Winston Waterways Vacations
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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.
Price found within the past 48 hours. Click for updated prices.
- Brickell Bay 3505
Jul 13 - Jul 16Brickell Bay 3505 + Flight
Brickell3 nights9.4/10 - Exceptional (3 reviews)"Great place and location! The pool was amazing."Reviewed May 9, 2026Roundtrip • Atlanta (ATL) - Miami (MIA)ATL - MIA • Nonstop MIA - ATL • Nonstop$1,192$417found 1 day agoper traveler - Brickell Bay 3318
Jul 17 - Jul 20Brickell Bay 3318 + Flight
Brickell3 nightsRoundtrip • New York (JFK) - Miami (MIA)JFK - MIA • Nonstop MIA - LGA • Nonstop$1,522$578found 21 hours agoper traveler - Family Pool Home by Hollywood Beach
Jun 24 - Jul 5Family Pool Home by Hollywood Beach + Flight
Hollywood Hills11 nightsRoundtrip • Atlanta (ATL) - Fort Lauderdale (FLL)ATL - FLL • Nonstop FLL - ATL • Nonstop$3,776$1,446found 1 day agoper traveler - 3BR Pool House Sleeps 8
Jul 6 - Jul 93BR Pool House Sleeps 8 + Flight
Driftwood3 nightsRoundtrip • New York (JFK) - Miami (MIA)JFK - MIA • Nonstop MIA - JFK • Nonstop$1,637$682found 0 hours agoper traveler - MirabileCondoDwntown MIA Brickell w PRKG
Jul 20 - Jul 22MirabileCondoDwntown MIA Brickell w PRKG + Flight
Downtown Miami2 nights2.0/10 - (2 reviews)"We were unable to stay at this property and the person at the door would not us in. The person I spoke to by phone insisted someone(unidentified) sent me an email saying there was no vacancy. There was no email and I prepaid for two nights. We had to find another place at 1:30 am. Glad we had rented a car."Reviewed December 12, 2023Roundtrip • New York (JFK) - Miami (MIA)JFK - MIA • Nonstop MIA - JFK • Nonstop$1,009$421found 23 hours agoper traveler
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
$299 nightly
The price is $331 total per night from May 21 to May 22
$331 total
May 21 - May 22
Total with taxes and fees
9.4/10 Exceptional! (1,433 reviews)
"Very nice property in Key Largo"
Reviewed on May 20, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$226 nightly
The price is $254 total per night from Jun 9 to Jun 10
$254 total
Jun 9 - Jun 10
Total with taxes and fees
9.2/10 Wonderful! (1,733 reviews)
"Everything was fine untill it wasn't. The bathroom my The pool was flooding out feces and urine all afternoon and night into and around the pool area and sidewalk and no one cares untill I said something. Its unsanitary! It never was sanitized or cleaned properly just hosed off. You can tell they've ..."
Reviewed on May 20, 2026
Marina Del Mar Resort and Marina
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $155 total per night from May 31 to Jun 1
$155 total
May 31 - Jun 1
Total with taxes and fees
8.6/10 Excellent! (1,796 reviews)
"Excelente"
Reviewed on May 20, 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.