Title: Book the Best BEACH RESORTS in Winston Waterways, Key Largo - Winston Waterways Hotels on the Beach| 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) ![Clearwater Beach Pier Panorama](https://images.trvl-media.com/place/553248635976481538/ecdd89c4-e539-4429-8ffb-e8e2551fcc04.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Beach Hotel in Winston Waterways, Key Largo - ![](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 Winston Waterways Beach Hotel Tonight [Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-12-05&endDate=2025-12-06&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [Dec 6 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-12-06&endDate=2025-12-07&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## Top Winston Waterways Beach Hotel ![A heated pool](https://images.trvl-media.com/lodging/60000000/59850000/59841600/59841531/dfbc577c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59850000/59841600/59841531/3557c6bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59850000/59841600/59841531/ca0b447d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/59850000/59841600/59841531/255494b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise on the Canal with Ocean Access including Pool & Spa Winston Waterways 10/10 Exceptional (1) "This is a neat and tidy property that is really close to a lot of things to do in Key Largo. The communication with the property managers was over the top good. Quick response to anything we inquired about with quick resolution. The owner is spending some money on the home updating things. It's already great and will be even better once it's all complete. This is a fantastic place to stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark M. [](https://www.expedia.ca/Key-Largo-Hotels-Paradise-On-The-Canal-With-Ocean-Access-Including-Pool-Spa.h59841531.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/104000000/103920000/103915800/103915745/c8c17eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/104000000/103920000/103915800/103915745/51efcaf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis](https://images.trvl-media.com/lodging/104000000/103920000/103915800/103915745/9d8ae4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103920000/103915800/103915745/89d6439c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 4-bedroom vacation home minutes to John Pennekamp Coral Reef State Park Winston Waterways 10/10 Exceptional (2) "The property was just as advertised! Beautifully furnished and appointed! Our first month long stay in the keys, our only complaint was that it wasn’t long enough! Gerard is a wonderful host that assisted us with any questions we had. Definitely going back!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth W. [](https://www.expedia.ca/Key-Largo-Hotels-Spacious-4-Bedroom-Vacation-Home-Minutes-To-John-Pennekamp-Coral-Reef-State-Park.h103915745.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/31000000/30090000/30083000/30082976/c40e03cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30090000/30083000/30082976/29eadb50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/31000000/30090000/30083000/30082976/7070bf87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30090000/30083000/30082976/02789fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LUXURY HOME, WATERFRONT, 5 MINS FROM OCEAN, 80FT DOCK, HOT TUB, GOURMET KITCHENT Winston Waterways 10/10 Exceptional (48) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy H. [](https://www.expedia.ca/Key-Largo-Hotels-LUXURY-HOME.h30082976.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117880000/117879200/117879131/9e989068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117880000/117879200/117879131/1c982d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117880000/117879200/117879131/ccc1dba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117880000/117879200/117879131/7eaf84ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keys Harbor 20% OFF: Waterfront, Private Boat Dock, Outdoor Oasis Winston Waterways [](https://www.expedia.ca/Key-Largo-Hotels-Keys-Harbor-Waterfront.h117879131.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88830000/88829100/88829040/dc4d7518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88830000/88829100/88829040/6c65392b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/89000000/88830000/88829100/88829040/8ce27bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88830000/88829100/88829040/18c38f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo home with breathtaking water views Winston Waterways 10/10 Exceptional (4) "Our second visit at this wonderful rental was just as great as our first, if not better. The home is just as described and the hosts are fantastic! Thoroughly enjoyed our time in Key Largo. Looking forward to returning once again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James K. [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Home-With-Breathtaking-Water-Views.h88829040.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33700000/33695400/33695396/6695194e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video-game console, books, stereo](https://images.trvl-media.com/lodging/34000000/33700000/33695400/33695396/27ed7664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33700000/33695400/33695396/6d358926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33700000/33695400/33695396/0187ef1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SPECTACULAR HOME IN Key Largo, Florida WITH EXCELLENT VIEWS Winston Waterways 9.4/10 Exceptional (11) "We had a great time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David D. [](https://www.expedia.ca/Key-Largo-Hotels-SPECTACULAR-HOME-IN-Key-Largo.h33695396.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/74000000/73250000/73240700/73240668/1483e3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73250000/73240700/73240668/d87ec5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Stovetop, coffee/tea maker, toaster, blender](https://images.trvl-media.com/lodging/74000000/73250000/73240700/73240668/cb3612ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/74000000/73250000/73240700/73240668/7c58a9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo Oasis. Winston Waterways [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Oasis.h73240668.Hotel-Information) ![House, 4 Bedrooms | Beach](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283613/98862765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283613/ecbdf21b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Living room](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283613/90571f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283613/274524cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cukoos Nest by Florida Keys Luxury Rentals Winston Waterways [](https://www.expedia.ca/Key-Largo-Hotels-Cukoos-Nest-By-Florida-Keys-Luxury-Rentals.h72283613.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-19&endDate=2025-12-20®ionId=553248635976481538&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Top Winston Waterways Hotel Reviews ![Drift Hotel](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/f3e504e7_y.jpg) ### Drift Hotel 10/10 Excellent "Everything good" [](https://expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.Hotel-Information) ![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Staff was amazing and food was excellent" [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Great property with boat slips " [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![The Pelican Key Largo Cottages](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg) ### The Pelican Key Largo Cottages 10/10 Excellent "Exellent " [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg) ### Creekside Inn 10/10 Excellent "Very basic amenities. Comfortable bed. Friendly staff. Pool clean. Able to use Freebie app to have rides around to restaurants and bars. Right on creek. " [](https://expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 10/10 Excellent "Lovely resort with dr" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Hadley Resort and Marina](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd_y.jpg) ### Hadley Resort and Marina 10/10 Excellent "Gisselle and her daughter who helped us were great. We enjoyed the property and thr room. Beautiful views, spacious and comfortable. Location was perfect. The front desk had just dealt with unkind clients but when it came to us they put aside whay they had just dealt with and greeted us with a smile. The ability to do thay was refreshing and they get A plus in customer serivce." [](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg) ### Fisher Inn Resort & Marina 10/10 Excellent "Recomendado el hotel tiene varios juegos que hacer con los ninos ademas puedes montar kayaks bicicleta." [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Bayside Inn Key Largo](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg) ### Bayside Inn Key Largo 10/10 Excellent "The room was clean, and the staff even folded the toilet paper in a cute bow. Loved that we could use the bikes and paddle boards at the hotel for free. The resturant next door was delicious, and show your room card for 10% off" [](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ## Frequently asked questions ### What is Winston Waterways like for travelers who love the beach? ### What is there to see and do around Winston Waterways? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Adults-Only-Resorts.0-n6240961-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Casino Hotels in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Casino-Hotel.0-n6240961-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Couples-Resorts-Hotels.0-n6240961-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Hotel-With-Early-Check-In.0-n6240961-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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