Winston Waterways Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 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 easyPlan, book, and manage your trip all in one place
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
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.
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 Jimmy Johnson's Big Chill.
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.
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.
Cross Key Waterways
When in Cross Key Waterways, you can plan a visit to MarineLab Undersea Laboratory and Caribbean Club Bar, some noteworthy sights in the nearby area.
Top hotels in Winston Waterways
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
฿7,203
฿9,420 total
9 Sept - 10 Sept
includes taxes & fees
9.2/10 Wonderful! (1,536 reviews)
"Great experience"
Reviewed on 8 Sept 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
฿7,795
฿10,582 total
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (1,186 reviews)
"It doesn’t have much to offer, upper floors have vacant spaces, should create spaces to entertain visitors, elevators too old, BORING HOTEL"
Reviewed on 8 Sept 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
฿3,922
฿6,263 total
9 Sept - 10 Sept
includes taxes & fees
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.
Frequently asked questions
How much does a Winston Waterways holiday package cost?
Our Winston Waterways holiday packages, which start at just , are the perfect way to save precious money. Choose your preferred flights, hotels and rental cars to create a personalized escape.
How do I get a cheap travel package to Winston Waterways?
If you love scoring a bargain, bundle your bookings into a Winston Waterways holiday package. Whether you need hotels, flights, tours or rental cars, you can browse and book everything in one place. You'll have plenty of choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 hotel options all over the world to pick from. Fly with who you prefer, stay where you like and save your hard-earned money — now that's the perfect escape!
Where should I stay in Winston Waterways?
With loads to discover in Winston Waterways, it'd be convenient for you to lock in a hotel close to its attractions. Jimmy Johnsons Big Chill, Caribbean Club Bar and MarineLab Undersea Laboratory are some fascinating ones to put on your to-do list.
How far in advance should I book my Winston Waterways holiday?
Search Expedia to compare international flights as soon as possible. You can normally purchase a ticket up to a year in advance. If it's too early for your preferred carrier, or you've left things to the last minute, don't despair. Cheap tickets to Winston Waterways sometimes emerge just weeks before the date of departure.
What does an Expedia Winston Waterways travel package include?
Select from any combination of flights, rental cars and hotels. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your fare class? That's possible too. The choice is yours when it comes to arranging your dream Winston Waterways getaway.
What should I know before booking a Winston Waterways travel package?
You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and score fantastic discounts. Hotels aren't your only choice, though. Book with us and take your pick of island resorts, cabins in the mountains and even ranches and treehouses!
Can I choose my airline with a Winston Waterways Expedia holiday package?
Most definitely. Expedia has access to more than 550 airlines all over the world, so you can customize your Winston Waterways holiday according to your travel needs.
If I'm not able to travel, can I cancel my Winston Waterways holiday package?
You can. We realise life happens, so we're happy to help if you need to make changes to your Winston Waterways holiday package. It may be possible to cancel or change your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
Things to do
Half Day Snorkel Trip on Reefs in the Florida Keys
฿2,460
per adult
94% of travellers recommend
Florida: Key West Overseas Highway App-Based Driving Audio Tour
฿557
per traveller
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.