Title: Book the Best HISTORIC Hotels in Osprey in 2025 | Expedia.ca [Hotels in Osprey](https://expedia.ca/Osprey-Hotels.d55888.Travel-Guide-Hotels)[Vacation Rentals in Osprey](https://expedia.ca/Osprey-Vacation-Rentals.d55888.Travel-Guide-VacationRentals)[Flights to Osprey](https://expedia.ca/Cheap-Flights-To-Osprey.d55888.Travel-Guide-Flights)[Osprey Car Rentals](https://expedia.ca/Car-Rentals-In-Osprey.d55888.Car-Rental-Guide)[Osprey Vacation Packages](https://expedia.ca/Osprey.d55888.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495790-osprey.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Osprey, FL from CA $322 - ![](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 Historic Hotels Tonight [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Osprey Historic Hotels ![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/6fb611a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/822b1606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/c128477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/edfdd191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Floridian cottage in Historic Gulf Village Olde Englewood Village 9.8/10 Exceptional (60) "Had a nice stay. Clean and well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debi D. CA $139 CA $353 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/8aa0ab0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/6b5f791e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/ba244c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/7c9280ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES Sarasota 9.6/10 Exceptional (35) "Looking forward to staying there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) aimen s. CA $113 CA $566 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Sarasota-Hotels-Extremely-Comfortableclean-VILLAS-Heated-Pool-And-Jacuzzi-SUMMER-SPECIAL-RATES.h33393742.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/5e0d8579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/b8cf3ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/4f7cba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/42000000/41380000/41375500/41375487/7b0de6bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Superb Waterfront Condo! 2 Pools~Lanai~Free WiFi. By IMG~Beaches~AMI~Restaurants Bradenton 9.8/10 Exceptional (112) "I stayed 1 night with 2 of my friends and honestlyEverything was amazing, place was super clean, the host was super quick to answer my questions and I would for sure booked again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenifer M. CA $125 CA $417 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Sarasota-Hotels-Newly-Listed-Upgraded-Waterfront-Condonear-Beachesimg-Academyanna-Mariasrq.h41375487.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/bfa1f244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/ea0f25fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/3810f46f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/36d1ce5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical, private, downtown Central Sarasota 9.6/10 Exceptional (78) "Clean, relaxing setting in a quaint neighborhood a short walk to downtown. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) FREDERICK W. CA $70 CA $354 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Sarasota-Hotels-Very-Tropical.h24253065.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/56d6d62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/7926e0c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/04dbd19f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156060/9cd77b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise Retreat with HEATED POOL-- Need We Say More South Bradenton 10/10 Exceptional (177) "Very close to the beaches and restaurants! Nice home and owners." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon L. CA $127 CA $429 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bradenton-Hotels-Paradise-Retreat-With-HEATED-POOL-Need-We-Say-More.h24156060.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/a6b1997c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/812fc075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/c848809a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/cdcfe3b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 2BR Condo! 2 Pools~Free WiFi. By IMG Academy~Beaches~AMI~Restaurants. Bradenton 9.8/10 Exceptional (144) "The location is great with stores very close, very close to IMG academy and for beaches.It had everything we needed for a short stay. There could be some improvements made but for the length of time we stayed it was okay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Salisha H. CA $125 CA $417 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Sarasota-Hotels-Cozy-Condo-Free-Wifi.h23592665.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/bca94bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/35a00a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/ac2ea9ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player, foosball](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/4235949a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SEPT OCT NOV DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK South Bradenton 9.8/10 Exceptional (137) "House and pool were great! Jackie is a great host! We really enjoyed our stay and plan to come again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandi C. CA $158 CA $736 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Bradenton-Hotels-APRIL-MAY-JUNE-DISCOUNTS-IMG-AMISLAND-BEACHES-KAYAK-FISHING-ON-LAKE-KIDS-PETS-OK.h30360582.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/af73f449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/4150dd9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/a0f04c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23060000/23058300/23058218/14c34a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Sands Serenity – Unit 234 at the Beach by RVA Longboat Key 9.4/10 Exceptional (29) "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Loved this place! Very friendly and helpful staff. Clean and well appointed condo. We will definitely come back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly L. CA $237 CA $494 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-234-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23058218.