He was married three times, to Kitty Jacob, Linda Kuechler, and Michele Metrinko, and had ten children including John W. Jr., James, Catherine, Patrick, Ted, Jeff, Michele, Monique, Michael and Marc, as well as eleven grandchildren, John III, Jamie, Fontayne, Charlie, Rachel, Katie, Sarah, Emma, Kaitlyn, William, and Morgan.

After World War II, Rollins and his wife Kitty moved to Lewes, Delaware, where he opened a Ford dealership.

The following year, the brothers founded Rollins Broadcasting and bought 1460 WRAD, an AM radio station based in the rural town of Radford, Virginia.

In the 1960s John Rollins who had been visiting Jamaica purchased a seven thousand acre sugar plantation Rose Hall near Montego Bay from Francis Kerr-Jarrett.

In 1956, Rollins was an alternate delegate to the Republican National Convention that nominated President Dwight D. Eisenhower for reelection.

In addition to contributing to multiple charities, he created the John W. Rollins Foundation, rated in 1999 to be one of the 50 largest charitable organizations in Delaware.

He sponsored the John W. Rollins, Sr. Award for health care philanthropy, and was a benefactor of the University of Delaware, despite never having attended the school himself.

The Horatio Alger Award recognized Rollins' rise from humble roots to preeminence in the world of business.

His philanthropy made the Horatio Alger Association into the largest privately funded scholarship in the US for underprivileged college students.