Title: The Best 4 Star Hotels in Osprey, FL from $157 | Expedia.com [Osprey Travel Guide](https://expedia.com/Osprey.dx55888)[Hotels in Osprey](https://expedia.com/Osprey-Hotels.d55888.Travel-Guide-Hotels)[Vacation Rentals in Osprey](https://expedia.com/Osprey-Vacation-Rentals.d55888.Travel-Guide-VacationRentals)[Flights to Osprey](https://expedia.com/Cheap-Flights-To-Osprey.d55888.Travel-Guide-Flights)[Things to do in Osprey](https://expedia.com/Things-To-Do-In-Osprey.d55888.Travel-Guide-Activities)[Car Rentals in Osprey](https://expedia.com/Car-Rentals-In-Osprey.d55888.Car-Rental-Guide)[Osprey Vacation Packages](https://expedia.com/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) ![](https://images.trvl-media.com/place/55888/92c919ca-2448-4c40-b1eb-f9207c3d50df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 [Mar 16 - Mar 17](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-03-16&endDate=2026-03-17&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 17 - Mar 18](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-03-17&endDate=2026-03-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-03-20&endDate=2026-03-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=55888&startDate=2026-03-27&endDate=2026-03-29&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Osprey 4-star hotels ![Property amenity](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/2384a13f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/c9bc57e8.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 [](https://www.expedia.com/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information) Central Sarasota 9.0/10 Wonderful (1,193 reviews) "Clean friendly staff, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra $331 nightly $374 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/adc14854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/86d1825b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/3517c29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Sarasota Bradenton Airport [](https://www.expedia.com/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) Sarasota 8.8/10 Excellent (1,578 reviews) "Our stay was excellent- room was clean and amenities were abundant - warm cookies at check in, dinner on property was reasonable and delicious. Would definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen $139 nightly $157 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d0399e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/9b658401.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) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/74878f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lido Beach Resort [](https://www.expedia.com/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) Lido Key 8.8/10 Excellent (1,002 reviews) "Beautiful resort and sunsets!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina $529 nightly $598 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/31e6e20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/094a6663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast (USD 18.00 per person)](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/ef052367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/c1b0fd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legacy Hotel at IMG Academy [](https://www.expedia.com/Sarasota-Hotels-Legacy-Hotel-At-IMG-Academy.h22882236.Hotel-Information) Bradenton 9.0/10 Wonderful (969 reviews) "Very nice hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bernard $259 nightly $293 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-Legacy-Hotel-At-IMG-Academy.h22882236.Hotel-Information) ![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) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/af42aafa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/07d4eefb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/79a4b428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zota Beach Resort [](https://www.expedia.com/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information) Longboat Key 9.0/10 Wonderful (1,006 reviews) "Yes absolutely perfect getaway. Super clean everywhere.. super friendly staff.. good food " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Corey $345 nightly $390 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/93021f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/04230bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Room | Pillowtop beds, minibar, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/21b61591.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) ### Casey Key Resorts - Mainland [](https://www.expedia.com/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) Osprey 8.8/10 Excellent (1,137 reviews) "The rooms were so clean, the staff were outstanding and we really enjoyed the poolside room with a table and chairs on our patio. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Althea $210 nightly $237 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Room, 1 King Bed, Ocean View | Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/a1349b0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/d63fa866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/670a9e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/22300/22224/76ce0480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cirque St. Armands Beachside [](https://www.expedia.com/Sarasota-Hotels-Cirque-St-Armands-Beachside.h22224.Hotel-Information) Lido Key 8.6/10 Excellent (1,009 reviews) "Wonderful staff, excellent location and the perfect size. Loved this hotel, it will be our choice for all upcoming trips to Sarasota." