Hemangiomas of the small intestine are rare and very difficult to diagnose preoperatively. Clinical presentations may include occult or massive gastrointestinal (GI) bleeding, obstruction, intussusception, and perforation. We report a 66-year-old Caucasian male patient with severe anemia secondary to occult GI bleeding from a cavernous hemangioma in the jejunum. A double balloon enteroscopy following capsule endoscopy was performed to obtain biopsy samples, which established the final diagnosis.