Winston Waterways Travel Guide

Key Largo



Top hotels in Winston Waterways

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ฿5,947 per night from 26 Jan to 27 Jan
฿5,947
฿8,459 total
26 Jan - 27 Jan
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! (1,632 reviews)
It was very nice place to stay resort nice and clean the ataff Vanessa very helpful and sweet. We very happy will come back again. Thank you Vanessa again .

Reviewed on 16 Jan 2026

Chesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
The price is ฿4,751 per night from 21 Jan to 22 Jan
฿4,751
฿6,230 total
21 Jan - 22 Jan
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. ...
8.8/10 Excellent! (1,184 reviews)
Floors greasy

Reviewed on 13 Jan 2026

Waterside Suites & Marina
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive Key Largo FL
The price is ฿3,716 per night from 19 Jan to 20 Jan
฿3,716
฿5,066 total
19 Jan - 20 Jan
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! (1,678 reviews)
Our room was huge and Clean. We arrived early and our room was ready. Saw a manatee in the Marina as well as a nurse shark. Plenty of pelicans to watch and great food and entertainment on the premises.

Reviewed on 12 Jan 2026

Marina Del Mar Resort and Marina
Reefhouse Resort & Marina

Reefhouse Resort & Marina

3.5 out of 5
103800 Overseas Hwy Key Largo FL
The price is ฿8,461 per night from 19 Jan to 20 Jan
฿8,461
฿10,777 total
19 Jan - 20 Jan
includes taxes & fees
Stay at this beach 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. ...
9.2/10 Wonderful! (1,327 reviews)
lovely resort style hotel and staff mostly very friendly. Stunning location on the water with heated pool

Reviewed on 13 Jan 2026

Reefhouse Resort & 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 ฿10,678 per night from 22 Jan to 23 Jan
฿10,678
฿13,747 total
22 Jan - 23 Jan
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! (1,001 reviews)
The rooms were ok, they were outdated with non working A/C, ripped curtains, old furniture and electrical outlets that does not hold the plugs. Towels smelled bad. However the staff except for one lady in the front was all amazing. They smiled and tried to help with everything. The resort is on an ...

Reviewed on 9 Jan 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo

3.5 out of 5
500 Burton Dr Tavernier FL
The price is ฿5,638 per night from 19 Jan to 20 Jan
฿5,638
฿6,909 total
19 Jan - 20 Jan
includes taxes & fees
Stay at this beach hotel in Tavernier. Enjoy free Wi-Fi, a private beach and 2 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
8.2/10 Very Good! (1,007 reviews)
While the condo unit we stayed in was fairly basic, it was clean and comfortable. The overall Ocean Pointe community was enjoyable with nice amenities. We enjoyed the pool, the beach, and the on site restaurant.

Reviewed on 11 Jan 2026

Ocean Pointe Suites at 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
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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
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Cross Key Waterways

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

Cross Key Waterways
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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

4.5/5(3 area reviews)

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.

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