Winston Waterways Vacations from $211
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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.
Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
per person
Oct 2 - Oct 8
found 2 days ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
High dollar with everything extra, restaurant stupid expensive plus a 22% surcharge on top of meal cost. View was fantastic, was nice that at least beach chairs were included.
Reviewed on Jul 13, 2025
Global Rent Apart
Hollywood Beach
Save 100% on your flight
per person
Aug 17 - Aug 21
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.8/10 Excellent! (22 reviews)
Property was nice, good location. Room was very basic. You get better amenities in a typical hotel room. Comfortable bed. Room always felt humid. Had an issue with the tv, we weren’t able to watch anything because the only service hooked up was Roku, but there was no Roku remote in the room. After calling and texting the host several times back and forth, and 2 visits from a technician we were provided a Roku remote. Chairs on the beach were all so close together, everyone is on top of each other. Have to pay for umbrella which is a rip off. Not sure what the $40/day extra resort fee actually gets you. The rooftop pool is nice but very crowded. The rooftop bar/restaurant is fun but very expensive. We probably wouldn’t stay here again.
Reviewed on Apr 21, 2025
iCoconutGrove Vacation Rentals
Coconut Grove
Save 100% on your flight
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
9.2/10 Wonderful! (1,003 reviews)
The property was in a very populated area with lots of shops, restaurants and nightlife (if that’s your thing). The studio was very clean and there were no issues at all. Unlike hotel rooms, I could not hear what was happening right next door, so it was quiet as well.
I would stay here again.
Reviewed on Jul 12, 2025
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
Key Largo Village
While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.
Winston Waterways Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $215 total per night from Aug 12 to Aug 13
$215 total
Aug 12 - Aug 13
Total includes taxes and fees
9/10 Wonderful! (1,492 reviews)
"Staff friendliness seemed a bit forced"
Reviewed on Jul 11, 2025
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$364 nightly
The price is $409 total per night from Aug 11 to Aug 12
$409 total
Aug 11 - Aug 12
Total includes taxes and fees
8.6/10 Excellent! (1,003 reviews)
"beautiful place and location but it could be more luxurious for the price"
Reviewed on Jul 8, 2025
Hampton Inn Key Largo Manatee Bay
102400 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $133 total per night from Aug 10 to Aug 11
$133 total
Aug 10 - Aug 11
Total includes taxes and fees
8.6/10 Excellent! (1,014 reviews)
"Great property"
Reviewed on Jul 13, 2025
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.