Winston Waterways Vacations from $596
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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.
Cavalier Hotel South Beach
South Beach
Price was $1,238, price is now $596 per person
$596
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Fantastic service, great restaurant downstairs, super convenient for beach access, shopping and dining!
Reviewed on Oct 13, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $3,004, price is now $1,353 per person
$1,353
per person
Dec 31 - Jan 4
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (31 reviews)
Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.
Reviewed on Oct 6, 2025
Bahama Beach Club Pompano
Price was $1,299, price is now $640 per person
$640
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (12 reviews)
Bahama Beach Club Pompano is going to my place to stay whenever I take trips to the Fort Lauderdale side of Florida.
The place was clean, close to the beach and provided all the amenities for anyone who loves the beach...beach chairs, towels, umbrella, cooler. The bbq grill was a plus as well and we actually did BBQed one day
Although Bahama Beach is walking distance from the beach, we drove and found parking easily.
Sandra was awesome and very quick with responses to our queries.
The personal welcome note, wine and snacks made us feel right at home.
I definitely rwcommend Bahama Beach to anyone traveling to Fort Lauderdale and neesa a nicr clean, quiet and safe place to stay.
Reviewed on Sep 29, 2025
Nomada Residences
Northeast Miami
Price was $1,931, price is now $970 per person
$970
per person
Jan 1 - Jan 8
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (522 reviews)
Clean modern location. Easy for us to get where we needed. Parking convenient.
Reviewed on Oct 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 John Pennekamp Coral Reef State Park.
Winston Waterways Hotel Deals
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$363 nightly
The price is $408 total per night from Oct 26 to Oct 27
$408 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (1,011 reviews)
"Clean room, nice staff and facilities"
Reviewed on Oct 12, 2025
Waterside Suites & Marina
201 Ocean Drive, Key Largo, FL
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $140 total per night from Oct 15 to Oct 16
$140 total
Oct 15 - Oct 16
Total with taxes and fees
8.8/10 Excellent! (1,095 reviews)
Love it
"Absolutely loved the hotel. The room was amazing. Great view of the boat cancel"
Reviewed on Oct 11, 2025
Reefhouse Resort & Marina
103800 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $286 total per night from Oct 15 to Oct 16
$286 total
Oct 15 - Oct 16
Total with taxes and fees
9.2/10 Wonderful! (1,311 reviews)
"Bartender should be more helpful Saturday 10/4/25 Carlos was very helpful"
Reviewed on Oct 6, 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.