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.
Beach Place Hotel

Beach Place Hotel

2 out of 5
North Beach
Price was CA $1,463, price is now CA $843 per person
CA $843
per person
Nov 8 - Nov 15
found 22 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Miami (MIA)
7.8/10 Good! (1,002 reviews)
Close to the beach and park

Reviewed on Sep. 2, 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
Price was CA $18,331, price is now CA $8,752 per person
CA $8,752
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Sunset Cove Beach Resort

Sunset Cove Beach Resort

2.5 out of 5
Price was CA $1,598, price is now CA $914 per person
CA $914
per person
Oct 20 - Oct 26
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (1,007 reviews)
Amazing place. Will definitely stay again. Super friendly staff, nice guests, everything was perfect.

Reviewed on Sep. 1, 2025

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Price was CA $2,654, price is now CA $1,520 per person
CA $1,520
per person
Nov 29 - Dec 5
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (364 reviews)
From the moment we checked in, it was delight to be staying at the Pelican! Everything was so convenient that it made our days of fun and exploring easy. We recommend staying here if you’re looking for something upper class yet personable and friendly. The food in the restaurant is impeccable!

Reviewed on Sep. 3, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $3,464, price is now CA $2,009 per person
CA $2,009
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (1,295 reviews)
The front desk staff went out of their way to make sure we had an excellent first time in a 1 Hotel, offering us a complimentary upgrade with champagne. The coffee shop is perfect for that quick breakfast option before heading to the beach or pool. The use of the house car was nice and saved us a ride share.

Reviewed on Sep. 6, 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 John Pennekamp Coral Reef State Park.

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 $169 per night from Sep 8 to Sep 9
CA $169
CA $268 total
Sep 8 - Sep 9
includes taxes & fees
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 $331 per night from Sep 8 to Sep 9
CA $331
CA $448 total
Sep 8 - Sep 9
includes taxes & fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Sep 8 to Sep 9
CA $139
CA $196 total
Sep 8 - Sep 9
includes taxes & fees
Waterside Suites & Marina
See all 2,275 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
Family Vacations

Frequently asked questions

How much does a Winston Waterways vacation package cost?
Our Winston Waterways vacation packages, which start at just CA $843, 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.