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.
Kimpton EPIC Hotel, an IHG Hotel

Kimpton EPIC Hotel, an IHG Hotel

5 out of 5
Downtown Miami
Save 100% on your flight
per person
Aug. 12 - Aug. 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,173 reviews)
Outside of no hot water in my room and the morning staff at Area 31 did not treat all of its guest the same or gave the same high level of service as they did others it was great.

Reviewed on May 26, 2024

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Aug. 12 - Aug. 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (1,006 reviews)
Beautiful stay!! Nice atmosphere

Reviewed on May 23, 2024

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
Aug. 15 - Aug. 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very Good! (1 review)
Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
Coconut Grove
Save 100% on your flight
per person
Aug. 17 - Aug. 23
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (502 reviews)
Beds are so comfy and everything just so perfect. The only thing missing is a fridge. Everything else is amazing

Reviewed on May 22, 2024

Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul. 29 - Aug. 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
9.2/10 Wonderful! (71 reviews)
Perfect place! The best place we have stayed in the Fort Lauderdale area. Very comfortable, clean, easy going and great people! We highly recommend!

Reviewed on Feb. 18, 2024

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 Park

Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.

Find hotel + flight trips in Key Largo Park

Winston Waterways Hotel Deals

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
8.6/10 Excellent! (1,005 reviews)
"Beautiful resort! Staff are very welcoming, polite and helpful. it has a private beach, marina with amazing sunset views, and champagne to go with the sunset watching. Restaurants and live music in the evening. There also activities for the kids throughout the day. I gave 3 stars for the favilities ..."

Reviewed on May 25, 2024

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Baker's Cay Resort Key Largo, Curio Collection by Hilton
Reefhouse Resort & Marina
Reefhouse Resort & Marina
3.5 out of 5
103800 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,181 reviews)
"This is a fantastic property that is all inclusive; beautiful landscaping and water front with a beach area and many chaise lounges, outdoor seating with fire pits and beautiful lighting, a tiki hut bar, beautiful pool and hot tub, two restaurants, and on-site rental of jet skis, kayaks etc. You ..."

Reviewed on May 23, 2024

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Reefhouse Resort & Marina
Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,326 reviews)
"Great Place, very friendly staff and hosts. Free breakfast sin sunrise room was great. Clean rooms and pools and beaches. Cleaning services were prompt and good, Hotel was quiet and clean. But upon checkout we noticed a 40$ daily service charge per day for Resort Fees. A little surprised, because ..."

Reviewed on May 21, 2024

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Chesapeake Beach Resort
See all 2,154 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.

Explore other types of vacation packages

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 $742, 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.