Winston Waterways Holidays from AU$2,599

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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.
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

Mid Beach
AU$2,599
per person
12 Sept - 18 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.2/10 Very good! (1,169 reviews)
Trump National Doral Miami

Trump National Doral Miami

Doral
AU$2,873
per person
12 Sept - 18 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
9.6/10 Exceptional! (1,502 reviews)
Bentley Hotel South Beach

Bentley Hotel South Beach

South Beach
AU$2,988
per person
12 Sept - 18 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
9.4/10 Exceptional! (1,036 reviews)
Eden Roc Miami Beach

Eden Roc Miami Beach

Mid Beach
AU$2,848
per person
12 Sept - 18 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.6/10 Excellent! (3,417 reviews)
They have so many hidden charge. So make sure everything before you book the hotel !

Reviewed on 13 Aug 2026

EAST Miami

EAST Miami

Brickell
AU$3,196
per person
12 Sept - 18 Sept
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (4,025 reviews)

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
A wooden pier extending into calm waters, with a covered area at the end.

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
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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 Pigeon Key.

Find hotels in Silver Shores
A white speedboat on a blue ocean with a tropical island in the background.

Key Largo Village

When in Key Largo Village, you can plan a visit to Jimmy Johnson's Big Chill and Jacob's Aquatic Center, some noteworthy sights in the nearby area.

Find hotels in Key Largo Village
An aerial view of a coastal area with RVs parked along the shore, a small beach, and a clear view of the ocean.

Key Largo Park

Key Largo Park might not have many top sights, but Jimmy Johnson's Big Chill and Jacob's Aquatic Center are two attractions nearby that you can check out.

Find hotels in Key Largo Park
A bridge over a river with boats docked along the shore.

Cross Key Waterways

When in Cross Key Waterways, you can plan a visit to Caribbean Club Bar and MarineLab Undersea Laboratory, some noteworthy sights in the nearby area.

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Our pick of the best Winston Waterways Hotel Deals

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
AU$482
24 Aug - 25 Aug
includes taxes & fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Waterside Suites & Marina

Waterside Suites & Marina

201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
AU$216
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,438 reviews)
"Very clean, good air, very comfortable"

Reviewed on 13 Aug 2026

Waterside Suites & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
AU$314
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (1,742 reviews)
"Nice ocean/beach view. Good property. Easy to find. Definitely worth it. Free ok breakfast."

Reviewed on 13 Aug 2026

Chesapeake Beach Resort
See all 2,267 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$2,599, 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

Key Largo Coral Reef Glass Bottom Boat Adventure

AU$64
per adult
96% of travellers recommend
Key Largo Coral Reef Glass Bottom Boat Adventure
Florida Keys Audio Guided Tour

Discover Florida Keys: A Self-Guided Tour

AU$3
per adult
Discover Florida Keys: A Self-Guided Tour
Key Largo: Deserted Island Tour Kayak Adventure

Key Largo: Deserted Island Tour Kayak Adventure

AU$60
per adult
Key Largo: Deserted Island Tour Kayak Adventure
See all activities in Key Largo
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.