Search Hotels in Winston Waterways, Key Largo

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10 Dec - 11 Dec
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12 Dec - 14 Dec
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Our top choices for Winston Waterways hotels

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, (1588)
"Great breakfast, great location, friendly staff, nice extras."
United States
Gary
The price is Rp3.152.598
Rp4.484.677 total
includes taxes & fees
15 Dec - 16 Dec
Chesapeake Beach 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, (1622)
"Friendly staff, clean room beautiful views from the private beach."
United States
Wanda
The price is Rp850.476
Rp1.373.686 total
includes taxes & fees
16 Dec - 17 Dec
Bayside Inn Key Largo
Exterior
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
26.7 km from Winston Waterways
9.0 out of 10, Wonderful, (149)
"Great place to stay! Clean, great location and great customer service. Very easy to check in, front desk was so sweet! Highly recommended!!! Had a great experience overall"
United States
Elaysi
The price is Rp2.536.420
Rp2.853.472 total
includes taxes & fees
14 Dec - 15 Dec
Coconut Cove Resort and Marina
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, (1069)
"Everything clean, friendly staff"
United States
Arlene
Rock Reef 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, (1648)
"Great location, amenities, service, places to eat. Very accommodating with extended stay."
United States
Joseph
The price is Rp1.828.523
Rp2.526.184 total
includes taxes & fees
14 Dec - 15 Dec
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
8.8 out of 10, Excellent, (1005)
"The beach area was wonderful"
United States
Sonya
The price is Rp1.624.868
Rp1.827.978 total
includes taxes & fees
16 Dec - 17 Dec
The Pelican Key Largo Cottages
Exterior
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
26.5 km from Winston Waterways
8.2 out of 10, Very good, (1001)
"Clean fresh rooms, facilities and property! Extraordinary customer service. Great kayaks and paddleboards to use free. I would definitely stay here again"
United States
Kristi
The price is Rp2.161.210
Rp2.975.499 total
includes taxes & fees
17 Dec - 18 Dec
Fisher Inn Resort & Marina
Dock
Hadley Resort and Marina

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
30.1 km from Winston Waterways
7.6 out of 10, Good, (1000)
"Comfortable stay. Great location. "
United States
Anand
The price is Rp2.311.294
Rp3.144.427 total
includes taxes & fees
14 Dec - 15 Dec
Hadley Resort and Marina
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, (114)
"Beautiful place to stay"
United States
Jonathan
The price is Rp3.529.475
Rp5.077.613 total
includes taxes & fees
17 Dec - 18 Dec
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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, (1150)
"Great place to stay!"
United States
Chad
The price is Rp2.518.910
Rp3.302.682 total
includes taxes & fees
14 Dec - 15 Dec
Waterside Suites & Marina
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 Rp4.385.788
Rp5.853.360 total
includes taxes & fees
17 Dec - 18 Dec
Playa Largo Resort & Spa, Autograph Collection
Exterior
Seafarer Key Largo

Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.4 out of 10, Exceptional, (129)
"The Seafarer stay was awesome! Great clean rooms and bathrooms! The kitchen was well equipped. The beach area was a beautiful spot to relax, swim and free kayaks to explore the beautiful water! The staff are all friendly and they keep the rooms and property super clean. Would definitely stay there again! "
United States
Laura
The price is Rp1.770.991
Rp2.226.871 total
includes taxes & fees
14 Dec - 15 Dec
Seafarer Key Largo
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor

Drop Anchor

Drop Anchor
3.0 star property
26.3 km from Winston Waterways
8.8 out of 10, Excellent, (1003)
"Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! "
United States
Laura
The price is Rp2.192.802
Rp3.050.562 total
includes taxes & fees
4 Jan - 5 Jan 2026
Drop Anchor
On the beach, sun-loungers, snorkelling, kayaking
Drift Hotel

Drift Hotel

Drift Hotel
2.5 star property
10.7 km from Winston Waterways
9.0 out of 10, Wonderful, (1000)
"we had a good time here, fabulous place"
United States
Kanishka
Drift Hotel
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, (1011)
"Excellent place to stay for a weekend "
United States
Carlos
The price is Rp2.834.920
Rp3.189.284 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Key Largo by IHG
Aerial view
Dove Creek Resort & Marina, Trademark Collection by Wyndham

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
7.6 out of 10, Good, (1002)
"The staff was courteous. "
United States
Natasha
The price is Rp1.686.777
Rp2.426.420 total
includes taxes & fees
17 Dec - 18 Dec
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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, (1012)
"Great resort"
United States
david
The price is Rp2.174.550
Rp2.446.370 total
includes taxes & fees
17 Dec - 18 Dec
Hampton Inn Key Largo Manatee Bay
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, (1004)
"Great service, spotless room, and the sunsets!!!"
United States
Peter
The price is Rp1.936.084
Rp2.647.190 total
includes taxes & fees
14 Dec - 15 Dec
Amoray Dive 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, (1009)
"Just a good place to stay."
United States
William
The price is Rp2.265.435
Rp2.848.782 total
includes taxes & fees
17 Dec - 18 Dec
Ocean Pointe Suites at Key Largo
Exterior
Ragged Edge Resort & Marina

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
24.2 km from Winston Waterways
9.4 out of 10, Exceptional, (205)
"Clean room, beautiful pool and quiet!"
United States
Robert
Ragged Edge 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.
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 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.

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.

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 Harry Harris Park.

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

Drift Hotel

Drift Hotel

10/10 Excellent
"The room was spotless. Small, but have everything. The little beach with the deck over the water is really beautiful, and the front desk person was very friendly and helpful."
Ada 1-night trip
Posted 2 days ago
Drift Hotel

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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.