Headley is a surname. Notable people with the surname include:
Chase Headley (born 1984), American professional baseball player
David Headley (born 1960), Pakistani-American terrorist
Dean Headley (born 1970), cricketer
Frederick Webb Headley (1856–1919), English naturalist
George Headley (1909–1983), West Indian cricketer
Heather Headley (born 1974), Trinidadian-American musician
Hubert Klyne Headley (1906–1996), American composer and musician
Justina Headley (born 1968), Taiwanese-American author
Ron Headley (born 1939), West Indian cricketer
Shari Headley (born 1964), American Actress
Victor Headley (born 1959), British author
Win Headley (born 1949), American football player
