Background: The objective of this study was to evaluate the long-term safety and efficacy of endovascular therapy (EVT) in complex aortoiliac occlusive disease (AIOD) treated with aortic bifurcation reconstruction using the kissing stent or Covered Endovascular Reconstruction of the Aortic Bifurcation (CERAB) technique. Methods: This retrospective single-center study included 201 patients (79.6% ASA stage ≥3) with symptomatic TASC-II C/D AIOD who underwent EVT between 2010 and 2019. Endpoints included technical success and procedural complications. Outcomes assessed over a 5-year follow-up included primary and secondary patency rates, major limb amputation, and survival. Kaplan–Meier (KM) estimates and Cox regression were used for analysis. Results: The cohort had a mean age of 61.9 ± 9.7 years, included 61 female patients (30.3%), and showed a low prevalence of obesity (body mass index >30: 7.5%), while cardiovascular risk factors were highly prevalent, including hypertension in 81.1% and hyperlipidemia in 79.6% of patients. Technical success was achieved in 96.0% (193/201), with 87.1% (175/201) of patients treated with kissing stents and 12.9% (26/201) with the CERAB technique. Overall, major complications were reported in 6.5% (13/201) and access site-related complications in 3.0% (6/201) of cases. Five-year KM estimates were: 72.1% for primary patency, 89.6% for secondary patency, and 79.6% for overall survival. No significant difference in primary patency was observed between techniques (p = 0.55), and one case of major limb amputation was reported after 5 years. Conclusions: EVT using the kissing stent or CERAB technique is a durable and safe treatment for complex AIOD in high-risk patients over 5 years, with favorable outcomes and low periinterventional morbidity and mortality.