Title: Book the Best Hotels with BARS in Winston Waterways in 2025 | Expedia.ca [Flights to Key Largo](https://expedia.ca/Cheap-Flights-To-Key-Largo.d8369.Travel-Guide-Flights)[Things to do in Key Largo](https://expedia.ca/Things-To-Do-In-Key-Largo.d8369.Travel-Guide-Activities)[Winston Waterways Car Rentals](https://expedia.ca/Car-Rentals-In-Winston-Waterways.d553248635976481538.Car-Rental-Guide)[Winston Waterways Vacations](https://expedia.ca/Winston-Waterways.d553248635976481538.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Winston Waterways, FL ![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 ## Check availability on Winston Waterways Hotels with Bar ## Top Winston Waterways Hotels with Bar ## Top Winston Waterways Hotel Reviews ![The Pelican Key Largo Cottages](//images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg) ### The Pelican Key Largo Cottages 10/10 Excellent "Our cottage was old school Florida charm which is exactly what I was looking for! The property had a nice little beach with loungers and umbrellas. The docks had adirondak chairs perfect for enjoying coffee in the morning and watching the sunset in the evening. I would definitely recommend this property!" [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Holiday Inn Key Largo by IHG](//images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg) ### Holiday Inn Key Largo by IHG 10/10 Excellent "September is the quietest month and this has been exceptionally quiet apparently, still staff were very attentive, no reason to think it unusual ," [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Excellent recommendation for a small budget." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Playa Largo Resort & Spa, Autograph Collection](//images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg) ### Playa Largo Resort & Spa, Autograph Collection 10/10 Excellent "The entire environment " [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Sunset Cove Beach Resort](//images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/fe271bae_y.jpg) ### Sunset Cove Beach Resort 10/10 Excellent "Staff was friendly, check in was a breeze. The cottage 2 was clean, updated, and stocked with a blender, dishes, paper towels, soap and a sponge. The shower and bathroom were great and everything was perfectly cleaned. Second furthest cottage from the beach and it took probably 1 minute to walk down to the water. The cabanas and seating was plentiful and again, up-kept very well. Only “3 star” rating was for eco-friendly because there was few trash/recycling bins on the beach or in the property, but if others were mindful that shouldn’t be an issue. We brought our dog, and had no issues with this, they even gave a nice “dog blanket” to cover the whole bed so there was not any contact with it for future guests. They also offered a dog bed and poop bags which was nice. Free coffee & pastries were set out every morning and there were lots of cute shady areas to sit around even aside from the beach. We ate out for lunch and dinner each night and easily could have walked to most of the places-great location, helpful and friendly staff, very clean. 10/10! " [](https://expedia.ca/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information) ![Hampton Inn Key Largo Manatee Bay](//images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233_y.jpg) ### Hampton Inn Key Largo Manatee Bay 10/10 Excellent "There’s a small but cozy beach area with the best view for sunset during happy hour at the tiki bar. We saw other guests have easy access to kayaks and paddle boarding and pets were welcomed!" [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Bayside Inn Key Largo](//images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg) ### Bayside Inn Key Largo 10/10 Excellent "Yes everything was just amazing i felt so safe It was just me and my sister and we would definitely come back " [](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](//images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 10/10 Excellent "Beautiful views, friendly staff. Great amenities " [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Ocean Pointe Suites at Key Largo](//images.trvl-media.com/lodging/1000000/10000/5600/5502/c6c81bd5_y.jpg) ### Ocean Pointe Suites at Key Largo 10/10 Excellent "Excelente beautiful " [](https://expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Winston Waterways? > Though you might not find a hotel in Winston Waterways well-known for its bar, you will find 18 properties to choose from, some of which will have an onsite bar where you can unwind with a beer after a day out and about. While you're here, consider a visit to John Pennekamp Coral Reef State Park. ### What are the best hotels with bars in Winston Waterways? > Below are some of top hotels with bars in and around Winston Waterways: [Chesapeake Beach Resort](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information): Enjoy the bar, free breakfast, and free WiFi. [Reefhouse Resort & Marina](https://www.expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information): Hotel with 3 restaurants. Enjoy the beach bar, poolside bar, and free parking. [Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information): Resort with 2 restaurants. Enjoy the beach bar, poolside bar, and 2 outdoor pools. [Waterside Suites & Marina](https://www.expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information): Hotel with 2 restaurants. Enjoy the bar, free WiFi, and free parking. [Marina Del Mar Resort and Marina](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information): Enjoy the bar, free breakfast, and free WiFi. ### What is there to do in Winston Waterways? > In the area, you can visit John Pennekamp Coral Reef State Park, MarineLab Undersea Laboratory, and Caribbean Club Bar, then find a cozy spot for a nightcap. Other places to see in the area include Jimmy Johnson's Big Chill and Harry Harris Park. ### How can I get to Winston Waterways and around the area? > You might want to make the most of these transportation choices in and around Winston Waterways: Fly into Miami Intl. Airport (MIA), which is located 47.6 mi (76.5 km) away. 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[Spa Hotels in Largo Gardens](https://www.expedia.ca/Largo-Gardens-Key-Largo-Hotels-Spa-Hotel.0-n553248635976471939-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Business-Hotel.0-0-d178286-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Miami](https://www.expedia.ca/Miami-Hotels-Couples-Resorts-Hotels.0-0-d178286-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Green Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Green-Sustainable.0-0-d178286-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with Wifi in Miami](https://www.expedia.ca/Miami-Hotels-Hotel-With-Wifi.0-0-d178286-tHotelwithwifi.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Miami](https://www.expedia.ca/Miami-Hotels-Hotels-With-Bar.0-0-d178286-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Miami](https://www.expedia.ca/Miami-Hotels-Hotels-With-Childcare.0-0-d178286-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Miami](https://www.expedia.ca/Miami-Hotels-Hotels-With-Smoking-Rooms.0-0-d178286-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Lake Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Lake-Hotels.0-0-d178286-tLakeHotels.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Mountain-Hotels.0-0-d178286-tMountainHotels.Travel-Guide-Filter-Hotels) - [Scuba Diving Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Scuba-Diving-Vacations.0-0-d178286-tscubadivingvacations.Travel-Guide-Filter-Hotels) - [Ski Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Ski-Hotel.0-0-d178286-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Waterpark-Hotels.0-0-d178286-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Winery-Hotel.0-0-d178286-tWineryHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in North Key Largo](https://www.expedia.ca/North-Key-Largo-Hotels-Cheap-Hotels.0-0-d553248635976475358-tCheapHotels.Travel-Guide-Filter-Hotels) - 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