The song was released on August 12, 2008 on USDA2DAY.com as a countdown to The Recession. Originally "Crazy World" was rumored to be the second single, but it was confirmed that "Vacation" would be the second single. He said that he chose "Vacation" as a single because "I need one, no one ever seen Jeezy have fun."
The music video was shot in Miami and was directed by Gil Green. Cameos include Rick Ross and Triple C's, Blood Raw, Slick Pulla, Slim Thug, Trey Songz and more. In the video, Jeezy is shown having fun on the beach with the FBI spying on him. He is then shown driving a Ferrari F430 Spider. Later he is at a club, having fun until the FBI cuts in and arrests him. This scene is part of an actual investigation the FBI conducted pertaining to the Black Mafia that police felt Jeezy had ties to.