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David $404 nightly $456 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-Cirque-St-Armands-Beachside.h22224.Hotel-Information) ![Outdoor pool, open 7:00 AM to 7:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/6c79dcd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/9e488af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, rooftop bar, lobby lounge](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/894b7c58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/49b22d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Ovation Hotel, Autograph Collection [](https://www.expedia.com/Sarasota-Hotels-Art-Ovation-Hotel.h19900973.Hotel-Information) Central Sarasota 9.4/10 Exceptional (1,002 reviews) "Nice hotel great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SHELLEY $299 nightly $338 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-Art-Ovation-Hotel.h19900973.Hotel-Information) ![Breakfast, lunch, dinner served; local and international cuisine ](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/3763f29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/28000000/27710000/27704600/27704596/698bb636.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/28000000/27710000/27704600/27704596/7122f3cb.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 [](https://www.expedia.com/Sarasota-Hotels-The-Sarasota-Modern.h27704596.Hotel-Information) Central Sarasota 8.2/10 Very Good (533 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara $190 nightly $215 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-The-Sarasota-Modern.h27704596.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27600/27542/12e41aae.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/1000000/30000/27600/27542/2ba8ee89.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/1000000/30000/27600/27542/00505e30.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 [](https://www.expedia.com/Sarasota-Hotels-The-Resort-At-Longboat-Key-Club.h27542.Hotel-Information) Longboat Key 9.0/10 Wonderful (699 reviews) "yes" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALAN $599 nightly $677 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-The-Resort-At-Longboat-Key-Club.h27542.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/105c6d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/7dab4f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/3e26fcd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Private kitchen | Full-size fridge, microwave, oven, stovetop](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 [](https://www.expedia.com/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information) Manasota Key 10/10 Exceptional (17 reviews) "Great place and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathy $641 nightly $694 total Mar 20 - Mar 21 Total with taxes and fees [](https://www.expedia.com/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.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) ![Exterior](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/4f87f0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living room | TV](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/455b2f06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | Living room | TV](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/017af173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bradenton Apartments by Landing [](https://www.expedia.com/Bradenton-Hotels-Barsala-At-Champions-Walk.h108753056.Hotel-Information) Bradenton 7.4/10 Good (58 reviews) "Perfect place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) chavelys [](https://www.expedia.com/Bradenton-Hotels-Barsala-At-Champions-Walk.h108753056.Hotel-Information) ![House, Multiple Beds (Bungalow 1) | Beach](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/0d7232c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Condo, 2 Bedrooms, Pool Access | Living room](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/d33c141c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds (Bungalow 1) | Outdoor dining](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/1cc6544e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds (Bungalow 1) | Exterior detail](https://images.trvl-media.com/lodging/102000000/101010000/101003900/101003898/8e57db2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Paradise by Beachside Management [](https://www.expedia.com/Siesta-Key-Hotels-Hidden-Paradise-By-Beachside-Management.h101003898.Hotel-Information) South Village 10/10 Exceptional (4 reviews) "Close to the beach and clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike Allen [](https://www.expedia.com/Siesta-Key-Hotels-Hidden-Paradise-By-Beachside-Management.h101003898.Hotel-Information) ![House, Multiple Beds (Vue B) | Beach | Beach nearby, white sand](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 | 3 bedrooms, individually decorated, individually furnished](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) | Living area | 32-inch TV with cable channels](https://images.trvl-media.com/lodging/94000000/93870000/93862600/93862595/w1800h1199x0y1-e4aa9864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds (Vue B) | Exterior](https://images.trvl-media.com/lodging/94000000/93870000/93862600/93862595/6ccbf680.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Vue By Beachside Management [](https://www.expedia.com/Siesta-Key-Hotels-Ocean-Vue-By-Beachside-Management.h93862595.Hotel-Information) Siesta Key 10/10 Exceptional (3 reviews) "It was a beautiful home and clean and very close to the beach!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malisa [](https://www.expedia.com/Siesta-Key-Hotels-Ocean-Vue-By-Beachside-Management.h93862595.