He was the son of Thomas Holland, 1st Earl of Kent and Joan of Kent, daughter of Edmund of Woodstock and granddaughter of Edward I. After his father's death his mother married Edward the Black Prince.
When his father died in 1460 he became Baron de Holland. His mother was still Countess of Kent in her own right. At sixteen, in 1366, Holland was appointed captain of the English forces in Aquitaine. He fought in various campaigns over the following years, and was made a Knight of the Garter in 1375.
Richard II became king in 1377, and soon Holland acquired great influence over his younger half-brother. This influence, in most historians view, was utilized primarily for Holland's own enrichment. In 1381 he was created Earl of Kent.