A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

Siesta Key Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Siesta Key holiday rentals

Property grounds

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,771 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is HK$1,041
HK$1,380 total
includes taxes & fees
20 Aug - 21 Aug
Tropical Beach Resorts
In-room safe, iron/ironing board, free WiFi

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (170 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is HK$1,617
HK$1,827 total
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,411 reviews)
"We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
United States
Justine
The price is HK$908
HK$1,026 total
includes taxes & fees
27 Aug - 28 Aug
Hibiscus Suites - Gateway to Siesta Key
Front of property – evening/night

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,299 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is HK$1,145
HK$1,427 total
includes taxes & fees
23 Aug - 24 Aug
Captiva Beach Resort
Private kitchen

5. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (78 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is HK$871
HK$2,630 total
includes taxes & fees
25 Aug - 26 Aug
Siesta Key Island Rentals
Beach nearby, white sand, beach umbrellas, beach towels

6. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (204 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The Inn On Siesta Key
Living area

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (383 reviews)
"Great place"
United States
Mario
The price is HK$613
HK$1,755 total
includes taxes & fees
22 Aug - 23 Aug
Tiny House Siesta
Front of property

8. The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (381 reviews)
"It was a perfect place for our family! Room for everyone and the private pool area was very nice and relaxing! We had zero issues and everything is close by. We will stay every year!"
United States
Rachel
The Ringling Beach House
Beach nearby

9. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (54 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
The price is HK$754
HK$2,001 total
includes taxes & fees
19 Aug - 20 Aug
Siesta Key, Sea Horse Villa, Pool. Daily rentals
2 bedrooms, iron/ironing board, WiFi, bed sheets

10. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is HK$727
HK$2,346 total
includes taxes & fees
24 Aug - 25 Aug
[escape to paradise] siesta key beach getaway
Beach

11. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.4 out of 10, Exceptional, (39 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is HK$881
HK$2,362 total
includes taxes & fees
24 Aug - 25 Aug
[Beach Elements] pool view withprivate beach access
Beach nearby

12. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Great stay."
United States
James J.
The price is HK$839
HK$1,761 total
includes taxes & fees
13 Sept - 14 Sept
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
Beach

13. [Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.6 out of 10, Exceptional, (14 reviews)
"Great location and accommodation. "
United States
ESTELEN
The price is HK$954
HK$2,499 total
includes taxes & fees
24 Aug - 25 Aug
[Sunny in Siesta] king bed + walk to beach
Sun-loungers, beach towels

14. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is HK$777
HK$2,386 total
includes taxes & fees
24 Aug - 25 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Living area

15. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is HK$761
HK$2,438 total
includes taxes & fees
24 Aug - 25 Aug
Siesta Heron Suites & Villas
Outdoor dining

16. Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
The price is HK$902
HK$2,950 total
includes taxes & fees
24 Aug - 25 Aug
Dolphin Villa - Pool - Steps to Siesta Key Village
Beach nearby

17. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is HK$1,093
HK$2,432 total
includes taxes & fees
24 Aug - 25 Aug
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Beach nearby, sun-loungers, beach towels

18. Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (77 reviews)
"Great stay"
United States
Allison H.
The price is HK$1,113
HK$2,972 total
includes taxes & fees
19 Aug - 20 Aug
Siesta Key Village-Suite #3: A Block to the Beach!
Exterior detail

19. Siesta Key Studio close to beaches, city, and airport.

Siesta Key Studio close to beaches, city, and airport.
Siesta Key
8.4 out of 10, Very good, (16 reviews)
"Great place to stay, very close to the beach and restaurants "
United States
Yeimy R.
The price is HK$777
HK$1,557 total
includes taxes & fees
24 Aug - 25 Aug
Siesta Key Studio close to beaches, city, and airport.
Beach nearby

20. Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (75 reviews)
"great location- clean "
United States
Jon W.
The price is HK$1,199
HK$3,090 total
includes taxes & fees
19 Aug - 20 Aug
Siesta Cooler: Only Minutes Walk to Siesta 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.
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Top Siesta Key Hotel Reviews

Captiva Beach Resort

Captiva Beach Resort

8/10 Good
"The proximity to the beach and the ambient of the place"
natalia 3-night trip
Posted 6 hours ago
Captiva Beach Resort

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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Look no further and take a look at our great range of rental properties in Siesta Key!

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 Luxury Siesta Key townhome close to village,beaches, city and airport and Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!.

How many holiday rentals are there in Siesta Key?

With 420 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 Shell 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 Venice Beach 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.