Winston Waterways Travel Guide
Key Largo
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Top hotels in Winston Waterways
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is £203 per night from 7 Jul to 8 Jul
£203
per night
7 Jul - 8 Jul
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! (1,764 reviews)
"My girlfriend and I really enjoyed our time at Chesapeake. The room was immaculate and the view from our balcony was amazing. The staff was extremely friendly and helpful. I was able to use fishing gear from the front office to fish the beachfront and harbor in the evenings and they have kayaks available ..."
Reviewed on 17 Jun 2026
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
The price is £197 per night from 24 Jun to 25 Jun
£197
per night
24 Jun - 25 Jun
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! (1,491 reviews)
"We had a great time. Walt during check was amazing."
Reviewed on 17 Jun 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
The price is £266 per night from 29 Jun to 30 Jun
£266
per night
29 Jun - 30 Jun
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! (1,096 reviews)
"Excelente servicio y todo muy limpio"
Reviewed on 16 Jun 2026
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is £135 per night from 23 Jun to 24 Jun
£135
per night
23 Jun - 24 Jun
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! (1,383 reviews)
"great, efficient check in, clean room, spacious area to stay in key largo. ample parking with plenty of shade ( which is hard to come by in the keys"
Reviewed on 16 Jun 2026
The Pelican Key Largo Cottages
99340 Overseas Highway Key Largo FL
The price is £87 per night from 24 Jun to 25 Jun
£87
per night
24 Jun - 25 Jun
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! (1,026 reviews)
"Love the dock and watched the most beautiful sunset right at the property. Very relaxing stay. Staff are super friendly, definitely recommend and will be back"
Reviewed on 17 Jun 2026
Playa Largo Resort & Spa, Autograph Collection
97450 Overseas Highway Key Largo FL
The price is £295 per night from 8 Jul to 9 Jul
£295
per night
8 Jul - 9 Jul
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! (1,002 reviews)
"The service was poor all around and the food was not fresh like you'd expect for the price and at a “resort.” The staff admitted the “fresh squeezed, orange juice“ was not fresh and from a can the guacamole was also from a can and not made out of actual fresh guacamoles. The menu variety was lacking, ..."
Reviewed on 13 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.
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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.