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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $19,502
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
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
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.
Silver Shores
If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit Bluefin Rock Harbor Marina and Harry Harris Park.
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 Jacob's Aquatic Center and Jimmy Johnson's Big Chill.
Key Largo Park
Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jacob's Aquatic Center and Jimmy Johnson's Big Chill.
Anglers Park
While there might not be top attractions in Anglers Park, you can explore the larger area and discover places like MarineLab Undersea Laboratory and Caribbean Club Bar.
Winston Waterways Hotel Deals
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
CA $154
CA $213 total
Nov 2 - Nov 3
includes taxes & fees
9/10 Wonderful! (1,501 reviews)
"Esther was really helpful. Very nice and professional. Room was spotless!! Balcony with a beautiful view."
Reviewed on Oct 14, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $196
CA $300 total
Nov 5 - Nov 6
includes taxes & fees
9.4/10 Exceptional! (1,799 reviews)
"Very professional reception, room clean staff very polite"
Reviewed on Oct 18, 2026
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
CA $281
CA $373 total
Oct 19 - Oct 20
includes taxes & fees
9.2/10 Wonderful! (1,548 reviews)
"Room are a little dated but overall nice. Pool and beach area were well maintained. We got couples massages and those were great. Pricing for them was reasonable. We would come back again!"
Reviewed on Oct 17, 2026
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.
Frequently asked questions
How much does a Winston Waterways vacation package cost?
Our Winston Waterways vacation packages, which start at just CA $1,221, 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.
Things to do
Florida: Key West Overseas Highway App-Based Driving Audio Tour
CA $24
per traveller
88% of travellers recommend
Key Largo Coral Reef Glass Bottom Boat Adventure
CA $93
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.