Winston Waterways Vacations from $528

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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.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was $1,117, price is now $528 per person
$528
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,418 reviews)
The location is great, but thats it. Everything else is average or below

Reviewed on Sep 1, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was $1,638, price is now $598 per person
$598
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (946 reviews)
Was going to rent a car but I’m so glad I didn’t. We Uber the whole time. Traffic was crazy fast. Seth stay was everything. Shopping was also everything.

Reviewed on Sep 2, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $32,233, price is now $14,800 per person
$14,800
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was $2,428, price is now $1,125 per person
$1,125
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (779 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!

Reviewed on Aug 23, 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was $1,845, price is now $870 per person
$870
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (300 reviews)
Every member of the staff was outstanding. Rooms were nice and spacious and clean. Location was excellent. The bikes were great.

Reviewed on Sep 1, 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
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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.

Find hotels in Key Largo Village

Winston Waterways Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $169 total per night from Sep 9 to Sep 10
$169 total
Sep 9 - Sep 10
Total with taxes and fees
Chesapeake Beach Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
$278 nightly
The price is $312 total per night from Sep 10 to Sep 11
$312 total
Sep 10 - Sep 11
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG

3 out of 5
99701 Overseas Hwy, Key Largo, FL
Fully refundable
$140 nightly
The price is $158 total per night from Sep 14 to Sep 15
$158 total
Sep 14 - Sep 15
Total with taxes and fees
Holiday Inn Key Largo by IHG
See all 2,265 properties in Winston Waterways
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.