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

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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, (6,033 reviews)
"Great resort and location!"
United States
Christine
The price is £134
includes taxes & fees
2 Dec - 3 Dec
Tropical Beach Resorts

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (204 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
The price is £176
includes taxes & fees
3 Nov - 4 Nov
SeaSpray Resort

3. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (391 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is £153
includes taxes & fees
18 Nov - 19 Nov
Tiny House Siesta

4. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,479 reviews)
"This place was perfect!"
United States
Kat
The price is £113
includes taxes & fees
4 Nov - 5 Nov
Hibiscus Suites - Gateway to Siesta Key

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,332 reviews)
"We liked the clean room, friendly staff, close to the beach and outdoor amenities."
United States
Andriy
The price is £143
includes taxes & fees
3 Nov - 4 Nov
Captiva Beach Resort

6. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is £262
includes taxes & fees
5 Nov - 6 Nov
Beach Tree Cottage,Walk To Beach& Siesta

7. 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 £183
includes taxes & fees
3 Nov - 4 Nov
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

8. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
The price is £292
includes taxes & fees
3 Nov - 4 Nov
PinkMango Cottage Steps to Beach&Village

9. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is £304
includes taxes & fees
5 Nov - 6 Nov
Beach View 100ft To Beach and SPA

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, (55 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 £183
includes taxes & fees
3 Nov - 4 Nov
Siesta Key, Sea Horse Villa, Pool. Daily rentals

11. Tiny House Calypso with 1st floor sleeping

Tiny House Calypso with 1st floor sleeping
Sarasota
9.0 out of 10, Wonderful, (11 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
The price is £123
includes taxes & fees
9 Nov - 10 Nov
Tiny House Calypso with 1st floor sleeping

12. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is £221
includes taxes & fees
3 Nov - 4 Nov
Siesta Heron Suites & Villas

13. [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)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is £229
includes taxes & fees
8 Nov - 9 Nov
[lounge like locals] walk to siesta beach +bikes

14. 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, (15 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is £288
includes taxes & fees
4 Nov - 5 Nov
Island Villa | Cozy Beach Retreat | Walk to Village

15. 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, (79 reviews)
"Great stay"
United States
Allison H.
The price is £300
includes taxes & fees
5 Nov - 6 Nov
Siesta Key Village-Suite #3: A Block to the Beach!

16. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (45 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 £216
includes taxes & fees
9 Nov - 10 Nov
[Beach Elements] pool view withprivate beach access

17. Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
9.0 out of 10, Wonderful, (168 reviews)
"No oven, but it was an excellent place to stay!"
United States
Brittany K.
The price is £235
includes taxes & fees
16 Nov - 17 Nov
Studio Retreat Across the Street from Beautiful Siesta Key Beach

18. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is £316
includes taxes & fees
6 Nov - 7 Nov
BlueDolphin Cottage Walk To Siesta Beach

19. Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (33 reviews)
"Very clean & tidy! The house stayed cool & comfortable the whole night! My husband & I enjoyed this unique place & would definitely book again!"
United States
Jennifer S.
The price is £137
includes taxes & fees
3 Nov - 4 Nov
Tiny House Green Lifeguard Stand - sleeps 5

20. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is £350
includes taxes & fees
6 Nov - 7 Nov
Yellow Palm Cottage, Heart of Siesta Key
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 £134 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 St. Boniface Episcopal Church Labyrinth, 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. Another good choice for your trip to Siesta Key is Siesta Heron Suites & Villas.

How many holiday rentals are there in Siesta Key?

With 401 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. While here, Safe Harbor Siesta Key and Point of Rocks are other places worth a visit.

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.