Title: 4 Stars Hotels in Osprey, Florida from CA $186 - Find Cheap Osprey Hotels With 4 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) # 4 Stars Hotels in Osprey, Florida from CA $186 ![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 4 Star Hotels Tonight [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-09-30&endDate=2025-10-01&adults=2&star=40&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&star=40&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&star=40&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&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Osprey 4 Star Hotels ![Serves lunch and dinner](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/764fdfc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/b7bacdeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/9034aec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Sarasota Central Sarasota 9.0/10 Wonderful (1090) "Very nice stay" CA $212 CA $274 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/406757f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/336c148c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, pay movies](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/b3010c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Sarasota Bradenton Airport Sarasota 8.8/10 Excellent (1446) "Amazing hotel" CA $164 CA $186 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/w4000h2662x0y0-652c5c90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/8c483fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, rooftop bar, lobby lounge](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/b1f69e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/3c9a9299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Ovation Hotel, Autograph Collection Central Sarasota 9.4/10 Exceptional (1012) "Great hotel with art in the lobby, artists in residence, phenomenal service and located near restaurants and bars." CA $249 CA $325 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Sarasota-Hotels-Art-Ovation-Hotel.h19900973.Hotel-Information) ![2 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/9d02e259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/74878f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/e35264a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lido Beach Resort Lido Key 8.8/10 Excellent (1016) "Great stay!" CA $346 CA $454 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/80dcbca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/ea63899d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/b6421168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/460d3141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legacy Hotel at IMG Academy Bradenton 9.0/10 Wonderful (896) "Great place to stay for campus visit. " CA $191 CA $250 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Sarasota-Hotels-Legacy-Hotel-At-IMG-Academy.h22882236.Hotel-Information) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/277458de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, Pool View](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/b9b12d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/94d8d980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/928bedb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zota Beach Resort Longboat Key 9.0/10 Wonderful (1001) "An amazing waterfront hotel, kind staff , clean and modern room " CA $277 CA $376 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information) ![3 outdoor pools, open 9:00 AM to 9:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/f22dde90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/e7fd7d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/3a54adfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Kitchen | View from room](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/29bd68d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sarasota Modern, a Tribute Portfolio Hotel Central Sarasota 8.0/10 Very good (510) "Really nice stylish hotel, enjoyed it " CA $200 CA $265 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Sarasota-Hotels-The-Sarasota-Modern.h27704596.Hotel-Information) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/b91ee19c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/d465f7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/97400825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/acedd7db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cirque St. Armands Beachside Lido Key 8.4/10 Very good (1006) "Beach View" CA $346 CA $446 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Sarasota-Hotels-Holiday-Inn-Lido-Beach.h22224.Hotel-Information) ![Deluxe Suite, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/62be52d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Room](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/1e7203ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | Terrace/patio](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/be5906a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/c5bfb01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SeaSpray Resort Siesta Key 9.4/10 Exceptional (43) "Our stay was beautiful this hotel. Staff were very great. Customer service was great." CA $346 CA $392 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Siesta-Key-Hotels-SeaSpray-Resort.h114189452.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/27600/27542/97bea551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/27600/27542/7d651380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/1000000/30000/27600/27542/492e9797.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/30000/27600/27542/80c7e20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Resort at Longboat Key Club Longboat Key 9.0/10 Wonderful (677) "The property offers exceptionally clean rooms and attentive staff who ensure a comfortable stay. Highly recommend!" CA $541 CA $675 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Sarasota-Hotels-The-Resort-At-Longboat-Key-Club.h27542.