Winston Waterways Holidays from AU$3,175

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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.
Renzzi Wynwood Apartments

Renzzi Wynwood Apartments

4 out of 5
Allapattah
Price was AU$3,922, price is now AU$3,175 per person
AU$3,175
per person
8 Apr - 15 Apr
found 6 hours ago
Return flight included
Brisbane (BNE) to Miami (MIA)
8/10 Very Good! (70 reviews)
Clean room, good neighborhood and Water was hot and the TV had netflix and Youtube

Reviewed on 15 Feb 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was AU$12,491, price is now AU$8,677 per person
AU$8,677
per person
8 Apr - 15 Apr
found 6 hours ago
Return flight included
Brisbane (BNE) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
The room was spotless and incredibly comfortable, so much attention to detail. The property had all the amenities that I look for during a beach getaway and the staff were so courteous and friendly. One of my favorite properties in the area!

Reviewed on 1 Mar 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was AU$6,502, price is now AU$4,547 per person
AU$4,547
per person
8 Apr - 15 Apr
found 6 hours ago
Return flight included
Brisbane (BNE) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Room was okay. The beds were smaller than we expected and there were only flat sheets on the mattress rather than fitted sheets. Breakfast was very good, pool and beach access were great.

Reviewed on 1 Mar 2026

Prestige Retreat by Renzzi

Prestige Retreat by Renzzi

3 out of 5
Little Havana
Price was AU$4,170, price is now AU$3,389 per person
AU$3,389
per person
8 Apr - 15 Apr
found 6 hours ago
Return flight included
Brisbane (BNE) to Miami (MIA)
No reviews
Great spot .. will be back

Reviewed on 4 Feb 2026

Loews Miami Beach Hotel – South Beach

Loews Miami Beach Hotel – South Beach

4.5 out of 5
South Beach
Save 100% on your flight
Price was AU$20,180, price is now AU$17,002 per person
AU$17,002
per person
8 Apr - 15 Apr
found 6 hours ago
Return flight included
Brisbane (BNE) to Miami (MIA)
9/10 Wonderful! (4,791 reviews)
Our check in experience and follow up by Caitlin was exceptional. She is professional and courteous.

Reviewed on 1 Mar 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

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$337 per night from 8 Mar to 9 Mar
AU$337
8 Mar - 9 Mar
includes taxes & fees
8.4/10 Very Good! (1,721 reviews)
Rooms are really run down. Staff is good, furniture and closet doors totally need replacement. Bathroom old and uninviting. Priced high for the condition of the building. Elevator got a facelift but not the rest.

Reviewed on 1 Mar 2026

Marina Del Mar Resort and 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$506 per night from 3 Mar to 4 Mar
AU$506
3 Mar - 4 Mar
includes taxes & fees
9.2/10 Wonderful! (1,661 reviews)
warm pool, beautiful view at the beach, pleasant front desk and breakfast staff

Reviewed on 28 Feb 2026

Chesapeake Beach Resort
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$608 per night from 3 Mar to 4 Mar
AU$608
3 Mar - 4 Mar
includes taxes & fees
9.4/10 Exceptional! (1,390 reviews)
Clean rooms nice staff beautiful grounds!!

Reviewed on 2 Mar 2026

Reefhouse Resort & Marina
See all 2,300 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$3,175, 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.