Vascular leiomyosarcoma is a rare malignant tumour of the smooth muscle connective tissue. Patients are usually asymptomatic in the early stages and only present when the lesion causes compressive or obstructive effects or has metastasized. We report a case of vascular pleomorphic leiomyosarcoma in a 70-year-old lady with a background history of squamous cell carcinoma of the cervix. She presented with a three-month history of low back pain, which radiated to the anterior bilateral thigh. Initial radiological findings revealed metastatic lesions involving the spine and lungs. Two spinal biopsies done were inconclusive. Increasing severity of pain over the right thigh prompted further imaging, which revealed bilateral femoral lesions. The patient underwent surgery which involved excision of the tumour in the right proximal femur with skeletal reconstruction using megaprosthesis. Proximal femoral nail was performed for the left femur. Intra-operatively, tumour was noted at the anteromedial aspect of the proximal right thigh surrounding the superficial femoral vein. Histopathological report of the right thigh mass finally confirmed a diagnosis of vascular pleomorphic leiomyosarcoma. The patient presented four months later with bilateral pulmonary embolism with deep vein thrombosis in addition to progression of the disease.