Winston Waterways, FL

Key Largo

A wooden pier extending into the ocean at dusk with a small house at the end.

Things to do

Key Largo: Deserted Island Tour Kayak Adventure

Key Largo: Deserted Island Tour Kayak Adventure

$42
per adult
Key Largo: Deserted Island Tour Kayak Adventure
Florida Keys Audio Guided Tour

Discover Florida Keys: A Self-Guided Tour

$2
per adult
Discover Florida Keys: A Self-Guided Tour
Florida: Key West Overseas Highway Self-Driving Tour

Florida: Key West Overseas Highway App-Based Driving Audio Tour

$17
per traveler
88% of travellers recommend
Florida: Key West Overseas Highway App-Based Driving Audio Tour
Small Group Florida Keys Eco Tour by Boat

Small Group Florida Keys Eco Tour by Boat

$60
per adult
100% of travellers recommend
Small Group Florida Keys Eco Tour by Boat
Key Largo Day/ Sunset Dolphin Jetski Tour

Key Largo Adventure Jetski Tour

$214
per traveler
Key Largo Adventure Jetski Tour
E-Bike Rental in the Florida Keys

E-Bike Rental in the Florida Keys

$65
per adult
E-Bike Rental in the Florida Keys
See all activities in Key Largo

Winston Waterways Hotel Deals

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
$259 nightly
The price is $286 total per night from Aug 5 to Aug 6
$286 total
Aug 5 - Aug 6
Total with taxes and fees
Book a stay at this luxury hotel in Key Largo. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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
$294 nightly
The price is $331 total per night from Aug 17 to Aug 18
$331 total
Aug 17 - Aug 18
Total with taxes and 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 ...
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
$134 nightly
The price is $151 total per night from Aug 10 to Aug 11
$151 total
Aug 10 - Aug 11
Total with taxes and 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. ...
Waterside Suites & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
$197 nightly
The price is $221 total per night from Aug 11 to Aug 12
$221 total
Aug 11 - Aug 12
Total with taxes and 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. ...
Chesapeake Beach Resort
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
$144 nightly
The price is $159 total per night from Aug 31 to Sep 1
$159 total
Aug 31 - Sep 1
Total with taxes and fees
Book a stay at this beach hotel in Key Largo. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,799 reviews)
"Kayaking was great!"

Reviewed on Aug 4, 2026

Bayside Inn Key Largo
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2 out of 5
99340 Overseas Highway Key Largo FL
$103 nightly
The price is $116 total per night from Aug 23 to Aug 24
$116 total
Aug 23 - Aug 24
Total with taxes and fees
Book a stay at this beach hotel in Key Largo. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,004 reviews)
"Cool place"

Reviewed on Aug 3, 2026

The Pelican Key Largo Cottages
See all 2,268 properties in Winston Waterways
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.

Where to stay in Winston Waterways

Find the best Winston Waterways areas and neighborhoods for the activities you enjoy most.
A beachside resort with lounge chairs, a thatched-roof hut, and palm trees.
Photo by Samantha Shoemaker
Open Photo by Samantha Shoemaker

Rock Harbor

While Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby.

Silver Shores

If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit Bluefin Rock Harbor Marina and Pigeon Key.

A white speedboat on a blue ocean with a tropical island in the background.

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.

An aerial view of a coastal area with RVs parked along the shore, a small beach, and a clear view of the ocean.

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.

Two manatees in a body of water.
Photo by Patricia Smith
Open Photo by Patricia Smith

Pirates Cove

While Pirates Cove might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

Winston Waterways, FL

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