Winston Waterways Holidays from NZ$3,037

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Top Holiday Package Deals in Winston Waterways

Price found within the past 48 hours. Click for updated prices.
Crest Hotel Suites

Crest Hotel Suites

3.5 out of 5
South Beach
Price was NZ$3,555, price is now NZ$3,037 per person
NZ$3,037
per person
11 June - 14 June
found 1 day ago
Return flight included
Wellington (WLG) to Miami (MIA)
7.8/10 Good! (1,000 reviews)
The staff was amazing!

Reviewed on 6 Apr 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was NZ$3,969, price is now NZ$3,132 per person
NZ$3,132
per person
11 June - 14 June
found 1 day ago
Return flight included
Wellington (WLG) to Miami (MIA)
8.4/10 Very Good! (2,145 reviews)
It was average No repeat for me

Reviewed on 10 Apr 2026

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was NZ$4,795, price is now NZ$3,833 per person
NZ$3,833
per person
11 June - 14 June
found 1 day ago
Return flight included
Wellington (WLG) to Miami (MIA)
9.4/10 Exceptional! (151 reviews)
While the hotel was great in all the different categories the staff going out of their way to help stood out the most. I had some issues with parking and really appreciated the efforts they went to resolve them!

Reviewed on 25 Mar 2026

EB Hotel Miami

EB Hotel Miami

4 out of 5
Price was NZ$4,528, price is now NZ$3,849 per person
NZ$3,849
per person
11 June - 14 June
found 1 day ago
Return flight included
Wellington (WLG) to Miami (MIA)
9.4/10 Exceptional! (2,863 reviews)
Clean room and the staff is extremely friendly

Reviewed on 9 Apr 2026

Gale Miami Hotel and Residences

Gale Miami Hotel and Residences

4 out of 5
Downtown Miami
Price was NZ$3,833, price is now NZ$3,280 per person
NZ$3,280
per person
11 June - 14 June
found 1 day ago
Return flight included
Wellington (WLG) to Miami (MIA)
8.8/10 Excellent! (1,617 reviews)
Great location. Great shops and bars/restaurants in the same block. Amazing vibe in sushi restaurant. Very clean. Helpful staff. Accommodating for early arrival and late checkout. Suites are roomy and affordable. Quiet rooms. Quiet floor. Easy 8 minute walk to port Miami for local shopping, bars and port experience. Only 15 minute Uber drive to ocean drive and south beach.

Reviewed on 11 Apr 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

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 NZ$645 per night from 21 Apr to 22 Apr
NZ$645
21 Apr - 22 Apr
includes taxes & fees
9.4/10 Exceptional! (1,408 reviews)
Ocean view is much nicer.

Reviewed on 8 Apr 2026

Reefhouse Resort & Marina
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is NZ$294 per night from 7 May to 8 May
NZ$294
7 May - 8 May
includes taxes & fees
9/10 Wonderful! (1,278 reviews)
Having a balcony one looking the canal was really nice. And, having two bathrooms in the suite was great.

Reviewed on 8 Apr 2026

Waterside Suites & 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 NZ$457 per night from 12 May to 13 May
NZ$457
12 May - 13 May
includes taxes & fees
9.2/10 Wonderful! (1,695 reviews)
This place was perfect for my family. The continental breakfast saved us a lot of money on food, the staff was friendly and the resort was clean. Will 100% be back here.

Reviewed on 11 Apr 2026

Chesapeake Beach Resort
See all 2,286 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.

Frequently asked questions

How much does a Winston Waterways holiday package cost?
Our Winston Waterways holiday packages, which start at just NZ$3,037, 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.