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/w2398h1348x2y6-214d5e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/2ec0e483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/0104cf78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/daf3f4ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bradenton Apartments by Landing Bradenton 7.4/10 Good (45) "Absolutely beautiful location has everything you need n makes you feel like home" [](https://www.expedia.ca/Bradenton-Hotels-Barsala-At-Champions-Walk.h108753056.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/08b5bced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/105c6d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/4fdb1405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/aa27a0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chadwick Cove Resort & Marina Englewood 10/10 Exceptional (14) "Great place and location " CA $97 CA $735 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information) ![Condo, Multiple Beds, Ocean View (604-E) | Beach](https://images.trvl-media.com/lodging/92000000/91350000/91348800/91348780/6720121f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, Multiple Beds, Ocean View (604-E) | Interior](https://images.trvl-media.com/lodging/92000000/91350000/91348800/91348780/ef01174f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, Multiple Beds, Ocean View (604-E) | Private kitchen](https://images.trvl-media.com/lodging/92000000/91350000/91348800/91348780/b64c98db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, Multiple Beds, Ocean View (604-E) | Outdoor dining](https://images.trvl-media.com/lodging/92000000/91350000/91348800/91348780/a2745eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Our House at the Beach 604E by Beachside Siesta Key 8.4/10 Very good (6) "We had wonderful time " [](https://www.expedia.ca/Siesta-Key-Hotels-Our-House-At-The-Beach-604E-By-Beachside.h91348780.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/b7daa6c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Condo, 2 Bedrooms, Pool Access](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/834ba8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Condo, 2 Bedrooms, Pool Access | Private kitchen](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/570b1753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds (Bungalow 1) | Private kitchen](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/c6251ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Paradise by Beachside Management South Village 10/10 Exceptional (2) "Beach was nearby.. Front office were great!! Everything was waslkable. Did not have too touch car." [](https://www.expedia.ca/Siesta-Key-Hotels-Hidden-Paradise-By-Beachside-Management.h101003898.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129823/29059d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129823/eb840da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129823/32082a8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129823/f6124d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Key Luxury Bayfront Home Steps from the World's Finest Beaches Siesta Key 9.8/10 Exceptional (34) "Enjoyed the house and the area. Did some fishing from the dock and the kids enjoyed the pool." [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Luxury-Bayfront-Home-Steps-From-The-Worlds-Finest-Beaches.h27129823.Hotel-Information) ![House, Multiple Beds (Vue B) | Beach](https://images.trvl-media.com/lodging/94000000/93870000/93862600/93862595/w1799h1199x1y1-251e8487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, 3 Bedrooms, Pool Access](https://images.trvl-media.com/lodging/94000000/93870000/93862600/93862595/w1800h1199x0y1-93912ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, 3 Bedrooms, Pool Access | Private kitchen](https://images.trvl-media.com/lodging/94000000/93870000/93862600/93862595/99d4d8c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds (Vue B) | Exterior](https://images.trvl-media.com/lodging/94000000/93870000/93862600/93862595/e6d7868c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Vue By Beachside Management Siesta Key 10/10 Exceptional (3) "It was a beautiful home and clean and very close to the beach!" [](https://www.expedia.ca/Siesta-Key-Hotels-Ocean-Vue-By-Beachside-Management.h93862595.Hotel-Information) ![Condo (Beach Club at Siesta Key Poolside D) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66883300/66883249/46f274c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66890000/66883300/66883249/9d21ae8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Beach Club at Siesta Key Poolside D) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66883300/66883249/3d950c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Beach Club at Siesta Key Poolside D) | Private kitchen](https://images.trvl-media.com/lodging/67000000/66890000/66883300/66883249/43017915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Club at Siesta Key Poolside D South Village 9.4/10 Exceptional (3) "Nice getaway. " [](https://www.expedia.ca/Sarasota-Hotels-Beach-Club-At-Siesta-Key-Poolside-D.h66883249.Hotel-Information) ![Deluxe Villa | Living area](https://images.trvl-media.com/lodging/116000000/115140000/115131000/115130957/w1270h862x20y1-2157a508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115140000/115131000/115130957/w1286h850x4y0-d4db1721.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115140000/115131000/115130957/600d6329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa | Private kitchen](https://images.trvl-media.com/lodging/116000000/115140000/115131000/115130957/w1286h860x4y2-e6289e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bradenton Breeze West Samoset 6.0/10 (2) "It was good! " CA $158 CA $454 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Bradenton-Hotels-Bradenton-Breeze.h115130957.