Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 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, (6,054 reviews)
"Great resort and location!"
United States
Christine
The price is P9,107
P11,930 total
includes taxes & fees
Nov 10 - Nov 11
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,482 reviews)
"This place was perfect!"
United States
Kat
The price is P9,393
P10,614 total
includes taxes & fees
Nov 10 - Nov 11
Hibiscus Suites - Gateway to Siesta Key
A bedroom with a view of a swimming pool and outdoor seating.

3. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (208 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
The price is P14,129
P15,966 total
includes taxes & fees
Nov 11 - Nov 12
SeaSpray Resort
A compact living space with a sofa, a television, a ceiling fan, and a door.

4. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (392 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 P3,826
P12,826 total
includes taxes & fees
Nov 22 - Nov 23
Tiny House Siesta
An outdoor dining area with clear plastic chairs and tables, surrounded by greenery and a building in the background.

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 P9,707
P12,037 total
includes taxes & fees
Nov 10 - Nov 11
Captiva Beach Resort
A hot tub surrounded by a wooden fence, with lounge chairs and an umbrella in the background.

6. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is P11,096
P29,281 total
includes taxes & fees
Nov 10 - Nov 11
Yellow Palm Cottage, Heart of Siesta Key
A cozy living room with a stone fireplace, a flat-screen TV, a sofa, a coffee table, and a dining area with chairs.

7. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (213 reviews)
"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...
United States
Karen Jean
The price is P14,422
P20,216 total
includes taxes & fees
Nov 10 - Nov 11
The Inn On Siesta Key
An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

8. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is P7,036
P22,200 total
includes taxes & fees
Nov 10 - Nov 11
Beach Tree Cottage,Walk To Beach& Siesta
A patio with a sun lounger, a table with chairs, and an umbrella.

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 P9,987
P25,534 total
includes taxes & fees
Nov 11 - Nov 12
Beach View 100ft To Beach and SPA
A small, single-story building with a porch, surrounded by tropical vegetation.

10. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
BlueDolphin Cottage Walk To Siesta Beach
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 P5,908
P19,357 total
includes taxes & fees
Nov 10 - Nov 11
Siesta Heron Suites & Villas
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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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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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.