Winston Waterways Holidays

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Price found within the past 48 hours. Click for updated prices.
  • 6 outdoor pools, free pool cabanas, pool umbrellas
    Jul 27 - Jul 31

    Oceans Edge Key West Resort, Hotel & Marina + Flight

    Stock Island
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,864 reviews)
    "Parking is not included in the stand and there are a lot of other fees that should be included. I wound up paying $375 more just to cover all the fees. Including a 29 dollar a day parking fee. Why is that not included. That was disappointing and the resort is in a weird part of town. Overall I would not stay there again."
    Reviewed May 31, 2026
    Return • Auckland (AKL) - Key West (EYW)
    AKL - EYW • 2 stops EYW - AKL • 2 stops
    NZ$4,748
    NZ$4,048
    per traveller
    found 0 hours ago
    Oceans Edge Key West Resort, Hotel & Marina
  • Outdoor pool
    Jul 27 - Jul 31

    The Key West Hotel + Flight

    Key West Historic District
    3 nights
    3.0 star property
    9.2/10 - Wonderful (556 reviews)
    Return • Auckland (AKL) - Key West (EYW)
    AKL - EYW • 2 stops EYW - AKL • 2 stops
    NZ$5,181
    NZ$4,244
    per traveller
    found 0 hours ago
    The Key West Hotel
  • Studio, Ocean View | Beach/ocean view
    Jul 27 - Jul 31

    Coconut Beach Resort + Flight

    Old Town Key West
    3 nights
    2.5 star property
    8.8/10 - Excellent (192 reviews)
    "This was a great place to stay! Clean and well-placed on Key West. Pool and patio were great for getting some sun."
    Reviewed May 29, 2026
    Return • Auckland (AKL) - Key West (EYW)
    AKL - EYW • 2 stops EYW - AKL • 2 stops
    NZ$5,061
    NZ$4,225
    per traveller
    found 0 hours ago
    Coconut Beach Resort
  • Terrace/patio
    Jul 27 - Jul 31

    Hyatt Vacation Club at Sunset Harbor, Key West + Flight

    Old Town Key West
    3 nights
    3.5 star property
    8.6/10 - Excellent (374 reviews)
    "Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail"
    Reviewed May 18, 2026
    Return • Auckland (AKL) - Key West (EYW)
    AKL - EYW • 2 stops EYW - AKL • 2 stops
    NZ$5,358
    NZ$4,494
    per traveller
    found 0 hours ago
    Hyatt Vacation Club at Sunset Harbor, Key West
  • Property grounds
    Jul 27 - Jul 31

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    3 nights
    3.5 star property
    9.4/10 - Exceptional (1,100 reviews)
    "The room and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street."
    Reviewed May 28, 2026
    Return • Auckland (AKL) - Key West (EYW)
    AKL - EYW • 2 stops EYW - AKL • 2 stops
    NZ$5,199
    NZ$4,382
    per traveller
    found 0 hours ago
    Hyatt Vacation Club at Windward Pointe, Key West

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$478 per night from 21 June to 22 June
NZ$478
21 June - 22 June
includes taxes & fees
9.4/10 Exceptional! (1,456 reviews)
"“Great place for traveling with small kids! Easy parking, a great pool and beach area, and good food. Room service was fast and the food arrived hot and fresh. We had a wonderful stay and will definitely be coming back!"

Reviewed on 30 May 2026

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 NZ$421 per night from 3 June to 4 June
NZ$421
3 June - 4 June
includes taxes & fees
9.2/10 Wonderful! (1,733 reviews)
"Property was clean and very smooth check in process. I would definitely return."

Reviewed on 31 May 2026

Chesapeake Beach Resort
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 NZ$599 per night from 17 June to 18 June
NZ$599
17 June - 18 June
includes taxes & fees
8.6/10 Excellent! (1,075 reviews)
"Very relaxing and chill. Easy access from rooms to beach. Super friendly staff."

Reviewed on 27 May 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,315 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 , 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.