Winston Waterways
Key Largo
Visit Winston Waterways
Things to do
Florida: Key West Overseas Highway App-Based Driving Audio Tour
CA $24
per traveller
88% of travellers recommend
Key Largo Coral Reef Glass Bottom Boat Adventure
CA $93
per adult
96% of travellers recommend
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle
CA $56
per traveller
100% of travellers recommend
Small Group Florida Keys Eco Tour by Boat
CA $84
per adult
100% of travellers recommend
Winston Waterways Hotel Deals
Waterside Suites & Marina
201 Ocean Drive Key Largo FL
The price is CA $153 per night from Nov 2 to Nov 3
CA $153
CA $212 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free WiFi, a marina, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (1,503 reviews)
"The hotel was conveniently located, close to all the main attractions in Key Largo, which made it easy to get around. The room was cozy and comfortable. The only downside was that the room was on the second floor, which was a bit inconvenient. Overall, it was a nice stay and a good location for exploring ..."
Reviewed on Oct 19, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is CA $205 per night from Oct 26 to Oct 27
CA $205
CA $310 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.4/10 Exceptional! (1,802 reviews)
"The room we had was exceptional, the view was awesome. The bar area was a nice amenity. Although this is a pet friendly hotel, seems like some people do not feel the need to pick up after their pets, if you know what I mean. So that was why I couldn’t give the grounds a five star."
Reviewed on Oct 19, 2026
Reefhouse Resort & Marina
103800 Overseas Hwy Key Largo FL
The price is CA $310 per night from Oct 22 to Oct 23
CA $310
CA $405 total
Oct 22 - Oct 23
includes taxes & fees
Book a stay at this luxury hotel in Key Largo. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in our ...
9.2/10 Wonderful! (1,549 reviews)
"Staff very friendly and helpful"
Reviewed on Oct 19, 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $382 per night from Oct 29 to Oct 30
CA $382
CA $507 total
Oct 29 - Oct 30
includes taxes & fees
Book a 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 ...
8.8/10 Excellent! (1,186 reviews)
"Clean rooms, responsive staff, the hallways were usually very wet due to overnight rain and needed extra caution when walking but overall very nice property"
Reviewed on Oct 19, 2026
The Pelican Key Largo Cottages
99340 Overseas Highway Key Largo FL
The price is CA $131 per night from Oct 26 to Oct 27
CA $131
CA $148 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this beach hotel in Key Largo. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,002 reviews)
"The Pelican was nice. It was a little dated. They have a tiki bar but no bar. I think music would be great when you’re sitting out by the dock. We booked 2 days but left after 1. There is not a whole lot to do around the property. No town to go to for restaurants."
Reviewed on Oct 19, 2026
Bayside Inn Key Largo
99490 Overseas Hwy Key Largo FL
The price is CA $176 per night from Nov 9 to Nov 10
CA $176
CA $233 total
Nov 9 - Nov 10
includes taxes & fees
Book a stay at this beach hotel in Key Largo. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
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 and neighborhoods for the activities you enjoy most.
Photo by Samantha Shoemaker
Open Photo by Samantha Shoemaker
Rock Harbor
While Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby.
Silver Shores
If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit Bluefin Rock Harbor Marina and Harry Harris Park.
Key Largo Village
While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jacob's Aquatic Center and Jimmy Johnson's Big Chill.
Key Largo Park
Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jacob's Aquatic Center and Jimmy Johnson's Big Chill.
Anglers Park
While there might not be top attractions in Anglers Park, you can explore the larger area and discover places like MarineLab Undersea Laboratory and Caribbean Club Bar.