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/97000000/96450000/96444100/96444007/c96ed58f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Partial Ocean View (100) | Living area](https://images.trvl-media.com/lodging/97000000/96450000/96444100/96444007/bf50475e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Partial Ocean View (100) | Living area](https://images.trvl-media.com/lodging/97000000/96450000/96444100/96444007/6559a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Partial Ocean View (100) | Living area](https://images.trvl-media.com/lodging/97000000/96450000/96444100/96444007/9742cd7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside of the Village by Beachside Siesta Key Village 9.6/10 Exceptional (4) "Loved how close it was to the beach and siesta village. My family really enjoyed everything about this property. " [](https://www.expedia.ca/Siesta-Key-Hotels-Beachside-Of-The-Village-By-Beachside.h96444007.Hotel-Information) ![Condo (House of Sun Siesta Key Crescent Beac) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882800/66882768/30fdbf70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (House of Sun Siesta Key Crescent Beac) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882800/66882768/f5385106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (House of Sun Siesta Key Crescent Beac) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882800/66882768/6fdcf274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (House of Sun Siesta Key Crescent Beac) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882800/66882768/61587577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House of The Sun Siesta Key Crescent Beach South Village 8.0/10 Very good (2) "The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . " [](https://www.expedia.ca/Sarasota-Hotels-House-Of-Sun-Siesta-Key-Crescent-Beach.h66882768.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%2F4Star-Osprey-Hotels.s40-0-d55888.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Osprey-Hotels.s40-0-d55888.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Osprey. ![The Ritz-Carlton, Sarasota](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/90558b2d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Ritz-Carlton, Sarasota 1111 Ritz Carlton Dr, Sarasota, FL CA $764 CA $954 total Oct 1 - Oct 2 includes taxes & fees 9/10 Wonderful! (1,006 reviews) [](https://expedia.ca/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) ![The St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/1e787841_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The St. Regis Longboat Key Resort 1601 Gulf Of Mexico Drive, Longboat Key, FL CA $917 CA $1,123 total Oct 1 - Oct 2 includes taxes & fees 9.6/10 Exceptional! (49 reviews) [](https://expedia.ca/Longboat-Key-Hotels-The-St-Regis-Longboat-Key-Resort.h5487.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=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=55888&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=55888&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=55888&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=55888&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=55888&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F10%2F2025&endDate=02%2F10%2F2025®ionId=55888&star=40&star=40&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=2025-10-14&endDate=2025-10-15&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 ![The Westin Sarasota](//images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg) ### The Westin Sarasota 10/10 Excellent "This is a valet only type of downtown hotel that offers a rooftop pool for a quick dip or fabulous sunset views. The whole hotel and the rooms are clean and well cared for. The staff anticipated your every need and the food from the rooftop bar to the on-site restaurant is top notch. An incredible deal to stay in the middle of all the action in downtown Sarasota." [](https://expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.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) ![Art Ovation Hotel, Autograph Collection](//images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/w4000h2662x0y0-652c5c90_y.jpg) ### Art Ovation Hotel, Autograph Collection 10/10 Excellent "Service was excellent" [](https://expedia.ca/Sarasota-Hotels-Art-Ovation-Hotel.h19900973.Hotel-Information) ## Find out more about Osprey If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Osprey are calling your name. Known for providing first-rate service in amazing locations, each of the Osprey 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Osprey. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Osprey, Florida, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Osprey hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### What are the best 4-star hotels in Osprey? > Kick back in comfortable luxury at [Siesta Key Palms Resort](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information). According to reviews by travellers, this is one of Osprey's popular 4-star hotels. ### How much does it cost to stay in a 4-star hotel in Osprey? > To book a 4-star hotel in Osprey that's within your budget, make use of Expedia's filter tool. Check out what's available during your preferred dates and use our pricing filter to set your maximum rate. You can also list your results by the most economical stay first. > > > > - Search for the lowest price from CA $954 ### What's the difference between 5-star and 4-star hotels in Osprey? > Give yourself the luxury treatment during your Osprey vacation by staying at a 4-star hotel. As well as featuring upmarket surroundings, these properties are typically packed with amenities such as complimentary bathrobes, large beds and plenty more. 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