Siesta Key Holiday Rentals: Short-Term Accommodations for Rent

Q: 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 .

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Holiday Rentals in Siesta Key

Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

"Excellent location, cute and clean rooms!! "

HK$1,452 total

includes taxes & fees

3 Aug - 4 Aug

"Nice place to stay in SK! "

HK$2,413 total

includes taxes & fees

3 Aug - 4 Aug

"Excellent property, excellent communication with Susan, i recommend it to anyone who wants to have an amazing vacation."

"The house was in great condition and near everything. "

"We love the property, beautiful, clean and we love that you can walked to the beach, that is a plus. "

"Fun place to stay for family vacation "

"I want use Expedia to select a vacation destination again."

HK$3,013 total

includes taxes & fees

29 Jul - 30 Jul

Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

"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. "

HK$2,798 total

includes taxes & fees

3 Aug - 4 Aug

"An outstanding experience — a place that leaves you with a strong desire to return."

"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!"

"Very nice location, clean, nice amenities"

"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!"

"It was perfect for my family of 4 for our beach vacation!!"

HK$2,737 total

includes taxes & fees

16 Aug - 17 Aug

On the beach, sun-loungers, beach towels

"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."

"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. "

"Enjoyable stay"

"We thoroughly enjoyed our stay at Casa mar number 15 plenty of towels sheets, very clean wonderful location. Owners were super responsive to any messages. Would highly recommend this place to anyone looking for a vacation on siesta key which is the most beautiful beach I’ve ever been to location was perfect. "

"Great location for all our visitors to walk to many various restaurants and shops"

HK$10,067 total

includes taxes & fees

7 Aug - 8 Aug

"Great owner, very easy to work with. "

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Top Siesta Key Hotel Reviews

Siesta Key Beach Resort and Suites

10/10 Excellent

"The location is excellent, with easy access to the beach and within walking distance to restaurants and shopping."

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

10/10 Excellent

"Great location! Loved the closeness of the beach and the private beach area was not too crowded. The townhouse was very comfortable had everything we needed. Alex was very kind and quick to respond to questions. We would definitely stay here again and absolutely loved Siesta Key!Request for two quick fixes: the master bed was quite squeaky and would be helpful to have that looked at. There was also an odd odor in the house, which we later discovered was the front load washing machine. "

Siesta Key Island Rentals

10/10 Excellent

"We had a very pleasant experience working with Siesta Key Island Rentals. Communication was smooth and professional from start to finish, making the entire booking process easy and stress-free. The unit itself was perfect—clean, comfortable, and ideally located. We were able to walk to the beach, restaurants, and shops without ever needing a car. Would definitely rent with them again and highly recommend to anyone visiting Siesta Key!"

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

10/10 Excellent

"This is a beautiful home in an amazing location. Short walk to the beach and all the bars and restaurants. We rented a golf cart for a day but quickly realized it wasn’t worth it as everything is so close. Bedrooms do vary greatly in size - there are a couple on the third floor that are very small but the other 4 are all a good size. Check in and out was very easy and convenient. Only real issue and nothing to do with the house or management were the Misquotes …. in July during our visit were pretty bad so I recommend bringing lots of spray and candles to keep the pool area usable. I would 100% stay here again "

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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All accommodation types in Siesta Key

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 798 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.

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Siesta Key Holiday Rentals

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Holiday Rentals in Siesta Key

Tropical Beach Resorts

SeaSpray Resort

The Ringling Beach House

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

Captiva Beach Resort

The Residences at Siesta Key Beach by Hyatt Vacation Club

Siesta Key Island Rentals

The Inn On Siesta Key

Siesta Palms By the Beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

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

VH106AMelissa

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

Siesta Heron Suites & Villas

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

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

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

Beachside Retreat with Pool and Beach Access

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

Top Siesta Key Hotel Reviews

Siesta Key Beach Resort and Suites

Siesta Palms By the Beach

Tropical Breeze Resort

Tropical Beach Resorts

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key Island Rentals

Siesta Key Inn

The Residences at Siesta Key Beach by Hyatt Vacation Club

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

Find out more about Siesta Key

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Frequently asked questions