Winston Waterways Vacation Packages

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Top Holiday Package Deals in Winston Waterways

Price found within the past 48 hours. Click for updated prices.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Overall, our stay was great. The resort was clean, quaint, and had a very relaxing atmosphere. The staff was friendly, and everything felt well-maintained and peaceful — perfect for a quiet getaway. That said, the pricing structure was a bit frustrating. While the base rate was already on the expensive side, we were surprised to find that many things you’d typically expect to be included — like beach access, pool use, and other basic amenities — came with additional charges. It felt like we were constantly paying extra for features that should be standard at this price point. Despite the added costs, we enjoyed our time there. Just be prepared to budget more than expected if you want to take full advantage of everything the property offers.

Reviewed on Jul. 20, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Oct 7 - Oct 13
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Overall, I enjoyed my stay would definitely go back

Reviewed on Jul. 20, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Good stay, hotel was accommodating whenever I needed something. Great location in south beach. Will be back

Reviewed on Jul. 20, 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Save 100% on your flight
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (3,202 reviews)
The area has so many things nearby, it is quite busy but it's an amazing area. The hotel was 10/10, enjoyed every bit me and my partner, WE WILL BE BACK!

Reviewed on Jul. 21, 2025

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

Winston Waterways Hotel Deals

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 CA $195 per night from Aug 20 to Aug 21
CA $195
CA $297 total
Aug 20 - Aug 21
includes taxes & fees
9/10 Wonderful! (1,481 reviews)
"Great view! Sweet ppl that work there!"

Reviewed on Jul. 19, 2025

Chesapeake Beach Resort
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 CA $432 per night from Aug 14 to Aug 15
CA $432
CA $561 total
Aug 14 - Aug 15
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"The resort was beautiful and although it was sold out it never seemed med to crowded."

Reviewed on Jul. 20, 2025

Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 CA $162 per night from Aug 17 to Aug 18
CA $162
CA $182 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Love this hotel. The staff is amazing and the room was large and comfortable. They property is a little older but it is very clean, renovated and maintained extremely well."

Reviewed on Jul. 19, 2025

Hampton Inn Key Largo Manatee Bay
See all 2,259 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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Frequently asked questions

How much does a Winston Waterways vacation package cost?
Our Winston Waterways vacation packages, which start at just CA $784, 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.