Title: 5 Stars Hotels in Bay Island, Siesta Key from CA $217 - Find Cheap Bay Island Hotels With 5 Stars | Expedia.ca [Bay Island Travel Guide](https://expedia.ca/Siesta-Key-Bay-Island.dx553248635976194864)[Flights to Siesta Key](https://expedia.ca/Cheap-Flights-To-Siesta-Key.d6881.Travel-Guide-Flights)[Things to do in Siesta Key](https://expedia.ca/Things-To-Do-In-Siesta-Key.d6881.Travel-Guide-Activities)[Bay Island Car Rentals](https://expedia.ca/Car-Rentals-In-Bay-Island.d553248635976194864.Car-Rental-Guide)[Bay Island Vacations](https://expedia.ca/Bay-Island-Sarasota.d553248635976194864.Vacation-Attraction) ![sunset over the bay, water, sky, red, intense, swirls, clouds, landscape, island, horizon, tropical, Siesta Key, Florida](https://images.trvl-media.com/place/553248635976194864/b2a5a03c-7b86-4d7a-9c34-4c8d8b677b76.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635976194864/b2a5a03c-7b86-4d7a-9c34-4c8d8b677b76.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Bay Island 5 Star Hotels Tonight [Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976194864&startDate=2026-01-17&endDate=2026-01-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976194864&startDate=2026-01-18&endDate=2026-01-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976194864&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976194864&startDate=2026-01-30&endDate=2026-02-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Bay Island 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) ![5 bars/lounges, tapas bar](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/3e02cf20.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) ### The Ritz-Carlton, Sarasota [](https://www.expedia.ca/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) Central Sarasota 9.2/10 Wonderful (1,001 reviews) "Excellent property and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) NINA CA $1,063 CA $1,292 total includes taxes & fees Feb 16 - Feb 17 [](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) ![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) ![John Jacob Astor Suite, 1 King Bed with Sofa bed, Non Smoking, Oceanfront | Living room](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/4e2f76c2.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) ### 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 (60 reviews) "Best of the best ! it was incredible! i want to go back again🙌♥️" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vasyl CA $1,515 CA $1,814 total includes taxes & fees Jan 18 - Jan 19 [](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-Bay-Island-Siesta-Key-Hotels.s50-n553248635976194864-0.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Bay-Island-Siesta-Key-Hotels.s50-n553248635976194864-0.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 Bay Island. ![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 $472 CA $568 total Jan 28 - Jan 29 includes taxes & fees 9/10 Wonderful! (1,171 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 $192 CA $217 total Jan 20 - Jan 21 includes taxes & fees 8.6/10 Excellent! (1,538 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 $265 CA $339 total Jan 25 - Jan 26 includes taxes & fees 9.4/10 Exceptional! (1,923 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 Bay Island.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=553248635976194864&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=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=553248635976194864&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=553248635976194864&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=553248635976194864&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=553248635976194864&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=553248635976194864&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. ## Top Bay Island Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - 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 Anna Maria Island ](https://www.expedia.ca/3Star-Anna-Maria-Island-Hotels.s30-0-d553248622847118534.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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