Title: 5 Stars Hotels in Legacy Trail, Florida from CA $159 - Find Cheap Legacy Trail Hotels With 5 Stars | Expedia.ca [Legacy Trail Travel Guide](https://expedia.ca/Legacy-Trail.dx553248621532652531)[Hotels in Legacy Trail](https://expedia.ca/Legacy-Trail-Hotels.d553248621532652531.Travel-Guide-Hotels)[Vacation Rentals in Legacy Trail](https://expedia.ca/Legacy-Trail-Vacation-Rentals.d553248621532652531.Travel-Guide-VacationRentals)[Flights to Legacy Trail](https://expedia.ca/Cheap-Flights-To-Legacy-Trail.d553248621532652531.Travel-Guide-Flights)[Legacy Trail Car Rentals](https://expedia.ca/Car-Rentals-In-Legacy-Trail.d553248621532652531.Car-Rental-Guide)[Legacy Trail Vacation Packages](https://expedia.ca/Legacy-Trail.d553248621532652531.Destination-Travel-Guides) ![Legacy Trail showing a garden](https://images.trvl-media.com/place/553248635975846806/d70ae022-0498-403c-94d8-dc8f29b7750f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Legacy Trail, Florida from CA $159 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Legacy Trail 5 Star Hotels Tonight [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-12-16&endDate=2025-12-17&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-12-17&endDate=2025-12-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-12-19&endDate=2025-12-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Legacy Trail 5-star hotels ![Private beach nearby, white sand, free beach shuttle, beach cabanas](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/90558b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/2c5129a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/3bd9c1f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/13a0ff16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Sarasota [](https://www.expedia.ca/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) Central Sarasota 9.2/10 Wonderful (1002) "Excellent property and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) NINA CA $756 CA $944 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/6b2968af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/1e787841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed with Sofa bed, Oceanfront | View from room](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/ec4c3b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/72c017f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The St. Regis Longboat Key Resort [](https://www.expedia.ca/Longboat-Key-Hotels-The-St-Regis-Longboat-Key-Resort.h5487.Hotel-Information) Longboat Key 9.8/10 Exceptional (59) "Fantastic stay . All servers were great. Staff very friendly and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $1,018 CA $1,251 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Longboat-Key-Hotels-The-St-Regis-Longboat-Key-Resort.h5487.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Legacy-Trail-Hotels.s50-0-d553248621532652531.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Legacy-Trail-Hotels.s50-0-d553248621532652531.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Legacy Trail. ![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Westin Sarasota 100 Marina View Drive Sarasota FL CA $329 CA $406 total Dec 18 - Dec 19 includes taxes & fees 9/10 Wonderful! (1,151 reviews) [](https://expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information) ![DoubleTree by Hilton Sarasota Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Sarasota Bradenton Airport 8009 15th Street E Sarasota FL CA $140 CA $159 total Dec 25 - Dec 26 includes taxes & fees 8.6/10 Excellent! (1,523 reviews) [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Compass Hotel by Margaritaville Anna Maria Sound](https://images.trvl-media.com/lodging/42000000/41970000/41961400/41961327/8b0dc5d5_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Compass Hotel by Margaritaville Anna Maria Sound 12324 Manatee Avenue West Bradenton FL CA $210 CA $276 total Dec 22 - Dec 23 includes taxes & fees 9.4/10 Exceptional! (1,882 reviews) [](https://expedia.ca/Sarasota-Hotels-Compass-Hotel-By-Margaritaville.h41961327.Hotel-Information) Still don't see what you're looking for? [See all properties in Legacy Trail.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=553248621532652531&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Legacy Trail Venture to Siesta Key Beach and Lido Beach—just two of the popular sights around Legacy Trail, a city also known for its beaches and sports teams. [See all hotels in Legacy Trail](https://www.expedia.ca/Hotel-Search?startDate=2025-12-30&endDate=2025-12-31&adults=2®ionId=553248621532652531) ![Legacy Trail showing a garden](https://images.trvl-media.com/place/553248635975846806/d70ae022-0498-403c-94d8-dc8f29b7750f.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Legacy Trail Hotel Reviews ![The St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/1e787841_y.jpg) ### The St. Regis Longboat Key Resort 10/10 Excellent "Everything was new, clean and the service was amazing! The best part is how many activities there are for kids. This is perfect for families to enjoy and relax! We'll be back very soon!" [](https://expedia.ca/Longboat-Key-Hotels-The-St-Regis-Longboat-Key-Resort.h5487.Hotel-Information) ## Find out more about Legacy Trail Luxury is the name of the game at the best 5 Stars hotels in Legacy Trail. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Legacy Trail 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Legacy Trail hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Legacy Trail without giving up even an inch of quality. 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