Winston Waterways Travel Guide

Key Largo

Clearwater Beach Pier Panorama


Top hotels in Winston Waterways

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ฿6,479 per night from 8 Jun to 9 Jun
฿6,479
฿9,125 total
8 Jun - 9 Jun
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! (1,736 reviews)
"This place is perfect"

Reviewed on 1 Jun 2026

Chesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
The price is ฿4,619 per night from 4 Jun to 5 Jun
฿4,619
฿6,114 total
4 Jun - 5 Jun
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! (1,373 reviews)
"The location is perfect. Being on a marina was fun and made being in the room an experience. The two stories was perfect. The bedroom upstairs helped when my one of us was still sleeping. We had two showers! After swimming we both could come in and shower at the same time. No waiting! The kitchen ..."

Reviewed on 2 Jun 2026

Waterside Suites & 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 ฿4,536 per night from 7 Jun to 8 Jun
฿4,536
฿6,021 total
7 Jun - 8 Jun
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! (1,806 reviews)
"Angela was so accommodating and was able to upgrade our stay. Every time we had a question she would have the answers and was very hospitable and welcoming to all of us. The room was clean and beautiful views, quiet and better than we could have imagined. Great location, food and service. We will ..."

Reviewed on 2 Jun 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 ฿9,478 per night from 15 Jun to 16 Jun
฿9,478
฿12,462 total
15 Jun - 16 Jun
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! (1,073 reviews)
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Reviewed on 1 Jun 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
The price is ฿6,494 per night from 10 Jun to 11 Jun
฿6,494
฿8,611 total
10 Jun - 11 Jun
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! (1,464 reviews)
"Large spacious rooms and great views."

Reviewed on 2 Jun 2026

Reefhouse Resort & Marina
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 ฿9,757 per night from 8 Jun to 9 Jun
฿9,757
฿13,363 total
8 Jun - 9 Jun
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! (202 reviews)
"The property was beautiful as soon as we pulled up we were greeted by a woman on a golf cart. She was so happy and helpful. It made us feel comfortable right away, showed us to the front desk and she was also so very friendly. I wish I remembered their names. We got an ocean view. It also overlooked ..."

Reviewed on 30 May 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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

4.5/5(3 area reviews)

If you're looking for some top things to see and do in Anglers Park and surrounding area, you can visit 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