Fall in love with Key West

You’ve already fallen in love with our Key West vacation rentals. Now it’s time to fall in love with exciting events in Key West this October and November!

Kick off your stay with the Southernmost Marathon, Half Marathon and 10K. Pick a distance and prepare to take in ocean views and pass by historical Key West landmarks. Race day is October 11th, but festivities begin the 9th and end the 13th. 

One of the largest fundraisers in Key West is the Royal Coronation Ball on October 17th. 2014 marks the 26th annual quest for the coveted crown. Contestants compete in the weeks leading up to this event in an effort to raise top dollar for AIDSHelp. Purchase tickets at KeysTix for reserved seating and dinner or standing room only. 

Fantasy Fest is our largest annual party held near the end of October with a new theme every year. This year’s theme of Anime-ted Dreams & Adventures kicks off October 17th with a week full of fun events. Check out the list of events and locations at FantasyFest.com. 

The 34th Annual Super Boat International will be held November 2nd-9th. Watch teams from all around the world compete in our beautiful Key West waters surrounding the Truman Waterfront. For schedule and details visit Super Boat International – Key West Schedule. 

Theatre season also kicks off November with The Beach Boys and the very special Key West version of the Nutcracker in December! See what shows and plays are coming to your favorite Key West theatre at Keystix.com.