Vaginal vault prolapse occurs in 0.2% to 1.0% of menopausal women with prior hysterectomy. Even rarer is the development of concurrent rectal prolapse seen in 0.03% to 0.1% of cases. This paper aimed to 1) present a rare case of concurrent prolapses of the vaginal vault and rectum in an 87-year old grandmultipara, 2) evaluate factors predisposing to vault prolapse and rectal prolapse and their manifestations, 3) introduce the new quantitative staging system of pelvic organ prolapse by the International Continence Society, 4) discuss the options of management, and 5) emphasize the need for multidisciplinary management approach. An 87-year old grandmultipara presented with two distinct prolapsing masses at the introitus and anus. Implicated factors such as prior hysterectomy, advanced age, multiple vaginal deliveries, menopausal state and history of heavy lifting were identified. Diagnosis was made clinically. The vaginal vault prolapse was categorized quantitatively according to the Pelvic Organ Prolapse Quantification System wherein she was diagnosed to be at stage IV C. Based on such stage, treatment options, both conservative and surgical, were discussed. She underwent perineal surgery for both lesions. Effective therapy for concurrent prolapses of vaginal vault and rectum requires in-depth knowledge of pelvic anatomy and physiology, a thorough physical examination, adequate preoperative planning and prudent selection of surgical procedures that will achieve the most anatomically complete repair that will prevent recurrence.