Search Hotels in Winston Waterways, Key Largo

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winston Waterways hotels

Treasure Harbor

Treasure Harbor
3.0 star property
24 km from Winston Waterways
9.0 out of 10, Wonderful, (150 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
The price is ฿5,460
฿10,632 total
includes taxes & fees
25 Apr - 26 Apr
Treasure Harbor

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, (1,003 reviews)
"The Tiki Bar was delightful, and the bartender very good."
United States
Cynthia
The price is ฿4,793
฿5,392 total
includes taxes & fees
3 May - 4 May
Hampton Inn Key Largo Manatee Bay

Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.4 out of 10, Exceptional, (170 reviews)
"It was very clean, well maintained and charming.The staff was very friendly and the morning breakfast was perfect. Room and bathroom were pretty small for the price but it meet our needs for a 1 night stay."
United States
Jason
The price is ฿4,426
฿5,428 total
includes taxes & fees
6 May - 7 May
Seafarer Key Largo

Drift Hotel

Drift Hotel
2.5 star property
10.7 km from Winston Waterways
9.0 out of 10, Wonderful, (1,005 reviews)
"Peaceful place to hang out at the beach. "
United States
brian
The price is ฿4,569
฿5,500 total
includes taxes & fees
20 Apr - 21 Apr
Drift Hotel

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,118 reviews)
"Rooms were clean, staff was friendly and the pool was impeccable. My family and I would stay there again."
United States
Michelle
The price is ฿6,293
฿7,080 total
includes taxes & fees
3 May - 4 May
Rock Reef Resort

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)
"Great place to stay. Room was clean and staff was nice. "
United States
Anna
The price is ฿5,431
฿6,110 total
includes taxes & fees
27 Apr - 28 Apr
Sunset Cove Beach Resort

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)
"Room, staff and location were all excellent. Would definitely stay there again. "
United States
Anthony
The price is ฿4,569
฿6,039 total
includes taxes & fees
22 Apr - 23 Apr
Amoray Dive Resort

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
24.2 km from Winston Waterways
9.6 out of 10, Exceptional, (242 reviews)
"Wonderful place, very clean and with stunning views. I will definitely stay there again."
United States
Karenia
The price is ฿7,177
฿8,074 total
includes taxes & fees
22 Apr - 23 Apr
Ragged Edge Resort & Marina

Largo Resort

Largo Resort
3.0 star property
0.9 km from Winston Waterways
9.4 out of 10, Exceptional, (304 reviews)
"The staff is extremely helpful! That is the one thing this “resort” has going for hit. "
United States
Wendy
The price is ฿7,827
฿13,762 total
includes taxes & fees
27 Apr - 28 Apr
Largo Resort

Azul del Mar

Azul del Mar
3.5 star property
3.8 km from Winston Waterways
9.0 out of 10, Wonderful, (845 reviews)
"Excellent location, close to essential amenities. Super responsive & friendly staff. Safe, comfortable & relaxing accommodations."
United States
Tim Kerry
The price is ฿6,006
฿6,757 total
includes taxes & fees
21 Apr - 22 Apr
Azul del Mar

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
28.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,690 reviews)
"Great location and beautiful beach"
United States
Jerrod
The price is ฿6,340
฿8,928 total
includes taxes & fees
10 May - 11 May
Chesapeake Beach Resort

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
3.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,297 reviews)
"Atmosphere out on the balcony watching the boats come and go made our stay well worth it. Would definitely stay again. "
United States
Julie
The price is ฿4,520
฿5,983 total
includes taxes & fees
4 May - 5 May
Waterside Suites & Marina

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, (1,002 reviews)
"Beautiful quiet place to stay! Rooms were very clean, view was amazing, perfect location. "
Canada
Melody
The price is ฿3,990
฿4,488 total
includes taxes & fees
26 Apr - 27 Apr
The Pelican Key Largo Cottages

Drop Anchor

Drop Anchor
3.0 star property
26.3 km from Winston Waterways
8.8 out of 10, Excellent, (1,001 reviews)
"We loved our stay and definitely will be back . Staff was great, hotel was clean and comfortable, the view amazing, great location. The only thing to improve is the water pressure when taking showers but everything else was fantastic . "
United States
vanessa
The price is ฿5,581
฿7,396 total
includes taxes & fees
23 Apr - 24 Apr
Drop Anchor

Gilbert's Resort

Gilbert's Resort
2.0 star property
7.7 km from Winston Waterways
8.6 out of 10, Excellent, (1,000 reviews)
"Great property yo spend time. Beach, pool, bar, food, entertainment, marina. Nicely remodel. Staff is very polite. Continental breakfast is very good, more than your normal. Nice variety. "
United States
dimitra
The price is ฿8,118
฿9,133 total
includes taxes & fees
22 Apr - 23 Apr
Gilbert's Resort

Dolphin Point Villas

Dolphin Point Villas
3.5 star property
0.7 km from Winston Waterways
9.6 out of 10, Exceptional, (490 reviews)
"Had a great time. Pool was heated which was super nice! Wonderful to watch the sunset from the beach. Very relaxing."
United States
Melissa
The price is ฿5,316
฿6,879 total
includes taxes & fees
21 Apr - 22 Apr
Dolphin Point Villas

Bay Harbor Lodge

Bay Harbor Lodge
3.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.4 out of 10, Exceptional, (680 reviews)
"Room was clean, staff is excellent, fresh made scones and coffee every morning, kayaks right on the beach for free where you can see a ton of wildlife! I don’t think I’ll stay at another place in the keys, this place was so perfect. "
United States
Rachel
The price is ฿7,823
฿8,801 total
includes taxes & fees
26 Apr - 27 Apr
Bay Harbor Lodge

Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
15.3 km from Winston Waterways
9.4 out of 10, Exceptional, (761 reviews)
"We loved our stay here. It was clean and quiet, and right on the water. It was beautiful! We would absolutely recommend this property and would stay here again anytime!"
United States
Katie
The price is ฿7,472
฿9,044 total
includes taxes & fees
4 May - 5 May
Atlantic Bay Resort

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, (1,003 reviews)
"Excellent stay. Love all the amenities this resort offers. You never even have to leave to have a wonderful stay"
United States
Robert
The price is ฿5,053
฿6,259 total
includes taxes & fees
5 May - 6 May
Ocean Pointe Suites at Key Largo

Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina
2.0 star property
3.5 km from Winston Waterways
8.4 out of 10, Very good, (1,743 reviews)
"Great family place and great views. Very friendly staff will definitely return "
United States
Ernesto
The price is ฿4,438
฿5,891 total
includes taxes & fees
21 Apr - 22 Apr
Marina Del Mar Resort and 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.

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.

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.

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.

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

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 17 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.