I had to do this name because my husband could easily be a stunt double for Orlando Bloom ( ^.^ ), the most famous namesake at the moment, who is married to Victoria's Secret model Miranda Kerr and named their son Flynn. Several athletes bear the name as well. Worldwide, the most easily recognizable place name is Orlando, Florida, home of Disney World, Sea World and Universal Studios. Orlando is an Italian and Spanish variant of the Old German name Roland, meaning "renowned/famous land." Roland was a famous and loved literary medieval knight (read Le Chanson de Roland for more info). It is possible Orlando and/or Roland originated as a place name.
Orlando is a literary name used a lot in the 19th century, which even Virginia Woolfe used as the title of one of her novels, and Shakespeare used it for one of his characters in "As You Like It." There was also a Saint Orlando. Orly and Lando are common nicknames, but Orrie or Andy can work well. Orlando currently ranks at #482, it's lowest ranking this decade, with 543 baby boys given the name in 2011. Only a handful of O names for boys actually ranked - Oliver, Oscar, Owen, Orion and Omar were the only names ahead of Orlando.