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/121000000/120460000/120453700/120453692/9f50a253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120460000/120453700/120453692/7a0cda88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Condo, 2 Bedrooms, Balcony, Lagoon View | Living area](https://images.trvl-media.com/lodging/121000000/120460000/120453700/120453692/w1024h682x0y1-3f469a5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Condo, 2 Bedrooms, Balcony, Lagoon View | Living area](https://images.trvl-media.com/lodging/121000000/120460000/120453700/120453692/cb9b9963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anchorage Resort [](https://www.expedia.com/Siesta-Key-Hotels-Anchorage-Resort.h120453692.Hotel-Information) South Village [](https://www.expedia.com/Siesta-Key-Hotels-Anchorage-Resort.h120453692.Hotel-Information) ![Beach nearby, white sand, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/67000000/66890000/66883300/66883249/c177b12e.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/da2c5654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66883300/66883249/22459dac.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) ### Beach Club at Siesta Key Poolside D [](https://www.expedia.com/Sarasota-Hotels-Beach-Club-At-Siesta-Key-Poolside-D.h66883249.Hotel-Information) South Village 9.4/10 Exceptional (3 reviews) "Nice getaway. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff $912 nightly $1,025 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-Beach-Club-At-Siesta-Key-Poolside-D.h66883249.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/67000000/66890000/66882800/66882768/151dbd0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882800/66882768/47cfbc1e.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/d411e3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House of The Sun Siesta Key Crescent Beach [](https://www.expedia.com/Sarasota-Hotels-House-Of-Sun-Siesta-Key-Crescent-Beach.h66882768.Hotel-Information) South Village 8.0/10 Very Good (2 reviews) "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 . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret Theresa $998 nightly $1,122 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Sarasota-Hotels-House-Of-Sun-Siesta-Key-Crescent-Beach.h66882768.Hotel-Information) ![On the beach, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/16000000/15610000/15603000/15602940/5912b755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool-Side Condo | Living area | Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/16000000/15610000/15603000/15602940/5c89b147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15610000/15603000/15602940/2044f88e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/16000000/15610000/15603000/15602940/6e669eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Del Mar Longboat Key [](https://www.expedia.com/Sarasota-Hotels-Casa-Del-Mar-Longboat-Key.h15602940.Hotel-Information) Longboat Key 9.4/10 Exceptional (159 reviews) "Great value, with easy access to beautiful beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy [](https://www.expedia.com/Sarasota-Hotels-Casa-Del-Mar-Longboat-Key.h15602940.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99570000/99566300/99566262/8b3e9756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/100000000/99570000/99566300/99566262/a5124d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99570000/99566300/99566262/c81651c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99570000/99566300/99566262/18175c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coastal Paradise Condo [](https://www.expedia.com/Siesta-Key-Hotels-Coastal-Paradise-Condo.h99566262.Hotel-Information) South Village 8.6/10 Excellent (4 reviews) "The condo was great. Clean, neighborhood was clean and safe. Was walking distance to the beach. Less than 10 min walk from the condo to the water. Kitchen well equipped. Property has a washer and dryer in common area. But you need quarters. There were 5 of us. It was big enough for all of us to be comfortable. Near walking distance to restaurants and some shopping. Short drive to anything else you need. I would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sergio [](https://www.expedia.com/Siesta-Key-Hotels-Coastal-Paradise-Condo.h99566262.Hotel-Information) ![Premier Condo | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100870000/100862900/100862818/b7942e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/101000000/100870000/100862900/100862818/w2044h1324x6y4-fcc07c5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100870000/100862900/100862818/dcb9909e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Condo | Living room | 40-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/101000000/100870000/100862900/100862818/972dc22c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Key [](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Key.h100862818.Hotel-Information) Siesta Key 10/10 Exceptional (6 reviews) "The property was well taken care of, well stocked, and just overall lovely. We enjoyed it very much!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John [](https://www.expedia.com/Siesta-Key-Hotels-Siesta-Key.h100862818.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.com/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.com/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 St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/6b2968af_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The St. Regis Longboat Key Resort 1601 Gulf Of Mexico Drive Longboat Key FL $1,434 nightly $1,620 total Apr 6 - Apr 7 Total with taxes and fees 9.8/10 Exceptional! (64 reviews) [](https://expedia.com/Longboat-Key-Hotels-The-St-Regis-Longboat-Key-Resort.h5487.Hotel-Information) ![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 $737 nightly $832 total Apr 15 - Apr 16 Total with taxes and fees 9.2/10 Wonderful! (1,001 reviews) [](https://expedia.com/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) Still don't see what you're looking for? [See all properties in Osprey.