We present a consecutive series of five patients with angioleiomyoma, a rare benign soft tissue tumor around the knee. Between 2005 and 2010, five patients with histopathologically confirmed diagnosis of angioleiomyoma of the knee underwent surgical excision. All five patients were Afro-caribbean in origin. The presenting feature was burning medial knee pain localized to a tender hyperesthetic swelling around the knee. The mean age of presentation was 45 years (range, 42 to 51 years), and the mean duration of symptom was 34 months (range, 12 to 96 months). Although magnetic resonance imaging (MRI) scans were helpful in locating and delineating the tumors, true diagnosis was established only by histopathology. All patients underwent surgical excision with complete resolution of symptoms. No recurrences were seen at an average follow-up of 16 months (range, 3 to 24 months). The treatment of these tumors, especially around the knee, is frequently delayed due to their late presentation and lack of awareness of this clinical condition. We recommend a high index of suspicion in patients, especially of Afro-caribbean origin, presenting with painful hyperesthetic subcutaneous swelling around the knee. Early investigation by MRI expedites the diagnosis, and surgical excision results in complete resolution of symptoms.