Uterine vascular remodeling is intrinsic to the cycling and early pregnant endometrium. Maternal regulatory factors such as ovarian hormones, VEGF, angiopoietins, Notch, and uterine natural killer cells significantly mediate these vascular changes. In the absence of pregnancy, changes in uterine vessel morphology and function correlate with different stages of the human menstrual cycle. During early pregnancy, vascular remodeling in rodents and humans results in decreased uterine vascular resistance and increased vascular permeability necessary for pregnancy success. Aberrations in these adaptive vascular processes contribute to increased risk of infertility, abnormal fetal growth, and/or preeclampsia. This Review comprehensively summarizes uterine vascular remodeling in the human menstrual cycle, and in the peri- and post-implantation stages in rodent species (mice and rats).