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Top Holiday Rentals in Siesta Key

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4830)
"Very nice stay"
The price is £136
includes taxes & fees
1 Sept - 2 Sept
Tropical Beach Resorts

SeaSpray Resort

4.0 star property
9.0 out of 10, Wonderful, (7)
"Nice place to stay in SK! "
The price is £190
includes taxes & fees
2 Sept - 3 Sept
SeaSpray Resort

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

10.0 out of 10, Exceptional, (22)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (317)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1120)
"We love the property, beautiful, clean and we love that you can walked to the beach, that is a plus. "
Captiva Beach Resort

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (274)
"Fun place to stay for family vacation "
The Residences at Siesta Key Beach by Hyatt Vacation Club

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (42)
"Quiet neighborhood, clean and well maintained property, responsive management."
Siesta Key Island Rentals

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The Inn On Siesta Key

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (124)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach

Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

9.4 out of 10, Exceptional, (34)
"Very nice location, clean, nice amenities"
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (17)
"We had a great stay at this property! We had five adults and one infant with plenty of room to be comfortable. We enjoyed the short walk to the beach and that beach chairs were provided by the HOA (umbrellas are not but there was one at the property). The owners were wonderful, fast responses to any messages and made sure we had everything we needed to have a great time! Definitely recommend this property if you’re in Siesta Key and looking to be very close to the beach!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

10.0 out of 10, Exceptional, (40)
"We were very pleased to stay at such a beautiful property. Everything was very clean, well maintained and comfortable. The hottub was a perfect fit as it was cooler in Florida when we arrived. Thank you!"
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
The price is £258
includes taxes & fees
6 Aug - 7 Aug
Siesta Heron Suites & Villas

5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING

10.0 out of 10, Exceptional, (140)
"This is a beautifully furnished and managed property. We stayed for a week with 7 adults and 4 small children, and we all had a great time."
5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING

Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course

10.0 out of 10, Exceptional, (45)
"This was an amazing house. It had everything you could want, walkable to everything, restaurant shopping , and the beach. We never needed to rent a car. So many things to do at this house. Every age range of people were completely satisfied. I would definitely stay at this house again it was beautiful top to bottom. "
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course

Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..

9.8 out of 10, Exceptional, (6)
"The rental was spacious and very clean!!I would definitely stay here again. Place looked exactly like the pictures!! "
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..

Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access

9.2 out of 10, Wonderful, (40)
"Enjoyable stay"
Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access

Tropical Green Cottage – Siesta Key, Just Cross the Street! Unit B

8.8 out of 10, Excellent, (41)
"Great owner, very easy to work with. "
Tropical Green Cottage – Siesta Key, Just Cross the Street! Unit B

Beachside Retreat with Pool and Beach Access

8.8 out of 10, Excellent, (40)
"Great location for all our visitors to walk to many various restaurants and shops"
The price is £873
includes taxes & fees
7 Aug - 8 Aug
Beachside Retreat with Pool and Beach Access

SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.6 out of 10, Exceptional, (49)
"This place has a great layout, it was so easy to walk to and from the beach and enjoy the porches and views. Thanks for all the beach equipment too!"
The price is £905
includes taxes & fees
6 Aug - 7 Aug
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
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

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 Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times and Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool.

How many holiday rentals are there in Siesta Key?

With 800 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. While here, Crescent Beach and Siesta Key Marina 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.