Winston Waterways Travel Guide

Key Largo

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


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 ₹20,567 per night from 29 Nov to 30 Nov
₹20,567
per night
29 Nov - 30 Nov
Stay at this luxury hotel in Key Largo. Enjoy free Wi-Fi, a full-service spa and 3 restaurants. Our guests praise the pool and the helpful staff in their reviews. ...
Reefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ₹13,462 per night from 10 Nov to 11 Nov
₹13,462
per night
10 Nov - 11 Nov
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
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
The price is ₹19,459 per night from 29 Nov to 30 Nov
₹19,459
per night
29 Nov - 30 Nov
Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (310 reviews)
"Amazing spot,super chill and beautiful"

Reviewed on 8 Nov 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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 ₹24,718 per night from 29 Nov to 30 Nov
₹24,718
per night
29 Nov - 30 Nov
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 ...
Baker's Cay Resort Key Largo, Curio Collection by Hilton
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2 out of 5
99340 Overseas Highway Key Largo FL
The price is ₹9,376 per night from 29 Nov to 30 Nov
₹9,376
per night
29 Nov - 30 Nov
Stay at this beach hotel in Key Largo. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (1,008 reviews)
"An older cottage type in an excellent location. Everything was fine except the window air conditioner was extremely loud and a little sleep disturbing. Fine beach and many nearby bars, restaurants and shopping."

Reviewed on 8 Nov 2026

The Pelican Key Largo Cottages
Rock Reef Resort

Rock Reef Resort

2.5 out of 5
97850 Overseas Hwy Key Largo FL
The price is ₹8,480 per night from 15 Nov to 16 Nov
₹8,480
per night
15 Nov - 16 Nov
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. ...
9.2/10 Wonderful! (1,207 reviews)
"Lovely room, really pleasant staff, suitable parking, lovely grounds, nice feel to the hotel. Clean. Lovely little beach area. We love it!"

Reviewed on 8 Nov 2026

Rock Reef Resort
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 Harry Harris Park.

Key Largo Village

When in Key Largo Village, you can plan a visit to Jacob's Aquatic Center and Jimmy Johnson's Big Chill, some noteworthy sights in the nearby area.

Key Largo Park

Key Largo Park might not have many top sights, but Jacob's Aquatic Center and Jimmy Johnson's Big Chill are two attractions nearby that you can check out.

Anglers Park

If you're looking for some top things to see and do in Anglers Park and surrounding area, you can visit MarineLab Undersea Laboratory and Caribbean Club Bar.



Winston Waterways Travel Guide