Winston Waterways Vacations from $287
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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.
Hyatt Place Miami Airport-East
Palmer Lake
Price was $629, price is now $287 per person
$287
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (2,247 reviews)
We checked in Wednesday to Saturday and Rooms were not clean during the stay..
Had to go to front desk each night for clean towels
Ran out tissue
Reviewed on Feb 1, 2026
Bay Breeze Premium Apartments By Eskape Collection
Price was $1,516, price is now $696 per person
$696
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
The staff was courteous and helpful. The apartment was equipped with basic essentials. The area was quiet. I would suggest adding oven mittens in the kitchen as there was nothing to use to take the pan out of the oven with.
Reviewed on Jan 21, 2026
Casablanca Miami Beach
North Beach
Price was $1,234, price is now $590 per person
$590
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly
Reviewed on Nov 12, 2025
Hotel Indigo Miami Brickell by IHG
Downtown Miami
Price was $858, price is now $412 per person
$412
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,005 reviews)
Don’t waste your time reading the negative reviews and psyching yourself out like I did… this place was fantastic! Staff members new and old were knowledgeable and provided information when needed!
Room was nice, all down to the scent of the lotions and soaps I loved lol. Had access to the gym, pool, everything!
Only complaint? I couldn’t stay longer! (And the beds were kinda soft lol not worth dropping a star though!
Reviewed on Jan 16, 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.
Winston Waterways Hotel Deals
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$349 nightly
The price is $388 total per night from Feb 2 to Feb 3
$388 total
Feb 2 - Feb 3
Total with taxes and fees
9.2/10 Wonderful! (1,337 reviews)
Yes
Reviewed on Jan 26, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$242 nightly
The price is $273 total per night from Feb 2 to Feb 3
$273 total
Feb 2 - Feb 3
Total with taxes and fees
9.2/10 Wonderful! (1,651 reviews)
Gorgeous view, very pleasant staff, clean room
Reviewed on Jan 30, 2026
Marina Del Mar Resort and Marina
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $220 total per night from Feb 2 to Feb 3
$220 total
Feb 2 - Feb 3
Total with taxes and fees
8.4/10 Very Good! (1,699 reviews)
Yep
Reviewed on Jan 29, 2026
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.