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
Price was CA $1,922, price is now CA $972 per person
CA $972
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,224 reviews)
I have been visiting pelican grand for well over a decade on and off and I hadnt been back in a few years and I thought the property looked much more run down! There were rust stains on walls near the pool and it just didnt feel as luxurious as it used to. I do think it might be time for a facelift for the pool area. Overall I do love this hotel and the room was comfortable and quiet. I love that the beach is right there and the dining options are nice.

Reviewed on Sep 8, 2025

Hotel Colonnade Coral Gables, Autograph Collection

Hotel Colonnade Coral Gables, Autograph Collection

4 out of 5
Coral Gables Section
Price was CA $4,464, price is now CA $1,434 per person
CA $1,434
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (1,004 reviews)
The mattress is soft and old very difficult to get good sleep AC was noise it . The pool are and the pool needs an upgrade, as well as the pump of the water fountain by the pool does not work and we can hear the noise from the 5th flloor

Reviewed on Sep 8, 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 $28,103, price is now CA $13,156 per person
CA $13,156
per person
Oct 19 - Oct 25
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $4,595, price is now CA $2,225 per person
CA $2,225
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (369 reviews)
This property is absolutely adorable! Room was clean and spacious. Front desk person was very nice and personable. The breakfast baskets that are delivered to your room are top notch! Will definitely be staying here again!

Reviewed on Aug 31, 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $3,366, price is now CA $1,680 per person
CA $1,680
per person
Oct 12 - Oct 19
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (815 reviews)
The staff were wonderful and we loved the breakfast and sangria hour and how walkable the area was! We walked everywhere during our stay. The only downsides were it is very noisy, since you can hear everything outside from in the room, and the AC in our room took about 2 days to cool down enough to be comfortable after the previous guests apparently had left the AC off and the windows open during their stay.

Reviewed on Sep 3, 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 10 to Sep 11
CA $169
CA $268 total
Sep 10 - Sep 11
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 $351 per night from Sep 16 to Sep 17
CA $351
CA $471 total
Sep 16 - Sep 17
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 $137 per night from Sep 28 to Sep 29
CA $137
CA $193 total
Sep 28 - Sep 29
includes taxes & fees
Waterside Suites & Marina
See all 2,285 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
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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 $972, 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.