Find Beach Hotel in Winston Waterways, Key Largo

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Winston Waterways Beach Hotel

Tonight
Aug 28 - Aug 29
Tomorrow
Aug 29 - Aug 30
This weekend
Aug 29 - Aug 31
Next weekend
Sep 5 - Sep 7

Top Winston Waterways Beach Hotel

Our top choices for Winston Waterways beach hotels

Paradise on the Canal with Ocean Access including Pool & Spa
A heated pool

Paradise on the Canal with Ocean Access including Pool & Spa

10.0 out of 10, Exceptional, (1)
"This is a neat and tidy property that is really close to a lot of things to do in Key Largo. The communication with the property managers was over the top good. Quick response to anything we inquired about with quick resolution. The owner is spending some money on the home updating things. It's already great and will be even better once it's all complete. This is a fantastic place to stay!!!"
Paradise on the Canal with Ocean Access including Pool & Spa
LUXURY HOME, WATERFRONT, 5 MINS FROM OCEAN, 80FT DOCK, HOT TUB, GOURMET KITCHENT
Exterior

LUXURY HOME, WATERFRONT, 5 MINS FROM OCEAN, 80FT DOCK, HOT TUB, GOURMET KITCHENT

10.0 out of 10, Exceptional, (48)
"Great place to stay"
LUXURY HOME, WATERFRONT, 5 MINS FROM OCEAN, 80FT DOCK, HOT TUB, GOURMET KITCHENT
Spacious 4-bedroom vacation home minutes to John Pennekamp Coral Reef State Park
Outdoor pool, a heated pool

Spacious 4-bedroom vacation home minutes to John Pennekamp Coral Reef State Park

10.0 out of 10, Exceptional, (2)
"The property was just as advertised! Beautifully furnished and appointed! Our first month long stay in the keys, our only complaint was that it wasn’t long enough! Gerard is a wonderful host that assisted us with any questions we had. Definitely going back!!!"
Spacious 4-bedroom vacation home minutes to John Pennekamp Coral Reef State Park
Key Largo home with breathtaking water views
Fridge, microwave, oven, stovetop

Key Largo home with breathtaking water views

10.0 out of 10, Exceptional, (4)
"Our second visit at this wonderful rental was just as great as our first, if not better. The home is just as described and the hosts are fantastic! Thoroughly enjoyed our time in Key Largo. Looking forward to returning once again."
Key Largo home with breathtaking water views
Keys Harbor: Waterfront, Private Boat Dock, Outdoor Oasis
Terrace/patio

Keys Harbor: Waterfront, Private Boat Dock, Outdoor Oasis

Keys Harbor: Waterfront, Private Boat Dock, Outdoor Oasis
Key Largo Oasis.
Marina

Key Largo Oasis.

Key Largo Oasis.
Family Tides
Smart TV, fireplace

Family Tides

Family Tides
Cukoos Nest by Florida Keys Luxury Rentals
House, 4 Bedrooms | Pool

Cukoos Nest by Florida Keys Luxury Rentals

4.0 star property
Cukoos Nest by Florida Keys Luxury Rentals
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.

Find out more about Winston Waterways

Find out more about Winston Waterways

Popular beach getaways

Most booked beach stays in Winston Waterways in 2025

Hotels with pools in Winston Waterways
Hotels with pools
Hotels with pools
Vacation rentals with pools in Winston Waterways
Vacation rentals with pools
Vacation rentals with pools
Pet-friendly beach stays in Winston Waterways
Pet-friendly beach stays
Pet-friendly beach stays

Top Winston Waterways Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia