Holiday Rentals Siesta Key from 3.653.953 ₫: Find Short-Term Rentals & Holiday Accommodations

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Top Holiday Rentals in Siesta Key

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

"Very nice stay"

4.721.044 ₫ total

includes taxes & fees

1 Sept - 2 Sept

"Nice place to stay in SK! "

6.190.488 ₫ total

includes taxes & fees

1 Sept - 2 Sept

"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "

"Everything was perfect with our stay. We will be back soon."

"Fun place to stay for family vacation "

13.379.548 ₫ total

includes taxes & fees

3 Sept - 4 Sept

Barefoot Bungalow W/Pool | Private kitchen

"Quiet neighborhood, clean and well maintained property, responsive management."

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. "

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

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Top Siesta Key Hotel Reviews

Siesta Key Beach Resort and Suites

10/10 Excellent

"We loved our stay. We had a room on the patio near the pool. It was a great room updated and super clean. We would definitely stay there again."

Tropical Breeze Resort

10/10 Excellent

"I truly don’t have the words to express how incredibly grateful I am to have discovered this hidden gem. From the moment we arrived, everything was beyond perfect—not just a five-star experience, but a 5000-star one. The unit was absolutely immaculate, and the entire resort, along with the surrounding area, was pristine and beautifully maintained. The front desk service was exceptional. I was warmly welcomed by someone who even shared my name, along with her wonderful colleague—both of whom made my family and me feel completely at home. Thank you from the bottom of my heart for such a remarkable experience and an unforgettable vacation. We will absolutely be back soon for more magical moments."

SeaSpray Resort

10/10 Excellent

"Really cute apartment/hotel. Had everything we needed. Nice individual patio area. Rooms also came with a wagon with beach chairs/umbrella/tote bag in it that you could lug to the beach. Pool was small & clean. Short walk to the beach. Close to the Village; took the free trolley. Would definitely stay there again."

Tropical Beach Resorts

10/10 Excellent

"The BEST place on the island. We’ve been coming here for 20 years and it just keeps getting better!!! The staff is so accommodating and will do anything for you. The new pool is absolutely amazing!!! We are sooo glad that they’ve been able to recover from the devastating hurricanes last year. "

Siesta Key Island Rentals

10/10 Excellent

"This is the best place to stay in Siesta Key and overall best place. Everything was very clean, the AC works so good specially during hot weather the room stays very cold. The bed was so comfortable and cleaned. This place has the best customer service I have ever experienced. Very sweet, helpful, and caring. There was a night were we forgot our password getting in and I sent them a email since it was after hours saying we needed the password and they called immediately after I sent the email, Checking if we were okay and if we needed help. This place is across from the beach like a 5 minute walk very close and the village is also right around the corner. I recommend this place 100%."

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.

How many holiday rentals are there in Siesta Key?

With 812 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.

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Top Holiday Rentals in Siesta Key

Tropical Beach Resorts

SeaSpray Resort

The Ringling Beach House

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

Siesta Heron Suites & Villas

Top Siesta Key Hotel Reviews

Siesta Key Beach Resort and Suites

Tropical Breeze Resort

SeaSpray Resort

Siesta Key Inn

Tropical Beach Resorts

Turtle Beach Resort

Siesta Palms By the Beach

Captiva Beach Resort

Siesta Key Island Rentals

Frequently asked questions

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