Headley \he(ad)-ley\ as a boy's name is a variant of Hedley (Old English), and the meaning of Headley is "heathered meadow".
The baby name Headley sounds like Hadley and Headly. Other similar baby names are Hadly, Hadlee, Hadlea, Hagley, Haley, Hayley, Halley, Hailey, Hanley, Henley, Handley, Harley, Hawley, Hedly, Radley, Redley and Wadley.