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 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 15 - Sep 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-09-15&endDate=2025-09-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 16 - Sep 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-09-16&endDate=2025-09-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 19 - Sep 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-09-19&endDate=2025-09-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2025-09-26&endDate=2025-09-28&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 ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "all good" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.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 "Very friendly staff, the room was clean and had all the essentials, the air conditioning ran super cold which was what was needed!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.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 "This resort is absolutely lovely. Our room was perfect. The pools and beach bar were also great. The views from anywhere were picture perfect. One thing that was not great was the beach access into the water. You couldn't walk in because it was too rocky. " [](https://expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](//images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent " Na" [](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.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 "Walkable to the beach. Shuttle to and from downtown with airport shuttle. " [](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.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 "Everything is great with the exception of being able to get in touch with the front desk!! Very difficult " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.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 "Pool, staff, clean" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.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 "The staff. the staff was helpful and kind. my room was clean,it was an amazing stay " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![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 "Beach view, safe, friendly" [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ## Explore a world of travel with Expedia - Explore a world of travel with Expedia ### More Themes - [All Inclusive Resorts and Hotels](https://expedia.ca/lp/t/hotels/All-Inclusive-Hotel) - [Hotels with Balconies](https://expedia.ca/lp/t/hotels/Hotels-with-Balconies) - [Hotels with Bar](https://expedia.ca/lp/t/hotels/Hotels-with-Bar) - [Beach Hotel](https://expedia.ca/lp/t/hotels/Beach-Hotel) - [Boutique Hotels](https://expedia.ca/lp/t/hotels/Boutique-Hotel) - [Cheap Hotels](https://expedia.ca/lp/t/hotels/Cheap-Hotels) - [Business Hotels](https://expedia.ca/lp/t/hotels/Business-Hotel) - [Casino Hotels](https://expedia.ca/lp/t/hotels/Casino-Hotel) - [Hotels with Childcare](https://expedia.ca/lp/t/hotels/Hotels-with-Childcare) - [Family Hotels](https://expedia.ca/lp/t/hotels/Family-Hotel) - [Hotels with Free Airport Shuttle](https://expedia.ca/lp/t/hotels/Hotels-with-Free-Airport-Shuttle) - [Hotels with Free Breakfast](https://expedia.ca/lp/t/hotels/Hotels-with-Free-Breakfast) - [Hotels with Free Parking](https://expedia.ca/lp/t/hotels/Hotels-with-Free-Parking) - 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[Condo Rentals in Monroe County](https://expedia.ca/Monroe-County-Condos.d553248635976430869-aaCondos.Travel-Guide-Accommodation) - [Apartments in Monroe County](https://expedia.ca/Monroe-County-Apartments.d553248635976430869-aaApartments.Travel-Guide-Accommodation) - [Cottages in Monroe County](https://expedia.ca/Monroe-County-Cottages.d553248635976430869-aaCottages.Travel-Guide-Accommodation) - [Villas in Monroe County](https://expedia.ca/Monroe-County-Villas.d553248635976430869-aaVillas.Travel-Guide-Accommodation) - [Resorts in Monroe County](https://expedia.ca/Monroe-County-Resort-Hotels.d553248635976430869-aaResortHotels.Travel-Guide-Accommodation) - [Houseboats in Monroe County](https://expedia.ca/Monroe-County-Houseboats.d553248635976430869-aaHouseboats.Travel-Guide-Accommodation) - [Aparthotels in Monroe County](https://expedia.ca/Monroe-County-Apart-Hotels.d553248635976430869-aaApartHotels.Travel-Guide-Accommodation) - [Guest Houses in Monroe County](https://expedia.ca/Monroe-County-Guest-Houses.d553248635976430869-aaGuestHouses.Travel-Guide-Accommodation) - [RV Parks in Monroe County](https://expedia.ca/Monroe-County-RV-Parks.d553248635976430869-aaRVParks.Travel-Guide-Accommodation) ### Hotels near Popular Monroe County Attractions - [Hotels near Duval Street](https://expedia.ca/Duval-Street-Hotels.0-l6068616-0.Travel-Guide-Filter-Hotels) - [Hotels near Everglades National Park](https://expedia.ca/Everglades-National-Park-Hotels.0-l54987-0.Travel-Guide-Filter-Hotels) - [Hotels near Southernmost Point](https://expedia.ca/Southernmost-Point-Hotels.0-l501380-0.Travel-Guide-Filter-Hotels) - [Hotels near Mallory Square](https://expedia.ca/Mallory-Square-Hotels.0-l501385-0.Travel-Guide-Filter-Hotels) - [Hotels near Smathers Beach](https://expedia.ca/Smathers-Beach-Hotels.0-l6069255-0.Travel-Guide-Filter-Hotels) - [Hotels