Aim: To identify different causes of vulvovaginal swelling and step-by-step identification and management options. Background: Vulvovaginal cysts may start as asymptomatic cysts but may enlarge to big sizes and varied histopathology, needing immediate as well as long-term medical attention. We have reviewed three cases of vulvovaginal cysts with unusual presentations. Case description: The first case presented was a giant dumbbell-shaped Bartholin cyst presenting as a labial cyst. The second case with a provisional diagnosis of Bartholin's cyst came out to be aggressive angiomyxoma on immune histopathology. The third case presented with pus in the urine, occasionally painful urination, and a vaginal cyst which turned out to be a urethral diverticulum on cystoscopy. Conclusion: A meticulous clinical history and examination of the patient supported by a few investigations help a gynecologist to formulate a plan of management to deliver the desired results to the patient. Clinical significance: The most important clinical parameter for the vulvovaginal cyst is the site of occurrence. Later differential diagnosis is made, and investigation and treatment (surgical or medical) are planned according to the suggested approaches and ideas mentioned in the paper. Management protocols can be as straightforward as cystectomy or may require a multiprong, multidisciplinary approach and multiple sitting.