoAnna
The price is HK$1,116
HK$1,437 total
includes taxes & fees
4 Jan - 5 Jan 2026
Tropical Beach Resorts
3.5 star property
9.6 out of 10, Exceptional, (302)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is HK$3,102
HK$3,901 total
includes taxes & fees
29 Jan - 30 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
2.5 star property
8.6 out of 10, Excellent, (2221)
"Very nice place !"
United States
Ivette
Hibiscus Suites - Gateway to Siesta Key

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 HK$832
HK$1,884 total
includes taxes & fees
5 Jan - 6 Jan 2026
Tiny House Siesta

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 HK$3,177
HK$4,021 total
includes taxes & fees
30 Dec - 31 Dec
The Inn On Siesta Key

Holiday Home in Sarasota

The Mermaid at Tiny House Siesta
2.0 star property
10.0 out of 10, Exceptional, (2)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
The price is HK$855
HK$1,560 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Mermaid at Tiny House Siesta

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 HK$1,417
HK$3,165 total
includes taxes & fees
5 Jan - 6 Jan 2026
Siesta Heron Suites & Villas
9.6 out of 10, Exceptional, (44)
"The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again."
United States
Mel S.
The price is HK$769
HK$1,910 total
includes taxes & fees
4 Jan - 5 Jan 2026
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3
9.2 out of 10, Wonderful, (132)
"Location was great! Can walk to shopping and restaraunts. Host was great with communication. Great stay!"
United States
Kristi R.
Free Activities Daily, Private Beach Front Modern Property | Tennis Court on the Beach | Heated Pool

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (82)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is HK$2,108
HK$2,383 total
includes taxes & fees
4 Jan - 5 Jan 2026
SeaSpray Resort
9.8 out of 10, Exceptional, (26)
"The property was very clean and conveniently located ."
United States
David
The price is HK$1,369
HK$3,162 total
includes taxes & fees
28 Jan - 29 Jan 2026
[lounge like locals] walk to siesta beach +bikes
9.6 out of 10, Exceptional, (21)
"Jayme was super helpful when needed with our stay "
United States
Gabby L.
The price is HK$1,105
HK$2,529 total
includes taxes & fees
4 Jan - 5 Jan 2026
[Beach Elements] pool view withprivate beach access
9.0 out of 10, Wonderful, (9)
"Third time here and best visit will book again in future "
United States
Desirae
The price is HK$886
HK$1,596 total
includes taxes & fees
4 Jan - 5 Jan 2026
Tiny House Calypso with 1st floor sleeping
9.6 out of 10, Exceptional, (9)
"Place is in a great location close to the beach and restaurants "
United States
Ellen C.
The price is HK$1,158
HK$2,588 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks
9.6 out of 10, Exceptional, (81)
"Wonderful experience! It was perfect for a girls’ weekend which included me, my mother & my 12 yr old daughters. There was enough restaurants in walking distance, the beach was in walking distance and we appreciated the trolley and frog hopper to get to Turtle Beach for kayaking. "
United States
Michelle A.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
8.0 out of 10, Very good, (4)
"We enjoyed our stay in this quiet neighborhood. With just a 4 to 5 minute drive to the main strip it was a perfect getaway. Walls are thin but with a sound machine or white noise from your phone you will hear nothing."
United States
A Positive Feel
Siesta Shores: Siesta Key Suite - Ground flr- King
9.4 out of 10, Exceptional, (3)
"Cute house. Clean and nicely decorated. Beautiful pool Location is so close to the ocean. (1 mile) Great experience very nice owner.. easy communication. Will definitely be back!"
United States
Misti H.
Beachside Bliss- 1 mi to the beach w/ heated pool
8.8 out of 10, Excellent, (6)
"Quiet and relaxed place and great hosts. "
United States
Michael
The price is HK$925
HK$2,117 total
includes taxes & fees
4 Jan - 5 Jan 2026
Relax & Recharge- Heated Pool and 1.7 mi to beach!
9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
The price is HK$1,158
HK$2,588 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.4 out of 10, Exceptional, (47)
"This is our second year staying at the villas i had a great time unit was cleaned ,pool was great,wahing machine worked good cant wait till next year"
United States
Edelmiro R.
The price is HK$769
HK$1,910 total
includes taxes & fees
4 Jan - 5 Jan 2026
Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS
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

Find out more about Siesta Key

Search for holiday rentals in Siesta Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Siesta Key using one of the methods below:

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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 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. Some other top choices in Siesta Key are 3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport. and Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village.

How many holiday rentals are there in Siesta Key?

With 394 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. You’ll find favourite places to visit such as Lido Beach and St. Armands Circle in the wider area.

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.