Winston Waterways Trips (flight + hotel)

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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

While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.

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 P13,918 per night from Jul 23 to Jul 24
P13,918
P18,839 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (1,482 reviews)
"The property is nice. Water pressure was not great. Water stopped completely while in the shower on multiple occasions. It was not off long but it was completely off. It was nice that breakfast was served a bit later, but even by 9 some things were gone. Overall nice stay."

Reviewed on Jul 6, 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 P6,959 per night from Aug 10 to Aug 11
P6,959
P7,829 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Great staff, very prompt"

Reviewed on Jul 7, 2025

Hampton Inn Key Largo Manatee Bay
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by Hilton
4 out of 5
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is P16,430 per night from Jul 13 to Jul 14
P16,430
P21,602 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"beautiful place and location but it could be more luxurious for the price"

Reviewed on Jul 8, 2025

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,251 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 vacation package cost?
Our Winston Waterways vacation 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 vacation 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 vacation?
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 vacation package?
Most definitely. Expedia has access to more than 550 airlines all over the world, so you can customize your Winston Waterways vacation according to your travel needs.
If I'm not able to travel, can I cancel my Winston Waterways vacation package?
You can. We realize life happens, so we're happy to help if you need to make changes to your Winston Waterways vacation 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.