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
The price is Rp3.861.408 per night from 10 Sept to 11 Sept
Rp3.861.408
Rp5.049.452 total
10 Sept - 11 Sept
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. ...
9.2/10 Wonderful! (1,538 reviews)
"Private beach, easy access to restaurants, water sports, state parks, museums, groceries etc The staff is super friendly and helpful! The check in and check out was a breeze and there’s lots of open and covered parking for your vehicle! Great place for families to relax and unwind!"

Reviewed on 9 Sept 2026

Reefhouse Resort & Marina
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 Rp4.178.431 per night from 28 Sept to 29 Sept
Rp4.178.431
Rp5.672.787 total
28 Sept - 29 Sept
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! (1,178 reviews)
"It doesn’t have much to offer, upper floors have vacant spaces, should create spaces to entertain visitors, elevators too old, BORING HOTEL"

Reviewed on 8 Sept 2026

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is Rp2.102.616 per night from 13 Sept to 14 Sept
Rp2.102.616
Rp3.357.243 total
13 Sept - 14 Sept
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. ...
Chesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
The price is Rp1.705.896 per night from 10 Sept to 11 Sept
Rp1.705.896
Rp2.415.032 total
10 Sept - 11 Sept
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. ...
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 Rp4.496.160 per night from 23 Sept to 24 Sept
Rp4.496.160
Rp6.030.231 total
23 Sept - 24 Sept
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! (1,002 reviews)
"Espectacular 🤗✨🤩 sigue siendo mi preferido"

Reviewed on 9 Sept 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 Rp2.034.204 per night from 10 Sept to 11 Sept
Rp2.034.204
Rp2.729.279 total
10 Sept - 11 Sept
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. ...
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.

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 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.

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 MarineLab Undersea Laboratory and Caribbean Club Bar, some noteworthy sights in the nearby area.



Winston Waterways Travel Guide