Winston Waterways Vacations from $378
Book a Hotel + Flight or Car together to unlock savings
Your Winston Waterways Vacation
Planning your next travel adventure just got a lot easier with a vacation package to Winston Waterways. Immerse yourself in the very best this neighborhood 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 vacation with Expedia and experience travel your way.
The Latest Winston Waterways Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Clinton Hotel South Beach
South Beach
Save 100% on your flight
Price was $713, price is now $378 per person
$378
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,698 reviews)
Enjoy my stay thanks to friendly helpful staff and clean rooms
Reviewed on Aug 3, 2026
Casablanca Miami Beach
North Beach
Price was $7,116, price is now $2,797 per person
$2,797
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
5.8/10 (326 reviews)
Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No beach chair, no wagon and the umbrella covered 1 person. I reached out to the person but never showed up with clean sheets. I had to invest in my stay detergent, sanitizing wipes, trash bags and toilet covers. Let me know forget to say, on my first stay the bottom of my feet was all black from the floors being super dirty. The only good thing of the place was the beach distance.
Reviewed on Jul 23, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $20,010, price is now $9,642 per person
$9,642
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
The Marlin Hotel
South Beach
Save 100% on your flight
Price was $1,168, price is now $619 per person
$619
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
The location was great, the bar convenient, the restaurant downstairs was great. Overnight parking was reasonable.
Reviewed on Aug 2, 2026
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
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.
Things to do
Key Largo: Deserted Island Tour Kayak Adventure
$42
per adult
Florida: Key West Overseas Highway App-Based Driving Audio Tour
$17
per traveler
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.