Siesta Key Holiday Rentals

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Holiday Rentals in Siesta Key

Aparthotel in South Village

3.5 star property
9.4 out of 10, Exceptional, (5109)
"The room was clean and the staff was very nice."
United States
Jill
The price is AU$218
includes taxes & fees
30 Nov - 1 Dec
Tropical Beach Resorts

Condo in South Village

3.0 star property
9.0 out of 10, Wonderful, (1160)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort

Aparthotel in South Village

3.5 star property
9.6 out of 10, Exceptional, (295)
"Loved our stay! "
United States
Michelle
The price is AU$672
includes taxes & fees
17 Dec - 18 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in Siesta Key

4.0 star property
9.4 out of 10, Exceptional, (69)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
The price is AU$436
includes taxes & fees
30 Nov - 1 Dec
SeaSpray Resort

Apartment in Siesta Key

3.5 star property
9.0 out of 10, Wonderful, (336)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House

Holiday Home in Siesta Key

3.0 star property
9.6 out of 10, Exceptional, (50)
"Very nice place, we loved it. Great location. "
United States
Derrick
The price is AU$450
includes taxes & fees
3 Dec - 4 Dec
Siesta Key Island Rentals

Cottage in Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (189)
"Great place to stay! "
United States
Carlos
The Inn On Siesta Key

Aparthotel in South Village

3.5 star property
9.4 out of 10, Exceptional, (136)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach

Holiday Home in Siesta Key

3.5 star property
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is AU$539
includes taxes & fees
28 Nov - 29 Nov
Siesta Heron Suites & Villas

Holiday Home in Siesta Key Village

10.0 out of 10, Exceptional, (40)
"This was the perfect place to stay for a large family with kids. The location to the beach and restaurants couldn't have been more convenient. Amazing vacation!"
United States
Frances E.
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Holiday Home in Siesta Key

9.8 out of 10, Exceptional, (8)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
United States
Michele B.
Private Home Directly on Siesta Key Beach!

Holiday Home in Siesta Key

9.6 out of 10, Exceptional, (28)
"Location was great! Alex was very helpful and quick to respond. Definitely recommend this place to stay in the beautiful Siesta Key!"
United States
Marla H.
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Condo in Siesta Key

9.4 out of 10, Exceptional, (68)
"Very clean and very quick to respond to any need. Would highly recommend. "
United States
Laura G.
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

Holiday Home in Siesta Key

9.6 out of 10, Exceptional, (55)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
United States
Rob M.
The price is AU$1,429
includes taxes & fees
24 Nov - 25 Nov
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Condo in Siesta Key

10.0 out of 10, Exceptional, (13)
"Had a great time with great accommodations"
United States
Henry P.
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Holiday Home in Siesta Key Village

9.8 out of 10, Exceptional, (45)
"This is a spectacular home with plenty of room and an amazing pool! We had 5 adults and two children and could have easily accomodated more. Everyone loved the outdoor space. Short walk to the beach and village."
United States
Bill & Jackie B.
Home Steps from Siesta Key Beach and Village with Waterslide! On The Rocks

Holiday Home in Siesta Key

10.0 out of 10, Exceptional, (142)
"Amazing stay with family! David was a fantastic host and gave us tips for 4th of a July weekend. This house has EVERYTHING you need. It was perfect!!"
United States
Raquel A.
5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING

Holiday Home in Siesta Key

10.0 out of 10, Exceptional, (48)
"Amazing property!! Perfect location right across from the beach, pool was amazing, house was so clean and well stocked with the essentials. They provide wagons, coolers, beach towels. The Vunique Vacation staff was excellent and communicated well throughout our stay. Cannot recommend this place enough. We will definitely be back! "
United States
Kristen T.
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course

Holiday Home in Siesta Key Village

9.6 out of 10, Exceptional, (142)
"Great location and fit all our boxes for beach getaway. "
United States
Lisa M.
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Condo in Siesta Key

9.2 out of 10, Wonderful, (23)
"We enjoyed the beautiful beach, pools and resort! The condo was a great place for our family to stay! We will definitely be back!"
United States
Lisa W.
Jamaica Royale Siesta Key Condo 109
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$218 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. 

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 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 Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village.

How many holiday rentals are there in Siesta Key?

With 815 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, Siesta Key Marina 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.