Background: Although pregnancy has been identified as one of the risk factors for venous disease, the mechanism of this interaction remains unclear. Possibly, pregnancy results in overstrain and vein dilatation, which exceed their durability and persist after pregnancy. The aim of this study was the assessment of the relationship between the number of pregnancies in women with venous disease and the selected parameters of their venous systems. Patients and methods: The retrospective assessment concerned 518 patients subjected to the diagnostics of the venous system in the lower limbs and the abdomen/pelvis using ultrasound scan and magnetic resonance or computed tomography. Results: We found that the occurrence of pelvic venous symptoms increases proportionally to the number of pregnancies and is correlated with ovarian and parauterine vein dilatation/incompetence (e.g., 13.5%of nulliparous women reported pelvic pain, and reflux in left ovarian veins was detected in 21.4% of the patients from that group, whereas in women after two pregnancies, pain and reflux concerned 22.8% and 90.6% of patients, respectively). In the nulliparous group, the development of venous disease resulted from the presence of anatomic abnormalities in abdominal/pelvic veins. Conclusions: Our report proved that the number of pregnancies is correlated with the incidence of pelvic vein insufficiency. Although not specifically addressed in this study, some correlation was found with saphenous disease as well. However, further studies are necessary to provide more evidence about the role of pelvic vein insufficiency in chronic venous disease of the lower limbs.