Winston Waterways Travel Guide

Tourist Guide

Clearwater Beach Pier Panorama


Our pick of the best Winston Waterways Hotel Deals

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
The price is AU$488 per night from 18 May to 19 May
AU$488
18 May - 19 May
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! (1,434 reviews)
Ask Questions if you have them or don’t go on the tours they are free I didn’t know

Reviewed on 9 May 2026

Reefhouse Resort & Marina
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2 out of 5
527 Caribbean Drive Key Largo FL
The price is AU$224 per night from 17 May to 18 May
AU$224
17 May - 18 May
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free Wi-Fi, free parking and 2 restaurants. Our guests praise the breakfast and the pool in their reviews. Popular attractions ...
8.6/10 Excellent! (1,782 reviews)
We went down for a quick one night stay for Mother’s Day.We were able to check in early to our room with the help of a super friendly staff member named Miguel. We sat and chatted with him for a while and couldn’t have been happier with his service. The hotel was clean. The bed was comfortable and ...

Reviewed on 10 May 2026

Marina Del Mar Resort and Marina
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 AU$597 per night from 19 May to 20 May
AU$597
19 May - 20 May
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! (1,071 reviews)
The beach at this hotel is the ultimate jewel. However, the hotel is overpriced Given the overall condition. Rooms are noisy with poor soundproof as they are all connecting rooms. The food is good but the wait time in the restaurant is very long for Every meal.

Reviewed on 10 May 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 AU$343 per night from 28 May to 29 May
AU$343
28 May - 29 May
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! (1,729 reviews)
Wow just wow Booked a king with ocean view They had a problem with door card reader. When I was checking in they were repairing it. So they upgraded me to a villa and holy cow now I know how rich people live!!! The staff were really friendly and knowledgeable about the area around the hotel. My wife ...

Reviewed on 8 May 2026

Chesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
The price is AU$252 per night from 12 May to 13 May
AU$252
12 May - 13 May
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! (1,342 reviews)
Wonderful accommodations. The deck is lovely to sit out on and watch the boats come back into dock. I would stay again.

Reviewed on 10 May 2026

Waterside Suites & Marina
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
The price is AU$251 per night from 10 June to 11 June
AU$251
10 June - 11 June
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! (1,739 reviews)
Room was very clean. Only stayed one night. It was a nice place to stay

Reviewed on 9 May 2026

Bayside Inn Key Largo
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.

Other neighbourhoods around Winston Waterways

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Largo Gardens

Though Largo Gardens may not have many top sights, you can venture to the surrounding area to see attractions like John Pennekamp Coral Reef State Park and MarineLab Undersea Laboratory.

Largo Gardens
Key West Florida - Sights and Sounds by the water and port

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.

Key Largo Village
Boats moored in a marina off the Highway 1 in  Key Largo, Floriday Keys, Florida, United States.

Cross Key Waterways

When in Cross Key Waterways, you can plan a visit to Caribbean Club Bar and MarineLab Undersea Laboratory, some noteworthy sights in the nearby area.

Cross Key Waterways
Coast of Islamorada, Florida Keys

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.

Key Largo Park
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Anglers Park

4/5(1 area review)

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

Anglers Park
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Largo Sound Village

Largo Sound Village might not have many top sights, but Caribbean Club Bar and MarineLab Undersea Laboratory are two attractions nearby that you can check out.

Largo Sound Village


Winston Waterways Travel Guide

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