Title: Winston Waterways Holidays 2026 | Expedia.co.uk [Hotels in Winston Waterways](https://expedia.co.uk/Winston-Waterways-Key-Largo-Hotels.0-n553248635976481538-0.Travel-Guide-Filter-Hotels)[Flights to Key Largo](https://expedia.co.uk/Cheap-Flights-To-Key-Largo.d8369.Travel-Guide-Flights)[Things to do in Key Largo](https://expedia.co.uk/Things-To-Do-In-Key-Largo.d8369.Travel-Guide-Activities)[Winston Waterways Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winston-Waterways.d553248635976481538.Car-Hire-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winston Waterways Holidays ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Packages with flights are ATOL protected ### Your Winston Waterways Holiday Book a Winston Waterways holiday package and experience the atmosphere and rhythm of this captivating neighbourhood. With all your travel plans worked out, the only thing you need to concentrate on here is having a good time. Hoping to explore the sights during your trip to Winston Waterways? Be sure to stop by nearby attractions such as [John Pennekamp Coral Reef State Park](https://www.expedia.co.uk/John-Pennekamp-Coral-Reef-State-Park-United-States-of-America.d6068611.Attraction), [Jimmy Johnsons Big Chill](https://www.expedia.co.uk/Jimmy-Johnsons-Big-Chill-Key-Largo.d553248621563219632.Attraction) and [Caribbean Club Bar](https://www.expedia.co.uk/Caribbean-Club-Bar-Key-Largo.d553248621533115829.Attraction). Stop daydreaming and start doing. When it's time to book your holiday to Winston Waterways, Expedia will help you get there. ## Where to stay in Winston Waterways Find the best Winston Waterways areas and neighborhoods for the activities you enjoy most. [Learn more about Winston Waterways](https://expedia.co.uk/Key-Largo-Winston-Waterways.dx553248635976481538) ![Safety Harbor, Florida](https://images.trvl-media.com/place/553248635975874039/2fee8556-a596-4748-bd3e-bcceb526467b.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Rock Harbor 1 out of top 10 points of interest in this area While there might not be top attractions in Rock Harbor, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill. [Find hotels in Rock Harbor](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635975874039) ![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) ### Silver Shores While there might not be top attractions in Silver Shores, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Pigeon Key. [Find hotels in Silver Shores](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635976471567) ![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 When in Key Largo Village, you can plan a visit to Jimmy Johnson's Big Chill and Jacob's Aquatic Center, some noteworthy sights in the nearby area. [Find hotels in Key Largo Village](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635976468738) ![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 Key Largo Park might not have many top sights, but Jimmy Johnson's Big Chill and Jacob's Aquatic Center are two attractions nearby that you can check out. [Find hotels in Key Largo Park](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635976481780) ![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 When in Cross Key Waterways, you can plan a visit to Caribbean Club Bar and MarineLab Undersea Laboratory, some noteworthy sights in the nearby area. [Find hotels in Cross Key Waterways](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635976480816) ## Top hotels in Winston Waterways ![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/e9f2dff3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Reefhouse Resort & Marina 103800 Overseas Hwy Key Largo FL Fully refundableReserve now, pay when you stay £364 12 Mar - 13 Mar includes taxes & fees 9.4/10 Exceptional! (1,405 reviews) Excellent we love it Reviewed on 9 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=3427&PinnedHotelID=3427&HadPinnedHotel=true®ionId=553248635976481538) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/e2f3e092_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterside Suites & Marina 201 Ocean Drive Key Largo FL Fully refundableReserve now, pay when you stay £174 11 Mar - 12 Mar includes taxes & fees 9/10 Wonderful! (1,247 reviews) I made a last minute reservation to stay just one night and found the room ready for me and staff very welcoming. All rooms are second floor level and there is no lift or elevator, but an excellent ramp makes it possible to wheel suitcases or a wheelchair to the room. The bedroom in my one-bed unit ... Reviewed on 10 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=13719&PinnedHotelID=13719&HadPinnedHotel=true®ionId=553248635976481538) ![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 Fully refundableReserve now, pay when you stay £293 6 Apr - 7 Apr includes taxes & fees 9.2/10 Wonderful! (1,677 reviews) little dated in the rooms but nice Reviewed on 10 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=4170&PinnedHotelID=4170&HadPinnedHotel=true®ionId=553248635976481538) [See all 2,295 properties in Winston Waterways](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F03%2F2026&endDate=12%2F03%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/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Frequently asked questions ### How much does a Winston Waterways travel package cost? ### If I'm not able to travel, can I cancel my Winston Waterways travel package? ### How do I get a cheap travel package to Winston Waterways? ### Does Expedia offer Book Now, Pay Later Winston Waterways holidays? > - Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams come true. > - Pay in instalments holidays: If you'd prefer to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna. > - Low deposit holidays: When you see an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you get what you want. ### Where should I stay in Winston Waterways? ### What are the top hotels in Winston Waterways? ### How far in advance should I book my Winston Waterways holiday? ### What does an Expedia Winston Waterways travel package include? ### What should I know before booking a Winston Waterways travel package? ### Can I choose my airline with a Winston Waterways Expedia travel package? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.