Leiomyomas may originate from any anatomic location of smooth muscle in the genitourinary system but are uncommon neoplasms. Five unusual cases of leiomyomas arising from the renal pelvis, bladder, spermatic cord, and glans penis are presented. The leiomyoma arising from the glans penis in a three-year-old boy is the first case of a leiomyoma in that location noted in the literature. A review of leiomyomas from each genitourinary structure of origin is presented.