Title: 5 Stars Hotels in Osprey, Florida from CA $187 - Find Cheap Osprey Hotels With 5 Stars | Expedia.ca [Osprey Travel Guide](https://expedia.ca/Osprey.dx55888)[Hotels in Osprey](https://expedia.ca/Osprey-Hotels.d55888.Travel-Guide-Hotels)[Vacation Rentals in Osprey](https://expedia.ca/Osprey-Vacation-Rentals.d55888.Travel-Guide-VacationRentals)[Flights to Osprey](https://expedia.ca/Cheap-Flights-To-Osprey.d55888.Travel-Guide-Flights)[Things to do in Osprey](https://expedia.ca/Things-To-Do-In-Osprey.d55888.Travel-Guide-Activities)[Osprey Car Rentals](https://expedia.ca/Car-Rentals-In-Osprey.d55888.Car-Rental-Guide)[Osprey Vacation Packages](https://expedia.ca/Osprey.d55888.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495790-osprey.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Osprey, Florida from CA $187 ![](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 Osprey 5 Star Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-12&endDate=2025-10-13&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Osprey 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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/36b8ca60.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) ![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) ### The Ritz-Carlton, Sarasota Central Sarasota 9.2/10 Wonderful (1005) "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 $785 CA $978 total includes taxes & fees Nov 11 - Nov 12 [](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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/72c017f9.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) ### 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 $1,035 CA $1,257 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-Osprey-Hotels.s50-0-d55888.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Osprey-Hotels.s50-0-d55888.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 Osprey. ![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 $261 CA $329 total Oct 26 - Oct 27 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 $165 CA $187 total Oct 30 - Oct 31 includes taxes & fees 8.6/10 Excellent! (1,456 reviews) [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Art Ovation Hotel, Autograph Collection](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/w4000h2662x0y0-652c5c90_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Art Ovation Hotel, Autograph Collection 1255 North Palm Avenue, Sarasota, FL CA $268 CA $347 total Oct 26 - Oct 27 includes taxes & fees 9.2/10 Wonderful! (1,000 reviews) [](https://expedia.ca/Sarasota-Hotels-Art-Ovation-Hotel.h19900973.Hotel-Information) Still don't see what you're looking for? [See all properties in Osprey.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=55888&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=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=55888&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=55888&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=55888&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=55888&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=55888&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 Osprey Paddle through Oscar Scherer State Park's serene waterways where you might spot eagles, turtles, and alligators along the way. Nearby Sarasota's white-sand beaches and Myakka River State Park offer perfect day trips from this peaceful Gulf Coast community. [See all hotels in Osprey](https://www.expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28&adults=2®ionId=55888) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495790-osprey.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Osprey Hotel Reviews ## Find out more about Osprey ## Five Star Hotels in Osprey There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Osprey so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Osprey and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Osprey Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Osprey The results are in, and Osprey 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Osprey! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Osprey today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Osprey? > How much you pay for a 5-star hotel in Osprey can vary according to when you prefer to travel and how long you plan to be away, among other factors. Use our price per night filter and other search tools to find the best rate on a luxurious getaway. > > > > - Search for the lowest price per night from CA $187 ### What makes a hotel 5 stars in Osprey? > In Osprey, a hotel must offer a certain level of upscale features to earn 5 stars. These may include on-site gyms, gourmet restaurants, saunas and spas, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their outstanding service. You'll enjoy things like concierge services, in-room massages and nightly turn-down services. Some may also offer additional touches like a welcome gift. ### Are there any 5-star all-inclusive resorts in Osprey? > Use Expedia's filters to find an upscale getaway in Osprey where most of what you need is included. From there, refine your results for hotels that have 5 stars and are described as "All inclusive." The first thing on the schedule at these stays? 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