He was educated at Westminster School under William Camden, where he excelled in classics and met playwright and poet Ben Jonson, with whom he established an "enduring friendship".
[2] On completion of his studies, he travelled abroad, as far as Rome, where unguarded remarks about Queen Elizabeth caused him some trouble, and Jerusalem, where he may have been made a Knight of the Holy Sepulchre.
He failed to secure preferment, but enjoyed the patronage of the Duke of Buckingham, George Villiers who introduced him to King James.
He was married to Ursula, widow of Robert Woodard of Burnham, Buckinghamshire, with whom he had three children: a daughter named Phil and two sons, Martin and Arbellinus.
Anthony à Wood recorded a copy of his epitaph, in which Holland described himself as Miserimus peccator, musarum et amicitiarum cultor sanctissimus.