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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Mar 15 - Mar 16
Tomorrow
Mar 16 - Mar 17
Next weekend
Mar 20 - Mar 22
In two weeks
Mar 27 - Mar 29

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winston Waterways hotels

Exterior

Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.4 out of 10, Exceptional, (156 reviews)
"Clean room, friendly staff "
United States
Quaid
The price is CA $281
CA $390 total
includes taxes & fees
Mar 17 - Mar 18
Seafarer Key Largo
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

Treasure Harbor
3.0 star property
24 km from Winston Waterways
9.0 out of 10, Wonderful, (144 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
The price is CA $249
CA $474 total
includes taxes & fees
Mar 26 - Mar 27
Treasure Harbor
Premier Cottage, Bay View | Terrace/patio

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,107 reviews)
"The view and the bay are beautiful. "
United States
Rosa
The price is CA $291
CA $328 total
includes taxes & fees
Apr 15 - Apr 16
Rock Reef Resort
BBQ/picnic area

Largo Resort

Largo Resort
3.0 star property
0.9 km from Winston Waterways
9.4 out of 10, Exceptional, (300 reviews)
"Alex was amazing and highly recommend for future stays. Bungalow serenity was so nice and spacious. Had some trouble with the getting the TV to work but the pool and views was stunning. A great place to get away from everyday stresses and relax. "
United States
Kevin
The price is CA $295
CA $423 total
includes taxes & fees
Apr 12 - Apr 13
Largo Resort
Exterior

Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
4.1 km from Winston Waterways
9.2 out of 10, Wonderful, (1,002 reviews)
"Clean, quite, friendly and easy walk to location for food and trinkets! "
United States
scott Alan
The price is CA $321
CA $361 total
includes taxes & fees
Mar 30 - Mar 31
Sunset Cove Beach Resort
Room, 1 King Bed, Bay View | Beach/ocean view

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, (1,007 reviews)
"The small beach was our favorite part. We really enjoyed seeing a manatee visit a few times as well as a small dolphin, watching the sunset, and sunbathing. Always plenty of sun loungers for everyone. Free parking and breakfast was a huge plus."
United States
Christopher
The price is CA $304
CA $342 total
includes taxes & fees
Apr 15 - Apr 16
Hampton Inn Key Largo Manatee Bay
Exterior

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
24.2 km from Winston Waterways
9.6 out of 10, Exceptional, (231 reviews)
"Place is great "
United States
Joel
The price is CA $349
CA $392 total
includes taxes & fees
Apr 12 - Apr 13
Ragged Edge Resort & Marina
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
28.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,668 reviews)
"Great modern resort, very clean, very friendly. "
United States
Steven
The price is CA $300
CA $415 total
includes taxes & fees
Apr 15 - Apr 16
Chesapeake Beach Resort
View from property

Creekside Inn

Creekside Inn
2.5 star property
17.7 km from Winston Waterways
7.8 out of 10, Good, (1,003 reviews)
"Great stay"
United States
Zach
The price is CA $328
CA $369 total
includes taxes & fees
Apr 2 - Apr 3
Creekside Inn
Beach/ocean view

Bay Harbor Lodge

Bay Harbor Lodge
3.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.4 out of 10, Exceptional, (673 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 CA $377
CA $424 total
includes taxes & fees
Mar 17 - Mar 18
Bay Harbor Lodge
Front of property

Gilbert's Resort

Gilbert's Resort
2.0 star property
7.7 km from Winston Waterways
8.6 out of 10, Excellent, (1,003 reviews)
"Great place to stay for relax and have fun! "
United States
Tatiana
The price is CA $450
CA $507 total
includes taxes & fees
Apr 14 - Apr 15
Gilbert's Resort
Lobby

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
7.8 km from Winston Waterways
8.8 out of 10, Excellent, (320 reviews)
"Room was spotless staff was nice "
United States
Jerquyitha
The price is CA $343
CA $386 total
includes taxes & fees
Mar 22 - Mar 23
Anchorage Resort & Yacht Club
Aerial view

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
3.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,245 reviews)
"Great place to stay! "
United States
Barbara
The price is CA $241
CA $310 total
includes taxes & fees
Apr 13 - Apr 14
Waterside Suites & Marina
Property grounds

Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
15.3 km from Winston Waterways
9.4 out of 10, Exceptional, (753 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 CA $434
CA $515 total
includes taxes & fees
Mar 17 - Mar 18
Atlantic Bay Resort
Terrace/patio

Bahia Bay Resort

Bahia Bay Resort
2.5 star property
Rock Harbor, 7.4 km from Winston Waterways
9.0 out of 10, Wonderful, (159 reviews)
"Excellent property, new like and very clean. Property mostly used for wedding but is used as hotel when not wedding."
United States
Kenneth
The price is CA $299
CA $337 total
includes taxes & fees
Mar 17 - Mar 18
Bahia Bay Resort
Classic Room, Patio, Garden View

The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
26.9 km from Winston Waterways
9.0 out of 10, Wonderful, (18 reviews)
"Great stay! Loved this property and staff. Clean and convenient. "
United States
Pamela
The price is CA $348
CA $392 total
includes taxes & fees
Mar 18 - Mar 19
The Ocean View Inn & Pub
Private beach, scuba diving, snorkeling, kayaking

Amoray Dive Resort

Amoray Dive Resort
2.0 star property
3.8 km from Winston Waterways
9.2 out of 10, Wonderful, (1,000 reviews)
"Very clean, gorgeous patio with hammock, kayaks and close to great food!"
United States
anne
The price is CA $344
CA $426 total
includes taxes & fees
Apr 14 - Apr 15
Amoray Dive Resort
On the beach, sun loungers, snorkeling, kayaking

Drift Hotel

Drift Hotel
2.5 star property
10.7 km from Winston Waterways
9.0 out of 10, Wonderful, (1,002 reviews)
"Great place"
United States
Jason
The price is CA $307
CA $361 total
includes taxes & fees
Apr 12 - Apr 13
Drift Hotel
Private beach, sun loungers, beach towels, kayaking

Dolphin Point Villas

Dolphin Point Villas
3.5 star property
0.7 km from Winston Waterways
9.6 out of 10, Exceptional, (488 reviews)
"The rooms were very clean. Beautiful view"
United States
Linda
The price is CA $370
CA $455 total
includes taxes & fees
Mar 24 - Mar 25
Dolphin Point Villas
Property grounds

Coconut Bay Resort Key Largo

Coconut Bay Resort Key Largo
2.0 star property
Rock Harbor, 6.6 km from Winston Waterways
9.6 out of 10, Exceptional, (199 reviews)
"Room was so clean and perfect! Staff was so nice and accommodating. Love how close to water we were and the breakfast truck was excellent! Must stay!"
United States
Lisandra
The price is CA $473
CA $532 total
includes taxes & fees
Mar 22 - Mar 23
Coconut Bay Resort 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.
View all properties

Where to stay in Winston Waterways

Find the best Winston Waterways areas and neighborhoods for the activities you enjoy most.
Baker's Cay is a gem within Key Largo. It has an incredible beach where are you likely to spot wildlife like manatees, dolphins, and sharks right from the beach or their own private pier. #LifeAtExpediaGroup
Photo by Samantha Shoemaker
Open Photo by Samantha Shoemaker

Rock Harbor

While Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby.

Silver Shores

If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit Bluefin Rock Harbor Marina and Pigeon Key.
Key West Florida - Sights and Sounds by the water and port

Key Largo Village

While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.
Coast of Islamorada, Florida Keys

Key Largo Park

Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.
Boats moored in a marina off the Highway 1 in Key Largo, Floriday Keys, Florida, United States.

Cross Key Waterways

While Cross Key Waterways might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Caribbean Club Bar and MarineLab Undersea Laboratory.

Top Winston Waterways Hotel Reviews

Rock Reef Resort

Rock Reef Resort

10/10 Excellent
"Convenient, quiet location. Well appointed rooms. "
Mallory 3-night trip
Posted 1 hour ago
Rock Reef Resort

Frequently asked questions

What's it like in Winston Waterways?
You'll be sure to have fun visiting Key Largo's Winston Waterways neighborhood. Consider a visit to John Pennekamp Coral Reef State Park as part of your Winston Waterways travel plans.
How many hotels will I be able to find in Winston Waterways?
With 17 Expedia hotels and other accommodations 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 hotel bookings are refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to review the best deals available 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.

Explore a world of travel with Expedia