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F17%2F2026&endDate=3%2F18%2F2026®ionId=55888&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F17%2F2026&endDate=3%2F18%2F2026®ionId=55888&star=40&star=40&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F17%2F2026&endDate=3%2F18%2F2026®ionId=55888&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F17%2F2026&endDate=3%2F18%2F2026®ionId=55888&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F17%2F2026&endDate=3%2F18%2F2026®ionId=55888&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F17%2F2026&endDate=3%2F18%2F2026®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.com/Hotel-Search?startDate=2026-03-30&endDate=2026-03-31&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 ![Casey Key Resorts - Mainland](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/93021f2f_y.jpg) ### Casey Key Resorts - Mainland 8/10 Good "The pool was enjoyable" [](https://expedia.com/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![DoubleTree by Hilton Sarasota Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg) ### DoubleTree by Hilton Sarasota Bradenton Airport 10/10 Excellent "yes the room was excellent, slept really good." [](https://expedia.com/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Legacy Hotel at IMG Academy](https://images.trvl-media.com/lodging/23000000/22890000/22882300/22882236/31e6e20e_y.jpg) ### Legacy Hotel at IMG Academy 4/10 Poor "The price of legacy is a resort price. but there is not enough pool chairs, they didn't light the firepits last night because the propane was out, the towels in the room are very thin and cheap. the restaurant is nice and convenient but closes at 10pm. and the hotel is isolated on the IMG campus, so you couldn't close the restaurant so early. they have a captive audience of teams coming to play in tournaments. but the hotel really should be so much nicer for the price" [](https://expedia.com/Sarasota-Hotels-Legacy-Hotel-At-IMG-Academy.h22882236.Hotel-Information) ![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/2384a13f_y.jpg) ### The Westin Sarasota 6/10 Okay "The hotel is in a great area… and I could tell that it had once been lovely… but it’s showing signs of age: stains, cracks, and water that just doesn’t get hot enough. The room configuration was awkward with not nearly enough storage space. And, while the bed was comfortable, the pillows were lifeless, flat, and floppy…and the comforter much (!!!) too heavy. It was more like a weighted blanket than something for sleeping. I could barely pull it up or down (and I work out 4 days a week… I’m no weakling). The gym was good. The staff was helpful. Sadly though, I’ll check out someplace else next time I’m in Sarasota." [](https://expedia.com/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information) ![Lido Beach Resort](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d0399e0e_y.jpg) ### Lido Beach Resort 10/10 Excellent "Beginning the day before we arrived, the staff was so attentive. They accommodated my last minute request for a dinner reservation, and the location for our room. We stayed on the upper level of the Tiki Tower. Room was spacious. Housekeeping great. We would have loved a balcony, but we booked late and only Tiki Tower rooms were available. The motel style entrance was different from what we’re used to, but it worked out fine. Easy access to pool, lobby, Tiki Bar, and beach. Pool area had plenty of chairs, and excellent food/beverage service. Lots of umbrellas for shade too. Music was even great! Beach was lovely, but there was a large pipe running the length of the beach. So you can’t see the water from the beach chairs. You can still walk over the pipe to the shoreline. Beautiful sunset views and dolphins too. We ate at Tiki Bar and Drift - both excellent. The live music at the beach near Tiki Bar was fun too. The shuttle to and from St Armand’s was also super convenient. " [](https://expedia.com/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Zota Beach Resort](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/928bedb0_y.jpg) ### Zota Beach Resort 10/10 Excellent "Great spot for a getaway. " [](https://expedia.com/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information) ## Find out more about Osprey ## Osprey Four Star Hotel Information When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Osprey, Florida are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Osprey 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service. Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Osprey. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Osprey, Florida, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop. Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Osprey hotels offer everything your heart desires. ## Frequently asked questions ### What are the best 4-star hotels in Osprey? ### How much does it cost to stay in a 4-star hotel in Osprey? > - Search for the lowest price from $832 ### What's the difference between 5-star and 4-star hotels in Osprey? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Historic Spanish Point ](https://www.expedia.com/Historic-Spanish-Point-Hotels.0-l6295820-0.Travel-Guide-Filter-Hotels) - [Hotels near The Oaks Club ](https://www.expedia.com/The-Oaks-Club-Hotels.0-l553248635976489805-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Vamo ](https://www.expedia.com/4Star-Vamo-Sarasota-Hotels.s40-n553248623282278448-0.Travel-Guide-Filter-Hotels) - [Hotels near Oscar Scherer State Park ](https://www.expedia.com/Oscar-Scherer-State-Park-Hotels.0-l6296013-0.Travel-Guide-Filter-Hotels) - 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