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

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 Rp5.205.334 per night from 17 Aug to 18 Aug
Rp5.205.334
Rp6.844.030 total
17 Aug - 18 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 ...
8.6/10 Excellent! (1,144 reviews)
"We had a wonderful time and the private beach area was clean. I was appreciative of the efforts the made to keep the water clear of sargassum. Thanks!"

Reviewed on 18 Jul 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 Rp2.196.219 per night from 21 Jul to 22 Jul
Rp2.196.219
Rp2.974.707 total
21 Jul - 22 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! (1,416 reviews)
"Amenities were nice and location of hotel was great"

Reviewed on 19 Jul 2026

Waterside Suites & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is Rp2.706.967 per night from 16 Aug to 17 Aug
Rp2.706.967
Rp4.053.393 total
16 Aug - 17 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! (1,745 reviews)
"The property was beautiful and well maintained. The check in staff and staff at the bar were not polite or helpful at all. Very disappointing. The food selection at 3 oclock was limited to two things when it didn’t close for two hours."

Reviewed on 18 Jul 2026

Chesapeake Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
The price is Rp3.924.699 per night from 27 Jul to 28 Jul
Rp3.924.699
Rp5.132.216 total
27 Jul - 28 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. ...
Reefhouse Resort & Marina
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
The price is Rp2.160.674 per night from 13 Aug to 14 Aug
Rp2.160.674
Rp2.878.783 total
13 Aug - 14 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. ...
8.6/10 Excellent! (1,779 reviews)
"Pleasant stay"

Reviewed on 19 Jul 2026

Bayside Inn Key Largo
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 Rp4.713.223 per night from 17 Aug to 18 Aug
Rp4.713.223
Rp6.290.362 total
17 Aug - 18 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 ...
9/10 Wonderful! (1,009 reviews)
"Great service."

Reviewed on 19 Jul 2026

Playa Largo Resort & Spa, Autograph Collection
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 Harry Harris Park.

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