Winston Waterways Travel Guide
Tourist Guide
Visit Winston Waterways
Activities
Key Largo Drive Your Own Mini Pontoon Boat Tour with Beach Pass
NZ$238
per adult
Snorkel Tours to Shallow Coral Reefs at Pennekamp Underwater Park
NZ$132
per adult
Key Largo Coral Reef Glass Bottom Boat Adventure
NZ$79
per adult
96% of travellers recommend
Florida: Key West Overseas Highway App-Based Driving Audio Tour
NZ$30
per traveller
88% of travellers recommend
Small Group Florida Keys Eco Tour by Boat
NZ$106
per adult
100% of travellers recommend
Our pick of the best Winston Waterways Hotel Deals
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
The price is NZ$477 per night from 26 July to 27 July
NZ$477
per night
26 July - 27 July
Stay at this luxury hotel in Key Largo. Enjoy free parking, a full-service spa and 3 restaurants. Our guests praise the pool and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,492 reviews)
"This was our second time staying here. This time was not as good only because we spent most of our time waiting on service at the restaurant and our food and drinks. One female bartender at the bar in the evening didn’t look like she wanted to be there at all and was rude and not friendly. Would ..."
Reviewed on 10 July 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is NZ$430 per night from 10 Aug to 11 Aug
NZ$430
per night
10 Aug - 11 Aug
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,752 reviews)
"This was a nice place to get away from the urban Key West. The staff was very friendly and solved any issues regardless of the time (noisy neighbor, needed blanket) and the shore was close by. There was staff routinely monitoring the beach and property so it was very secure. The location has easy ..."
Reviewed on 10 July 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
The price is NZ$698 per night from 22 July to 23 July
NZ$698
per night
22 July - 23 July
Stay at this beach resort in Key Largo. Enjoy 2 outdoor pools, 2 restaurants and a private beach. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,134 reviews)
"My stay at this hotel was wonderful! We had a great time, and the staff was friendly and welcoming. The only suggestion I have is that the rooms could use a little updating. Overall, it was a great experience, and I would definitely stay here again."
Reviewed on 9 July 2026
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
The price is NZ$264 per night from 19 July to 20 July
NZ$264
per night
19 July - 20 July
Stay at this hotel in Key Largo. Enjoy free Wi-Fi, a marina and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (1,415 reviews)
"We stayed for the 4th of July with our family and friends and enjoyed our stay this is our second time staying here and we love the space the pool and bbq area. We will definitely return"
Reviewed on 7 July 2026
Playa Largo Resort & Spa, Autograph Collection
97450 Overseas Highway Key Largo FL
The price is NZ$688 per night from 26 July to 27 July
NZ$688
per night
26 July - 27 July
Stay at this luxury resort in Key Largo. Enjoy free Wi-Fi, a full-service spa and 3 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (1,012 reviews)
"Amazing Hotel and Staff! However kids shouldn’t have been charged for fun activities on the 4th of July! Also fishing poles and bait were excellent and free however super far away from fishing deck… made no sense! Food and Staff was Excellent but those two things should have been more accessible ..."
Reviewed on 6 July 2026
Bayside Inn Key Largo
99490 Overseas Hwy Key Largo FL
The price is NZ$277 per night from 11 Aug to 12 Aug
NZ$277
per night
11 Aug - 12 Aug
Stay at this beach hotel in Key Largo. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the pool and the helpful staff in their reviews. ...
8.6/10 Excellent! (1,777 reviews)
"Was very disappointed! Photos on web site were very misleading. Was not told housekeeping was by request! On third day we requested housekeeping/water/towels and we're assured housekeeping would do our room at 10:00am, returned at 3:00pm and room had not been touched! Went to front desk and was told ..."
Reviewed on 10 July 2026
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.
Our guide on where to stay in Winston Waterways
Find the best Winston Waterways areas for the activities you enjoy most.
Photo by Samantha Shoemaker
Open Photo by Samantha Shoemaker
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 Harry Harris Park.
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 MarineLab Undersea Laboratory and Caribbean Club Bar, some noteworthy sights in the nearby area.
