Intravenous lobular capillary hemangioma is a rare benign lesion that can mimic other intravascular lesions encountered by vascular surgeons, such as angiosarcoma, papillary endothelial hyperplasia, and deep vein thrombus. These lesions have been described originating in the veins of the head, neck, and upper extremities. To our knowledge, there are no reported cases of intravenous capillary hemangioma arising from within a pelvic vein. We report a case of an elderly woman found to have an extensive intravenous lobular capillary hemangioma originating in the internal iliac vein. She was successfully treated with resection, including the tumor and normal iliac vein. Diagnosis of these lesions can be difficult. We describe the utility of duplex ultrasound and magnetic resonance venography in aiding preoperative diagnosis and surgical planning. The diagnosis is ultimately confirmed with histology that demonstrates multiple capillaries lined with flattened endothelial cells grouped in a lobular fashion admixed with fibromyxoid stroma containing collagenous fibers, spindle cells, and mitotic figures. Preoperative work-up should include a duplex ultrasound and magnetic resonance venogram. Treatment should be with resection and specimen processing to rule-out malignant vascular tumors.