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Objective: Ambulatory Arterial Stiffness Index (AASI) and symmetric AASI (sAASI) have been proposed as indices of arterial stiffness obtained by 24-hour ambulatory blood pressure monitoring (ABPM). ABPM allows the analysis of indices of BP variability like day and night SD, BP dipping, weighted 24-h SD (wSD), average real variability (ARV). Aim of the present study was to address the relationship between these indices and other markers of vascular subclinical damage in children. Design and Method: 45 obese children were included. Children underwent vascular measurements, including: (i) office and 24-hour ambulatory BP; (ii) brachial flow-mediated dilatation (FMD), carotid intima media thickness (cIMT), and distensibility (cDC); (iii) systemic arterial stiffness (SIDVP). From ABPM we calculate AASI, sAASI, ARV, SD, SD, systolic and diastolic dipping and wSD. Results: ARV showed a significant correlation with SIDVP (r = 0.379; p = 0.023). AASI but not sAASI correlated with FMD (r = 0.361; p = 0.031). In the population divided in hypertensive (n = 11)/normotensive (n = 34), ARV was associated with SIDVP only in normotensive (r = 0.446; p = 0.015). In normotensive, z score-BMI was correlated with both sAASI and wSD (respectively 0.340; p = 0.049 and 0.423; p = 0.014), wSD correlated with FMD (r = 0.384; p = 0.048); in hypertensive children, ARV correlated with FMD (r = 0.828; p = 0.011; rspearman = 0.738; p = 0.037). No indices of BP variability correlated with cIMT or cDC. Conclusions: BP variability, in particular ARV, shows a correlation with systemic but not local vascular stiffness in a sample of obese children, suggesting a relation between daily BP variability and arterial elastic properties. Further studies, especially perspective ones, are needed to clarify the pathophysiological significance of these relations.