Title: 4 Stars Hotels in Winston Waterways, Key Largo from CA $608 - Find Cheap Winston Waterways Hotels With 4 Stars | Expedia.ca [Winston Waterways Travel Guide](https://expedia.ca/Key-Largo-Winston-Waterways.dx553248635976481538)[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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 ## Check availability on Winston Waterways 4 Star Hotels Tonight [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-01-18&endDate=2026-01-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-01-19&endDate=2026-01-20&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976481538&startDate=2026-01-30&endDate=2026-02-01&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winston Waterways 4-star hotels ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/7c755dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/3b0a2582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/0df3bfb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/4de34d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 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) Key Largo 8.6/10 Excellent (1,004 reviews) "Everything about this place was perfect, location, staff, comfort, and amenities. Can’t wait to go back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fabiane CA $472 CA $608 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/8c74658c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/ba58782b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/bb9d7ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/92d23e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Largo Resort & Spa, Autograph Collection [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) Rock Harbor 8.8/10 Excellent (1,003 reviews) "Everything was great. Very clean and excellent location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) peter CA $611 CA $764 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fcc01350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a064415d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) Matecumbe 9.8/10 Exceptional (70 reviews) "Amazing stay, can’t wait to stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $763 CA $935 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![House, 3 Bedrooms | Dining](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284316/8791240b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284316/aef7d17c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Pool](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284316/69d8167a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284316/7ec2eb24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lime Key by Florida Keys Luxury Rentals [](https://www.expedia.ca/Key-Largo-Hotels-Lime-Key-By-Florida-Keys-Luxury-Rentals.h72284316.Hotel-Information) Buccaneer Point [](https://www.expedia.ca/Key-Largo-Hotels-Lime-Key-By-Florida-Keys-Luxury-Rentals.h72284316.Hotel-Information) ![House, 3 Bedrooms | Balcony](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284318/81b644b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284318/477ebb36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Pool](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284318/87ec301a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Balcony](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284318/177ebf94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sanctuary Islet by Florida Keys Luxury Rentals [](https://www.expedia.ca/Key-Largo-Hotels-The-Sanctuary-Islet-By-Florida-Keys-Luxury-Rentals.h72284318.Hotel-Information) Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-The-Sanctuary-Islet-By-Florida-Keys-Luxury-Rentals.h72284318.Hotel-Information) ![House, 5 Bedrooms | Balcony](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284315/1f429a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Dining](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284315/a0ec2dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Pool](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284315/6c262c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Exterior](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284315/dc20dcc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Midnight Runner by Florida Keys Luxury Rentals [](https://www.expedia.ca/Tavernier-Hotels-Midnight-Runner-By-Florida-Keys-Luxury-Rentals.h72284315.Hotel-Information) Tavernier [](https://www.expedia.ca/Tavernier-Hotels-Midnight-Runner-By-Florida-Keys-Luxury-Rentals.h72284315.Hotel-Information) ![House, 5 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/9cd307d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Balcony](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/c5120887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Exterior](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/17e25e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/73000000/72290000/72284400/72284313/4bb0823d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pineapple Beach by Florida Keys Luxury Rentals [](https://www.expedia.ca/Islamorada-Hotels-Pineapple-Beach-By-Florida-Keys-Luxury-Rentals.h72284313.Hotel-Information) Islamorada [](https://www.expedia.ca/Islamorada-Hotels-Pineapple-Beach-By-Florida-Keys-Luxury-Rentals.h72284313.Hotel-Information) ![House, 5 Bedrooms | Exterior](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283612/6e67804b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283612/6278eb8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283612/e5adec7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Pool](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283612/01839bea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bay Beach by Florida Keys Luxury Rentals [](https://www.expedia.ca/Key-Largo-Hotels-Bay-Beach-By-Florida-Keys-Luxury-Rentals.h72283612.Hotel-Information) Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-Bay-Beach-By-Florida-Keys-Luxury-Rentals.h72283612.Hotel-Information) ![House, 4 Bedrooms | Pool](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283611/d3246cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283611/2729607c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283611/eb6743db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Interior](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283611/cc4a66b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coral Palm's Estate by Florida Keys Luxury Rentals [](https://www.expedia.ca/Key-Largo-Hotels-Coral-Palms-Estate-By-Florida-Keys-Luxury-Rentals.h72283611.Hotel-Information) Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-Coral-Palms-Estate-By-Florida-Keys-Luxury-Rentals.h72283611.Hotel-Information) ![House, 4 Bedrooms | Pool](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283613/185a994e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Beach](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283613/e4561dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 | Beach/ocean view](https://images.trvl-media.com/lodging/73000000/72290000/72283700/72283613/98fb16a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cukoos Nest by Florida Keys Luxury Rentals [](https://www.expedia.ca/Key-Largo-Hotels-Cukoos-Nest-By-Florida-Keys-Luxury-Rentals.h72283613.Hotel-Information) Winston Waterways [](https://www.expedia.ca/Key-Largo-Hotels-Cukoos-Nest-By-Florida-Keys-Luxury-Rentals.h72283613.Hotel-Information) ![](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%2F4Star-Winston-Waterways-Key-Largo-Hotels.s40-n553248635976481538-0.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Winston-Waterways-Key-Largo-Hotels.s40-n553248635976481538-0.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Winston Waterways. ![Condo in the Keys](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/9b3c41b7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Condo in the Keys 500 Burton Dr Tavernier FL [Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=93061348&PinnedHotelID=93061348&HadPinnedHotel=true®ionId=553248635976481538) 7.8/10 Good! (13 reviews) [](https://expedia.ca/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) ![Waterfront House with Boat Dock](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/5d9195bd_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Waterfront House with Boat Dock 213 Aberdeen Ct Tavernier FL [Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=109724487&PinnedHotelID=109724487&HadPinnedHotel=true®ionId=553248635976481538) 7/10 Good! (2 reviews) [](https://expedia.ca/Tavernier-Hotels-Waterfront-House-With-Boat-Dock.h109724487.Hotel-Information) Still don't see what you're looking for? [See all properties in Winston Waterways.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976481538&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976481538&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976481538&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976481538&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976481538&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976481538&star=40&star=40&amenities=WATER_PARK) 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. ## Top Winston Waterways Hotel Reviews ![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 "Everything about this place was perfect, location, staff, comfort, and amenities. Can’t wait to go back!" 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