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 £214 per night from 30 Nov to 1 Dec
£214
30 Nov - 1 Dec
includes taxes & fees
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. ...
9.2/10 Wonderful! (1,559 reviews)
"Very nice"

Reviewed on 2 Nov 2026

Reefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is £160 per night from 10 Nov to 11 Nov
£160
10 Nov - 11 Nov
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
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 £250 per night from 12 Nov to 13 Nov
£250
12 Nov - 13 Nov
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 ...
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
The price is £109 per night from 4 Nov to 5 Nov
£109
4 Nov - 5 Nov
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. ...
8.4/10 Very good! (1,865 reviews)
"Excellent location but room quality, service and amenities have declined compared to previous visits."

Reviewed on 2 Nov 2026

Bayside Inn Key Largo
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2 out of 5
99340 Overseas Highway Key Largo FL
The price is £84 per night from 23 Nov to 24 Nov
£84
23 Nov - 24 Nov
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 helpful staff and the clean rooms in their reviews. ...
The Pelican Key Largo Cottages
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 £229 per night from 29 Nov to 30 Nov
£229
29 Nov - 30 Nov
includes taxes & fees
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 ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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

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