Winston Waterways Holidays

Book a Hotel + Flight or Car together to unlock savings

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 John Pennekamp Coral Reef State Park, 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 3.230.173 ₫ per night from 26 Aug to 27 Aug
3.230.173 ₫
5.116.582 ₫ total
26 Aug - 27 Aug
includes taxes & fees
9/10 Wonderful! (1,498 reviews)
"All good unless the beach"

Reviewed on 23 Aug 2025

Chesapeake Beach Resort
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 5.772.402 ₫ per night from 26 Aug to 27 Aug
5.772.402 ₫
7.548.404 ₫ total
26 Aug - 27 Aug
includes taxes & fees
9.2/10 Wonderful! (1,301 reviews)
"Loved it"

Reviewed on 22 Aug 2025

Reefhouse Resort & Marina
Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG

3 out of 5
99701 Overseas Hwy, Key Largo, FL
Fully refundable
The price is 3.769.194 ₫ per night from 7 Sept to 8 Sept
3.769.194 ₫
4.240.343 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Quiet and close to attractions. Very clean. Far enough away from bar/party area but still walkable if that’s what you want."

Reviewed on 23 Aug 2025

Holiday Inn Key Largo by IHG
See all 2,262 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 1null000null000 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.