Winston Waterways Holidays from AU$3,619

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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.
Sonesta Select Boca Raton Town Center

Sonesta Select Boca Raton Town Center

3 out of 5
Price was AU$4,105, price is now AU$3,619 per person
AU$3,619
per person
29 Dec - 4 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.4/10 Very Good! (1,721 reviews)
average - the room had no safe!!!, no free breakfast. water pressure in shower was AWEFUL

Reviewed on 15 Nov 2025

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Price was AU$7,246, price is now AU$5,522 per person
AU$5,522
per person
29 Dec - 4 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
16.8/10 Exceptional! (1,931 reviews)
Overall an amazing experience, the staff was incredible and the resort was beautiful!

Reviewed on 14 Nov 2025

Ocean Sky Hotel and Resort

Ocean Sky Hotel and Resort

4 out of 5
East Fort Lauderdale
Price was AU$5,482, price is now AU$4,651 per person
AU$4,651
per person
29 Dec - 4 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
16/10 Exceptional! (2,681 reviews)
Beach chairs were to old ,didn't look good for the hotel

Reviewed on 14 Nov 2025

Costa Hollywood Beach Resort

Costa Hollywood Beach Resort

4 out of 5
Hollywood Beach
Price was AU$5,465, price is now AU$4,640 per person
AU$4,640
per person
29 Dec - 4 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
18/10 Exceptional! (3,814 reviews)
Yes it was very clean, we enjoyed our stayed. Thank you

Reviewed on 14 Nov 2025

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
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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.

Find hotels in Rock Harbor

Our pick of the best Winston Waterways Hotel Deals

Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is AU$455 per night from 18 Nov to 19 Nov
AU$455
18 Nov - 19 Nov
includes taxes & fees
9.2/10 Wonderful! (1,310 reviews)
Very nice

Reviewed on 2 Nov 2025

Reefhouse Resort & Marina
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 AU$317 per night from 17 Nov to 18 Nov
AU$317
17 Nov - 18 Nov
includes taxes & fees
9.2/10 Wonderful! (1,563 reviews)
Nice place, good location, friendly staff, clean room, good food, beat views, easy access to pool and beach.

Reviewed on 9 Nov 2025

Chesapeake Beach Resort
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 7 Dec to 8 Dec
AU$206
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (1,624 reviews)
Great location for walking to restaurants, dive boats. Fun to watch activity in the canal. Great swimming pool, hot tub, beautiful landscaping!

Reviewed on 8 Nov 2025

Marina Del Mar Resort and Marina
See all 2,319 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.
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Frequently asked questions

How much does a Winston Waterways holiday package cost?
Our Winston Waterways holiday packages, which start at just AU$3,619, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.