Title: Book the Best Osprey LUXURY Hotels - Upscale Hotels in Osprey, FL | Expedia.ca [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)[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) # Find luxury hotels in Osprey, FL ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Luxury Hotels Tonight [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-09-30&endDate=2025-10-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-01&endDate=2025-10-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Osprey Luxury Hotels ![Outdoor dining](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Suite](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/c4f21556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/68922696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Room](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/b68095b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casey Key Resorts - Mainland Osprey 8.6/10 Excellent (1049) "Great location, friendly staff." CA $155 CA $175 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/13100/13062/54080f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/13100/13062/dc2b5b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/13100/13062/ec2878ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/1000000/20000/13100/13062/8911b765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bentley's Boutique Hotel, BW Premier Collection Osprey 8.6/10 Excellent (1000) "Check in was backed up a bit at 7:00 p.m. Room was nice. Bar area outside was enjoyable with live music..drinks..the bright moon. Enjoyed the pool ...good temperature. Breakfast was good. Love the Coffee machine in the lobby area." [](https://www.expedia.ca/Osprey-Hotels-Bentleys-Boutique-Hotel.h13062.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-14&endDate=2025-10-15®ionId=55888&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Osprey Hotel Reviews ![Hyatt Place Sarasota/Bradenton Airport](//images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg) ### Hyatt Place Sarasota/Bradenton Airport 10/10 Excellent "All was excellent 👍" [](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information) ![Casey Key Resorts - Mainland](//images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9_y.jpg) ### Casey Key Resorts - Mainland 10/10 Excellent "Clean room , friendly staff . " [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Lido Beach Resort](//images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "Loved our stay, beautiful amenities that are staffed with great people, the Tiki bar on the beach - chairside service, adult pool for those that prefer quieter swims - easy rinse station at the beach entrance- breakfast in-house with a stunning view Shopping circle a 10 min walk or 2 min drive away Nothing here I didn't love " [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![DoubleTree by Hilton Sarasota Bradenton Airport](//images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg) ### DoubleTree by Hilton Sarasota Bradenton Airport 10/10 Excellent "We flew in for a quick two nights and this was convenient and nice so we booked it. The staff was friendly and helpful and breakfast at the restaurant was great! Compton was awesome!" [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Tropical Beach Resorts](//images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Nice quiet parking spot in front of room 2 minutes from beach definitely if I came back to Siesta Key I would come back here.." [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Tropical Breeze Resort](//images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg) ### Tropical Breeze Resort 10/10 Excellent "Great place! Come here everytime we come to Siesta Key. So glad they opened back up after the hurricane. Its beautiful!" [](https://expedia.ca/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.Hotel-Information) ![Spark by Hilton Sarasota Siesta Key Gateway](//images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg) ### Spark by Hilton Sarasota Siesta Key Gateway 10/10 Excellent "WE loved the location very close to where we wanted to go The set up was very comfortable and the staff were very friendly" [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![Golden Host Resort - Sarasota](//images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "Good price " [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![voco Sarasota by IHG](//images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/dc3c2bf5_y.jpg) ### voco Sarasota by IHG 10/10 Excellent "Enjoyed our stay at the property. It was very clean and safe. Staff extremely helpful and friendly. " [](https://expedia.ca/Sarasota-Hotels-Voco-Sarasota.h1577382.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your stay in Osprey? > Use Expedia and let us help you arrange a flight to Sarasota-Bradenton Intl. Airport (SRQ) airport, and then select from different places to stay that will deliver the luxury you want. Amenities are important when you plan a vacation, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel that has a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Osprey has to offer. During your visit, you might want to enjoy the restaurants and bars which Osprey is known for. ### When can I expect good weather in Osprey? > Planning for the weather is a good way to make your trip to Osprey relaxing and enjoyable, especially when you're splurging. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 66°F. Average annual precipitation for Osprey is 44 inches. ### What's there to see and do in Osprey? > Enjoy all that Osprey has to offer and visit Oscar Scherer State Park, Turtle Beach, and Nokomis Beach. 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