Steven Spielberg was the executive producer of the film, which was written by Paul Dini, Nicholas Hollander, Tom Ruegger, and Sherri Stoner. Japanese animation studio Tokyo Movie Shinsha (now known as TMS Entertainment) produced the animation for the film. How I Spent My Vacation was released on both VHS and LaserDisc formats on Wednesday, March 11, 1992. It was the first animated film to be released direct-to-video in the United States. The film was later aired on television as four separate Tiny Toon Adventures episodes.
The film was one of the highest selling videos in the United States, listing on Billboard magazine's 40 "Top Video Sales" for 16 weeks as of July 1992. Points of praise by critics included the film's jokes and celebrity caricatures, while points of criticism included the segmented plot. Themes of the film included parodies of pop culture and summer vacations.