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
7 Jul - 8 Jul
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! (1,763 reviews)
"Breakfast selection each day was excellent. Room was clean, just a little noisy from upstairs kids footsteps in the morning. 2 pools were great although main pool in need of resurfacing and a bit too warm, understandable due to 90+ temps. Love the free kayaks and paddle boards. Staff was very friendly ..."
Reviewed on 16 Jun 2026
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
The price is £197 per night from 24 Jun to 25 Jun
£197
24 Jun - 25 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! (1,491 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 £261 per night from 30 Jun to 1 Jul
£261
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! (1,095 reviews)
"Excelente servicio y todo muy limpio"
Reviewed on 16 Jun 2026
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
The price is £134 per night from 22 Jun to 23 Jun
£134
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! (1,383 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
24 Jun - 25 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! (1,025 reviews)
"We. Absolutely LOVED staying here. The staff was friendly and helpful. We got discounts on local food and a pamphlet on things to do in the area. The rolms were clean with working A/C in both rooms. Worked so well we were cold in FL so that was nice. Private beach was beautiful to watch sunsets and ..."
Reviewed on 16 Jun 2026
Playa Largo Resort & Spa, Autograph Collection
97450 Overseas Highway Key Largo FL
The price is £295 per night from 7 Jul to 8 Jul
£295
7 Jul - 8 Jul
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! (1,001 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.
Check Winston Waterways hotel availability
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.
