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 Rp3.959.520 per night from 27 Oct to 28 Oct
Rp3.959.520
Rp5.177.750 total
27 Oct - 28 Oct
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! (1,555 reviews)
"Had a wonderful time, everything was neat and clean and not super crowded. Food options were delicious, room was very comfortable, only complaint would be the water pressure in the shower was terrible!! Other than that, we had a wonderful weekend. thank you."

Reviewed on 26 Oct 2026

Reefhouse Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is Rp2.730.984 per night from 3 Nov to 4 Nov
Rp2.730.984
Rp4.089.357 total
3 Nov - 4 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 Rp4.432.854 per night from 9 Nov to 10 Nov
Rp4.432.854
Rp5.983.711 total
9 Nov - 10 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 ...
8.8/10 Excellent! (1,193 reviews)
"Amazing hotel with lots of on-site amenities and options for dinner. Loved the fishing in the morning."

Reviewed on 26 Oct 2026

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 Rp2.085.890 per night from 27 Oct to 28 Oct
Rp2.085.890
Rp2.798.627 total
27 Oct - 28 Oct
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! (1,867 reviews)
"The property looks much nicer online. The room was musty, the toilet kept malfunctioning, the door lock died so we couldn’t get in our room until maintenance came to replace batteries, the shower water pressure was abysmal - I appreciate wanting to conserve water but it was little more than a trickle. ..."

Reviewed on 26 Oct 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
Fully refundable
The price is Rp1.805.105 per night from 1 Nov to 2 Nov
Rp1.805.105
Rp2.030.743 total
1 Nov - 2 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. ...
9/10 Wonderful! (1,002 reviews)
"Absolutely loved our trip. The pelican reef was wonderful. The staff was excellent. It was clean comfortable and we really enjoyed the time we spent there."

Reviewed on 25 Oct 2026

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 Rp4.324.736 per night from 2 Nov to 3 Nov
Rp4.324.736
Rp6.187.518 total
2 Nov - 3 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