Winston Waterways Travel Guide
Key Largo
Visit Winston Waterways
Top hotels in Winston Waterways
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is ฿6,177 per night from 9 Jun to 10 Jun
฿6,177
฿8,787 total
9 Jun - 10 Jun
includes taxes & fees
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! (1,739 reviews)
"We really enjoyed the resort! They offered snacks and champagne during the day by the pool with live music. Also the breakfast was amazing! Especially the omelettes. We will definitely be back and bring the boat."
Reviewed on 4 Jun 2026
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
The price is ฿4,625 per night from 8 Jun to 9 Jun
฿4,625
฿6,122 total
8 Jun - 9 Jun
includes taxes & fees
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! (1,377 reviews)
"Clean and friendly"
Reviewed on 4 Jun 2026
Marina Del Mar Resort and Marina
527 Caribbean Drive Key Largo FL
The price is ฿4,541 per night from 8 Jun to 9 Jun
฿4,541
฿6,028 total
8 Jun - 9 Jun
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free Wi-Fi, free parking and 2 restaurants. Our guests praise the breakfast and the pool in their reviews. Popular attractions ...
8.6/10 Excellent! (1,807 reviews)
"Angela was so accommodating and was able to upgrade our stay. Every time we had a question she would have the answers and was very hospitable and welcoming to all of us. The room was clean and beautiful views, quiet and better than we could have imagined. Great location, food and service. We will ..."
Reviewed on 2 Jun 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
The price is ฿8,283 per night from 30 Jun to 1 Jul
฿8,283
฿11,120 total
30 Jun - 1 Jul
includes taxes & fees
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! (1,074 reviews)
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Reviewed on 1 Jun 2026
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
The price is ฿6,828 per night from 15 Jun to 16 Jun
฿6,828
฿8,989 total
15 Jun - 16 Jun
includes taxes & fees
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! (1,467 reviews)
"Nice hotel at the entry of the FL keys"
Reviewed on 4 Jun 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
The price is ฿9,137 per night from 5 Jul to 6 Jul
฿9,137
฿12,668 total
5 Jul - 6 Jul
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (203 reviews)
"This hotel was my favorite. If I come to the keys I will be returning to this hotel and this hotel only. We stayed in the cove (21 age plus) and loved it. So quiet and you even had your own pool and gym. Even the other amenities were great."
Reviewed on 3 Jun 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.
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 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.
Photo by Patricia Smith
Open Photo by Patricia Smith
Pirates Cove
While there might not be top attractions in Pirates Cove, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.
