Title: Visit Winston Waterways: Best of Winston Waterways, Key Largo Travel 2026 | Expedia Tourism - Expedia.ca [Hotels in Winston Waterways](https://expedia.ca/Winston-Waterways-Key-Largo-Hotels.0-n553248635976481538-0.Travel-Guide-Filter-Hotels)[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) # Winston Waterways ## Key Largo ![Clearwater Beach Pier Panorama](https://images.trvl-media.com/place/553248635976481538/ecdd89c4-e539-4429-8ffb-e8e2551fcc04.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Clearwater Beach Pier Panorama](https://images.trvl-media.com/place/553248635976481538/ecdd89c4-e539-4429-8ffb-e8e2551fcc04.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Winston Waterways Hotels Where to stay --- --- ## Winston Waterways Hotel Deals ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Beach Resort 83409 Overseas Hwy Islamorada FL CA $568 per night Mar 12 - Mar 13 Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ... 9.2/10 Wonderful! (1,675 reviews) Nice stay Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=4170&PinnedHotelID=4170&HadPinnedHotel=true®ionId=553248635976481538) ![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Reefhouse Resort & Marina 103800 Overseas Hwy Key Largo FL CA $474 per night Feb 23 - Feb 24 Book a stay at this beach hotel in Key Largo. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in ... 9.2/10 Wonderful! (1,354 reviews) Staff were great and very helpful. This is a beautiful resort! Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=3427&PinnedHotelID=3427&HadPinnedHotel=true®ionId=553248635976481538) ![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marina Del Mar Resort and Marina 527 Caribbean Drive Key Largo FL CA $294 per night Mar 4 - Mar 5 Stay at this hotel in Key Largo. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions ... 8.4/10 Very Good! (1,732 reviews) Staff was wonderful and ver accommodating! Room was very clean and the grounds are beautiful. Breakfast by pool is wonderful! Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=5114&PinnedHotelID=5114&HadPinnedHotel=true®ionId=553248635976481538) ![Bayside Inn Key Largo](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bayside Inn Key Largo 99490 Overseas Hwy Key Largo FL CA $329 per night Mar 2 - Mar 3 Book a stay at this beach hotel in Key Largo. Enjoy free WiFi, a private beach, and a 24-hour fitness center. Our guests praise the pool and the helpful staff ... 8.4/10 Very Good! (1,664 reviews) Such a great location! The view to the bay is incredible! The rooms are a bit old and the water pressure could be better but everything was clean and the staff were very nice. Very walkable to several restaurants (Snooks is great!) Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=22657&PinnedHotelID=22657&HadPinnedHotel=true®ionId=553248635976481538) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterside Suites & Marina 201 Ocean Drive Key Largo FL CA $321 per night Mar 1 - Mar 2 Stay at this hotel in Key Largo. Enjoy free WiFi, a marina, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ... 8.8/10 Excellent! (1,207 reviews) The room was nice with sitting area downstairs and bedroom upstairs. Lots of room with a kitchen and balcony. Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=13719&PinnedHotelID=13719&HadPinnedHotel=true®ionId=553248635976481538) ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 97000 Overseas Hwy Key Largo FL CA $726 per night Mar 5 - Mar 6 Book a stay at this beach resort in Key Largo. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms ... 8.4/10 Very Good! (1,002 reviews) Loved the beach and the included beach activies Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&selected=14042&PinnedHotelID=14042&HadPinnedHotel=true®ionId=553248635976481538) [See all 2,313 properties in Winston Waterways](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=14%2F02%2F2026&endDate=15%2F02%2F2026®ionId=553248635976481538) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=DX-NH_SPRING_PROMO_553248635976481538) ## Check Winston Waterways hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481538&startDate=2026-02-13&endDate=2026-02-14)[Feb 13 - Feb 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481538&startDate=2026-02-13&endDate=2026-02-14) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481538&startDate=2026-02-14&endDate=2026-02-15)[Feb 14 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481538&startDate=2026-02-14&endDate=2026-02-15) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481538&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481538&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) --- ### Other neighbourhoods around Winston Waterways ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Largo Gardens While Largo Gardens might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like John Pennekamp Coral Reef State Park and MarineLab Undersea Laboratory. [](https://expedia.ca/Key-Largo-Largo-Gardens.dx553248635976471939) ![Key West Florida - Sights and Sounds by the water and port](https://images.trvl-media.com/place/553248635976468738/e4cdcb39-8599-4d99-85bd-253ccbd56c96.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Key Largo Village While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jimmy Johnson's Big Chill and Jacob's Aquatic Center. [](https://expedia.ca/Key-Largo-Key-Largo-Village.dx553248635976468738) ![Boats moored in a marina off the Highway 1 in Key Largo, Floriday Keys, Florida, United States.](https://images.trvl-media.com/place/553248635976480816/7291e4bb-f266-4907-b7b1-59d72a523003.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Cross Key Waterways While Cross Key Waterways might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Caribbean Club Bar and MarineLab Undersea Laboratory. [](https://expedia.ca/Key-Largo-Cross-Key-Waterways.dx553248635976480816) ![Coast of Islamorada, Florida Keys](https://images.trvl-media.com/place/553248635976481780/88fa8714-c73f-4dd9-80be-c5fe469e99a3.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Key Largo Park Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jimmy Johnson's Big Chill and Jacob's Aquatic Center. [](https://expedia.ca/Key-Largo-Key-Largo-Park.dx553248635976481780) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Anglers Park 5/5(2 area reviews) While there might not be top attractions in Anglers Park, you can explore the larger area and discover places like MarineLab Undersea Laboratory and Caribbean Club Bar. [](https://expedia.ca/Key-Largo-Anglers-Park.dx553248635976468912) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Largo Sound Village While there might not be top attractions in Largo Sound Village, you can explore the larger area and discover places like Caribbean Club Bar and MarineLab Undersea Laboratory. [](https://expedia.ca/Key-Largo-Largo-Sound-Village.dx553248635976481003) --- --- - [Stays](?pwaLob=wizard-hotel-pwa-v2) - [Packages](?pwaLob=wizard-package-pwa) - [Flights](?pwaLob=wizard-flight-pwa) - [Things to do](?pwaLob=wizard-lx-pwa) - [Cruises](?pwaLob=wizard-cruise-pwa) - [Cars](?pwaLob=wizard-car-pwa) # Winston Waterways ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app