Title: 4 Stars Hotels in Osprey, Florida from CA $187 - 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 $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 4 Star Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-15&endDate=2025-10-16&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-24&endDate=2025-10-26&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) ![Outdoor pool](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/9034aec0.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/b7bacdeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Sarasota Central Sarasota 9.0/10 Wonderful (1106) "Very nice stay" CA $261 CA $330 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/336c148c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Sarasota Bradenton Airport Sarasota 8.8/10 Excellent (1463) "Staff was amazing the rooms were cozy and comfy!" CA $166 CA $187 total includes taxes & fees Oct 30 - Oct 31 [](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) ![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) ![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) ### Art Ovation Hotel, Autograph Collection Central Sarasota 9.4/10 Exceptional (1002) "Great hotel with art in the lobby, artists in residence, phenomenal service and located near restaurants and bars." CA $268 CA $347 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/0566c4a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lido Beach Resort Lido Key 8.8/10 Excellent (1009) "Great stay!" CA $378 CA $490 total includes taxes & fees Oct 15 - Oct 16 [](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) ![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) ![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) ### Legacy Hotel at IMG Academy Bradenton 9.0/10 Wonderful (900) "Great place to stay for campus visit. " CA $208 CA $275 total includes taxes & fees Nov 12 - Nov 13 [](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) ![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) ![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) ### Zota Beach Resort Longboat Key 9.0/10 Wonderful (1005) "Great place" CA $274 CA $373 total includes taxes & fees Oct 30 - Oct 31 [](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) ![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) ![Breakfast, lunch, dinner served; local and international cuisine ](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/7017aba3.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) ### The Sarasota Modern, a Tribute Portfolio Hotel Central Sarasota 8.0/10 Very good (512) "Really nice stylish hotel, enjoyed it " CA $261 CA $335 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/d465f7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/8c24890a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cirque St. Armands Beachside Lido Key 8.4/10 Very good (1007) "Beautiful hotel. Stunning views from the ocean view rooms. Pool area lovely and the restaurant very nice. Staff extremely helpful " CA $378 CA $482 total includes taxes & fees Oct 15 - Oct 16 [](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/115000000/114190000/114189500/114189452/9d53ae34.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) ![Signature Room](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/1e7203ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SeaSpray Resort Siesta Key 9.4/10 Exceptional (49) "Pleasant stay, walk to beach and the Village. Good size mini apartment " CA $321 CA $363 total includes taxes & fees Oct 20 - Oct 21 [](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) ![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) ![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) ![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 (683) "The property offers exceptionally clean rooms and attentive staff who ensure a comfortable stay. Highly recommend!" CA $546 CA $680 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, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/ed4ab08b.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) ![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) ### Bradenton Apartments by Landing Bradenton 7.6/10 Good (47) "Perfect place " [](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/113000000/112390000/112387400/112387358/4fdb1405.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) ![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/105c6d3d.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 $98 CA $741 total includes taxes & fees Oct 15 - Oct 16 [](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) | Outdoor dining](https://images.trvl-media.com/lodging/92000000/91350000/91348800/91348780/a2745eaf.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) ### 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) ![House, Multiple Beds (Bungalow 1) | Private kitchen](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/d4e66e3c.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) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129823/fb7b9d0e.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) ![Exterior](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129823/eb840da4.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 | Private kitchen](https://images.trvl-media.com/lodging/94000000/93870000/93862600/93862595/99d4d8c8.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) ![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) ![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 nearby, white sand, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/67000000/66890000/66883300/66883249/da89a02e.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) ### 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) ![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) ![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 | 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 $128 CA $422 total includes taxes & fees Oct 15 - Oct 16 [](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/97000000/96450000/96444100/96444007/9742cd7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Partial Ocean View (100) | Private kitchen](https://images.trvl-media.com/lodging/97000000/96450000/96444100/96444007/7b3fe600.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) ### 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/67000000/66890000/66882800/66882768/61587577.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) ### 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 $786 CA $980 total Nov 12 - Nov 13 includes taxes & fees 9/10 Wonderful! (1,002 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 $1,037 CA $1,259 total Oct 20 - Oct 21 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=15%2F10%2F2025&endDate=16%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=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=55888&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%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=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=55888&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=55888&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%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=2025-10-28&endDate=2025-10-29&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 ![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 "Room was clean and staff was great" [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![The Westin Sarasota](//images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg) ### The Westin Sarasota 10/10 Excellent "A wonderful compact property right near the water. Close to downtown and Marina Jack's. Spa is great. Roof top pool is very nice, views are insane. Would recommend this property. " [](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 "The property is situated right on the beach. Very well maintained hotel with all the amenities possible. Staff is friendly and helpful! " [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.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 "ALL was great other than their pillows (super uncomfortable and flat) & they need to improve on overall appearance of rooms like the bed head board/furniture were damaged and bathroom lighting was terrible! AC were loud and turned off when your sleeping. Highly recommend to turn off the eco-motion sensors for guest comfort with the FL Heat. Overall, The staff are incredible & the service was great. " [](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 $980 ### 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. A 5-star hotel will go above and beyond to make your stay an even more lavish and unforgettable one. 24-hour front desk, luxurious spas and gourmet dining are only the start of the exclusive conveniences and services you'll likely get access to. ## 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) - [3 Star Hotels in North Sarasota](https://www.expedia.ca/3Star-North-Sarasota-Sarasota-Hotels.s30-n553248635975847442-0.Travel-Guide-Filter-Hotels) - 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