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

Siesta Key Holiday Rentals

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Our top choices for Siesta Key holiday rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,780 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is AU$237
includes taxes & fees
26 Aug - 27 Aug
Tropical Beach Resorts

2. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (384 reviews)
"Great place"
United States
Mario
The price is AU$323
includes taxes & fees
12 Sept - 13 Sept
Tiny House Siesta

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,300 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is AU$261
includes taxes & fees
9 Sept - 10 Sept
Captiva Beach Resort

4. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (173 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is AU$301
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort

5. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,417 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 AU$201
includes taxes & fees
20 Sept - 21 Sept
Hibiscus Suites - Gateway to Siesta Key

6. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is AU$499
includes taxes & fees
23 Aug - 24 Aug
Siesta Key Island Rentals

7. The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
8.8 out of 10, Excellent, (384 reviews)
"was amazing"
United States
Thomas
The Ringling Beach House

8. [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 AU$390
includes taxes & fees
24 Aug - 25 Aug
[Beach Elements] pool view withprivate beach access

9. 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 AU$440
includes taxes & fees
24 Aug - 25 Aug
Siesta Heron Suites & Villas

10. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is AU$447
includes taxes & fees
23 Aug - 24 Aug
[lounge like locals] walk to siesta beach +bikes

11. 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 AU$515
includes taxes & fees
23 Aug - 24 Aug
Siesta Key Village-Suite #3: A Block to the Beach!

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 AU$420
includes taxes & fees
30 Aug - 31 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

13. 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 AU$418
includes taxes & fees
22 Sept - 23 Sept
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

14. Tiny Coral Oasis- beachy tiny house for your getaway

Tiny Coral Oasis- beachy tiny house for your getaway
Sarasota
9.0 out of 10, Wonderful, (20 reviews)
"Cute tiny house Clean and comfortable Had a great time"
United States
DeAnna T.
The price is AU$302
includes taxes & fees
25 Aug - 26 Aug
Tiny Coral Oasis- beachy tiny house for your getaway

15. Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!
Siesta Key Village
9.0 out of 10, Wonderful, (43 reviews)
"Great stay! "
United States
Mason M.
The price is AU$515
includes taxes & fees
23 Aug - 24 Aug
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

16. 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 AU$428
includes taxes & fees
23 Aug - 24 Aug
Siesta Key, Sea Horse Villa, Pool. Daily rentals

17. 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.
The price is AU$401
includes taxes & fees
3 Sept - 4 Sept
Canalfront Siesta key entire King suite

18. 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 AU$474
includes taxes & fees
23 Aug - 24 Aug
Dolphin Villa - Pool - Steps to Siesta Key Village

19. 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 AU$518
includes taxes & fees
16 Sept - 17 Sept
Siesta Key Condo: Beach, Pool & Village Fun!

20. Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (169 reviews)
"The rental had everything promised. The bed and couch were very comfortable. Everything was clean. Beach access was great. The chairs, cooler, and canopy were were just what was needed to maximize our enjoyment on a great beach."
United States
Karen G.
The price is AU$376
includes taxes & fees
26 Aug - 27 Aug
Beachside Studio Located Across from Main Beach and Half Mile to Village
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

Everything you need to know about Siesta Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Siesta Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Siesta Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Siesta Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Siesta Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Siesta Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Siesta Key holiday rentals we have selected for you start as low as AU$237 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Siesta Key rentals

At Expedia, we put the best Siesta Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Siesta Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Siesta Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Siesta Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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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 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.