Winston Waterways Travel Guide
Tourist Guide
Visit Winston Waterways
Activities
Key Largo Coral Reef Glass Bottom Boat Adventure
AU$64
per adult
96% of travellers recommend
Key Largo: Deserted Island Tour Kayak Adventure
AU$60
per adult
Small Group Florida Keys Eco Tour by Boat
AU$86
per adult
100% of travellers recommend
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle
AU$57
per traveller
100% of travellers recommend
1.5 Hour Bay Side Key Largo Sunset Cruise on a Spacious Catamaran
AU$99
per adult
80% of travellers recommend
Our pick of the best Winston Waterways Hotel Deals
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
The price is AU$482 per night from 24 Aug to 25 Aug
AU$482
24 Aug - 25 Aug
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 ...
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
The price is AU$216 per night from 17 Aug to 18 Aug
AU$216
17 Aug - 18 Aug
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. ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is AU$314 per night from 24 Aug to 25 Aug
AU$314
24 Aug - 25 Aug
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! (1,742 reviews)
"Nice ocean/beach view. Good property. Easy to find. Definitely worth it. Free ok breakfast."
Reviewed on 13 Aug 2026
Bayside Inn Key Largo
99490 Overseas Hwy Key Largo FL
The price is AU$238 per night from 23 Aug to 24 Aug
AU$238
23 Aug - 24 Aug
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 pool and the helpful staff in their reviews. ...
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
The price is AU$405 per night from 16 Aug to 17 Aug
AU$405
16 Aug - 17 Aug
includes taxes & fees
Stay at this luxury hotel in Key Largo. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,499 reviews)
"Had the best time ever"
Reviewed on 13 Aug 2026
Playa Largo Resort & Spa, Autograph Collection
97450 Overseas Highway Key Largo FL
The price is AU$459 per night from 30 Aug to 31 Aug
AU$459
30 Aug - 31 Aug
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 ...
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
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.
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 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.
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 Caribbean Club Bar and MarineLab Undersea Laboratory, some noteworthy sights in the nearby area.
