Title: 10 Historic Hotels in Monroe County for 2026 | Expedia.ca [Monroe County Hotels](https://expedia.ca/Destinations-In-Monroe-County.d553248635976430869.Hotel-Destinations)[Vacation Rentals in Monroe County](https://expedia.ca/Destinations-In-Monroe-County.d553248635976430869.Vacation-Rental-Destinations)[Monroe County Car Rentals](https://expedia.ca/Destinations-In-Monroe-County.d553248635976430869.Car-Rental-Destinations)[Monroe County Vacations](https://expedia.ca/Monroe-County.d553248635976430869.Destination-Travel-Guides) ![Mallory Dock](https://images.trvl-media.com/place/553248621563220296/e155ce65-e05d-4828-bad4-09cc4a36ce98.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Historic Hotels in Monroe County - ![](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 ## Top Cities in Monroe County ![Everglades National Park featuring wetlands](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/175000/175817-Southeast-Florida.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Flamingo [](https://expedia.ca/Flamingo-Hotels-Historic-Hotel.0-0-d553248635074842070-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497918-south-beach-fm.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Key West [](https://expedia.ca/Key-West-Hotels-Historic-Hotel.0-0-d1187-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Marathon which includes swimming, tropical scenes and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63837-Marathon.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Marathon [](https://expedia.ca/Marathon-Hotels-Historic-Hotel.0-0-d2437-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Key Largo showing outdoor eating and café scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/190000/190949-Key-Largo.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Key Largo [](https://expedia.ca/Key-Largo-Hotels-Historic-Hotel.0-0-d8369-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Islamorada which includes tropical scenes and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63860-Islamorada.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Islamorada [](https://expedia.ca/Islamorada-Hotels-Historic-Hotel.0-0-d10768-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Big Pine Key featuring a bay or harbour, general coastal views and a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63852-Big-Pine-Key.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Big Pine Key [](https://expedia.ca/Big-Pine-Key-Hotels-Historic-Hotel.0-0-d7195-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340394-Florida-Keys-Wild-Bird-Rehabilitation-Center.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Tavernier [](https://expedia.ca/Tavernier-Hotels-Historic-Hotel.0-0-d10047-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340342-Sunset-Park-Beach-Florida.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Key Colony Beach [](https://expedia.ca/Key-Colony-Beach-Hotels-Historic-Hotel.0-0-d121486-tHistoricHotel.Travel-Guide-Filter-Hotels) ## Check availability on Monroe County Historic Hotels Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Monroe-County-Historic-Hotel.0-0-d553248635976430869-tHistoricHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Monroe-County-Historic-Hotel.0-0-d553248635976430869-tHistoricHotel.Hotel-Filter-Destinations) ## Top Monroe County Hotel Reviews ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "They went the extra mile! Was a lovely stay" [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Rooms were beautiful" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg) ### The Reach Key West, Curio Collection by Hilton 10/10 Excellent "Great view, amazing room and friendly staff" [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "All the staff is amazing and helpful! Room was clean and roomy. " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Beautiful room and amazing reception staff of Annette, Sara, Jody and Richardo. They were very accommodating. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Our Birthday Club recently stayed at the resort while in town celebrating our Sister Audrey's 60th Birthday. The resort staff were very friendly and accommodating. The front desk team were helpful, the shuttle drivers were friendly and went the extra mile to make sure we got to our destinations, the pool area was beautiful, we felt like we were on a resort in the Caribbean. The bar staff were nice and fun and the breakfast buffet was delicious and had lots of variety. The wait staff were super nice and attentive. I almost forgot, the famous warm cookies did not disappoint!! Lastly, our balcony with the pool view was spacious, had a ceiling fan and provided a great view of the resort courtyard and pool. Overall, our stay was great. We would recommend this resort to others. " [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Isla Bella Beach Resort & Spa](https://images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/f4f56036_y.jpg) ### Isla Bella Beach Resort & Spa 10/10 Excellent "My wife and I celebrated our 25th wedding anniversary at Isla Bella, and could not have been more pleased. From the moment we checked in to the moment we left, we thoroughly enjoyed our stay. The grounds were perfectly maintained, offering beautiful ocean views. Dining at Mahina during sunset is an unforgettable moment, and highly recommended. Wait staff were attentive at every restaurant on the grounds, and we never felt rushed or unimportant. Other patrons of the resort were quiet and respectful, unlike some other locations you may often encounter in the Keys. This is not a party atmosphere, but rather a place to enjoy peace, quiet and perfect scenery. Our room was spacious and comfortable, and was serviced every day making it feel like new each time we opened the door. Key West is a fun place to visit, but if you want to relax in luxury and avoid the crowds, plan a trip to Marathon, Isla Bella will not disappoint. " [](https://expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.Hotel-Information) ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg) ### Winslow's Bungalows - Key West Historic Inns 10/10 Excellent "Room was very private everything was within walking distance. Only down side was the breakfast it was very basic. " [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Great view and unit was large and very clean. 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