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) ![](https://images.trvl-media.com/place/553248621563220296/e155ce65-e05d-4828-bad4-09cc4a36ce98.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248621563220296/e155ce65-e05d-4828-bad4-09cc4a36ce98.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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://images.trvl-media.com/place/6246827/1df1ca27-0c09-4c02-a20a-892bfe87b325.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) ![Aerial Key Colony Marathon Florida Keys](https://images.trvl-media.com/place/121486/6746c800-d35f-465b-9341-fafb5e3cd1d9.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) ![Striking sunrise viewed on a tropical sandy beach at the Atlantic Ocean Shore. Plantation Key, Florida Keys, Florida, United States.](https://images.trvl-media.com/place/10047/c3213b0e-e385-4951-809c-014f7d7ac83b.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) ![](https://images.trvl-media.com/place/7195/453b5f3b-21ff-43f4-af99-caa27959ad08.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) ## Check availability on Monroe County Winery Hotels Tonight [Apr 7 - Apr 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2026-04-07&endDate=2026-04-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 8 - Apr 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2026-04-08&endDate=2026-04-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2026-04-10&endDate=2026-04-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976430869&startDate=2026-04-17&endDate=2026-04-19&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 ![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 "The property was well kept. Most all rooms over look the pools and marina. It is a very comfortable and safe place. The on site restaurant had great food and drinks for the whole family. We will go back!!" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "We had a fantastic stay at the Reef House in Key Largo! They won us over right from the start—when we asked about a possible upgrade, they went above and beyond. We had originally booked a one-room with two beds and were pleasantly surprised to be upgraded to a spacious two-bedroom with a kitchen and living room. We were so impressed! The amenities were excellent—great pool and hot tub, right on the beach, plus fun extras like cornhole and other games. While we didn’t eat on-site since we enjoyed exploring local restaurants, everything the property offered made our stay easy and relaxing. One of the highlights was being able to have our fishing charter pick us up from the dock—so convenient! Overall, a wonderful experience and we would definitely go back." [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.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 8/10 Good "The property was very nice, with a lot of amenities: 2 pools, 3 bars, an exercise room, outdoor lawn games such as jumbo chess, shuffleboard, bean bag toss, and foosball. The front desk was very friendly and helpful. One disappointment was the lack of an airport shuttle. We flew directly into Key West and chose the Blue Flamingo partially because we read they had a free shuttle service. Unfortunately, the shuttle doesn't pick up or drop off guests at the airport. It has one location in the downtown area it shuttles guests to every hour on the hour (which needs to be reserved in advance), and offers pick up from the same location every hour on the 1/2 hour. We ended up using Uber most of the time. Another disappointment was the elevator. The property is quite large, with one main 6-story building and another smaller 2-story building. There are 2 elevators, one of which was inoperable during our entire stay. That meant that all guests plus housekeeping were limited to one small elevator. We ended up taking the stairs for our many trips up and down, which got to be a bit much since we were on the 5th floor. A broken coffee maker was promptly fixed, and a weird situation with our door mechanism (neither we nor housekeeping could get into our room) was addressed, but we didn't get housekeeping during our stay even when we asked for it. I noticed a mysterious charge on my bill. When I called to ask about it I was told someone would call me back. They didn't." [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Had great time on a girls trip" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Havana Cabana at Key West ](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/62539afb_y.jpg) ### Havana Cabana at Key West 10/10 Excellent "Great resort!" [](https://expedia.ca/Key-West-Hotels-Havana-Cabana-At-Key-West.h21241090.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg) ### Pier House Resort & Spa 6/10 Okay "Not worth the price. Nice but not great" [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Beautiful property and the beach is nice, calm, and quiet. The made to order breakfasts every morning were absolutely amazing and delicious! My only complaint was that we explored Islamorada and did adventures during the day off the property. When we came back after dinnertime, we wanted to use some of the amenities such as fishing or having a drink from the bar and everything closed early (4:00-7:00 it was closed by). Would've been nice to have those things open till dark. " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![The Laureate Key West](https://images.trvl-media.com/lodging/28000000/27160000/27156600/27156592/cba0d59f_y.jpg) ### The Laureate Key West 10/10 Excellent "This was a very nice place we really enjoyed it. Very clean and quiet. Beautiful view from the balcony. Staff was very helpful. Dislike: Elevator was too slow!!" [](https://expedia.ca/Key-West-Hotels-The-Laureate-Key-West.h27156592.Hotel-Information) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/e2f3e092_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Fantastic " [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.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) - 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