Title: Monroe County Winery Hotels : Book the Right Winery Hotels Room in Monroe County, Florida - 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) # Monroe County Winery Hotels - ![](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 ![](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-Winery-Hotel.0-0-d1187-tWineryHotel.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-Winery-Hotel.0-0-d7195-tWineryHotel.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-Winery-Hotel.0-0-d10047-tWineryHotel.Travel-Guide-Filter-Hotels) ![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-Winery-Hotel.0-0-d553248635074842070-tWineryHotel.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-Winery-Hotel.0-0-d121486-tWineryHotel.Travel-Guide-Filter-Hotels) ## Check availability on Monroe County Winery Hotels Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This 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) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-12-26&endDate=2025-12-28&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-Winery-Hotel.0-0-d553248635976430869-tWineryHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Monroe-County-Winery-Hotel.0-0-d553248635976430869-tWineryHotel.Hotel-Filter-Destinations) ## Top Monroe County Hotel Reviews ![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg) ### Hyatt Vacation Club at Beach House, Key West 10/10 Excellent "Absolutely loved this resort and everything was perfect. The 2 bedroom villa as beautiful and the screen in deck was perfect! We will definitely be back! Thank you for making our anniversary great!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "The room and amenities at Hyatt Windward were top notch!!!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.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 "Yes and view was ok. Next time we will request the marina view" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "Very spacious, neat rooms. Great vibe" [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![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 "." [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.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 "shuttle" [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg) ### Margaritaville Beach House Key West 10/10 Excellent "Beautiful property that cant be described in words. The staff was welcoming and very helpful. I honestly did not want to leave. " [](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) ![Fairfield Inn and Suites by Marriott Key West](https://images.trvl-media.com/lodging/1000000/10000/9000/8946/7b2c8a2c_y.jpg) ### Fairfield Inn and Suites by Marriott Key West 10/10 Excellent "Good budget hotel. Nice pool. Breakfast wasn’t that great. Friendly staff. We had an unexpected visitor while we were at the pool. Largest iguana I’ve ever see. " [](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.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 "Beach and pool - bar, music and great staff" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Beachside ](https://www.expedia.ca/Beachside-Key-West-Hotels-All-Inclusive-Hotel.0-n864982244484468736-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - 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