Title: The 10 Best 5 Star Hotels in Legacy Trail - 2026 Updated Prices | Expedia.co.uk [Legacy Trail Travel Guide](https://expedia.co.uk/Legacy-Trail.dx553248621532652531)[Hotels in Legacy Trail](https://expedia.co.uk/Legacy-Trail-Hotels.d553248621532652531.Travel-Guide-Hotels)[Holiday Rentals in Legacy Trail](https://expedia.co.uk/Legacy-Trail-Holiday-Rentals.d553248621532652531.Travel-Guide-HolidayRentals)[Flights to Legacy Trail](https://expedia.co.uk/Cheap-Flights-To-Legacy-Trail.d553248621532652531.Travel-Guide-Flights)[Legacy Trail Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Legacy-Trail.d553248621532652531.Car-Hire-Guide)[Legacy Trail Holidays](https://expedia.co.uk/Legacy-Trail.d553248621532652531.Holidays-City-Breaks) ![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) # Compare and book 5 Star hotels in Legacy Trail, Florida - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [28 Dec - 29 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248621532652531&startDate=2025-12-28&endDate=2025-12-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [29 Dec - 30 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248621532652531&startDate=2025-12-29&endDate=2025-12-30&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [2 Jan - 4 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248621532652531&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [9 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248621532652531&startDate=2026-01-09&endDate=2026-01-11&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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/36b8ca60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Sarasota [](https://www.expedia.co.uk/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) Central Sarasota 9.2/10 Wonderful (1003) "Excellent property and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) NINA £595 includes taxes & fees 28 Jan - 29 Jan 2026 [](https://www.expedia.co.uk/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) ![Presidential Suite, 3 Bedrooms, 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) ![Outdoor pool, 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) ![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.co.uk/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 £966 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/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.co.uk/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.co.uk/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 £294 5 Jan - 6 Jan 2026 includes taxes & fees 9/10 Wonderful! (1,155 reviews) [](https://expedia.co.uk/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 £102 31 Dec - 1 Jan 2026 includes taxes & fees 8.6/10 Excellent! (1,527 reviews) [](https://expedia.co.uk/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 £191 4 Jan - 5 Jan 2026 includes taxes & fees 9.4/10 Exceptional! (1,884 reviews) [](https://expedia.co.uk/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.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=553248621532652531&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=553248621532652531&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%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 top sights around Legacy Trail, a city also notable for its beaches and wildlife. [See all hotels in Legacy Trail](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-12&endDate=2026-01-13&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 ## Find out more about Legacy Trail ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [2 Star Hotels in Casey Key ](https://www.expedia.co.uk/2Star-Casey-Key-Hotels.s20-0-d6167273.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Anna Maria Island ](https://www.expedia.co.uk/3Star-Anna-Maria-Island-Hotels.s30-0-d553248622847118534.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Bradenton ](https://www.expedia.co.uk/3Star-Bradenton-Hotels.s30-0-d6020.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Longboat Key ](https://www.expedia.co.uk/3Star-Longboat-Key-Hotels.s30-0-d8409.Travel-Guide-Filter-Hotels) - 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[5 Star Hotels in Anna Maria ](https://www.expedia.co.uk/5Star-Anna-Maria-Hotels.s50-0-d74028.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Anna Maria Island ](https://www.expedia.co.uk/5Star-Anna-Maria-Island-Hotels.s50-0-d553248622847118534.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Boca Grande ](https://www.expedia.co.uk/5Star-Boca-Grande-Hotels.s50-0-d183083.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Lido Key ](https://www.expedia.co.uk/5Star-Lido-Key-Hotels.s50-0-d6138897.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Longboat Key ](https://www.expedia.co.uk/5Star-Longboat-Key-Hotels.s50-0-d8409.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sarasota ](https://www.expedia.co.uk/5Star-Sarasota-Hotels.s50-0-d602719.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Siesta Key ](https://www.expedia.co.uk/5Star-Siesta-Key-Hotels.s50-0-d6881.Travel-Guide-Filter-Hotels) - [5 Star Hotels in St. Pete Beach ](https://www.expedia.co.uk/5Star-St-Pete-Beach-Hotels.s50-0-d9802.Travel-Guide-Filter-Hotels) - 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