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 $248 ![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 Historic Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-02&endDate=2025-10-03&adults=2&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&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&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Osprey Historic Hotels ![A heated pool](https://images.trvl-media.com/lodging/24000000/23980000/23973100/23973025/c8fb5056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23980000/23973100/23973025/5c96e242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23980000/23973100/23973025/3dea3e3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23973100/23973025/c08d6442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2nd Floor Retreat Overlooking the Pool & Gulf Silver Sands #251 Resort by RVA Longboat Key 8.6/10 Excellent (41) "Beautiful place with a private beach and a really nice clean condo. Had everything we needed for a relaxing weekend. Will definitely come back! Thank you." CA $181 CA $418 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-251-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23973025.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19520000/19512800/19512749/286a6f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/20000000/19520000/19512800/19512749/f7e6f10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19520000/19512800/19512749/8c2c4edc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/20000000/19520000/19512800/19512749/w801h737x0y0-2dd841c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Very tropical, private and peaceful, short walk to everything happening downtown Central Sarasota 9.6/10 Exceptional (59) "Stayed here for two nights and was very happy with it. Very easy walk to downtown area. Nice quiet street. Property was clean. " CA $85 CA $327 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Sarasota-Hotels-Very-Tropical.h19512749.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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/1da0f055.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) ![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) ### Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES Sarasota 9.6/10 Exceptional (35) "Looking forward to staying there again." CA $139 CA $596 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Sarasota-Hotels-Extremely-Comfortableclean-VILLAS-Heated-Pool-And-Jacuzzi-SUMMER-SPECIAL-RATES.h33393742.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/24000000/23520000/23515800/23515758/a5117df9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23520000/23515800/23515758/3618bc6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23520000/23515800/23515758/2bc24b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23520000/23515800/23515758/191faeed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Affordable Beach Escape – Studio at Silver Sands in LBK #257A Resort by RVA Longboat Key 9.6/10 Exceptional (74) "Great place on the beach. Quiet and relaxing." CA $167 CA $400 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-257a-Hotel-1-BA-Resort-On-Longboat-Key-By-Rva.h23515758.Hotel-Information) ![Beach nearby, beach umbrellas](https://images.trvl-media.com/lodging/24000000/23040000/23032200/23032118/3fb1808b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player, stereo](https://images.trvl-media.com/lodging/24000000/23040000/23032200/23032118/a12de0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23040000/23032200/23032118/7b483057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/24000000/23040000/23032200/23032118/90e7d057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Waters & Magical Sunsets-The Beach Club at Siesta Key #106B by RVA South Village 8.6/10 Excellent (65) "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Fantastic location with a fun pool. Apartment bedrooms and bathrooms very comfortable. The office is very kind and helpful. Thanks for a solid week in Siesta Key!" CA $195 CA $541 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Sarasota-Hotels-The-Beach-Club-At-Siesta-Key-106b-2-BR-2-BA-Resort-By-Rva.h23032118.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/24000000/23980000/23973400/23973386/72ba5d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23980000/23973400/23973386/52e9ca4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23980000/23973400/23973386/abe85b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23973400/23973386/dfc22000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Beachside Studio Escape - Silver Sands #251A Resort by RVA Longboat Key 8.6/10 Excellent (49) "all good , an ice machine would have been nice" CA $167 CA $400 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-251a-Hotel-1-BA-Resort-On-Longboat-Key-By-Rva.h23973386.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/24000000/23980000/23973300/23973268/7f909a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23980000/23973300/23973268/ec28b2ef_edited_7206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23973300/23973268/9a67acc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23980000/23973300/23973268/6b6c6e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Sands #245A Resort by RVA Longboat Key 8.8/10 Excellent (59) "Rating Details: 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: Couple getaway" CA $167 CA $402 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Longboat-Key-Hotels-Silver-Sands-245A-HOTEL-1-BA-Resort-On-Longboat-Key-By-RVA.h23973268.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/37000000/36360000/36358600/36358504/w1400h930x0y3-969270a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36360000/36358600/36358504/3c43f7cf.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/37000000/36360000/36358600/36358504/e6fb9ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/37000000/36360000/36358600/36358504/311350e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historically Significant, 2nd floor, 1 BR, 1 Private BA Close to Everything Central Sarasota 9.2/10 Wonderful (14) "Cute place .. excellent food" CA $174 CA $248 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Sarasota-Hotels-Historically-Significant-1-BR.h36358504.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) ![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) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/31000000/30370000/30360600/30360582/efdcbaed.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 (134) "House and pool were great! Jackie is a great host! We really enjoyed our stay and plan to come again!" CA $99 CA $655 total includes taxes & fees Oct 15 - Oct 16 [](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/24000000/23550000/23547100/23547098/0d958ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23550000/23547100/23547098/9a2ea3e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23550000/23547100/23547098/7ddb3b42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23550000/23547100/23547098/43db1448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ground Floor, Steps to the Sand Silver Sands #243A Resort by RVA Longboat Key 8.6/10 Excellent (59) "Clean, cozy and right in the beach!! Was a perfect little getaway! " CA $167 CA $399 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-243a-Hotel-1-BA-Resort-On-Longboat-Key-By-Rva.h23547098.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=2025-10-15&endDate=2025-10-16®ionId=55888&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Osprey Hotel Reviews ![Tropical Beach Resorts](//images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Rooms very clean. Close to lots of places to eat." [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.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 "Andrew at the front desk was wonderful and Lisa at the Sand Dollar was very informative. I would recommend this location to anyone. " [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![voco Sarasota by IHG](//images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/dc3c2bf5_y.jpg) ### voco Sarasota by IHG 10/10 Excellent "Great area and transportation from hotel " [](https://expedia.ca/Sarasota-Hotels-Voco-Sarasota.h1577382.Hotel-Information) ![Lido Beach Resort](//images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "Great view from the balcony Very comfortable room Everything I needed" [](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 "Clean room and comfy stay." [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Lantern Inn & Suites](//images.trvl-media.com/lodging/1000000/450000/448500/448416/4f77412a_y.jpg) ### Lantern Inn & Suites 10/10 Excellent "Very clean and nice rooms. " [](https://expedia.ca/Sarasota-Hotels-Lantern-Inn-Suites.h448416.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 "All was excellent 👍" [](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 "Clean room , friendly staff . " [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.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 "This is the second time staying at this property the staff is very helpful and polite. The beds are very comfortable. The pool is also a plus." [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.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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