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Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
  • 20 min drive from Siesta Key Beach
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
9/10 Wonderful! (4,480 reviews)
"I really like the Views either side. I've stayed there more than 20 times annually whenever I'm in town. Trendy and clean. I feel connected."

Reviewed on Oct 16, 2025

Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
  • 27 min walk from Siesta Key Beach
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (5,031 reviews)
"The room was lovely good size had everything you needed. It was very clean the property was in good order. Most of the staff were friendly. My only issue was with the one swimming pool that you had to wear a paper waistband to attend, I’m all for having to prove you are staying at the residence. ..."

Reviewed on Oct 17, 2025

Tropical Beach Resorts
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
6600 S Tamiami Trl, Sarasota, FL
  • 25 min walk from Siesta Key Beach
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.2/10 Very Good! (1,771 reviews)
Enjoyable stay.
"Very comfy beds. Would have been nice to have a microwave but it wasn’t a huge issue."

Reviewed on Oct 16, 2025

Spark by Hilton Sarasota Siesta Key Gateway
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West, Bradenton, FL
  • 41 min drive from Siesta Key Beach
Stay at this 4-star hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,803 reviews)
"What a wonderful property and location. Not a bad room in the house. Ocean views out both sides, nice, clean marina, easy access into town or Anna Marie Island, and the hotel itself has wonderful in-house amentities with as a store and restaurant. Will book again and again, whenever I am in the ..."

Reviewed on Oct 16, 2025

Compass Hotel by Margaritaville Anna Maria Sound
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl, Sarasota, FL
  • 18 min drive from Siesta Key Beach
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the bar in our ...
8.4/10 Very Good! (2,134 reviews)
"We enjoyed our stay, the highlights for us were the live music ( Friday night, he was incredibly talented 10/10 musician) and the drag queen bingo on Sunday! Drinks were well made and entertain was 10/10 at Bahi Hut tiki bar on site. Clean rooms. Comfortable bed. Easy parking. Very pleasant staff. ..."

Reviewed on Oct 14, 2025

Golden Host Resort - Sarasota
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL
  • 17 min walk from Siesta Key Beach
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,004 reviews)
"Awesome space"

Reviewed on Oct 9, 2025

Tropical Breeze Resort
The Westin Sarasota

The Westin Sarasota

4 out of 5
100 Marina View Drive, Sarasota, FL
  • 12 min drive from Siesta Key Beach
Stay at this 4-star spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,110 reviews)
"Great staff"

Reviewed on Oct 15, 2025

The Westin Sarasota
Carlisle Inn

Carlisle Inn

3.5 out of 5
3727 Bahia Vista, Sarasota, FL
  • 11 min drive from Siesta Key Beach
Stay at this 3.5-star hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.8/10 Exceptional! (2,060 reviews)
"A little stronger water pressure would be great."

Reviewed on Oct 15, 2025

Carlisle Inn
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

4 out of 5
8009 15th Street E, Sarasota, FL
  • 22 min drive from Siesta Key Beach
Stay at this 4-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,467 reviews)
"VERY PLEASANT EXPERIENCE"

Reviewed on Oct 14, 2025

DoubleTree by Hilton Sarasota Bradenton Airport
Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

3.5 out of 5
202 North Tamiami Trail, Sarasota, FL
  • 12 min drive from Siesta Key Beach
Stay at this 3.5-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in ...
8.6/10 Excellent! (1,639 reviews)
"Enjoyed our stay for the week. Friendly staff all around. We loved the breakfast, happy hour, and restaurant. Everything you could want or need is in one spot. Short drive to the beach and shops…things to do. I would definitely recommend."

Reviewed on Oct 1, 2025

Embassy Suites by Hilton Sarasota, FL
Extended Stay America Premier Suites - Bradenton

Extended Stay America Premier Suites - Bradenton

2.5 out of 5
4550 53rd Ave E, Bradenton, FL
  • 31 min drive from Siesta Key Beach
Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mall at University Town Center and Rosedale Golf and ...
8.8/10 Excellent! (280 reviews)
"Very clean and comfortable"

Reviewed on Oct 12, 2025

Extended Stay America Premier Suites - Bradenton
Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

3 out of 5
950 University Parkway, Sarasota, FL
  • 19 min drive from Siesta Key Beach
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,025 reviews)
"The staff was nice and we enjoyed our stay."

Reviewed on Oct 15, 2025

Hyatt Place Sarasota/Bradenton Airport
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.

Find cheap hotels in Legacy Trail

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Frequently Asked Questions About Legacy Trail hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in Legacy Trail?

With over 16,855 hotels in Legacy Trail, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $82.

How to find cheap car rentals in Legacy Trail?

Finding a cheap car rental deal in Legacy Trail is as easy as scoring cheap hotels in Legacy Trail. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.