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

Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Siesta Key vacation rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,973 reviews)
"Amazing resort,"
United States
kurt
The price is NT$4,091
NT$5,459 total
includes taxes & fees
Oct 19 - Oct 20
Tropical Beach Resorts
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (197 reviews)
"Best short vacation"
United States
Rommel
The price is NT$7,207
NT$8,144 total
includes taxes & fees
Nov 2 - Nov 3
SeaSpray Resort
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,468 reviews)
"This place was perfect!"
United States
Kat
The price is NT$4,376
NT$4,945 total
includes taxes & fees
Oct 15 - Oct 16
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,321 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is NT$5,502
NT$6,762 total
includes taxes & fees
Oct 18 - Oct 19
Captiva Beach Resort
A hotel with a balcony and palm trees.

5. The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
8.8 out of 10, Excellent, (398 reviews)
"Nice kitchen and clean place"
United States
Ricardo
The price is NT$3,751
NT$7,510 total
includes taxes & fees
Oct 15 - Oct 16
The Ringling Beach House
A compact living space with a kitchen, a dining area, and a sofa with cushions.

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 NT$1,760
NT$6,319 total
includes taxes & fees
Oct 17 - Oct 18
Tiny House Siesta
A covered outdoor area with a wooden table and chairs, a white door, and a yellow wall.

7. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is NT$4,747
NT$11,796 total
includes taxes & fees
Oct 15 - Oct 16
Yellow Palm Cottage, Heart of Siesta Key
A room with a dining table, chairs, a television, a sofa, and a lamp.

8. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is NT$5,442
NT$12,581 total
includes taxes & fees
Oct 19 - Oct 20
BlueDolphin Cottage Walk To Siesta Beach
A living room with a sofa, armchair, coffee table, and a potted plant.

9. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is NT$3,842
NT$12,543 total
includes taxes & fees
Oct 15 - Oct 16
Siesta Vibe Pool Walk To Crescent Beach
A patio area with a grill, potted plants, and a building with a teal door.

10. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is NT$4,631
NT$11,665 total
includes taxes & fees
Oct 18 - Oct 19
Beach Tree Cottage,Walk To Beach& Siesta
A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

11. 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 NT$3,271
NT$10,165 total
includes taxes & fees
Oct 15 - Oct 16
Siesta Heron Suites & Villas
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

12. Siesta Sands Beach Resort 4th Floor With Elevator

Siesta Sands Beach Resort 4th Floor With Elevator
3.5 star property
South Village
The price is NT$12,146
NT$27,542 total
includes taxes & fees
Nov 10 - Nov 11
Siesta Sands Beach Resort 4th Floor With Elevator
A beach with a wooden picnic table, palm trees, and a clear blue sky.

13. Beach Road - Capri

Beach Road - Capri
2.5 star property
Siesta Key
The price is NT$17,206
NT$22,361 total
includes taxes & fees
Oct 25 - Oct 26
Beach Road - Capri
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

14. Siesta Sands Beach Resort Gulf View

Siesta Sands Beach Resort Gulf View
2.5 star property
South Village
10.0 out of 10, Exceptional, (1 review)
"Loved to property! Clean and accommodating. Had a beautiful ocean view and could walk right out to the beach. Pool area was clean."
United States
Jessica
The price is NT$10,599
NT$24,382 total
includes taxes & fees
Nov 8 - Nov 9
Siesta Sands Beach Resort Gulf View
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

15. House of The Sun Siesta Key Crescent Beach

House of The Sun Siesta Key Crescent Beach
4.0 star property
South Village
8.0 out of 10, Very good, (2 reviews)
"The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . "
United States
Margaret Theresa
The price is NT$8,968
NT$24,209 total
includes taxes & fees
Oct 22 - Oct 23
House of The Sun Siesta Key Crescent Beach
A beach with tall grasses and a sunset sky.

16. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is NT$12,478
NT$22,586 total
includes taxes & fees
Oct 26 - Oct 27
Siesta Heron 6 / Sunset
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a ceiling fan.

17. 4 Mi to Siesta Key Beach: Condo w/ Pool Access

4 Mi to Siesta Key Beach: Condo w/ Pool Access
4.0 star property
Sarasota
10.0 out of 10, Exceptional, (1 review)
"The property was clean and decorated so cute. It was easy to find and simple check in. We had a problem with the ac and they fixed it right away. The host was great and communicated very well. Highly recommended!"
United States
Lori
The price is NT$2,637
NT$9,204 total
includes taxes & fees
Oct 15 - Oct 16
4 Mi to Siesta Key Beach: Condo w/ Pool Access
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

18. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (692 reviews)
"Enjoyed our stay"
United States
Robin
The price is NT$5,926
NT$6,697 total
includes taxes & fees
Nov 4 - Nov 5
A Beach Retreat
A modern living room with a sofa, coffee table, and artwork on the walls.

19. Pineapple Paradise 1 13 min to Beach Fire Pit

Pineapple Paradise 1 13 min to Beach Fire Pit
2.0 star property
Central Sarasota
The price is NT$3,592
NT$11,385 total
includes taxes & fees
Oct 18 - Oct 19
Pineapple Paradise 1 13 min to Beach Fire Pit
A multi-story building with a light blue facade, featuring a restaurant named 'Bridge Street Bistro' and a sign for 'Island Time.'

20. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (839 reviews)
"I loved this hotel"
United States
Raisare
The price is NT$9,295
NT$11,411 total
includes taxes & fees
Oct 15 - Oct 16
Bridgewalk Resort
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

The Capri at Siesta

The Capri at Siesta

10/10 Excellent
"Wonderful trip! Would absolutely stay again! Room was very clean and way more spacious than the pictures even show!"
Elizabeth 3-night trip
Posted 1 hour ago
The Capri at Siesta

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 vacation rental in Siesta Key?

Yes, we give you a choice of vacation rentals in Siesta Key close to St. Boniface Episcopal Church Labyrinth, or you can go with a more secluded option if you'd like a relaxing place to 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 vacation rentals in Siesta Key?

Siesta Key Island Rentals: Visitors give good reviews to this Siesta Key vacation home rental, which comes with free WiFi so you can feel at home during your trip. This vacation 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 vacation rentals are there in Siesta Key?

With 401 Expedia vacation rentals, you're sure 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 vacation rentals like in Siesta Key?

Vacation rentals are private accommodations you can stay in for several days or longer in Siesta Key. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.