near Florida Keys Beaches](https://expedia.ca/Florida-Keys-Beaches-Hotels.0-l553248635976496782-0.Travel-Guide-Filter-Hotels) - [Hotels near John Pennekamp Coral Reef State Park](https://expedia.ca/John-Pennekamp-Coral-Reef-State-Park-Hotels.0-l6068611-0.Travel-Guide-Filter-Hotels) - [Hotels near Sombrero Beach](https://expedia.ca/Sombrero-Beach-Hotels.0-l6069239-0.Travel-Guide-Filter-Hotels) - [Hotels near South Beach](https://expedia.ca/South-Beach-Hotels.0-l6246827-0.Travel-Guide-Filter-Hotels) - [Hotels near Ernest Hemingway Home and Museum](https://expedia.ca/Ernest-Hemingway-Home-And-Museum-Hotels.0-l501376-0.Travel-Guide-Filter-Hotels) ### Discover hotels close to Monroe County with room rates, reviews, and availability. Most hotels are fully refundable. - [Oceans Edge Key West Resort, Hotel & Marina](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) - [Beachside Resort & Residences](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) - [Margaritaville Beach House Key West](https://expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) - [Hyatt Centric Key West Resort and Spa](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) - [Southernmost Beach Resort and Guesthouses](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) - [Hilton Garden Inn Key West / The Keys Collection](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) - [Parrot Key Hotel & Villas](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) - [Fairfield Inn and Suites by Marriott Key West](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.Hotel-Information) - [Blue Flamingo Resort Key West](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) - [Cheeca Lodge & Spa](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) [See a list of all hotels in Monroe County](https://expedia.ca/All-Monroe-County-Hotels.d553248635976430869.Travel-Guide-City-All-Hotels) ### Expedia's Latest Trends Hotels - [Hotels in Kissimmee](https://expedia.ca/Kissimmee-Hotels.d7927.Travel-Guide-Hotels) - [Brickell hotels](https://expedia.ca/Brickell-Miami-Hotels.0-n6240961-0.Travel-Guide-Filter-Hotels) - [Hotels near Port of Miami](https://expedia.ca/Port-Of-Miami-Hotels.0-l6125791-0.Travel-Guide-Filter-Hotels) - [Hotels in Clearwater](https://expedia.ca/Clearwater-Hotels.d6033.Travel-Guide-Hotels) - [Hotels in Miami Beach](https://expedia.ca/Miami-Beach-Hotels.d8833.Travel-Guide-Hotels) - [Hotels in Clearwater Beach](https://expedia.ca/Clearwater-Beach-Hotels.d10759.Travel-Guide-Hotels) - [Hotels near Port Everglades](https://expedia.ca/Port-Everglades-Hotels.0-l6124927-0.Travel-Guide-Filter-Hotels) - [Downtown Miami hotels](https://expedia.ca/Downtown-Miami-Miami-Hotels.0-n800070-0.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Hollywood](https://expedia.ca/Hollywood-Hotels-Oceanfront-Hotels.0-0-d6076-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Hotels near Walt Disney World® Resort](https://expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels) - [Hotels in Dunedin](https://expedia.ca/Dunedin-Hotels.d7932.Travel-Guide-Hotels) - [Hotels in St. Pete Beach](https://expedia.ca/St-Pete-Beach-Hotels.d9802.Travel-Guide-Hotels) - [Port Canaveral hotels](https://expedia.ca/Port-Canaveral-Cape-Canaveral-Hotels.0-n6127851-0.Travel-Guide-Filter-Hotels) - [Hotels in Lauderdale-by-the-Sea](https://expedia.ca/Lauderdale-By-The-Sea-Hotels.d10652.Travel-Guide-Hotels) - [South Beach hotels](https://expedia.ca/South-Beach-Miami-Hotels.0-n6138745-0.Travel-Guide-Filter-Hotels) Cars - [Car rental Tampa Airport (TPA)](https://expedia.ca/Car-Rentals-In-Tampa-Intl.d4280404.Car-Rental-Guide) - [Car rental Orlando Airport (MCO)](https://expedia.ca/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide) - [Car rental Sanford Airport (SFB)](https://expedia.ca/Car-Rentals-In-Orlando-Sanford-Intl.d6031813.Car-Rental-Guide) - [Car rental Miami Airport (MIA)](https://expedia.ca/Car-Rentals-In-Miami-Intl.d4278605.Car-Rental-Guide) - [Car rental Fort Myers Airport (RSW)](https://expedia.ca/Car-Rentals-In-Southwest-Florida-Intl.d5722962.Car-Rental-Guide) - [Car rental Fort Lauderdale Airport (FLL)](https://expedia.ca/Car-Rentals-In-Fort-Lauderdale-Hollywood-Intl.d5000262.Car-Rental-Guide) Cruises - [Cruises from Port Canaveral](https://expedia.ca/Cruises-from-Port-Canaveral.d6127851.Cruise-Departure-Port) Activities - [Things to do in Boca Chica Key](https://expedia.ca/Things-To-Do-In-Boca-Chica-Key.d553248635083916609.Travel-Guide-Activities) - [Things to do in Levy County](https://expedia.ca/Things-To-Do-In-Levy-County.d553248635976432502.Travel-Guide-Activities) Packages - [Aventura Vacations](https://expedia.ca/Aventura.d7176.Destination-Travel-Guides) - [Miami Beach Vacations](https://expedia.ca/Miami-Beach.d8833.Destination-Travel-Guides) - [Clearwater Beach Vacations](https://expedia.ca/Clearwater-Beach.d10759.Destination-Travel-Guides) - [Walt Disney World® Resort](https://expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction) Vacation Rentals - [Kissimmee Vacation Rentals](https://expedia.ca/Kissimmee-Vacation-Rentals.d7927.Travel-Guide-VacationRentals) General - [Visit Downtown Miami](https://expedia.ca/Miami-Downtown-Miami.dx800070) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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