Winston Waterways Hotels, Key Largo

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Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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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 NZ$347
includes taxes & fees
6 Jan - 7 Jan 2026
Atlantic Bay Resort
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, (1329)
"Very relaxing with nice on-site activities. Bed can be better for better sleep"
United States
Jing
The price is NZ$590
includes taxes & fees
4 Jan - 5 Jan 2026
Reefhouse Resort & Marina
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, (1180)
"Clean room and staff was great"
United States
Jim
The price is NZ$323
includes taxes & fees
19 Jan - 20 Jan 2026
Waterside Suites & Marina
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, (1011)
"Very comfortable stay Local dining walking distance many amenities close by Room was very clean and AC worked great "
United States
Roy
The price is NZ$295
includes taxes & fees
5 Jan - 6 Jan 2026
Creekside Inn
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, (1002)
"One of the nicest hotels we have stayed at. Amazing staff, food, activities and property "
United States
Sara
The price is NZ$760
includes taxes & fees
6 Jan - 7 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 NZ$779
includes taxes & fees
1 Jan - 2 Jan 2026
Island Bay Resort
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 NZ$914
includes taxes & fees
13 Jan - 14 Jan 2026
Playa Largo Resort & Spa, Autograph Collection
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, (1011)
"It is best..very nice place..very clean... beautiful place with ocean view"
United States
nazliya
The price is NZ$337
includes taxes & fees
7 Jan - 8 Jan 2026
Ocean Pointe Suites at Key Largo
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, (1019)
"Wonderful hotel. Great location Pool is amazing the staff was very friendly In all very good.. highly recommend "
United States
Christopher
The price is NZ$364
includes taxes & fees
27 Jan - 28 Jan 2026
Holiday Inn Key Largo by IHG
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, (1607)
"The entire resort was wonderful."
Canada
Mat
The price is NZ$441
includes taxes & fees
28 Jan - 29 Jan 2026
Chesapeake Beach 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, (122)
"Beautiful chilled out hotel"
United Kingdom
Jacqueline
The price is NZ$722
includes taxes & fees
6 Jan - 7 Jan 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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, (1669)
"Excellent staff! Breakfast was outstanding!"
United States
David
The price is NZ$274
includes taxes & fees
5 Jan - 6 Jan 2026
Marina Del Mar Resort and Marina
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, (1005)
"Great place"
United States
Marc
The price is NZ$260
includes taxes & fees
5 Jan - 6 Jan 2026
The Pelican Key Largo Cottages
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, (1075)
"Great room, friendly staff "
United States
Chengdao
Rock Reef 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, (1003)
"warm pool, great clean room"
United States
Heidi
The price is NZ$289
includes taxes & fees
5 Jan - 6 Jan 2026
Amoray Dive Resort
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, (1000)
"Great place to stay for relax and have fun! "
United States
Tatiana
Gilbert's Resort
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, (128)
"Location is perfect and we just keep coming back "
United States
Jason
Bahia Bay Resort
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)
"Great hotel"
United States
Elior
The price is NZ$307
includes taxes & fees
13 Jan - 14 Jan 2026
Hampton Inn Key Largo Manatee Bay
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers
The Islands of Islamorada

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
29.9 km from Winston Waterways
9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
United States
Dixania
The price is NZ$1,268
includes taxes & fees
14 Jan - 15 Jan 2026
The Islands of Islamorada
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, (1630)
"Great location, Relaxing friendly atmosphere. Very basic room amenities but beautiful beach, pool, experience "
United States
Rebecca
The price is NZ$351
includes taxes & fees
4 Jan - 5 Jan 2026
Bayside Inn Key Largo
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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Our guide on 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.

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.

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.

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.

Top Winston Waterways Hotel Reviews

Treasure Harbor

Treasure Harbor

10/10 Excellent
"Great spot! Will be back someday hopefully. "
Diane 1-night trip
Posted 1 day ago
Treasure Harbor

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.

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