Winston Waterways Travel Guide
Key Largo
Visit Winston Waterways
Top hotels in Winston Waterways
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
The price is ฿7,549 per night from 30 Jun to 1 Jul
฿7,549
฿9,811 total
30 Jun - 1 Jul
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! (1,463 reviews)
"All the staff members were extremely helpful and very friendly!! Room very clean, Pool area great! My wife said the lobster Ravioli was the best she ever had!! So now the only bad part of our stay was we were celebrating 30th wedding anniversary and having dinner in the restaurant and a few families ..."
Reviewed on 20 Jun 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is ฿6,545 per night from 23 Jun to 24 Jun
฿6,545
฿9,218 total
23 Jun - 24 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! (1,734 reviews)
"We had a fabulous stay, would stay again!!"
Reviewed on 20 Jun 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
The price is ฿9,372 per night from 12 Jul to 13 Jul
฿9,372
฿12,361 total
12 Jul - 13 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! (1,103 reviews)
"Beautiful resort and common areas...friendliest staff."
Reviewed on 19 Jun 2026
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is ฿4,666 per night from 22 Jun to 23 Jun
฿4,666
฿6,177 total
22 Jun - 23 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! (1,397 reviews)
"We absolutely loved our stay. Check-in was simple and hassle free, staff is helpful and always reachable if you need anything. The room was huge, clean, full kitchen and a great view from the balcony. Highly recommend and will definitely return on future trips."
Reviewed on 20 Jun 2026
Playa Largo Resort & Spa, Autograph Collection
97450 Overseas Highway Key Largo FL
The price is ฿11,505 per night from 24 Jun to 25 Jun
฿11,505
฿14,760 total
24 Jun - 25 Jun
includes taxes & fees
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! (1,003 reviews)
"Beautiful property!"
Reviewed on 17 Jun 2026
The Pelican Key Largo Cottages
99340 Overseas Highway Key Largo FL
The price is ฿3,427 per night from 28 Jun to 29 Jun
฿3,427
฿3,855 total
28 Jun - 29 Jun
includes taxes & fees
Stay at this beach hotel in Key Largo. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (1,001 reviews)
"Absolutely love this place. The staff was amazing. We will definitely be going back. The sunset from the docks were beautiful. We arrived early for our stay. Had a great time using the kayaks and relaxing on the docks while we were waiting for our room to be ready. Highly recommend"
Reviewed on 18 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.
