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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 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, (5,756 reviews)
"Clean quiet and close to the beach. Best place for a quiet weekend getaway in a cute quiet beach town"
United States
Lindy
The price is HK$1,061
HK$1,403 total
includes taxes & fees
18 Aug - 19 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, (166 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, (2,402 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$987
HK$1,115 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, (1,297 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is HK$1,278
HK$1,577 total
includes taxes & fees
27 Aug - 28 Aug
Captiva Beach Resort
Beach nearby, white sand, beach umbrellas, beach towels

5. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (203 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

6. 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$671
HK$1,823 total
includes taxes & fees
23 Aug - 24 Aug
Tiny House Siesta
Beach

7. [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$1,043
HK$2,561 total
includes taxes & fees
14 Aug - 15 Aug
[Beach Elements] pool view withprivate beach access
Living area

8. 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$963
HK$2,667 total
includes taxes & fees
17 Aug - 18 Aug
Siesta Heron Suites & Villas
Beach nearby, sun-loungers, beach towels

9. Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Brad S.
The price is HK$1,113
HK$2,973 total
includes taxes & fees
18 Aug - 19 Aug
Siesta Key Village-Suite #1: A block to the Beach!
Beach nearby

10. 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$2,002 total
includes taxes & fees
16 Aug - 17 Aug
Siesta Key, Sea Horse Villa, Pool. Daily rentals
Beach nearby

11. 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.
Siesta Cooler: Only Minutes Walk to Siesta Beach!
Sun-loungers, beach towels

12. 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
17 Aug - 18 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Beach nearby

13. 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$1,263
HK$2,600 total
includes taxes & fees
11 Sept - 12 Sept
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Beach nearby, beach umbrellas

14. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
The price is HK$1,193
HK$2,627 total
includes taxes & fees
16 Aug - 17 Aug
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
Sun-loungers, beach towels

15. Canalfront Siesta key entire King suite

Canalfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (12 reviews)
"Great location, spacious parking, clean."
United States
Norma C.
Canalfront Siesta key entire King suite
Beach nearby

16. Siesta Key Condo: Beach, Pool & Village Fun!

Siesta Key Condo: Beach, Pool & Village Fun!
Siesta Key Village
9.2 out of 10, Wonderful, (16 reviews)
"Love the place. Perfect location. Close to village, close to beach. Highly suggest and will definitely be back in the future. Host was very friendly and accommodating."
United States
Jeffrey B.
The price is HK$847
HK$2,698 total
includes taxes & fees
16 Aug - 17 Aug
Siesta Key Condo: Beach, Pool & Village Fun!
2 bedrooms, iron/ironing board, WiFi, bed sheets

17. [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$1,212
HK$3,076 total
includes taxes & fees
11 Sept - 12 Sept
[escape to paradise] siesta key beach getaway
Coffee/tea maker, fridge, microwave, oven

18. Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Siesta Key
9.2 out of 10, Wonderful, (48 reviews)
"Perfect spot for beach vacation "
United States
Megan C.
Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Beach nearby

19. 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$898
HK$1,867 total
includes taxes & fees
17 Aug - 18 Aug
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
Beach nearby, beach umbrellas

20. Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA

Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
South Village
9.0 out of 10, Wonderful, (76 reviews)
"Great stay. As advertised and very clean!"
United States
Seth S.
The price is HK$1,365
HK$2,851 total
includes taxes & fees
25 Aug - 26 Aug
Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
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 Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Todo me encantó lo que si eres alérgico a la picadura de jejenes tienes que llevar repelente"
Maidel 4-night trip
Posted 3 hours ago
Tropical Beach Resorts

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 421 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.