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) ![Key Largo which includes a river or creek and mangroves](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63593-Key-Largo.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 ## Check availability on Monroe County Winery Hotels Tonight [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Monroe County Winery Hotels ![](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 ![Casa Marina Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "Beautiful property far enough away from duval to be quiet but close enough to walk and right on its own private beach. You can rent bikes and jet skis and everything on site." [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.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 "Acceptable prices " [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Margaritaville Beach House Key West](//images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/32e70782_y.jpg) ### Margaritaville Beach House Key West 10/10 Excellent "Great place, loved it " [](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) ![The Perry Hotel & Marina Key West](//images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "The rooms were very clean the staff was extremely nice and helpful. Would definitely stay here again" [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Isla Bella Beach Resort & Spa](//images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/1b2ea44f_y.jpg) ### Isla Bella Beach Resort & Spa 10/10 Excellent "Really nice place and the rooms and amenities were excellent." [](https://expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.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 "This was my 4th year in a row staying at this property. Great views and a great location. " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](//images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Great stay and place , only thing that would make it better is a larger and more equipped gym. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Beachside Resort & Residences](//images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "A real nice hotel away from the crowds and real nice room decor .. Tavern n Town is an A+ restaurant " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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) - [Beach Hotel Hotels in Beachside](https://www.expedia.ca/Beachside-Key-West-Hotels-Beach-Hotel.0-n864982244484468736-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Beachside](https://www.expedia.ca/Beachside-Key-West-Hotels-Cheap-Hotels.0-n864982244484468736-0-tCheapHotels.Travel-Guide-Filter-Hotels) - 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