Winston Waterways Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ฿4,531 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, 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
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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

Top hotels in Winston Waterways

Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ฿8,007 per night from 23 Jul to 24 Jul
฿8,007
฿10,838 total
23 Jul - 24 Jul
includes taxes & fees
9/10 Wonderful! (1,470 reviews)
"An absolute dream! This place is absolutely amazing. Price point was great too. I can’t wait to come back!"

Reviewed on 24 Jun 2025

Chesapeake Beach Resort
Hampton Inn Key Largo Manatee Bay
Hampton Inn Key Largo Manatee Bay
2.5 out of 5
102400 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is ฿4,287 per night from 16 Jul to 17 Jul
฿4,287
฿4,823 total
16 Jul - 17 Jul
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"Staff was great and gave us a recommendation for sunset meal that was great. Hotel is dated but nice and has a great view of the bay."

Reviewed on 25 Jun 2025

Hampton Inn Key Largo Manatee Bay
Reefhouse Resort & Marina
Reefhouse Resort & Marina
3.5 out of 5
103800 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is ฿9,079 per night from 29 Jun to 30 Jun
฿9,079
฿11,516 total
29 Jun - 30 Jun
includes taxes & fees
9.2/10 Wonderful! (1,311 reviews)
"I had a great stay! The check-in process was quick and smooth, and there was plenty of parking available. The staff was warm, welcoming, and went above and beyond-surprising me with a complimentary bottle of champagne, which was such a thoughtful touch. The tiki bartenders were fantastic, and the ..."

Reviewed on 25 Jun 2025

Reefhouse Resort & Marina
See all 2,249 properties in Winston Waterways
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.