Aims This study aims to report a rare case of concurrent vestibular schwannoma and tonsillar schwannoma in a 62 year-old female, emphasizing the significance of the incidental finding of tonsillar schwannoma and its implications for diagnosis and treatment in the case of a dual pathology. Methodology The patient initially presented with imbalance, leading to a CT scan revealing a large right cerebellopontine angle mass, suggestive of vestibular schwannoma. A subsequent MRI for preoperative workup identified an incompletely imaged right tonsillar mass. Dedicated CT imaging of the tonsillar mass was conducted, alongside a staging CT scan. Examination revealed a grade IV right tonsil and profound hearing loss on the same side, but no systemic symptoms or lymphadenopathy were noted. The patient first underwent an uncomplicated tonsillectomy for histopathological diagnosis of the tonsillar mass, and subsequently a translabyrinthine approach vestibular schwannoma excision. The patient’s clinical course was closely monitored postoperatively. Results Histological analysis of the tonsil revealed a well-circumscribed, thinly encapsulated proliferation of spindle cells consistent with schwannoma, showing no evidence of malignancy. While the vestibular schwannoma was successfully removed, the operation was complicated by a CSF leak and facial nerve palsy, which were actively managed with a lumbosacral drain and gold weight with lateral canthoplasty, and the patient demonstrated gradual recovery over several months. Conclusion Tonsillar schwannomas are a rare entity with only several cases described in literature to date. This report contributes to the limited knowledge on tonsillar schwannomas as a cause of a unilateral tonsillar mass, and the potential association with vestibular schwannomas. To our knowledge, this is the first case of tonsillar schwannoma that presented concurrently with a vestibular schwannoma.