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! (1,143 reviews)
"The cleaning service did not come to our room for three days. We thought it might be on request only, but the front desk attendant said they should be there every day. There was a large group of children playing the outdoor games that were available outside of our window late at night. We had to ..."

Reviewed on 17 Jul 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 Rp2.706.967 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. ...
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 26 Jul to 27 Jul
Rp3.924.699
Rp5.132.216 total
26 Jul - 27 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. ...
9.4/10 Exceptional! (1,486 reviews)
"Room was clean. Loved the daily water, coffee and chocolates. Staff was amazing. Had a nice breakfast at Gus’. Food was plentiful and yummy but the restaurant itself needs updating and to be cleaned. There is dirt build up on the floors, benches were torn, fans were filthy. Staff at the restaurant ..."

Reviewed on 17 Jul 2026

Reefhouse Resort & Marina
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
The price is Rp2.168.511 per night from 13 Aug to 14 Aug
Rp2.168.511
Rp2.889.225 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! (1,776 reviews)
"Beautiful place on the Bay. Very convenient to activities."

Reviewed on 17 Jul 2026

Bayside Inn Key Largo
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 Rp3.713.231 per night from 13 Aug to 14 Aug
Rp3.713.231
Rp5.487.948 total
13 Aug - 14 Aug
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 ...
9/10 Wonderful! (228 reviews)
"We had a schizophrenic experience at this resort. Some elements are well done....the food is great (particularly Kindler and also The Lemon) and we encountered some supportive, friendly and helpful team members. But....the renovation attempted to tie together multiple old dingy Key's resorts into ..."

Reviewed on 13 Jul 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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 Rp5.896.009 per night from 17 Aug to 18 Aug
Rp5.896.009
Rp7.620.995 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 ...
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