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) ![Great Heron](https://images.trvl-media.com/place/55888/92c919ca-2448-4c40-b1eb-f9207c3d50df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Osprey, FL - ![](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 Luxury Hotels Tonight [Nov 28 - Nov 29](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-28&endDate=2025-11-29&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 29 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-29&endDate=2025-11-30&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-28&endDate=2025-11-30&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-05&endDate=2025-12-07&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## 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) ![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 Suite](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/c4f21556.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 (1090) "Nice little get away spot, rooms are comfy and clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Busisiwe CA $231 CA $261 total includes taxes & fees Dec 1 - Dec 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) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/13100/13062/6bd84450.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/13100/13062/dc2b5b49.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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](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=2025-12-12&endDate=2025-12-13®ionId=55888&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_55888) ## Top Osprey Hotel Reviews ![Casey Key Resorts - Mainland](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9_y.jpg) ### Casey Key Resorts - Mainland 10/10 Excellent "Nice pool solid clean rooms quiet atmosphere" [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Hibiscus Suites - Gateway to Siesta Key](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/6ff58e07_y.jpg) ### Hibiscus Suites - Gateway to Siesta Key 10/10 Excellent "The room was perfect. It was a last minute trip just for a night, will definitely return. Staff was great!!" [](https://expedia.ca/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.Hotel-Information) ![Captiva Beach Resort](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375_y.jpg) ### Captiva Beach Resort 10/10 Excellent "This is great place to stay. Clean, amenities are great. The staff is super friendly. We borrow from them the beach bench to enjoy the sunset at their private beach. We love it!" [](https://expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information) ![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Not what I expected, smallish motel like. But nice and clean rooms with good ac and nice kitchenette. Small but cozy little pool. Beach very close. Is good for the price tbh." [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Spark by Hilton Sarasota Siesta Key Gateway](https://images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg) ### Spark by Hilton Sarasota Siesta Key Gateway 10/10 Excellent "Everything we needed with great value, the whole hotel was well maintained. Staff was friendly and helpful. The pool area is so relaxing even has a bar area to watch games and order drinks. The pool was heated and the jacuzzi was nice and hot. Just a shirt drive to the beaches and village. Beds are comfortable and the large TV was very nice." [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "Cute room, nice and large. Loved the balcony view. Right next to Sarasota airport. " [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![Hampton Inn & Suites Sarasota/Bradenton-Airport, FL](https://images.trvl-media.com/lodging/3000000/2860000/2853000/2852995/fc398fad_y.jpg) ### Hampton Inn & Suites Sarasota/Bradenton-Airport, FL 10/10 Excellent "Great staff, kept very clean, good location, staff seemed happy to be working and appeared to not be stressed out and had assistance. Good amenities. CLEAN SHEETS AND TOWELS" [](https://expedia.ca/Sarasota-Hotels-Hampton-Inn-Suites-SarasotaBradenton-Airport.h2852995.Hotel-Information) ![Lido Beach Resort](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "Ocean view and beach view. I'd do it again." [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Hyatt Place Sarasota/Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg) ### Hyatt Place Sarasota/Bradenton Airport 10/10 Excellent "Nice stay" [](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information) ## Frequently asked questions ### How much does a luxury hotel in Osprey cost? > Luxury hotel prices in Osprey vary, but you can find a great deal from CA $261 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates. ### What luxury activities and experiences are there in Osprey? > The best areas to stay in Osprey are along the Gulf of Mexico coastline, particularly around Casey Key Road and the adjacent mainland for luxury experiences. > > > > This area offers a refined coastal experience, with many high-end properties situated directly on the water or just a short stroll from private beach access. You'll find exclusive residential areas and boutique resorts here, providing a quiet and sophisticated setting. > > > > Couples looking for a private and serene getaway will find the properties along Casey Key Road particularly appealing. Many of these accommodations offer direct beach access, allowing for secluded walks and stunning sunset views over the Gulf. It's an ideal spot for those who appreciate privacy and the natural beauty of the coastline. > > > > For those seeking an active yet luxurious escape, staying near the waterfront on the mainland, close to areas like Blackburn Point Road, provides excellent access to water-based activities. You can easily arrange private boat charters, kayaking through the intercoastal waterways, or paddleboarding. ### How can I save on a luxury hotel in Osprey with Expedia? > There are plenty of ways to save on a luxury hotel in Osprey. Unlock our lowest prices by joining [One Key™](https://www.expedia.ca/welcome-one-key), Expedia's travel rewards program. It's free and easy to sign up, and you can access member perks too. Typically, booking in advance will help you save on your luxury hotel booking. If you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book a luxury Osprey hotel and flights as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### Can I cancel my luxury hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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