Title: 5 Stars Hotels in Oyster Bay, Sarasota from CA $188 - Find Cheap Oyster Bay Hotels With 5 Stars | Expedia.ca [Oyster Bay Travel Guide](https://expedia.ca/Sarasota-Oyster-Bay.dx553248635976482297)[Vacation Rentals in Sarasota](https://expedia.ca/Sarasota-Vacation-Rentals.d602719.Travel-Guide-VacationRentals)[Flights to Sarasota](https://expedia.ca/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)[Things to do in Sarasota](https://expedia.ca/Things-To-Do-In-Sarasota.d602719.Travel-Guide-Activities)[Oyster Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Oyster-Bay.d553248635976482297.Car-Rental-Guide)[Oyster Bay Vacations](https://expedia.ca/Oyster-Bay.d553248635976482297.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Oyster Bay, Sarasota from CA $188 ![](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 Oyster Bay 5 Star Hotels Tonight [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=553248635976482297&startDate=2025-10-09&endDate=2025-10-10&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976482297&startDate=2025-10-10&endDate=2025-10-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976482297&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976482297&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oyster Bay 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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/36b8ca60.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 Central Sarasota 9.2/10 Wonderful (1004) "Loved staying at this hotel! I was hesitant because it wasn’t on the beach but they have a shuttle that takes you straight to their beach location with a great pool! Staff was incredibly friendly " CA $781 CA $974 total includes taxes & fees Nov 9 - Nov 10 [](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) ![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) ![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 | 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" CA $1,031 CA $1,252 total includes taxes & fees Oct 20 - Oct 21 [](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-Oyster-Bay-Sarasota-Hotels.s50-n553248635976482297-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Oyster-Bay-Sarasota-Hotels.s50-n553248635976482297-0.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 Oyster Bay. ![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 $248 CA $315 total Oct 13 - Oct 14 includes taxes & fees 9/10 Wonderful! (1,099 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 $166 CA $188 total Oct 12 - Oct 13 includes taxes & fees 8.6/10 Excellent! (1,456 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 $248 CA $319 total Oct 12 - Oct 13 includes taxes & fees 9.4/10 Exceptional! (1,785 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 Oyster Bay.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635976482297&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=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635976482297&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635976482297&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635976482297&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635976482297&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635976482297&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 Oyster Bay Hotel Reviews ![The St. Regis Longboat Key Resort](//images.trvl-media.com/lodging/1000000/10000/5500/5487/1e787841_y.jpg) ### The St. Regis Longboat Key Resort 10/10 Excellent "Great customer service, excell" [](https://expedia.ca/Longboat-Key-Hotels-The-St-Regis-Longboat-Key-Resort.h5487.Hotel-Information) ## 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) - 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[Hotels with Free Breakfast in Southgate](https://www.expedia.ca/Southgate-Sarasota-Hotels-Hotels-With-Free-Breakfast.0-n553248623282278413-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Southgate](https://www.expedia.ca/Southgate-Sarasota-Hotels-Hotels-With-Waterslides.0-n553248623282278413-0-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Southgate Hotels](https://www.expedia.ca/Southgate-Sarasota-Hotels.0-n553248623282278413-0.Travel-Guide-Filter-Hotels) - [Hotels near St. Boniface Episcopal Church Labyrinth](https://www.expedia.ca/St-Boniface-Episcopal-Church-Labyrinth-Hotels.0-l6295832-0.Travel-Guide-Filter-Hotels) - [Flights to Sarasota](https://www.expedia.ca/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights) - [Flights to Siesta Key](https://www.expedia.ca/Cheap-Flights-To-Siesta-Key.d6881.Travel-Guide-Flights) - [Visit Arlington Park](https://www.expedia.ca/Sarasota-Arlington-Park.dx553248635976473965) - [Visit Cherokee Park](https://www.expedia.ca/Sarasota-Cherokee-Park.dx553248635976481007) - [Siesta Key Beach](https://www.expedia.ca/Siesta-Key-Beach-Siesta-Key.d6066003.Vacation-Attraction) - [Visit Siesta Key Village](https://www.expedia.ca/Siesta-Key-Siesta-Key-Village.dx6296072) - [Siesta Key Vacations](https://www.expedia.ca/Siesta-Key.d6881.Destination-Travel-Guides) - [Visit Siesta Key](https://www.expedia.ca/Siesta-Key.dx6881) - [St. Boniface Episcopal Church Labyrinth](https://www.expedia.ca/St-Boniface-Episcopal-Church-Labyrinth-Siesta-Key.d6295832.Vacation-Attraction) - [All inclusive Vacation Packages Siesta Key](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/6881/Siesta-Key) - [Car rentals near Siesta Key Beach](https://www.expedia.ca/Car-Rentals-In-Siesta-Key-Beach.d6066003.Car-Rental-Guide) - [Car rental Siesta Key](https://www.expedia.ca/Car-Rentals-In-Siesta-Key.d6881.Car-Rental-Guide) - [Midsize Car Rentals near Siesta Key Beach](https://www.expedia.ca/Midsize-Car-Rentals-In-Siesta-Key-Beach.d6066003-tMidsize.Car-Rental-Guide-Class) - [Siesta Key Vacation Rentals](https://www.expedia.ca/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals) - [Things to do in Siesta Key](https://www.expedia.ca/Things-To-Do-In-Siesta-Key.d6881.Travel-Guide-Activities) - [Book Hotels in Oyster Bay on Expedia.com](https://www.expedia.com/5Star-Oyster-Bay-Sarasota-Hotels.s50-n553248635976482297-0.Travel-Guide-Filter-Hotels)