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 NZ$653 per night from 19 Apr to 20 Apr
NZ$653
19 Apr - 20 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! (1,386 reviews)
Average stay with average views and limited amenities. Room was decent. Beach was quite small. On-site restaurant is pricey with average tasting food.

Reviewed on 27 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 NZ$388 per night from 12 Apr to 13 Apr
NZ$388
12 Apr - 13 Apr
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! (1,265 reviews)
Great for a low key extended stay.

Reviewed on 27 Mar 2026

Waterside Suites & 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 NZ$886 per night from 27 Apr to 28 Apr
NZ$886
27 Apr - 28 Apr
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! (1,014 reviews)
I recently stayed at this hotel in Key Largo, and overall, it’s a mixed experience with some clear highlights. The biggest plus is how genuinely pet-friendly the property is. Not just “allowed,” but truly welcoming—something that’s rare and very appreciated. The atmosphere is incredibly peaceful ...

Reviewed on 27 Mar 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 NZ$525 per night from 14 Apr to 15 Apr
NZ$525
14 Apr - 15 Apr
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! (1,669 reviews)
Every aspect of our stay was awesome for our first time visiting The Keys. Everyone in the front office, to the people that maintained the property and guest rooms, and especially to the two gentlemen making made to order omelettes were wonderful. We loved our room and the view of the ocean was spectacular ...

Reviewed on 26 Mar 2026

Chesapeake Beach Resort
Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG

3 out of 5
99701 Overseas Hwy Key Largo FL
Fully refundable
The price is NZ$463 per night from 13 Apr to 14 Apr
NZ$463
13 Apr - 14 Apr
includes taxes & fees
Stay at this beach hotel in Key Largo. Enjoy free Wi-Fi, free parking and 2 restaurants. Our guests praise the pool and the helpful staff in their reviews. Popular ...
8.6/10 Excellent! (1,051 reviews)
Property was fine air seemed to cycle off and in and make a lot of extra noise periodically. Older property. Breakfast buffet was good. Oil are and tiki bar good music was exceptional and Skippers restaurant was good with good service behind the hotel. Would book again by maybe a pool side lower ...

Reviewed on 23 Mar 2026

Holiday Inn Key Largo by IHG
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
The price is NZ$422 per night from 30 Mar to 31 Mar
NZ$422
30 Mar - 31 Mar
includes taxes & fees
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! (1,689 reviews)
Overpriced by a long shot. Old,needs an upgrade. Elevator was not working so had to lug all our luggage up 3 flights. Room took 2 extra hours after check in and we got up there and girl at desk never activated our key. Avoid this place.

Reviewed on 25 Mar 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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