Have a question? Call 305.296.4440

Annual Events in Key West

October 2016

Key West Halloween Half Marathon & 5K Run

October 21, 2016
A unique running experience that is so characteristic of the eclectic style of Key West and all who live there.

37th Annual Key West Fantasy Fest

October 21-30, 2016
Events and Festivals
Florida’s premier masking and costuming celebration is one of the most popular events in all of south Florida.

Goombay Festival

October 21-22  2016
Events and Festivals
Part of the annual and highly anticipated Fantasy Fest, the Goombay Festival is an exuberant street party and family-friendly event. Activities include island arts and crafts, music, and food.

Visit Website for More Details

Make a Reservation

Manage Reservations
Need assistance? Call 305.296.4440
Pool and garden at our key west bed and breakfast

Photo Gallery

Tour our beautiful Key West hotel through photos in our gallery. View the lush grounds and gardens, our cozy rooms, and unique features like our library and pools.

Learn More

On the Beach after a wedding in key west

Wedding Gallery

You’ve always pictured your perfect wedding day. View the photos in our Wedding Gallery to see what your destination wedding can be like at Westwinds Inn.

Learn More

Key West beach and palm tree

Calendar of Events

There’s always something going on in Key West, from food and literary festivals to fishing and sailing tournaments. View our Events Calendar for the latest happenings.

Learn More