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19300000/19297800/19297785/w1400h930x0y3-6866132b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19300000/19297800/19297785/615f082b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/20000000/19300000/19297800/19297785/4f39f7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19300000/19297800/19297785/09ec13c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR King/ensuite with Kitchen 5 Mins. To Beach/Downtown Central Sarasota 10/10 Exceptional (11) "good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edwin B. CA $210 CA $322 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Sarasota-Hotels-1BR-Kingensuite-With-Kitchen-5-Mins-To-Beachdowntown.h19297785.Hotel-Information) ![Beach nearby, beach umbrellas](https://images.trvl-media.com/lodging/24000000/23040000/23032000/23031918/d07ad619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/24000000/23040000/23032000/23031918/48d74cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/24000000/23040000/23032000/23031918/cbf34a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23040000/23032000/23031918/59877761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright and Beachy–Beach Club at Siesta Key #100A Resort by RVA South Village 9.0/10 Wonderful (113) "This is a perfect studio for a few day stay. Very clean with modern finishes. Great location close to beach and South Island end for nightlife and the 7-11 for quick grabs. Resort is clean and although we did not use the pool it was very nice. We highly recommend this unit!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jennifer s. CA $252 CA $512 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Sarasota-Hotels-The-Beach-Club-At-Siesta-Key-100a-Studio-1-BA-Resort-By-Rva.h23031918.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=2025-11-17&endDate=2025-11-18®ionId=55888&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Osprey Hotel Reviews ![Lido Beach Resort](//images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "Our room was wonderful with fantastic view!!" [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Golden Host Resort - Sarasota](//images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "Reception staff was very friendly." [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![Hyatt Place Sarasota/Bradenton Airport](//images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg) ### Hyatt Place Sarasota/Bradenton Airport 10/10 Excellent "Management Service was the best! " [](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information) ![Casey Key Resorts - Mainland](//images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9_y.jpg) ### Casey Key Resorts - Mainland 10/10 Excellent "Staff were very friendly & accommodating, rooms are clean. " [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Comfort Suites Sarasota - Siesta Key](//images.trvl-media.com/lodging/6000000/5640000/5637500/5637457/a4f997ef_y.jpg) ### Comfort Suites Sarasota - Siesta Key 10/10 Excellent "The hotel was good and staff was great" [](https://expedia.ca/Sarasota-Hotels-Comfort-Suites-Sarasota-Siesta-Key.h5637457.Hotel-Information) ![Spark by Hilton Sarasota Siesta Key Gateway](//images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg) ### Spark by Hilton Sarasota Siesta Key Gateway 10/10 Excellent "I love the bartender girl from the pool bar… so sweet" [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![Lantern Inn & Suites](//images.trvl-media.com/lodging/1000000/450000/448500/448416/4f77412a_y.jpg) ### Lantern Inn & Suites 10/10 Excellent "I didn't use the laundry facility and didn't drink in the bar" [](https://expedia.ca/Sarasota-Hotels-Lantern-Inn-Suites.h448416.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 "Loved this hotel " [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Captiva Beach Resort](//images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375_y.jpg) ### Captiva Beach Resort 10/10 Excellent "Very good stay, clean, safe, and steps from the beach" [](https://expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information) ## Frequently asked questions ### What should I expect on my historical trip to Osprey? > The historical places in Osprey are probably at the top of your sightseeing list. While you're in town, you can check out the popular beaches and top-notch restaurants. You can also relish a trip to the lively bars. ### How many historically relevant hotels will I find in Osprey? > Osprey is home to 66 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels. ### What are the top historical sites and other places to visit in Osprey? > Osprey is notable for landmarks like Historic Spanish Point. The natural setting is picturesque, namely the stunning beaches, and these places to see: Turtle Beach, Nokomis Beach, and Jim Neville Marine Preserve. Additionally, in the area you'll find Siesta Key Beach and Lido Beach. ### What is a historic hotel like in Osprey? > Guests who book a historic hotel can stay someplace that has an officially recognized historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be identified as a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically found in the guestrooms or communal spaces of such hotels in Osprey, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and building of a historic hotel tends to be the most important aspect. For a heritage hotel, it's often the cultural value as well as how it inspired the community. ### Do historic hotels in Osprey have modern facilities? > Hotels have the safety features and modern conveniences you expect to find, though efforts have been made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found at a contemporary hotel will also be available in a historic hotel. When you choose a historic hotel in Osprey, don't worry that you'll find yourself staying at a place that's uncomfortable for guests or simply rundown. ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Bay Acres](https://www.expedia.ca/Bay-Acres-Osprey-Hotels-Beach-Hotel.0-n553248635976472153-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Casey Key](https://www.expedia.ca/Casey-Key-Hotels-Beach-Hotel.0-0-d6167273-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Casey Key](https://www.expedia.ca/Casey-Key-Hotels-Boutique-Hotel.0-0-d6167273-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Casey Key](https://www.expedia.ca/Casey-Key-Hotels-Casino-Hotel.0-0-d6167273-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Casey Key](https://www.expedia.ca/Casey-Key-Hotels-Cheap-Hotels.0-0-d6167273-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Casey Key](https://www.expedia.ca/Casey-Key-Hotels-Couples-Resorts-Hotels.0-0-d6167273-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - 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