From a structural standpoint, living systems exhibit a hierarchical pattern of organization in which structures are nested within one another. From a temporal point of view, this type of organization is the outcome of a ‘history’ resulting from a set of developmental steps. Recently, it has been suggested that some auto similarity prevails at each nested level or time step and a principle of “self-similarity logic” has been proposed to convey the concept of a multi-level organization in which very similar rules (logic) apply at each level. In this study, the hypothesis is put forward that such a principle is particularly apparent in many morphological and developmental aspects of the vascular system. In fact, not only the morphology of the vascular system exhibits a high degree of geometrical self-similarity, but its remodelling processes also seem to be characterized by the application of almost the same rules, from the macroscopic to the endothelial cell to the sub-cellular levels, potentially allowing a unitary description of features such as sprouting and intussusceptive angiogenesis, and phenotypic differences of endothelial cells. The influence of the “self-similarity logic” shaping the vascular system on the organogenesis has been also discussed.