Winston Waterways Holidays from AU$2,010

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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.
Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
Price was AU$2,603, price is now AU$2,010 per person
AU$2,010
per person
21 July - 27 July
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
9.4/10 Exceptional! (221 reviews)
I would 100% recommend this accommodation. For the price I paid, it was excellent value. The room is spacious and clean with a powerful aircon. The location is fantastic, literally metres from Española Way and just a short walk to Lincoln Road and Ocean Drive. My flight was cancelled, which meant I had to stay an extra 12 hours in South Beach. The manager was incredibly kind and allowed me to stay in the room until I needed to leave. Not many hotels would do that, so I really must thank the manager for their kindness and flexibility. If I return to South Beach, I will definitely stay here again, as it truly felt like a home away from home.

Reviewed on 8 June 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Price was AU$3,694, price is now AU$2,620 per person
AU$2,620
per person
21 July - 27 July
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.4/10 Very Good! (8,366 reviews)
The room was clean and the service was exceptional! I will be back.

Reviewed on 18 June 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was AU$2,961, price is now AU$2,152 per person
AU$2,152
per person
21 July - 27 July
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
I enjoyed my stay. The room was clean. The staff was helpful and friendly. The food was great!

Reviewed on 18 June 2026

Andaz Miami Beach Resort & Spa

Andaz Miami Beach Resort & Spa

5 out of 5
Mid Beach
Price was AU$3,177, price is now AU$2,408 per person
AU$2,408
per person
21 July - 27 July
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
9/10 Wonderful! (305 reviews)
Very clean room, friendly staff, and easy access to the beach.

Reviewed on 16 June 2026

EAST Miami

EAST Miami

5 out of 5
Brickell
Price was AU$3,672, price is now AU$2,787 per person
AU$2,787
per person
21 July - 27 July
found 1 day ago
Return flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (3,845 reviews)
As always, the property was amazing, and the views did not disappoint.

Reviewed on 17 June 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
Safety Harbor, Florida

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

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$367 per night from 7 July to 8 July
AU$367
7 July - 8 July
includes taxes & fees
9.2/10 Wonderful! (1,728 reviews)
"Great resort with friendly staff. Very clean!"

Reviewed on 19 June 2026

Chesapeake Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is AU$376 per night from 24 June to 25 June
AU$376
24 June - 25 June
includes taxes & fees
9.4/10 Exceptional! (1,460 reviews)
"We had a great time. Walt during check was amazing."

Reviewed on 17 June 2026

Reefhouse Resort & Marina
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
The price is AU$498 per night from 30 June to 1 July
AU$498
30 June - 1 July
includes taxes & fees
8.6/10 Excellent! (1,102 reviews)
"Beautiful resort and common areas...friendliest staff."

Reviewed on 19 June 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,268 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$2,010, 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.