Winston Waterways Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Winston Waterways

Price found within the past 48 hours. Click for updated prices.
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was CA $2,412, price is now CA $964 per person
CA $964
per person
Jun 23 - Jun 27
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
6/10 (2 reviews)
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Price was CA $2,691, price is now CA $971 per person
CA $971
per person
Jul 16 - Jul 20
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (2 reviews)
The room was clean, there was a problem at the check out time as all the guest have the same check out and all the elevators collapse, it took us more than an hour to get down. The parking is really a problem as we had to go up almost 20 floors. Location is pretty good.

Reviewed on Apr 14, 2026

Brickell Bay 3304

Brickell Bay 3304

3 out of 5
Brickell
Price was CA $2,950, price is now CA $1,124 per person
CA $1,124
per person
Jun 23 - Jun 28
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
No reviews
Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was CA $3,365, price is now CA $1,336 per person
CA $1,336
per person
Jun 23 - Jun 29
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
No reviews
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $7,699, price is now CA $3,475 per person
CA $3,475
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (323 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

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
Safety Harbor, Florida

Rock Harbor

1 out of top 10 points of interest in this area

While Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby.

Find hotels in Rock Harbor

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 $243 per night from May 11 to May 12
CA $243
CA $351 total
May 11 - May 12
includes taxes & fees
9.2/10 Wonderful! (1,714 reviews)
Great location. Peaceful.

Reviewed on May 5, 2026

Chesapeake Beach Resort
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 $179 per night from May 13 to May 14
CA $179
CA $239 total
May 13 - May 14
includes taxes & fees
9/10 Wonderful! (1,330 reviews)
We were in a 2 bedroom suite. Thought there was a lounge, but no. So nowhere to sit for 4 except balcony which was ok good view of passing boats .It would have been good if it had been catered for 4 people, ie glasses, cutlery. Kitchen basic but ok, good fridge.

Reviewed on May 4, 2026

Waterside Suites & Marina
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 $427 per night from Jun 2 to Jun 3
CA $427
CA $556 total
Jun 2 - Jun 3
includes taxes & fees
8.6/10 Excellent! (1,060 reviews)
Rooms seem outdated , bathtub was horrendous , I might’ve got fungus on my feet , staff very unprofessional and unpleasant to talk too disgustingly rude like they were raised on a farm with no parents. Beach view was stunning Room view was waterfront but had a big tree infront Bar was okay they dropped ...

Reviewed on May 5, 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,303 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 $964, 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.