Title: 5 Stars Hotels in Legacy Trail, Florida from CA $181 - 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495922-south-venice.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Legacy Trail, Florida from CA $181 ![](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 [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-10-22&endDate=2025-10-23&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-10-23&endDate=2025-10-24&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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/1000000/810000/806200/806101/3e724949.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) ![Private beach nearby, white sand, free beach shuttle, beach cabanas](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/8d484916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Sarasota Central Sarasota 9.2/10 Wonderful (1008) "Everything and everyone was wonderful. The street was a bit loud sometimes at night. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Doris CA $785 CA $979 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) ![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) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/68d9d3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed with Sofa bed, Non Smoking, Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/4e06c5f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed with Sofa bed, Non Smoking, 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) ### The St. Regis Longboat Key Resort Longboat Key 9.8/10 Exceptional (49) "Absolutely beautiful property! Lovely pools and impeccable beach. Restaurants are good, housekeeping was the only miss - no turndown one night and had to request cleaning at 3 pm after having had the service sign on all day" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) carrie CA $1,036 CA $1,258 total includes taxes & fees Oct 26 - Oct 27 [](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 $307 CA $382 total Oct 26 - Oct 27 includes taxes & fees 9/10 Wonderful! (1,112 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 $160 CA $181 total Oct 26 - Oct 27 includes taxes & fees 8.6/10 Excellent! (1,471 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 $249 CA $321 total Oct 23 - Oct 24 includes taxes & fees 9.4/10 Exceptional! (1,810 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=23%2F10%2F2025&endDate=24%2F10%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=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=553248621532652531&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=553248621532652531&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=553248621532652531&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=553248621532652531&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%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=2025-11-05&endDate=2025-11-06&adults=2®ionId=553248621532652531) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495922-south-venice.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Legacy Trail Hotel Reviews ## 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. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Legacy Trail. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [1 Star Hotels in Bellevue Terrace](https://www.expedia.ca/1Star-Bellevue-Terrace-Sarasota-Hotels.s10-n553248635976477541-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Main Street Merchants](https://www.expedia.ca/1Star-Main-Street-Merchants-Sarasota-Hotels.s10-n553248635976474790-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Sunny Shores](https://www.expedia.ca/1Star-Sunny-Shores-Bradenton-Hotels.s10-n553248635976469851-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Bradenton](https://www.expedia.ca/3Star-Bradenton-Hotels.s30-0-d6020.Travel-Guide-Filter-Hotels) - [3 Star Hotels in North Sarasota](https://www.expedia.ca/3Star-North-Sarasota-Sarasota-Hotels.s30-n553248635975847442-0.Travel-Guide-Filter-Hotels) - 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