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.
  • Jul 13 - Jul 16

    Brickell Bay 3505 + Flight

    Brickell
    3 nights
    3.0 star property
    9.4/10 - Exceptional (3 reviews)
    "Great place and location! The pool was amazing."
    Reviewed May 9, 2026
    Roundtrip Atlanta (ATL) - Miami (MIA)
    ATL - MIANonstop MIA - ATLNonstop
    $1,192
    $417
    per traveler
    found 1 day ago
    Brickell Bay 3505
  • Jul 17 - Jul 20

    Brickell Bay 3318 + Flight

    Brickell
    3 nights
    3.0 star property
    Roundtrip New York (JFK) - Miami (MIA)
    JFK - MIANonstop MIA - LGANonstop
    $1,522
    $578
    per traveler
    found 21 hours ago
    Brickell Bay 3318
  • Jun 24 - Jul 5

    Family Pool Home by Hollywood Beach + Flight

    Hollywood Hills
    11 nights
    2.5 star property
    Roundtrip Atlanta (ATL) - Fort Lauderdale (FLL)
    ATL - FLLNonstop FLL - ATLNonstop
    $3,776
    $1,446
    per traveler
    found 1 day ago
    Family Pool Home by Hollywood Beach
  • Jul 6 - Jul 9

    3BR Pool House Sleeps 8 + Flight

    Driftwood
    3 nights
    3.0 star property
    Roundtrip New York (JFK) - Miami (MIA)
    JFK - MIANonstop MIA - JFKNonstop
    $1,637
    $682
    per traveler
    found 0 hours ago
    3BR Pool House Sleeps 8
  • Jul 20 - Jul 22

    MirabileCondoDwntown MIA Brickell w PRKG + Flight

    Downtown Miami
    2 nights
    5.0 star property
    2.0/10 - (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, 2023
    Roundtrip New York (JFK) - Miami (MIA)
    JFK - MIANonstop MIA - JFKNonstop
    $1,009
    $421
    per traveler
    found 23 hours ago
    MirabileCondoDwntown MIA Brickell w PRKG

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

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
$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

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
$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

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
$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

Marina Del Mar Resort and Marina
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.