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
per night
18 May - 19 May
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! (1,435 reviews)
I love staying at the Reef House. The site is beautiful and so relaxing. The drinks at the bar are excellent and the grounds are well maintained and clean. Every single staff member I encountered during my stay were incredibly helpful and friendly. The facility is also pet friendly and even provided ...

Reviewed on 11 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 26 May to 27 May
AU$224
per night
26 May - 27 May
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! (1,784 reviews)
didn't use the kitchen, but it was alright

Reviewed on 11 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$615 per night from 2 June to 3 June
AU$615
per night
2 June - 3 June
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
per night
28 May - 29 May
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! (1,733 reviews)
Breakfast the best ! Staff wonderful!

Reviewed on 11 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 13 May to 14 May
AU$252
per night
13 May - 14 May
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! (1,344 reviews)
We loved our stay at Waterside. We were able to have our fur babies vacationing with us and our suite was so big and convenient. Only thing missing was the kayaks in the picture on property but beside that one minor thing I would definitely recommend to stay here.. we will be back.. place is clean ...

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
per night
10 June - 11 June
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! (1,741 reviews)
Our room was very clean and the office staff was very nice and helpful. It is located in the perfect location with a restaurant/bar just next door. The sunset was beautiful from the property. We would definitely stay there again.

Reviewed on 10 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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