Search Hotels in Winston Waterways, Key Largo

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23 Dec - 24 Dec
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26 Dec - 28 Dec
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Our top choices for Winston Waterways hotels

Property grounds
Atlantic Bay Resort

Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
15.3 km from Winston Waterways
9.4 out of 10, Exceptional, (717)
"Great location with friendly staff"
United States
enrique
The price is 4.668.018 ₫
5.777.722 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Atlantic Bay Resort
Water view
Creekside Inn

Creekside Inn

Creekside Inn
2.5 star property
17.7 km from Winston Waterways
8.0 out of 10, Very good, (1006)
"The room was nice, but walking out to the pier from door was excellent "
United States
Anthony
The price is 4.005.227 ₫
4.505.881 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Creekside Inn
Terrace/patio
Waterside Suites & Marina

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
3.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1172)
"Always a great experience every time we go to key largo we stay there "
United States
AMYRSA
The price is 3.974.881 ₫
5.211.851 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Waterside Suites & Marina
3 restaurants, breakfast, lunch, dinner served; American cuisine
Reefhouse Resort & Marina

Reefhouse Resort & Marina

Reefhouse Resort & Marina
3.5 star property
2.9 km from Winston Waterways
9.2 out of 10, Wonderful, (1331)
"Nice hotel with great staff."
United States
David
The price is 6.556.917 ₫
8.429.983 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Reefhouse Resort & Marina
32-inch LCD TV with satellite channels, TV, iPod dock
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
8.3 km from Winston Waterways
8.6 out of 10, Excellent, (1008)
"Beautiful Hotel and Calusa Restaurant was outstanding "
United States
Darlene
The price is 10.559.006 ₫
13.330.619 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Private beach, sun-loungers, beach umbrellas, beach towels
Island Bay Resort

Island Bay Resort

Island Bay Resort
2.5 star property
15.1 km from Winston Waterways
10.0 out of 10, Exceptional, (141)
"Very quiet and the outdoor spaces are very nice. Staff was very friendly also."
United States
Jacob
The price is 11.153.039 ₫
12.547.169 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Island Bay Resort
BBQ/picnic Area
Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
14.2 km from Winston Waterways
8.4 out of 10, Very good, (1007)
"Just a good place to stay."
United States
William
The price is 5.117.819 ₫
6.231.540 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Ocean Pointe Suites at Key Largo
Outdoor pool, pool cabanas (surcharge), pool umbrellas
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor, 7.1 km from Winston Waterways
8.8 out of 10, Excellent, (1000)
"Beautiful location, great views, very clean property, room was great (great bed), friendly staff."
United States
Scott
The price is 9.032.219 ₫
11.612.985 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Playa Largo Resort & Spa, Autograph Collection
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

Holiday Inn Key Largo by IHG
3.0 star property
3.6 km from Winston Waterways
8.6 out of 10, Excellent, (1015)
"Excellent place to stay for a weekend "
United States
Carlos
The price is 4.976.937 ₫
5.599.054 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Key Largo by IHG
Sun deck
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1071)
"Wish we stayed a little longer to enjoy the oroperty"
United States
Vicki
Rock Reef Resort
Marina
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
4.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1004)
"Great place"
United States
Marc
The price is 3.862.195 ₫
4.344.969 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
The Pelican Key Largo Cottages
Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
28.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1601)
"The entire resort was wonderful."
Canada
Mat
The price is 4.978.254 ₫
7.081.734 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Chesapeake Beach Resort
Exterior
Amoray Dive Resort

Amoray Dive Resort

Amoray Dive Resort
2.0 star property
3.7 km from Winston Waterways
9.2 out of 10, Wonderful, (1008)
"Great place, beautiful location. Every staff member I encountered was friendly and professional, even January. We are going to try and make this a annual trip."
United States
Jonathan
The price is 3.705.908 ₫
4.909.894 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Amoray Dive Resort
Exterior
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina
2.5 star property
3.5 km from Winston Waterways
8.4 out of 10, Very good, (1656)
"Great location, amenities, service, places to eat. Very accommodating with extended stay."
United States
Joseph
The price is 3.782.735 ₫
4.996.323 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Marina Del Mar Resort and Marina
Room, 1 King Bed, Bay View | Beach/ocean view
Hampton Inn Key Largo Manatee Bay

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, (1010)
"Clean room, welcoming staff, nice stay."
Germany
Verena
The price is 4.299.126 ₫
4.836.517 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Key Largo Manatee Bay
Exterior
Gilbert's Resort

Gilbert's Resort

Gilbert's Resort
2.0 star property
7.7 km from Winston Waterways
8.6 out of 10, Excellent, (1003)
"Great place to stay for relax and have fun! "
United States
Tatiana
Gilbert's Resort
Terrace/patio
Bayside Inn Key Largo

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
3.9 km from Winston Waterways
8.6 out of 10, Excellent, (1628)
"Great location, Relaxing friendly atmosphere. Very basic room amenities but beautiful beach, pool, experience "
United States
Rebecca
The price is 4.080.658 ₫
5.248.615 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Bayside Inn Key Largo
Terrace/patio
Bahia Bay Resort

Bahia Bay Resort

Bahia Bay Resort
2.5 star property
Rock Harbor, 7.4 km from Winston Waterways
8.8 out of 10, Excellent, (126)
"Location is perfect and we just keep coming back "
United States
Jason
Bahia Bay Resort
Private beach, sun-loungers, beach towels, scuba diving
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
27.6 km from Winston Waterways
9.0 out of 10, Wonderful, (119)
"Beautiful place to stay"
United States
Jonathan
The price is 8.035.515 ₫
10.787.938 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior
Dolphin Point Villas

Dolphin Point Villas

Dolphin Point Villas
3.5 star property
0.7 km from Winston Waterways
9.6 out of 10, Exceptional, (472)
"Spacious room and beautiful grounds. Confusing check in and out procedures. "
United States
Daniel
The price is 5.660.356 ₫
7.108.142 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Dolphin Point Villas
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

Where to stay in Winston Waterways

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

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.

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.

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 Jimmy Johnson's Big Chill.

Cross Key Waterways

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

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
"The beds were incredibly soft and comfortable, the marina view was great and we really appreciated the breakfast spot being so close to our room. Fun spaces to gather around our room, very modern and stylish. The only glitch: the beautiful pool located just off the ocean was unheated and consequently, freezing. "
Carol 2-night trip
Posted 4 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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.