Holland was born in Bartow, Florida, the son of Benjamin Franklin and Virginia Spessard Holland, a teacher.
He attended public schools, entering the Summerlin Institute (now Bartow High School) in 1909.
Holland graduated magna cum laude from Emory College (currently Emory University) in 1912, where he was a member of the Alpha Tau Omega fraternity.
Holland would go on to teach high school in Warrenton, Georgia for four years.

In 1916, Holland began attending law school at the University of Florida.
There he taught in the "sub-freshman department" (high school) of the university.
He also became the first elected student body president and a member of the debating society.
During his time at Emory and UF, he participated in track and field, football, basketball, and baseball; 
on one occasion, he played so well as a pitcher in an exhibition game against the Philadelphia Athletics that Connie Mack (the grandfather of Connie Mack III, who would one day hold the Senate seat Holland once occupied) offered him a contract (he declined).
Holland was born in Bartow, Florida, the son of Benjamin Franklin and Virginia Spessard Holland, a teacher. He attended public schools, entering the Summerlin Institute (now Bartow High School) in 1909. Holland graduated magna cum laude from Emory College (currently Emory University) in 1912, where he was a member of the Alpha Tau Omega fraternity. Holland would go on to teach high school in Warrenton, Georgia for four years.
In 1916, Holland began attending law school at the University of Florida. There he taught in the "sub-freshman department" (high school) of the university. He also became the first elected student body president and a member of the debating society. During his time at Emory and UF, he participated in track and field, football, basketball, and baseball; 
on one occasion, he played so well as a pitcher in an exhibition game against the Philadelphia Athletics that Connie Mack (the grandfather of Connie Mack III, who would one day hold the Senate seat Holland once occupied) offered him a contract (he declined).
Spessard Holland