Winston Waterways, FL

Key Largo

Clearwater Beach Pier Panorama


Winston Waterways Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ¥29,797 per night from Jun 9 to Jun 10
¥29,797
¥42,502 total
Jun 9 - Jun 10
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,736 reviews)
"This place is perfect"

Reviewed on Jun 1, 2026

Chesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is ¥21,017 per night from Jun 4 to Jun 5
¥21,017
¥28,133 total
Jun 4 - Jun 5
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free WiFi, a marina, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our 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 Jun 2, 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 ¥21,525 per night from Jun 7 to Jun 8
¥21,525
¥28,707 total
Jun 7 - Jun 8
includes taxes & fees
Stay at this hotel in Key Largo. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the pool in our 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 Jun 2, 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 ¥46,372 per night from Jun 16 to Jun 17
¥46,372
¥60,971 total
Jun 16 - Jun 17
includes taxes & fees
Book a 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 ...
8.6/10 Excellent! (1,073 reviews)
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Reviewed on Jun 1, 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 ¥31,770 per night from Jun 10 to Jun 11
¥31,770
¥42,128 total
Jun 10 - Jun 11
includes taxes & fees
Book a 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 ...
9.4/10 Exceptional! (1,464 reviews)
"Large spacious rooms and great views."

Reviewed on Jun 2, 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 ¥47,735 per night from Jun 8 to Jun 9
¥47,735
¥65,378 total
Jun 8 - Jun 9
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
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 May 30, 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 neighborhoods around Winston Waterways

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Largo Gardens

While Largo Gardens might not have many sights to explore, venturing just a little farther will lead you to top things to see and do 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

While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.

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

Cross Key Waterways

While Cross Key Waterways might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Caribbean Club Bar and MarineLab Undersea Laboratory.

Cross Key Waterways
Coast of Islamorada, Florida Keys

Key Largo Park

Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jimmy Johnson's Big Chill and Jacob's Aquatic Center.

Key Largo Park
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Anglers Park

4.5/5(33 area reviews)

While there might not be top attractions in Anglers Park, you can explore the larger area and discover places like Caribbean Club Bar and MarineLab Undersea Laboratory.

Anglers Park
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Largo Sound Village

While there might not be top attractions in Largo Sound Village, you can explore the larger area and discover places like Caribbean Club Bar and MarineLab Undersea Laboratory.

Largo Sound Village


Winston Waterways, FL