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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, (5,725 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is £140
includes taxes & fees
23 Aug - 24 Aug
Tropical Beach Resorts

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (161 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is £170
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,294 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is £144
includes taxes & fees
10 Aug - 11 Aug
Captiva Beach Resort

4. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (382 reviews)
"Great place"
United States
Mario
The price is £168
includes taxes & fees
6 Aug - 7 Aug
Tiny House Siesta

5. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,393 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 £102
includes taxes & fees
10 Aug - 11 Aug
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, (75 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is £476
includes taxes & fees
7 Aug - 8 Aug
Siesta Key Island Rentals

7. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (202 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

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

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (36 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is £235
includes taxes & fees
10 Aug - 11 Aug
[lounge like locals] walk to siesta beach +bikes

9. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (37 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 £256
includes taxes & fees
12 Aug - 13 Aug
[Beach Elements] pool view withprivate beach access

10. 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 £256
includes taxes & fees
9 Aug - 10 Aug
Siesta Heron Suites & Villas

11. [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 £201
includes taxes & fees
6 Aug - 7 Aug
[Sunny in Siesta] king bed + walk to 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, (89 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 £228
includes taxes & fees
10 Aug - 11 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

13. 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 £295
includes taxes & fees
18 Aug - 19 Aug
Dolphin Villa - Pool - Steps to Siesta Key Village

14. 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 location was incredible, right across from the best beach. It was perfect size for two people and really really priced affordable. The refrigerator was roomy and the bathroom had a nice shower. It was clean. "
United States
Mojo R.
The price is £211
includes taxes & fees
26 Aug - 27 Aug
Beachside Studio Located Across from Main Beach and Half Mile to Village

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.
The price is £217
includes taxes & fees
12 Aug - 13 Aug
Canalfront Siesta key entire King suite

16. 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, (104 reviews)
"Awesome location and the staff was great!"
United States
John F.
The price is £246
includes taxes & fees
17 Aug - 18 Aug
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

17. 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 £331
includes taxes & fees
20 Aug - 21 Aug
Siesta Key Condo: Beach, Pool & Village Fun!

18. 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)
"Great location. Very clean, quiet. "
United States
Earl M.
The price is £224
includes taxes & fees
16 Aug - 17 Aug
Siesta Key, Sea Horse Villa, Pool. Daily rentals

19. Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village
Siesta Key Village
8.4 out of 10, Very good, (13 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is £350
includes taxes & fees
19 Aug - 20 Aug
Island Villa | Cozy Beach Retreat | Walk to Village

20. 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 £296
includes taxes & fees
12 Aug - 13 Aug
Siesta Key Village-Suite #1: A block to the 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

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, apart-hotels, 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 favorite 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 depends 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 £140 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

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 free 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 bed 2 Bath, heated pool, walk to beach and village and 3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport.

How many holiday rentals are there in Siesta Key?

With 416 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 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.