Prior to the arrival of the railroad and the establishment of Kenansville, a farming community called Whittier existed dating from the late 1800s. In 1910, while surveying a route for the Okeechobee Spur of his Florida East Coast Railroad, Henry Flagler made a deal with Whittier: he would bring the railroad near town to help turpentine and cattle operations, if they relocated to the rails and renamed the town 'Kenansville,' after his wife Mary Lily Kenan Flagler. Flagler also promised that if the town followed through, he would donate $10,000 for construction of a new school.

Needless to say, the town was renamed and relocated to Flagler's new rail line. Unfortunately, in 1913 Flagler died after falling down a flight of stairs at his home in Palm Beach. Mary Flagler kept her husband's promise in 1914 and donated five acres of land as well as $6,000 for a new brick schoolhouse that was completed in 1917. For a time, the school would be recognized as one of Florida's most outstanding rural school.

Over the next few decades Kenansville thrived as a cattle town. However, after rail service ended in 1947 the town quietly declined. The school finally closed in 1961 (though it reopened briefly from 1992-2003). A small farming population still remains, and the community has a handful of historic buildings - including Webb's Heartbreak Hotel, supposedly the inspiration behind the famed Elvis Presley song.