Title: Book the Best HISTORIC Hotels in Cudjoe Key in 2025 | Expedia.ca [Cudjoe Key Travel Guide](https://expedia.ca/Cudjoe-Key.dx3000430966)[Hotels in Cudjoe Key](https://expedia.ca/Cudjoe-Key-Hotels.d3000430966.Travel-Guide-Hotels)[Vacation Rentals in Cudjoe Key](https://expedia.ca/Cudjoe-Key-Vacation-Rentals.d3000430966.Travel-Guide-VacationRentals)[Flights to Cudjoe Key](https://expedia.ca/Cheap-Flights-To-Cudjoe-Key.d3000430966.Travel-Guide-Flights)[Things to do in Cudjoe Key](https://expedia.ca/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities)[Cudjoe Key Car Rentals](https://expedia.ca/Car-Rentals-In-Cudjoe-Key.d3000430966.Car-Rental-Guide)[Cudjoe Key Vacation Packages](https://expedia.ca/Cudjoe-Key.d3000430966.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/1d07342ba59eb2e04b3a99e373967cc5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Cudjoe Key, FL ![](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 Cudjoe Key Historic Hotels Tonight [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2025-10-10&endDate=2025-10-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cudjoe 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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/ec0614f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/10da66f5.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) "Good Fishing, Good local eateries. " CA $210 CA $443 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.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) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19710000/19709400/19709378/90-4f9fb4dc.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) ### Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes Cudjoe Key 9.8/10 Exceptional (237) "Lovely property. Well equipped, nicely decorated, perfect for our stay." CA $491 CA $1,146 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Summerland-Key-Hotels-Gated-Community-On-Open-Water-With-Dock.h19709378.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) ![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) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/7c5d926a.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 " CA $314 CA $752 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/9d11031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/4dc70db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/156e79e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/f7bd180e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED Stock Island 9.8/10 Exceptional (113) "Great location. Clean and beautifully decorated. " CA $379 CA $814 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/18689dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/3a23829d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/bbc45f19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/70000000/69730000/69725500/69725473/b8a0e487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West! Stock Island 10/10 Exceptional (36) "The stay was amazing. Mike was very easy to communicate with. The condo had everything you needed. Beds were comfortable and the unit was huge. Would definitely stay again. " CA $628 CA $1,241 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Key-West-Hotels-Gorgeous-Ocean-View-Three-Bedroom-Condo-In-Paradise-Minutes-From-Key-West.h69725473.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=2025-10-24&endDate=2025-10-25®ionId=3000430966&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Cudjoe Key Hotel Reviews ![Blue Flamingo Resort Key West](//images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "We loved this resort and will be back!" [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](//images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Exceeded our expectations. Restaurant was amazing, everything was clean and up to date. They kept open communication via text messages daily. I am a night shift health care provider, I cannot tell you how much I needed this mini-vacay. " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](//images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "Great views from our room excellent staff service. Would definitely stay again" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Courtyard by Marriott Key West Waterfront](//images.trvl-media.com/lodging/1000000/670000/663200/663132/f56e20a1_y.jpg) ### Courtyard by Marriott Key West Waterfront 10/10 Excellent "We had a great time use the pool a lot out at the beach" [](https://expedia.ca/Key-West-Hotels-Courtyard-By-Marriott-Key-West-Waterfront.h663132.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Super clean. The pool was amazing..friendly staff.." [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Beachside Resort & Residences](//images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "We had a great time. Everything was clean and very comfortable " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Parrot Key Hotel & Villas](//images.trvl-media.com/lodging/1000000/30000/24700/24615/b83a5985_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "Impeccable service" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](//images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "Clean grounds, clean room, loved the shuttle service to town and back to hotel, access to all 3 properties and pools which were wonderful and staff professional and courteous." [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![Hampton Inn Key West FL](//images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "Wonderful stay. Bar staff could be more friendly but overall very decent for the price. 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[Mountain Hotels in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Hotels-Mountain-Hotels.0-0-d183126-tMountainHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Hotels-Oceanfront-Hotels.0-0-d183126-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Hotels-Pet-Friendly-Hotel.0-0-d183126-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Sugarloaf Key](https://www.expedia.ca/Sugarloaf-Key-Hotels-Spa-Hotel.0-0-d183126-tSpaHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Sugarloaf Shores](https://www.expedia.ca/Sugarloaf-Shores-Summerland-Key-Hotels-Adults-Only-Resorts.0-n6270983-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Adults-Only-Resorts.0-0-d6177802-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-All-Inclusive-Hotel.0-0-d6177802-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Beach-Hotel.0-0-d6177802-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Cheap-Hotels.0-0-d6177802-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Hotel-With-Pool.0-0-d6177802-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Hotels-With-Free-Breakfast.0-0-d6177802-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Hotels-With-Kitchenettes.0-0-d6177802-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Luxury-Hotel.0-0-d6177802-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-Hotels.0-0-d6177802-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Summerland Key](https://www.expedia.ca/Summerland-Key-Hotels-Waterpark-Hotels.0-0-d6177802-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Adults-Only-Resorts.0-n553248635976481798-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-All-Inclusive-Hotel.0-n553248635976481798-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Beach-Hotel.0-n553248635976481798-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Boutique-Hotel.0-n553248635976481798-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Casino-Hotel.0-n553248635976481798-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Cheap-Hotels.0-n553248635976481798-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Couples-Resorts-Hotels.0-n553248635976481798-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Family-Hotel.0-n553248635976481798-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Golf-Hotel.0-n553248635976481798-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Honeymoon-Hotels.0-n553248635976481798-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Sunset Key](https://www.expedia.ca/Sunset-Key-Key-West-Hotels-Hotel-With-Early-Check-In.0-n553248635976481798-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [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)