Title: Book the Best HISTORIC Hotels in Big Pine Key in 2025 | Expedia.ca [Big Pine Key Travel Guide](https://expedia.ca/Big-Pine-Key.dx7195)[Hotels in Big Pine Key](https://expedia.ca/Big-Pine-Key-Hotels.d7195.Travel-Guide-Hotels)[Vacation Rentals in Big Pine Key](https://expedia.ca/Big-Pine-Key-Vacation-Rentals.d7195.Travel-Guide-VacationRentals)[Flights to Big Pine Key](https://expedia.ca/Cheap-Flights-To-Big-Pine-Key.d7195.Travel-Guide-Flights)[Things to do in Big Pine Key](https://expedia.ca/Things-To-Do-In-Big-Pine-Key.d7195.Travel-Guide-Activities)[Big Pine Key Car Rentals](https://expedia.ca/Car-Rentals-In-Big-Pine-Key.d7195.Car-Rental-Guide)[Big Pine Key Vacation Packages](https://expedia.ca/Big-Pine-Key.d7195.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497701-big-pine-key.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Big Pine Key, FL from CA $442 ![](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 Big Pine Key Historic Hotels Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=7195&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7195&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7195&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7195&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Big Pine Key Historic Hotels ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/6e8a6b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/ec0614f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/88047f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/8879ca02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Dockage, just minutes to Key West Cudjoe Key 9.2/10 Wonderful (155) "A beautiful stay, we plan to come back again in the future!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabastian M. CA $210 CA $442 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/7c5d926a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool Cutthroat Harbor Estates 8.4/10 Very good (117) "Deer in the front yard, perfect location, clean and friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara H. CA $315 CA $754 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![On the beach, beach towels](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/f3afeb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/94858c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/356d9302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/5796fc96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes Cudjoe Key 9.8/10 Exceptional (238) "Lovely property. Well equipped, nicely decorated, perfect for our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen M. CA $490 CA $1,144 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Summerland-Key-Hotels-Gated-Community-On-Open-Water-With-Dock.h19709378.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=2025-11-07&endDate=2025-11-08®ionId=7195&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Big Pine Key Hotel Reviews ## Frequently asked questions ### What can a history enthusiast expect from a trip to Big Pine Key? > You're already probably planning a visit to historically relevant sites while you're staying in Big Pine Key. During your vacation, why not also discover the many sights including the beaches? ### How many historical hotels are located in Big Pine Key? > In Big Pine Key, there are 165 lodging options bookable on Expedia but not many designated as historic hotels. ### What are the must-see historical places and other sights to visit in Big Pine Key? > Favorite places to visit include Calusa Beach, Bahia Honda State Park, and Big Pine Key Flea Market. A couple of additional sights to add to your agenda are Coupon Bight Aquatic Preserve and Cook Island. ### What is a historic hotel like in Big Pine Key? > When you choose a historic hotel, you'll enjoy a vacation in a building that has an officially recognized historic designation. A castle, a palace or even a pub or an old police station can be transformed into a historic hotel as long as it has special significance. Traditional architecture and period features can be admired in the guestrooms or communal spaces of these historic hotels in Big Pine Key, giving a sense of history. ### 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. overall though the terms are similar. The building and architecture of historic hotels are generally the most important aspect. For a heritage hotel, mainly, it's cultural value along with how it inspired the community. ### Do historic hotels in Big Pine Key have modern facilities? > Hotels have the safety features and modern conveniences you might expect, but every effort is made to preserve historic facades and treasured traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the popular amenities found in any hotel should be available at a historic hotel. Rest assured that when you choose a historic hotel in Big Pine Key, you won't be staying at a place that's uncomfortable or rundown. ## Explore a world of travel with Expedia - Lodging - More ways to book - [All Inclusive Resorts and in Atlantis Estates](https://www.expedia.ca/Atlantis-Estates-Big-Pine-Key-Hotels-All-Inclusive-Hotel.0-n553248635976480034-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Atlantis Estates](https://www.expedia.ca/Atlantis-Estates-Big-Pine-Key-Hotels-Cheap-Hotels.0-n553248635976480034-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Atlantis Estates](https://www.expedia.ca/Atlantis-Estates-Big-Pine-Key-Hotels-Hotels-With-Free-Airport-Shuttle.0-n553248635976480034-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Atlantis Estates](https://www.expedia.ca/Atlantis-Estates-Big-Pine-Key-Hotels-Pet-Friendly-Hotel.0-n553248635976480034-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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[Hotels with a Lazy River in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Hotels-With-A-Lazy-River.0-n553248635976481798-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Hotels-With-Balconies.0-n553248635976481798-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Hotels-With-Smoking-Rooms.0-n553248635976481798-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Hotels-With-Tennis-Courts.0-n553248635976481798-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Luxury-Hotel.0-n553248635976481798-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Mountain-Hotels.0-n553248635976481798-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Oceanfront-Hotels.0-n553248635976481798-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Pet-Friendly-Hotel.0-n553248635976481798-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Romantic-Hotel.0-n553248635976481798-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Shopping-Hotel.0-n553248635976481798-0-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Ski-Hotel.0-n553248635976481798-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Spa-Hotel.0-n553248635976481798-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Wedding-Hotels.0-n553248635976481798-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Winery-Hotel.0-n553248635976481798-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Whispering Pines](https://www.expedia.ca/Whispering-Pines-Big-Pine-Key-Hotels-Adults-Only-Resorts.0-n553248635976471032-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Golf Hotels in Whispering Pines](https://www.expedia.ca/Whispering-Pines-Big-Pine-Key-Hotels-Golf-Hotel.0-n553248635976471032-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Whispering Pines](https://www.expedia.ca/Whispering-Pines-Big-Pine-Key-Hotels-Mountain-Hotels.0-n553248635976471032-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Whispering Pines](https://www.expedia.ca/Whispering-Pines-Big-Pine-Key-Hotels-Pet-Friendly-Hotel.0-n553248635976471032-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Whispering Pines](https://www.expedia.ca/Whispering-Pines-Big-Pine-Key-Hotels-Waterpark-Hotels.0-n553248635976471032-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Book Historic Hotels in Big Pine Key on Expedia.com](https://www.expedia.com/Big-Pine-Key-Hotels-Historic-Hotel.0-0-d7195-tHistoricHotel.Travel-Guide-Filter-Hotels)