The appearance of severe vulvovaginal varicosities (VVs) is challenging in pregnancy. The management of VVs may require a multidisciplinary approach, including radiologists, vascular surgeons, and obstetricians. We report a rare case of enormous VVs and pubic varicosities and summarize similar cases in the literature. A woman in her 20s with a full-term pregnancy visited our hospital for severe VVs and pubic varicosities. She had been in a spoke maternity unit where a cesarean section was scheduled. After a multidisciplinary evaluation, we offered her the chance to have a vaginal delivery (VD). The woman had an uneventful VD, and VVs disappeared after 40 days. A comprehensive literature search on this topic showed 11 cases of VVs during pregnancy (five VDs and six cesarean sections). The presence of VVs represented the indication for surgery in 70% of cases. Severe complications occurred in 20% of VDs vs. 50% of CSs. In pregnant women with VVs, the risk-benefit ratio suggests a chance of having VD.