Title: 5 Stars Hotels in Osprey, Florida from CA $207 - 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) ![Great Heron](https://images.trvl-media.com/place/55888/92c919ca-2448-4c40-b1eb-f9207c3d50df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Osprey, Florida from CA $207 - ![](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 [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-29&endDate=2025-12-30&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-30&endDate=2025-12-31&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-09&endDate=2026-01-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![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 [](https://www.expedia.ca/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 CA $894 CA $1,099 total includes taxes & fees Jan 28 - Jan 29, 2026 [](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, 3 Bedrooms, Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/4e06c5f1.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) ### 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 (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 CA $1,489 CA $1,783 total includes taxes & fees Jan 4 - Jan 5, 2026 [](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 $450 CA $542 total Jan 5 - Jan 6, 2026 includes taxes & fees 9/10 Wonderful! (1,155 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 $183 CA $207 total Jan 5 - Jan 6, 2026 includes taxes & fees 8.6/10 Excellent! (1,531 reviews) [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Lido Beach Resort](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Lido Beach Resort 700 Benjamin Franklin Dr Sarasota FL CA $381 CA $493 total Jan 6 - Jan 7, 2026 includes taxes & fees 8.8/10 Excellent! (1,002 reviews) [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.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=30%2F12%2F2025&endDate=31%2F12%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=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=55888&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=55888&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=55888&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=55888&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F12%2F2025&endDate=31%2F12%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=2026-01-12&endDate=2026-01-13&adults=2®ionId=55888) ![Great Heron](https://images.trvl-media.com/place/55888/92c919ca-2448-4c40-b1eb-f9207c3d50df.jpg?impolicy=fcrop&w=900&h=582&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? > - Search for the lowest price per night from CA $207 ### What makes a hotel 5 stars in Osprey? ### Are there any 5-star all-inclusive resorts in Osprey? ## Explore a world of travel with Expedia - Lodging - 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 Bradenton ](https://www.expedia.ca/3Star-Bradenton-Hotels.s30-0-d6020.Travel-Guide-Filter-Hotels) - 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