Winston Waterways, FL

Key Largo

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

Things to do

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
E-Bike Rental in the Florida Keys

E-Bike Rental in the Florida Keys

$65
per adult
E-Bike Rental in the Florida Keys
Key Largo Day/ Sunset Dolphin Jetski Tour

Key Largo Adventure Jetski Tour

$214
per traveler
Key Largo Adventure Jetski Tour
1.5 Hour Bay Side Key Largo Sunset Cruise on a Spacious Catamaran

1.5 Hour Bay Side Key Largo Sunset Cruise on a Spacious Catamaran

$69
per adult
80% of travellers recommend
1.5 Hour Bay Side Key Largo Sunset Cruise on a Spacious Catamaran
Florida Keys Audio Guided Tour

Discover Florida Keys: A Self-Guided Tour

$5
per adult
Discover Florida Keys: A Self-Guided Tour
See all activities in Key Largo

Winston Waterways Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
$186 nightly
The price is $209 total per night from Oct 6 to Oct 7
$209 total
Oct 6 - Oct 7
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. ...
9.2/10 Wonderful! (1,785 reviews)
"Loved the kayak, and breakfast and the view! Everything!"

Reviewed on Sep 26, 2026

Chesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
$133 nightly
The price is $150 total per night from Oct 4 to Oct 5
$150 total
Oct 4 - Oct 5
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
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
$239 nightly
The price is $264 total per night from Sep 28 to Sep 29
$264 total
Sep 28 - Sep 29
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
$311 nightly
The price is $350 total per night from Sep 30 to Oct 1
$350 total
Sep 30 - Oct 1
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
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2 out of 5
99340 Overseas Highway Key Largo FL
$82 nightly
The price is $92 total per night from Oct 5 to Oct 6
$92 total
Oct 5 - Oct 6
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! (1,006 reviews)
"Great experience!!"

Reviewed on Sep 27, 2026

The Pelican Key Largo Cottages
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
$140 nightly
The price is $155 total per night from Oct 5 to Oct 6
$155 total
Oct 5 - Oct 6
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. ...
Bayside Inn Key Largo
See all 2,259 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 Harry Harris Park.

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 Jacob's Aquatic Center and Jimmy Johnson's Big Chill.

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 Jacob's Aquatic Center and Jimmy Johnson's Big Chill.

A bridge over a river with boats docked along the shore.

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 MarineLab Undersea Laboratory and Caribbean Club Bar.

Winston Waterways, FL

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