Winston Waterways Vacations

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    Save up to ￥109,000 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 16 - Jul 20

    Cavalier Hotel South Beach + Flight

    South Beach
    4 nights
    3.5 star property
    8.6/10 - Excellent (1,001 reviews)
    "The staff was very helpful and accommodating."
    Reviewed May 25, 2026
    Roundtrip • Tokyo (HND) - Miami (MIA)
    HND - MIA • 1 stop MIA - HND • 1 stop
    ￥425,080
    ￥335,784
    per traveler
    found 1 day ago
    Cavalier Hotel South Beach
  • 4 outdoor pools, sun loungers
    Jul 16 - Jul 20

    Nobu Hotel Miami Beach + Flight

    Mid Beach
    4 nights
    5.0 star property
    8.6/10 - Excellent (1,372 reviews)
    "Overall property is really nice, I will stay here again."
    Reviewed May 26, 2026
    Roundtrip • Tokyo (HND) - Miami (MIA)
    HND - MIA • 1 stop MIA - HND • 1 stop
    ￥519,722
    ￥410,824
    per traveler
    found 1 day ago
    Nobu Hotel Miami Beach
  • Exterior
    Jul 16 - Jul 20

    Fontainebleau Miami Beach + Flight

    Mid Beach
    4 nights
    4.5 star property
    8.4/10 - Very Good (8,246 reviews)
    "Very nice getaway at the Fountainbleau in Miami! We enjoyed the property very much and always love visiting the resort! The only thing I found annoying is that some of the servers asked for additional gratuity in addition to the 20 percent that they automatically add to your bill. I believe that the gratuity expectation is getting out of hand and management needs to reevaluate how they compensate their employees. Gratuity is a personal choice and customers should not be pressured to give..."
    Reviewed May 27, 2026
    Roundtrip • Tokyo (HND) - Miami (MIA)
    HND - MIA • 1 stop MIA - HND • 1 stop
    ￥565,315
    ￥447,491
    per traveler
    found 1 day ago
    Fontainebleau Miami Beach
  • Bay Plus King | View from room
    Jul 16 - Jul 20

    EAST Miami + Flight

    Brickell
    4 nights
    5.0 star property
    9.2/10 - Wonderful (3,822 reviews)
    "Absolutely loved my stay at EAST Miami! From the moment we arrived, the staff made us feel so welcomed and genuinely cared for. Every single person was kind, helpful, and went above and beyond to make our stay special. The hotel itself was spotless, modern, and had such an amazing atmosphere. The food was also incredible — everything we had was delicious. This was one of those trips where everything just felt easy and enjoyable. I had the best time and can already see myself coming back again..."
    Reviewed May 25, 2026
    Roundtrip • Tokyo (HND) - Miami (MIA)
    HND - MIA • 1 stop MIA - HND • 1 stop
    ￥522,561
    ￥420,841
    per traveler
    found 1 day ago
    EAST Miami
  • Penthouse, 1 King Bed, Terrace | In-room safe, individually decorated, blackout drapes
    Jul 16 - Jul 20

    President Hotel + Flight

    South Beach
    4 nights
    3.5 star property
    8.4/10 - Very Good (2,407 reviews)
    "The hotel is nice and cozey… it’s worth the cost"
    Reviewed May 27, 2026
    Roundtrip • Tokyo (HND) - Miami (MIA)
    HND - MIA • 1 stop MIA - HND • 1 stop
    ￥415,513
    ￥337,753
    per traveler
    found 1 day ago
    President Hotel

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 Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby.

Find hotels in Rock Harbor

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 ￥34,878 per night from Jun 21 to Jun 22
￥34,878
￥45,609 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (1,449 reviews)
"The property was nice. I had requested a view room and believed I paid for one through Expedia but got a room without a balcony or a window to open and it faced a wall. No view. I was offered to move for my last 2 days and I would have had to pay more."

Reviewed on May 27, 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 ￥31,621 per night from Jun 8 to Jun 9
￥31,621
￥44,533 total
Jun 8 - Jun 9
includes taxes & fees
9.2/10 Wonderful! (1,738 reviews)
"I had a wonderful time on my getaway. The view from my room was beautiful. Everything was quite and pleasant perfect for a family. Everyone was polite, and the breakfast was delicious. The view of the breakfast was phenomenal."

Reviewed on May 26, 2026

Chesapeake Beach Resort
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2 out of 5
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is ￥19,702 per night from May 31 to Jun 1
￥19,702
￥26,645 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (1,800 reviews)
"Property was family friendly. Had many dining option within walking distance."

Reviewed on May 27, 2026

Marina Del Mar Resort and Marina
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 vacation package cost?
Our Winston Waterways vacation 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 vacation 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 vacation?
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 vacation package?
Most definitely. Expedia has access to more than 550 airlines all over the world, so you can customize your Winston Waterways vacation according to your travel needs.
If I'm not able to travel, can I cancel my Winston Waterways vacation package?
You can. We realize life happens, so we're happy to help if you need to make changes to your Winston Waterways vacation 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.