The incidence of multiple pregnancies has increased dramatically over the last few years in developed countries, largely attributed to delayed childbearing and the increasing use of assisted reproduction technologies and ovulation inducing hormones. Relatively few countries have population-based statistics covering birth statistics. Of those that do, the numbers of quintuplet pregnancies rose sharply in the nineties while, at the same time, their delivery rates decreased greatly because of the use of fetal reduction. Fetal reduction is not possible or legal in some countries, Poland being one of them, and therefore obstetricians are faced with the challenges of quintuplet deliveries. Conservative treatment and management is difficult, and outcomes often vary greatly. Despite this, expert care provided at tertiary care centers can positively influence outcomes. The objective of this article is to present different care options and their consequences in two illustrative cases, as well as to establish a set of obstetric care and management goals that would allow prolongation of the gestation time. Quintuplet pregnancy is rare but poses relevant clinical problems to both the obstetrician and the neonatologist. It should be managed with close cooperation between all concerned. Due to the extreme and invariable risk of premature delivery associated with quintuplet pregnancies, we recommend early diagnosis, adequate prenatal care at one tertiary medical center, routine hospitalization and bed rest, repeated ante partum ultrasound surveillance with tests of fetal well-being, tocolytic therapy at first signs of the risk of premature labor, and specialized neonatology care after delivery.