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, (5,948 reviews)
"Amazing resort,"
United States
kurt
The price is AU$256
includes taxes & fees
8 Oct - 9 Oct
Tropical Beach Resorts

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (189 reviews)
"Great place with a bunch of little touches that put it above and beyond"
United States
Rafe
The price is AU$341
includes taxes & fees
3 Nov - 4 Nov
SeaSpray Resort

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,459 reviews)
"This place was perfect!"
United States
Kat
The price is AU$218
includes taxes & fees
18 Oct - 19 Oct
Hibiscus Suites - Gateway to Siesta Key

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,317 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is AU$267
includes taxes & fees
15 Oct - 16 Oct
Captiva Beach Resort

5. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is AU$504
includes taxes & fees
8 Oct - 9 Oct
Beach View 100ft To Beach and SPA

6. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 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 AU$293
includes taxes & fees
1 Nov - 2 Nov
Tiny House Siesta

7. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is AU$559
includes taxes & fees
15 Oct - 16 Oct
Siesta Vibe Pool Walk To Crescent Beach

8. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (43 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$366
includes taxes & fees
8 Oct - 9 Oct
[Beach Elements] pool view withprivate beach access

9. 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 AU$259
includes taxes & fees
13 Oct - 14 Oct
Tiny House Calypso with 1st floor sleeping

10. Siesta Key APT On OceanW/FREE WIFI, BEACH AMENTITIES, ONSITE MANAGER, &LAUNDRY

Siesta Key APT On OceanW/FREE WIFI, BEACH AMENTITIES, ONSITE MANAGER, &LAUNDRY
Siesta Key
8.4 out of 10, Very good, (15 reviews)
"Great place to stay, very close to the beach and restaurants "
United States
Yeimy R.
The price is AU$293
includes taxes & fees
31 Oct - 1 Nov
Siesta Key APT On OceanW/FREE WIFI, BEACH AMENTITIES, ONSITE MANAGER, &LAUNDRY

11. 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)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is AU$518
includes taxes & fees
13 Oct - 14 Oct
Dolphin Villa - Pool - Steps to Siesta Key Village

12. [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 AU$462
includes taxes & fees
13 Oct - 14 Oct
[lounge like locals] walk to siesta beach +bikes

13. 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, (14 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is AU$577
includes taxes & fees
12 Oct - 13 Oct
Island Villa | Cozy Beach Retreat | Walk to Village

14. 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.
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

15. 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 AU$446
includes taxes & fees
8 Oct - 9 Oct
Siesta Heron Suites & Villas

16. Canalfront Siesta key entire King suite

Canalfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (13 reviews)
"Great location, spacious parking, clean."
United States
Norma C.
The price is AU$418
includes taxes & fees
24 Oct - 25 Oct
Canalfront Siesta key entire King suite

17. 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$421
includes taxes & fees
11 Oct - 12 Oct
Siesta Key, Sea Horse Villa, Pool. Daily rentals

18. Heart of Village: Dog-Friendly w/ Pool & Parking

Heart of Village: Dog-Friendly w/ Pool & Parking
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$494
includes taxes & fees
8 Oct - 9 Oct
Heart of Village: Dog-Friendly w/ Pool & Parking

19. Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village
Siesta Key Village
9.4 out of 10, Exceptional, (92 reviews)
"Fantastic stay for our family’s 4th of July getaway! The condo was perfect—an easy walk to both the beach and town, which made everything super convenient. The pool was clean and refreshing, and we loved having the outdoor picnic tables for meals and games. Beds were very comfortable, and everyone slept great. Would happily stay here again!"
United States
Kim S.
The price is AU$967
includes taxes & fees
10 Oct - 11 Oct
Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village

20. 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$363
includes taxes & fees
11 Oct - 12 Oct
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to 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, 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$256 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 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.