Hotels in Winston Waterways

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

Filter by

Guest rating
Guest rating
Property class

Top 10 Hotels in Winston Waterways

Azul del Mar
On the beach, kayaking

Azul del Mar

3.5 star property
9.0 out of 10, Wonderful, (748)
"Easy access and several locations to eat or explore waterside nearby. "
Azul del Mar
Hampton Inn Key Largo Manatee Bay
Beach/ocean view

Hampton Inn Key Largo Manatee Bay

2.5 star property
8.8 out of 10, Excellent, (1011)
"Very nice hotel, the plus is the private beach!!"
The price is S$164
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn Key Largo Manatee Bay
Chesapeake Beach Resort
Private beach, white sand, sun-loungers, beach towels

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1502)
"Excellent location on the ocean and everything was really perfect. will stay there again"
The price is S$243
includes taxes & fees
1 Sept - 2 Sept
Chesapeake Beach Resort
Drift Hotel
On the beach, sun-loungers, snorkelling, kayaking

Drift Hotel

2.5 star property
9.0 out of 10, Wonderful, (1008)
"Great stay, nice property. Staff was awesome. "
Drift Hotel
Rock Reef Resort
Sun deck

Rock Reef Resort

2.5 star property
9.2 out of 10, Wonderful, (1013)
"It was a very quite and a relaxing stay."
Rock Reef Resort
Amoray Dive Resort
Exterior

Amoray Dive Resort

2.0 star property
9.0 out of 10, Wonderful, (1005)
"Great place!"
The price is S$141
includes taxes & fees
28 Aug - 29 Aug
Amoray Dive Resort
The Pelican Key Largo Cottages
Marina

The Pelican Key Largo Cottages

2.0 star property
8.8 out of 10, Excellent, (1007)
"Beautiful beachfront, gorgeous views, convenient snorkeling, delicious food, kind and helpful staff, we're already planning to come back "
The price is S$128
includes taxes & fees
27 Aug - 28 Aug
The Pelican Key Largo Cottages
Ragged Edge Resort & Marina
Exterior

Ragged Edge Resort & Marina

2.5 star property
9.4 out of 10, Exceptional, (190)
"We enjoyed our stay very much and have already recommended this hotel to friends. Thanks for accommodating our check in and check out. "
Ragged Edge Resort & Marina
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Aerial view

Dove Creek Resort & Marina, Trademark Collection by Wyndham

3.0 star property
7.6 out of 10, Good, (1002)
"Loved staying in this hotel"
The price is S$174
includes taxes & fees
1 Sept - 2 Sept
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Seafarer Key Largo
Exterior

Seafarer Key Largo

2.0 star property
9.6 out of 10, Exceptional, (107)
"This is a great place to stay! The beach front area is beautiful and relaxing and the view is spectacular. The breakfast is also delicious. "
The price is S$158
includes taxes & fees
1 Sept - 2 Sept
Seafarer Key Largo
Dolphin Point Villas
Property entrance

Dolphin Point Villas

3.5 star property
9.6 out of 10, Exceptional, (457)
"Had a great stay. Staff was very friendly and enjoyed use of the kayaks and paddleboards with the kids. "
Dolphin Point Villas
Creekside Inn Islamorada
Water view

Creekside Inn Islamorada

2.5 star property
8.0 out of 10, Very good, (1002)
"Loved staying here, amazing friendly staff, great location, would surely stay here again"
The price is S$180
includes taxes & fees
1 Sept - 2 Sept
Creekside Inn Islamorada
Kona Kai Resort and Gallery - Adults Only
Exterior

Kona Kai Resort and Gallery - Adults Only

2.5 star property
9.8 out of 10, Exceptional, (252)
"I truly enjoyed this resort. Extremely friendly staff, beautiful room and the view on the water is grwat"
Kona Kai Resort and Gallery - Adults Only
Atlantic Bay Resort
Property grounds

Atlantic Bay Resort

3.0 star property
9.4 out of 10, Exceptional, (695)
"Great spot and a hidden gem!"
The price is S$230
includes taxes & fees
2 Sept - 3 Sept
Atlantic Bay Resort
Waterside Suites & Marina
Terrace/patio

Waterside Suites & Marina

3.5 star property
8.8 out of 10, Excellent, (1050)
"Loved staying here!"
The price is S$185
includes taxes & fees
1 Sept - 2 Sept
Waterside Suites & Marina
Largo Resort
Outdoor pool, pool umbrellas, pool loungers

Largo Resort

3.0 star property
9.4 out of 10, Exceptional, (290)
"Amazing place to stay "
The price is S$379
includes taxes & fees
8 Sept - 9 Sept
Largo Resort
Bayside Inn Key Largo
Terrace/patio

Bayside Inn Key Largo

3.0 star property
8.6 out of 10, Excellent, (1553)
"Great place to stay! Enjoyed our time there"
The price is S$196
includes taxes & fees
3 Sept - 4 Sept
Bayside Inn Key Largo
Marina Del Mar Resort and Marina
Exterior

Marina Del Mar Resort and Marina

2.5 star property
8.4 out of 10, Very good, (1589)
"Have stayed many times and will be back many times"
The price is S$157
includes taxes & fees
1 Sept - 2 Sept
Marina Del Mar Resort and Marina
Kings Kamp
Fishing

Kings Kamp

2.5 star property
8.6 out of 10, Excellent, (22)
"The property is beautiful, nicely renovated and clean. A true gem is a covered patio with grill and a small beach right outside the door. There is plenty of local attractions to choose from near by. We had a fantastic stay and would highly recommend this property. We hope to come back again some day. Thank you!"
Kings Kamp
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
8.0 out of 10, Very good, (1001)
"Great views manatees cruising by very relaxing"
The price is S$183
includes taxes & fees
14 Sept - 15 Sept
Fisher Inn Resort & 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.

Where to stay in Winston Waterways

Find the best Winston Waterways areas for the activities you enjoy most.

Key Largo Village

When in Key Largo Village, you can plan a visit to Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park, some noteworthy sights in the nearby area.

Key Largo Park

Key Largo Park might not have many top sights, but Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park are two attractions nearby that you can check out.

Cross Key Waterways

When in Cross Key Waterways, you can plan a visit to MarineLab Undersea Laboratory and Caribbean Club Bar, some noteworthy sights in the nearby area.

Sexton Cove Estates

When in Sexton Cove Estates, you can plan a visit to Key Largo Baptist Church and Caribbean Club Bar, some noteworthy sights in the nearby area.

Largo Gardens

Though Largo Gardens may not have many top sights, you can venture to the surrounding area to see attractions like John Pennekamp Coral Reef State Park and MarineLab Undersea Laboratory.

Top Winston Waterways Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"We were only there a couple of days but we had a great time! It's typical Key West layed back vibe!"
Karen 2-night trip
Posted 11 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Winston Waterways?

You'll be sure to have fun exploring Key Largo's Winston Waterways neighbourhood. Consider a visit to John Pennekamp Coral Reef State Park as part of your Winston Waterways travel plans.

How many hotels are there in Winston Waterways?

With 18 Expedia hotels and other accommodation options in Winston Waterways to choose from, this is a good starting point for exploring the greater Key Largo area.

If I need to cancel my hotel reservation in Winston Waterways, will I receive a refund?

Yes! The majority of room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to view top deals in Winston Waterways.

What are the top things to see and do in Winston Waterways?

John Pennekamp Coral Reef State Park is an attraction you might want to check out while you're in Winston Waterways. When you're sightseeing in Key Largo, Lower Sound Point and MarineLab Undersea Laboratory are also worth a stop.