This chapter explores a variety of diseases affecting the vagina and vulva, with a focus on diagnosis and management through imaging techniques. Congenital anomalies such as agenesis and duplication, as well as cystic lesions like Bartholin’s gland cysts, Gartner’s duct cysts, and Skene’s duct cysts, are discussed. Benign tumors, including hidradenoma, leiomyoma, and fibroma, are examined alongside malignant conditions such as vulvar and vaginal cancers, which encompass squamous cell carcinoma, melanoma, and other rare metastatic tumors. Detailed descriptions of the imaging characteristics of these diseases are provided for ultrasonography (US), computed tomography (CT), and magnetic resonance (MR) imaging, highlighting the strengths of each modality in detecting and differentiating these conditions. The chapter also covers the imaging evaluation of fistulas, offering insights into their assessment and aiding in effective treatment planning for various vaginal and vulvar pathologies.