Background/Objectives: Kidney transplantation is the treatment of choice for children with end-stage renal disease (ESRD), but its outcome can be affected by urological complications, with incidence rates of 2.5–25%. The aim of this study was to evaluate the occurrence of urological complications and their management in a cohort of pediatric kidney transplant recipients. Materials and Methods: A retrospective analysis on 178 patients who received a renal transplant at our Pediatric Kidney Transplant Center between 2011 and 2023 was conducted. Demographic and clinical data were analyzed. Urological complications were categorized as early, intermediate, or late based on their onset time. Results: Out of 178 patients, 28 (15.7%) experienced urological complications. Most patients (61%) had a pre-existing uropathy. Early complications (7–30 days) were all obstructive, namely, ureterovesical junction obstruction and perirenal collections. Intermediate complications (1–3 months) comprised ureteral stenosis, symptomatic vesicoureteral reflux (VUR), and obstructive lymphocele. Late complications (>3 months) included symptomatic VUR and ureteral stenosis, with one case leading to ureteral rupture. Early complications were often detected due to acute graft dysfunction, while late ones were mainly identified during routine clinical, laboratory, or ultrasound follow-up. Urological complications requiring surgical or endoscopic therapy were 13.4%. Most ureteral stenoses were treated with initial endoscopic stents, followed by definitive surgery. VUR was treated with endoscopic correction with a high success rate (75%), while open surgery was reserved for cases where initial treatments failed or complications recurred. No clear correlations were found between patient characteristics and risk of urological complication. Urological complications required multiple diagnostic procedures and therapeutic interventions (+2.5 admissions in mean and approximately +EUR 24,000) compared to an uncomplicated post-transplant course. However, they did not significantly impact transplant outcomes, with a graft survival rate comparable to that of the control group. Conclusions: Regular post-transplant follow-up is crucial, especially for patients with known risk factors, to allow for timely detection and treatment of urological complications, avoiding detrimental effects on graft function and improving transplantation outcomes.