Hotels in Winston Waterways, Key Largo

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29 Dec - 30 Dec
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30 Dec - 31 Dec
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2 Jan - 4 Jan
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9 Jan - 11 Jan

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Our top choices for Winston Waterways hotels

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 RM612
RM802 total
includes taxes & fees
4 Jan - 5 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, (1329)
"Very relaxing with nice on-site activities. Bed can be better for better sleep"
United States
Jing
The price is RM1,090
RM1,388 total
includes taxes & fees
4 Jan - 5 Jan 2026
Reefhouse Resort & Marina
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 RM644
RM826 total
includes taxes & fees
5 Jan - 6 Jan 2026
Bayside Inn Key Largo
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, (1604)
"The entire resort was wonderful."
Canada
Mat
The price is RM766
RM1,089 total
includes taxes & fees
18 Jan - 19 Jan 2026
Chesapeake Beach Resort
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, (1002)
"Always a great stay"
United States
Ashley
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, (1018)
"Wonderful hotel. Great location Pool is amazing the staff was very friendly In all very good.. highly recommend "
United States
Christopher
The price is RM766
RM861 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Key Largo by IHG
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, (1008)
"Great hotel"
United States
Elior
The price is RM691
RM778 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hampton Inn Key Largo Manatee Bay
Gazebo
Sunset Cove Beach Resort

Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
4.1 km from Winston Waterways
9.0 out of 10, Wonderful, (1005)
"Always a great stay"
United States
Richard
The price is RM842
RM948 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sunset Cove 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, (1003)
"warm pool, great clean room"
United States
Heidi
The price is RM503
RM680 total
includes taxes & fees
5 Jan - 6 Jan 2026
Amoray Dive Resort
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
Courtyard by Marriott Key Largo

Courtyard by Marriott Key Largo

Courtyard by Marriott Key Largo
3.0 star property
3.4 km from Winston Waterways
8.2 out of 10, Very good, (1001)
"Everything was very clean and chill. The breakfast was delicious, and the staff was very kind & respectful."
United States
Danay
The price is RM798
RM898 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Key Largo
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, (1666)
"Excellent staff! Breakfast was outstanding!"
United States
David
The price is RM547
RM730 total
includes taxes & fees
4 Jan - 5 Jan 2026
Marina Del Mar Resort and 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, (1003)
"Beautiful location, great views, very clean property, room was great (great bed), friendly staff."
United States
Scott
The price is RM1,389
RM1,786 total
includes taxes & fees
19 Jan - 20 Jan 2026
Playa Largo Resort & Spa, Autograph Collection
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, (1008)
"Great room with beautiful sunrise over the ocean! "
Canada
Heather
The price is RM547
RM744 total
includes taxes & fees
7 Jan - 8 Jan 2026
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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 RM594
RM668 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Pelican Key Largo Cottages
On the beach, kayaking
Azul del Mar

Azul del Mar

Azul del Mar
3.5 star property
3.8 km from Winston Waterways
9.0 out of 10, Wonderful, (805)
"one of the best hotel experiences I've had very quiet and right on the water "
United States
todd
Azul del Mar
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, (1006)
"Patio nice , pool area good , good walk to things to do ,dive museum , brewery, shopping. "
United States
John
The price is RM602
RM810 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hadley Resort and Marina
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, (137)
"Nice, quiet and the staff were great. Loved the breakfast!"
United States
Michael
The price is RM649
RM787 total
includes taxes & fees
6 Jan - 7 Jan 2026
Seafarer Key Largo
Outdoor pool, pool umbrellas, pool loungers
Largo Resort

Largo Resort

Largo Resort
3.0 star property
0.8 km from Winston Waterways
9.4 out of 10, Exceptional, (295)
"Absolutely beautiful resort! Quiet, and peaceful! "
United States
Shana
The price is RM850
RM1,225 total
includes taxes & fees
25 Jan - 26 Jan 2026
Largo 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 RM1,339
RM1,776 total
includes taxes & fees
5 Jan - 6 Jan 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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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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

Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

10/10 Excellent
"Hanging out on your balcony was great, very fun place with a great vibe. Will be back. "
David 2-night trip
Posted 2 days ago
Marina Del Mar Resort and 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?
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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