Venous aneurysms of the head and neck, and in particular the facial vein, are rare lesions that present as soft, compressible masses. We describe a case of an idiopathic aneurysm of the facial vein. A comprehensive literature review of this entity was conducted to better understand the disease process. A 51-year-old female presented with a one-year history of a prominent but painless right submandibular mass that was more noticeable with maneuvers such as straining. An exam showed a painless, soft, compressible, right level 1b neck mass that enlarged with Valsalva. A computed tomography scan of the neck revealed a 2.7 cm enhancing mass adjacent to the right submandibular gland. Further workup included a direct puncture venography, which demonstrated an unruptured 3 cm venous aneurysm involving the right facial vein. Surgical excision was offered to the patient, which was completed without complications. Histopathology of the mass was consistent with a facial vein aneurysm and confirmed the suspected diagnosis. The patient was seen postoperatively in follow-up and was healing well. While facial vein aneurysms are rare, it is important to recognize, work up, and treat them appropriately. A painless compressible mass that enlarges with Valsalva is suggestive of the diagnosis. Management may vary on a case-by-case basis with surgical resection being the definitive treatment of choice.