
Winston Waterways Holidays from £1,016
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages 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, Jimmy Johnsons Big Chill and Caribbean Club Bar. Stop daydreaming and start doing. When it's time to book your holiday to Winston Waterways, Expedia will help you get there.


The Retreat Collection at 1 Hotel & Homes South Beach
Reviewed on 22 Jun 2016



YotelPad Miami
Reviewed on 2 Nov 2026
Where to stay in Winston Waterways

Rock Harbor
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.
Top hotels in Winston Waterways

Reefhouse Resort & Marina
"Very nice"
Reviewed on 2 Nov 2026

Chesapeake Beach Resort
"This resort was the perfect getaway for us!! Ocean front! Beautiful views!!"
Reviewed on 2 Nov 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Frequently asked questions
Things to do

Florida: Key West Overseas Highway App-Based Driving Audio Tour

Key Largo Coral Reef Glass Bottom Boat Adventure

Small Group Florida Keys Eco Tour by Boat
* 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.












