Winston Waterways Travel Guide

Tourist Guide

Clearwater Beach Pier Panorama
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$687 per night from 9 Apr to 10 Apr
AU$687
9 Apr - 10 Apr
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! (1,406 reviews)
From the moment I walked in the door to the moment I left it was absolutely perfect. The food was fantastic and the pool bar made excellent drinks.

Reviewed on 11 Mar 2026

Reefhouse Resort & Marina
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
The price is AU$383 per night from 12 Mar to 13 Mar
AU$383
12 Mar - 13 Mar
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! (1,233 reviews)
Pool down for 2 days after being shocked with chemicals. I got no reason, but suspect a baby in non swim diapersmay have pooped causing the closure. When opened back up all was greart. The floors look clean, but are actually dirty. I tried to explain that yes a new mop rag used each time but the ...

Reviewed on 11 Mar 2026

Waterside Suites & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is AU$559 per night from 24 Mar to 25 Mar
AU$559
24 Mar - 25 Mar
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! (1,680 reviews)
The staff was always available and helpful. The breakfast and chefs were outstanding. Our ocean view room could not have been better!

Reviewed on 11 Mar 2026

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 AU$882 per night from 12 Mar to 13 Mar
AU$882
12 Mar - 13 Mar
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! (1,000 reviews)
We were placed in a room far away from most things. The pool was a short walk away. The room was surface clean but not deep cleaned. There was a stain on the couch cushion when we made the pull out couch for our child. There wasn’t a vent in the bathroom and the bathroom was in between the two bedrooms ...

Reviewed on 10 Mar 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 AU$423 per night from 9 Apr to 10 Apr
AU$423
9 Apr - 10 Apr
includes taxes & fees
Stay at this beach hotel in Key Largo. Enjoy free Wi-Fi, a private beach and a 24-hour fitness centre. Our guests praise the pool and the helpful staff in their ...
8.6/10 Excellent! (1,680 reviews)
Sheets and pillowcases felt dirty. Washcloths were ripped. Hotel Ran low on coffee and towels. Room wasn’t cleaned after request was made.

Reviewed on 11 Mar 2026

Bayside Inn Key Largo
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$317 per night from 17 Mar to 18 Mar
AU$317
17 Mar - 18 Mar
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 ...
8.4/10 Very Good! (1,737 reviews)
Good

Reviewed on 10 Mar 2026

Marina Del Mar Resort and Marina
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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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