Lodging Image

Winston Waterways Hotels, Key Largo

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
3 July - 5 July
In two weeks
10 July - 12 July

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winston Waterways hotels

Room, 1 King Bed, Bay View | Beach/ocean view

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
0.6 km from Winston Waterways
8.8 out of 10, Excellent, (1,005 reviews)
"Super fun place"
United States
Dylan Robert
The price is AU$231
includes taxes & fees
29 July - 30 July
Hampton Inn Key Largo Manatee Bay
3 restaurants; breakfast, lunch and dinner served

Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
2.9 km from Winston Waterways
9.4 out of 10, Exceptional, (1,478 reviews)
"We loved this place! The view, the access to everything, the food, would definitely stay here again!"
United States
Thomas
The price is AU$448
includes taxes & fees
12 July - 13 July
Reefhouse Resort & Marina
Front of property

Gilbert's Resort

Gilbert's Resort
2.0 star property
7.7 km from Winston Waterways
8.6 out of 10, Excellent, (1,003 reviews)
"You have it all at this place pool,little beach area , restuarant , kayaks and jet ski rental"
United States
LASARO
The price is AU$359
includes taxes & fees
2 July - 3 July
Gilbert's Resort
View from property

Creekside Inn

Creekside Inn
2.5 star property
17.7 km from Winston Waterways
7.8 out of 10, Good, (1,004 reviews)
"It was quaint, clean, and conveniently located."
United States
HEATHER
The price is AU$207
includes taxes & fees
6 July - 7 July
Creekside Inn
Exterior

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor, 7.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,009 reviews)
"Our favorite hotel in the FL Keys"
United States
Jose
The price is AU$574
includes taxes & fees
22 July - 23 July
Playa Largo Resort & Spa, Autograph Collection
Sun deck

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,158 reviews)
"Nice relaxing resort"
United States
Benjamin jacob
The price is AU$286
includes taxes & fees
14 July - 15 July
Rock Reef Resort
Private beach, white sand, sun-loungers, beach towels

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
28.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,742 reviews)
"Very attentive service great breakfast and beautiful room."
United States
Patrick
The price is AU$383
includes taxes & fees
5 July - 6 July
Chesapeake Beach Resort
On the beach, sun-loungers, snorkelling, kayaking

Drift Hotel

Drift Hotel
2.5 star property
10.7 km from Winston Waterways
9.0 out of 10, Wonderful, (1,005 reviews)
"Clean and super cute"
United States
Daniel
The price is AU$338
includes taxes & fees
2 July - 3 July
Drift Hotel
Property grounds

Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
15.3 km from Winston Waterways
9.4 out of 10, Exceptional, (789 reviews)
"Cute place very clean and lovely staff."
Canada
Juanita
The price is AU$320
includes taxes & fees
1 July - 2 July
Atlantic Bay Resort
BBQ/picnic Area

Largo Resort

Largo Resort
3.0 star property
0.9 km from Winston Waterways
9.4 out of 10, Exceptional, (312 reviews)
"The Largo was very nice."
United States
William R
The price is AU$500
includes taxes & fees
14 July - 15 July
Largo Resort
Exterior

Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
4.1 km from Winston Waterways
9.2 out of 10, Wonderful, (1,006 reviews)
"It was great, beautiful location, friendly staff, all the right things. Would stay again!"
United States
Dawn
The price is AU$285
includes taxes & fees
28 July - 29 July
Sunset Cove Beach Resort
Exterior

Key Largo Inn

Key Largo Inn
3.0 star property
4.5 km from Winston Waterways
6.8 out of 10, (1,003 reviews)
"Good price great location "
United States
Kristin
The price is AU$171
includes taxes & fees
30 June - 1 July
Key Largo Inn
Exterior

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
11.9 km from Winston Waterways
7.8 out of 10, Good, (1,002 reviews)
"Very nice place"
United States
Mae L
The price is AU$279
includes taxes & fees
5 July - 6 July
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Private beach, sun-loungers, beach towels, kayaking

Dolphin Point Villas

Dolphin Point Villas
3.5 star property
0.7 km from Winston Waterways
9.6 out of 10, Exceptional, (502 reviews)
"Wonderful place"
United States
Patrick
The price is AU$321
includes taxes & fees
30 June - 1 July
Dolphin Point Villas
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers

Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG
3.0 star property
3.6 km from Winston Waterways
8.6 out of 10, Excellent, (1,065 reviews)
"Always a great stay"
United States
Karen
The price is AU$308
includes taxes & fees
12 July - 13 July
Holiday Inn Key Largo by IHG
Single Room | Terrace/patio

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.8 out of 10, Exceptional, (329 reviews)
"What a wonderful stay we had at Kona Kai Resort. It is a true gem set amidst beautiful beachfront landscape that offers both tranquility and breathtaking scenery."
United States
Christine
The price is AU$406
includes taxes & fees
1 July - 2 July
Kona Kai Resort and Gallery - Adults Only
Terrace/patio

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
3.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,402 reviews)
"We loved the location and pool"
United States
Tara
The price is AU$236
includes taxes & fees
2 July - 3 July
Waterside Suites & Marina
Exterior

Amoray Dive Resort

Amoray Dive Resort
2.0 star property
3.8 km from Winston Waterways
9.2 out of 10, Wonderful, (1,001 reviews)
"everything was great"
United States
alex
The price is AU$168
includes taxes & fees
1 July - 2 July
Amoray Dive Resort
Exterior

Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.2 out of 10, Wonderful, (204 reviews)
"The play is absolutely perfect beautiful located the breakfast is awesome quiet and peaceful recommend 100 percent will be going back"
United States
Donald Andrew
The price is AU$207
includes taxes & fees
30 June - 1 July
Seafarer Key Largo
Exterior

Coconut Palm Inn

Coconut Palm Inn
3.0 star property
15.8 km from Winston Waterways
9.4 out of 10, Exceptional, (545 reviews)
"Nice quiet family friendly place to stay"
United States
James
The price is AU$307
includes taxes & fees
30 June - 1 July
Coconut Palm Inn
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.
View all properties

Our guide on where to stay in Winston Waterways

Find the best Winston Waterways areas for the activities you enjoy most.
A beachside resort with lounge chairs, a thatched-roof hut, and palm trees.
Photo by Samantha Shoemaker
Open Photo by Samantha Shoemaker

Rock Harbor

While there might not be top attractions in Rock Harbor, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

A white speedboat on a blue ocean with a tropical island in the background.

Key Largo Village

When in Key Largo Village, you can plan a visit to Jimmy Johnson's Big Chill and Jacob's Aquatic Center, some noteworthy sights in the nearby area.

Silver Shores

While there might not be top attractions in Silver Shores, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Pigeon Key.

An aerial view of a coastal area with RVs parked along the shore, a small beach, and a clear view of the ocean.

Key Largo Park

Key Largo Park might not have many top sights, but Jimmy Johnson's Big Chill and Jacob's Aquatic Center are two attractions nearby that you can check out.

Two manatees in a body of water.
Photo by Patricia Smith
Open Photo by Patricia Smith

Pirates Cove

While there might not be top attractions in Pirates Cove, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

Top Winston Waterways Hotel Reviews

Recent Reviews in Winston Waterways

Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Great job!"
John 2-night trip
Posted 1 hour ago
Reefhouse Resort & Marina

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?
If you're searching for places to stay in Key Largo, Expedia has something to meet your needs with 20 Winston Waterways hotels and other accommodation options to choose from.
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.

Explore a world of travel with Expedia