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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/beach.jpeg?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 [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-13&endDate=2025-10-14&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-14&endDate=2025-10-15&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## 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) ![Property grounds](https://images.trvl-media.com/lodging/60000000/59850000/59841600/59841531/255494b7.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) ![Smart TV, fireplace, DVD player, music library](https://images.trvl-media.com/lodging/60000000/59850000/59841600/59841531/68549e70.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!!!" [](https://www.expedia.ca/Key-Largo-Hotels-Paradise-On-The-Canal-With-Ocean-Access-Including-Pool-Spa.h59841531.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) ![Marina](https://images.trvl-media.com/lodging/31000000/30090000/30083000/30082976/042a3fad.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) ### LUXURY HOME, WATERFRONT, 5 MINS FROM OCEAN, 80FT DOCK, HOT TUB, GOURMET KITCHENT Winston Waterways 10/10 Exceptional (48) "Great place to stay" [](https://www.expedia.ca/Key-Largo-Hotels-LUXURY-HOME.h30082976.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) ![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) ![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) ### 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!!!" [](https://www.expedia.ca/Key-Largo-Hotels-Spacious-4-Bedroom-Vacation-Home-Minutes-To-John-Pennekamp-Coral-Reef-State-Park.h103915745.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) ![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) ![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) ### 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) ![Outdoor pool](https://images.trvl-media.com/lodging/74000000/73250000/73240700/73240668/1483e3ed.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) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73250000/73240700/73240668/8a3770a3.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) ### Key Largo Oasis. Winston Waterways [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Oasis.h73240668.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33700000/33695400/33695396/6d358926.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) ### SPECTACULAR HOME IN Key Largo, Florida WITH EXCELLENT VIEWS Winston Waterways 9.4/10 Exceptional (11) "We had a great time" [](https://www.expedia.ca/Key-Largo-Hotels-SPECTACULAR-HOME-IN-Key-Largo.h33695396.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) ![Exterior](https://images.trvl-media.com/lodging/89000000/88830000/88829100/88829040/d17af949.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." [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Home-With-Breathtaking-Water-Views.h88829040.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 | 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 | 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 | Pool](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283613/21d11928.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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/80000000/79390000/79390000/79389994/9fc936df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/80000000/79390000/79390000/79389994/w507h683x259y0-b8e3d20f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/80000000/79390000/79390000/79389994/w506h683x259y0-5b2932c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/80000000/79390000/79390000/79389994/w906h683x59y0-164f91df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Tides Winston Waterways [](https://www.expedia.ca/Key-Largo-Hotels-Family-Tides.h79389994.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=2025-10-27&endDate=2025-10-28®ionId=553248635976481538&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Top Winston Waterways Hotel Reviews ![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 "Awesome trip stayed there for seven days had a blast down by the pool and the tiki hut and the iguanas are fun to watch as are the curly tail lizards no problem we had in the room was the toilet didn’t flush very well. It did flush but it was slow. The restaurant next-door within walking distance is nice pool tables and some other games and all we had a great time if you do go here make sure you go to Rob’s Marina feed the tarpon and go along the snorkeling trip to the lighthouse. You will be amazed. Happy travels." [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ![Waterside Suites & Marina](//images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "The rooms have 2 levels. There’s living room and kitchen downstairs. The couch downstairs makes into bed and then the main bedroom is up stairs. If you have a friend that snores you can get away to another bedroom " [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.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 "The staff was so nice and I loved the little beach/ pool area!" [](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 "view was great ,service was great also" [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.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 "Staff was great, pool area was beautiful. Great Food and drink options. Very relaxing, did not need to leave the resort. Shout out to Matt the bartender who was amazing!" [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Hadley Resort and Marina](//images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd_y.jpg) ### Hadley Resort and Marina 10/10 Excellent "Super " [](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.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 "First time there and it was very nice and clean. Staff was great!" [](https://expedia.ca/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information) ![Creekside Inn Islamorada](//images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg) ### Creekside Inn Islamorada 10/10 Excellent "Great little place on the water. Easy access for boating. Hidden Gem. We will definitely be booking again soon. " [](https://expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Bartender should be more helpful Saturday 10/4/25 Carlos was very helpful " [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ## Frequently asked questions ### What is Winston Waterways like for travelers who love the beach? > Discover your ideal place to stay in Winston Waterways, which has a lot to offer the traveler looking for a beach getaway. ### What is there to see and do around Winston Waterways? > After checking into your accommodation of choice, you'll probably want to venture out and explore. Discover a variety of local attractions, which include John Pennekamp Coral Reef State Park and MarineLab Undersea Laboratory. 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