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Hotels in Legacy Trail

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Choose from 16032 Legacy Trail Hotel Deals

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
The price is $154 per night from Mar 3 to Mar 4
$154
includes taxes & fees
Mar 3 - Mar 4
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! (1,729 reviews)
Nicely restored motel with friendly staff
"This is a restored older motel with all the comforts you need. The staff was very friendly and helpful as well."

Reviewed on Feb 21, 2025

Golden Host Resort - Sarasota
Hyatt Regency Sarasota
Hyatt Regency Sarasota
4 out of 5
1000 Blvd Of The Arts, Sarasota, FL
  • 13 min drive from Siesta Key Beach
The price is $304 per night from Mar 9 to Mar 10
$304
includes taxes & fees
Mar 9 - Mar 10
Book a stay at this eco-certified hotel in Sarasota. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
8/10 Very Good! (1,003 reviews)
"Stop the smokers"

Reviewed on Feb 19, 2025

Hyatt Regency Sarasota
Kompose Boutique Hotel
Kompose Boutique Hotel
3 out of 5
965 University Pkwy, Sarasota, FL
  • 20 min drive from Siesta Key Beach
The price is $252 per night from Mar 3 to Mar 4
$252
includes taxes & fees
Mar 3 - Mar 4
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 ...
8.8/10 Excellent! (3,647 reviews)
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Reviewed on Feb 21, 2025

Kompose Boutique Hotel
Palmetto Marriott Resort & Spa
Palmetto Marriott Resort & Spa
4.5 out of 5
600 US HIGHWAY 41, Palmetto, FL
  • 42 min drive from Siesta Key Beach
The price is $214 per night from Mar 11 to Mar 12
$214
includes taxes & fees
Mar 11 - Mar 12
Stay at this 4.5-star luxury hotel in Palmetto. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Popular attractions LECOM Park and Palmetto Historical ...
9/10 Wonderful! (85 reviews)
"Everything was great … except the $45/night for resort fee and parking"

Reviewed on Feb 16, 2025

Palmetto Marriott Resort & Spa
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
The price is $269 per night from Mar 23 to Mar 24
$269
includes taxes & fees
Mar 23 - Mar 24
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 ...
8.2/10 Very Good! (1,170 reviews)
"Good location. Access to pool and hot tub. Be advised. The website says breakfast and shuttle available. While this is true, potential guests should be aware that the shuttle is not free; tips only. And breakfast consists of bagels, cereal - hot and cold - muffins, coffee, OJ, and water. No eggs, ..."

Reviewed on Feb 19, 2025

Spark by Hilton Sarasota Siesta Key Gateway
Anna Maria Beach Resort
Anna Maria Beach Resort
3.5 out of 5
6306 Gulf Dr, Holmes Beach, FL
  • 45 min drive from Siesta Key Beach
The price is $857 per night from Feb 27 to Feb 28
$857
includes taxes & fees
Feb 27 - Feb 28
Stay at this 3.5-star beach aparthotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (188 reviews)
"All stay was friendly, very clean. Rooms cleaned daily. Would rate 5"

Reviewed on Feb 9, 2025

Anna Maria Beach Resort
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
The price is $1,533 per night from Feb 24 to Feb 25
$1,533
includes taxes & fees
Feb 24 - Feb 25
Stay at this 5-star luxury hotel in Longboat Key. Enjoy a full-service spa, 3 restaurants, and a private beach. Popular attractions St. Armands Circle and Lido ...
10/10 Exceptional! (13 reviews)
"Darin and the staff at the beach, pool, valet, housekeeping, butler, FD, restaurants were all fabulous. loved nightly turndown service. room was clean and comfortable. balcony large. food at CW prime, Aura were excellent as was breakfast at Riva and the coffee/baked goods at Carolinas. loved the ..."

Reviewed on Feb 6, 2025

The St. Regis Longboat Key Resort
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
The price is $479 per night from Mar 5 to Mar 6
$479
includes taxes & fees
Mar 5 - Mar 6
Book a stay at this beach motel in Siesta Key. Enjoy free WiFi, free bicycles on site, and parking (surcharge). Our guests praise the pool and the helpful staff ...
8.6/10 Excellent! (1,005 reviews)
"Make sure you know where your room is located on the facility. "Bar side" rooms are literally in the bar (Big Tiki). You'll walk through the bar and upstairs to your room. When you exit your room you'll exit into the bar. Music...loud music (live and DJ) are on all day until 9/10pm and can very clearly ..."

Reviewed on Feb 21, 2025

Siesta Key Beach Resort and Suites
Carlisle Inn
Carlisle Inn
3.5 out of 5
3727 Bahia Vista, Sarasota, FL
  • 11 min drive from Siesta Key Beach
The price is $315 per night from Mar 16 to Mar 17
$315
includes taxes & fees
Mar 16 - Mar 17
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! (1,726 reviews)
"Very clean! Friendly staff."

Reviewed on Feb 19, 2025

Carlisle Inn
Siesta Key Palms Resort
Siesta Key Palms Resort
4 out of 5
1800 Stickney Point Rd, Sarasota, FL
  • 23 min walk from Siesta Key Beach
The price is $389 per night from Feb 24 to Feb 25
$389
includes taxes & fees
Feb 24 - Feb 25
Stay at this 4-star hotel in Sarasota. Enjoy 2 outdoor pools, free bicycles on site, and a garden. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,000 reviews)
"A hidden gem! Easy walk to Siesta Key, property was cute, beautifully landscaped and full of lounges, hammocks, fire pits - all sorts of spaces to socialize or enjoy quiet time alone. Rooms were cute and comfortable and well-equipped. Facial tissues would have been nice to have. Staff were friendly ..."

Reviewed on Feb 14, 2025

Siesta Key Palms Resort
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
The price is $363 per night from Feb 26 to Feb 27
$363
includes taxes & fees
Feb 26 - Feb 27
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! (1,284 reviews)
"Loved it! Can’t wait to come back next year."

Reviewed on Feb 19, 2025

Compass Hotel by Margaritaville Anna Maria Sound
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! (4,557 reviews)
"Perfect location!"

Reviewed on Feb 20, 2025

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Tropical Beach Resorts
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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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