Winston Waterways Travel Guide

Key Largo

A wooden pier extending into the ocean at dusk with a small house at the end.

Things to do


Top hotels in Winston Waterways

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is ฿7,284 per night from 26 Jul to 27 Jul
฿7,284
฿9,525 total
26 Jul - 27 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! (1,481 reviews)
"Clean room staff nice"

Reviewed on 29 Jun 2026

Reefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ฿6,604 per night from 5 Jul to 6 Jul
฿6,604
฿9,300 total
5 Jul - 6 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! (1,744 reviews)
"Muy bonito el lugar"

Reviewed on 29 Jun 2026

Chesapeake Beach Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy Key Largo FL
The price is ฿9,625 per night from 21 Jul to 22 Jul
฿9,625
฿12,662 total
21 Jul - 22 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! (1,122 reviews)
"Perfect beach. Great rooms. Wish they had better food to pick from, too expensive for barley nothing. Family with Kids have to go outside the resort and eat. They have bikes but only a bike trail beside the main highway- that’s a C minus. Overall we loved it minus the food selection was very limited ..."

Reviewed on 29 Jun 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
The price is ฿4,708 per night from 2 Jul to 3 Jul
฿4,708
฿6,232 total
2 Jul - 3 Jul
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! (1,404 reviews)
"The staff texted with updates or answered any questions I had promptly. Very convenient location. Comfortable sleep and 2 story living"

Reviewed on 29 Jun 2026

Waterside Suites & Marina
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
The price is ฿10,077 per night from 16 Jul to 17 Jul
฿10,077
฿13,171 total
16 Jul - 17 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! (1,011 reviews)
"Really good"

Reviewed on 29 Jun 2026

Playa Largo Resort & Spa, Autograph Collection
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
The price is ฿4,133 per night from 14 Jul to 15 Jul
฿4,133
฿5,481 total
14 Jul - 15 Jul
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. ...
8.6/10 Excellent! (1,764 reviews)
"Was a good time kind people"

Reviewed on 28 Jun 2026

Bayside Inn Key Largo
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.

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.

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.



Winston Waterways Travel Guide