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Hotels in Legacy Trail

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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, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
9/10 Wonderful! (4,153 reviews)
"Everything was amazing. I did not expect this hotel to be this nice. I had never heard of Kompose. We will definitely recommend this place to anyone staying in Sarasota. And my husband said the breakfast was extremely good. 10/10"

Reviewed on Jul 19, 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! (4,778 reviews)
"The bed was firm, but the property was quiet, clean, and comfortable. This was one if the most relaxing getaways I've been on. I would definitely stay here again!"

Reviewed on Jul 17, 2025

Tropical Beach Resorts
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! (1,519 reviews)
"The property was good , surrounded area was very poor a lot of closed down buildings and a lot of homeless people"

Reviewed on Jul 18, 2025

Embassy Suites by Hilton Sarasota, FL
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! (1,581 reviews)
"The manager was very nice to allow me to cancel my second night because my family from out of state all flew in to surprise me for my 70 birthday. She helped to make my birthday the best I ever had. Thank you"

Reviewed on Jul 21, 2025

Compass Hotel by Margaritaville Anna Maria Sound
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! (1,462 reviews)
"This was my first time staying at this hotel. On the first day, the bathtub was clogged, but the staff acted quickly and switched us to a different room right away. Other than that, everything was great. The staff were incredibly friendly and helpful, always checking in to see if we needed anything. ..."

Reviewed on Jul 19, 2025

Spark by Hilton Sarasota Siesta Key Gateway
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! (1,035 reviews)
"Great people. From the valet stand to my check-in and out. Comfortable room and bed. I’ll be back"

Reviewed on Jul 19, 2025

The Westin Sarasota
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! (1,355 reviews)
"So far the hotel is great. Very friendly staff and nice room"

Reviewed on Jul 20, 2025

DoubleTree by Hilton Sarasota Bradenton Airport
The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

5 out of 5
1601 Gulf Of Mexico Drive, Longboat Key, FL
  • 16 min drive from Siesta Key Beach
Stay at this 5-star luxury hotel in Longboat Key. Enjoy a full-service spa, 3 restaurants, and a private beach. Popular attractions Lido Beach and St. Armands ...
9.6/10 Exceptional! (32 reviews)
"Very nice resort but not suitable for kids/babies. There was not much to do for our infant."

Reviewed on Jul 16, 2025

The St. Regis Longboat Key Resort
Lido Beach Resort

Lido Beach Resort

4 out of 5
700 Benjamin Franklin Dr, Sarasota, FL
  • 8 min drive from Siesta Key Beach
Book a stay at this beach resort in Sarasota. Enjoy free WiFi, 2 outdoor pools, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,003 reviews)
Decent with a few complaints
"Had an ok time at this resort. Just a few complaints….our toilet didn’t flush great, water constantly ran. Some items in the room could use updating. The luggage rack was not sturdy enough to hold a suitcase. Fan speed could not be adjusted. One night walking back to our room, we walked past a room ..."

Reviewed on Jul 16, 2025

Lido Beach Resort
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 ...
8.2/10 Very Good! (2,066 reviews)
"Everything was good Better than pics on the website I really like want to come back."

Reviewed on Jul 20, 2025

Golden Host Resort - Sarasota
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd, Siesta Key, FL
  • 13 min walk from Siesta Key Beach
Stay at this resort in Siesta Key. Enjoy free WiFi, free bicycles on site, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,006 reviews)
"Perfect location for everything. Did not have to use our car for anything because everything was walking distances."

Reviewed on Jul 19, 2025

Siesta Key Beach Resort and Suites
SeaSpray Resort

SeaSpray Resort

4 out of 5
574 Canal Rd, Siesta Key, FL
  • 7 min walk from Siesta Key Beach
Stay at this 4-star aparthotel in Siesta Key. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Siesta Key Beach and Lido Beach are ...
9.6/10 Exceptional! (4 reviews)
"Great place! 1 min walk to the beach, 10 min walk to siesta village, place was clean, provided cart & umbrella, great location!"

Reviewed on Jun 28, 2025

SeaSpray Resort
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 16,375 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 $84.

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.