Winston Waterways Holidays from AU$2,049
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Your Winston Waterways Holiday
Planning your next travel adventure just got a lot easier with a holiday package to Winston Waterways. Immerse yourself in the very best this neighbourhood has to offer while creating fond memories you'll replay for years. Begin your trip to Winston Waterways by visiting nearby attractions such as Jimmy Johnsons Big Chill, John Pennekamp Coral Reef State Park and Caribbean Club Bar. Don't just imagine it — make it happen! Book your perfect Winston Waterways holiday with Expedia and experience travel your way.
Top Holiday Package Deals in Winston Waterways
Price found within the past 48 hours. Click for updated prices.
Greenview Hotel by Lowkl
South Beach
AU$2,160
per person
2 Nov - 8 Nov
found 2 hours ago
Return flight included
Adelaide (ADL) to Miami (MIA)
7.6/10 Good! (559 reviews)
It was really close and convenient to everything. My only issue was the noise volume. It felt like everyone was slamming doors, music was loud the entire stay. Due to me and my family not staying long I didn’t matter much and we were in and out our room also.
Reviewed on 27 Sept 2026
Our guide on 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 there might not be top attractions in Rock Harbor, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.
Silver Shores
While there might not be top attractions in Silver Shores, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Harry Harris Park.
Key Largo Park
Key Largo Park might not have many top sights, but Jacob's Aquatic Center and Jimmy Johnson's Big Chill are two attractions nearby that you can check out.
Key Largo Village
When in Key Largo Village, you can plan a visit to Jacob's Aquatic Center and Jimmy Johnson's Big Chill, some noteworthy sights in the nearby area.
Cross Key Waterways
When in Cross Key Waterways, you can plan a visit to MarineLab Undersea Laboratory and Caribbean Club Bar, some noteworthy sights in the nearby area.
Our pick of the best Winston Waterways Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
AU$305
8 Oct - 9 Oct
includes taxes & fees
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
AU$219
8 Oct - 9 Oct
includes taxes & fees
9/10 Wonderful! (1,494 reviews)
"i loved this place beautiful hotel full kitchen perfect for a little trip 100% recommend"
Reviewed on 28 Sept 2026
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
AU$376
1 Oct - 2 Oct
includes taxes & fees
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 holiday package cost?
Our Winston Waterways holiday packages, which start at just AU$2,049, 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 holiday 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 holiday?
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 holiday package?
Most definitely. Expedia has access to more than 550 airlines all over the world, so you can customize your Winston Waterways holiday according to your travel needs.
If I'm not able to travel, can I cancel my Winston Waterways holiday package?
You can. We realise life happens, so we're happy to help if you need to make changes to your Winston Waterways holiday 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.
Activities
Key Largo Coral Reef Glass Bottom Boat Adventure
AU$94
per adult
96% of travellers recommend
Small Group Florida Keys Eco Tour by Boat
AU$84
per adult
100% of travellers recommend
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle
AU$56
per traveller
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.