Name: Holiday Inn Key Largo by IHG
Price range: $158 total
Rating: 8.4

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

South Beach

Save 100% on your flight

$383

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,414 reviews)

I would definitely stay at this property again. The only thing, is you have to walk next door to eat breakfast. And the pool that you have to use is also on another property but it’s closed right now. However the woman that checked us in gave us extra drink vouchers to make up for it. Great little hotel with friendly staff

Reviewed on Aug 28, 2025

Park Central South Beach

South Beach

$543

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (930 reviews)

stayed here for our SB vacay super friendly staff lovely hotel everything is within walking distance the beach everything and the shrimp pasta omg the best!!! a must try the next time i am in south beach this will be my first hotel choice.

Reviewed on Aug 27, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,262

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

President Villa

South Beach

Save 100% on your flight

$396

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,000 reviews)

Hospitable staff, clean, location ideal to walking distance to beach and shopping. Safe place!

Reviewed on Aug 8, 2025

President Hotel

South Beach

Save 100% on your flight

$389

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,773 reviews)

Amazing. Great breakfast and complementary drinks.

Reviewed on Aug 25, 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

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

$150 nightly

$169 total

Sep 4 - Sep 5

Total with taxes and fees

9/10 Wonderful! (1,499 reviews)

"Fresh new rooms. Location was right on the ocean. Great breakfast, made for you. Front desk staff was amazing. Super accommodating and great communication. The only thing I would have recommended is that during construction they should have instated a bathroom vanity. Would return there again!!"

Reviewed on Aug 24, 2025

Reefhouse Resort & Marina

103800 Overseas Hwy, Key Largo, FL

Fully refundableReserve now, pay when you stay

$259 nightly

$286 total

Sep 1 - Sep 2

Total with taxes and fees

9.2/10 Wonderful! (1,301 reviews)

"Loved it"

Reviewed on Aug 22, 2025

Holiday Inn Key Largo by IHG

99701 Overseas Hwy, Key Largo, FL

Fully refundable

$140 nightly

$158 total

Sep 7 - Sep 8

Total with taxes and fees

8.4/10 Very Good! (1,004 reviews)

"Great location and two beautiful pools. Very comfortable bed as well"

Reviewed on Aug 26, 2025

See all 2,262 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.