Background: Laparoscopic sacral colpopexy (LSC) is the gold standard treatment for women with apical/anterior pelvic organ prolapse (POP). For isolated posterior vaginal prolapse, instead, the literature suggests fascial native tissue repair. This is a retrospective 2-year quality-of-life follow-up study after laparoscopic posterior plication (LPP) combined with LSC in patients with anterior/apical prolapse combined with severe posterior colpocele. The primary endpoint was to evaluate the subjective outcomes quality of life (QoL), sexual function, and patient satisfaction rate. The secondary endpoint was to evaluate perioperative and anatomical outcomes at the 2-year follow-up. Methods: A total of 139 consecutive patients with anterior and/or apical prolapse (POP-Q stage ≥ II) and severe posterior vaginal prolapse (posterior POP-Q stage ≥ III) were retrospectively selected from our database among women who underwent, from November 2018 to February 2021, a “two-meshes” LSC. The patients were classified into Group A (81 patients; LSC plus LPP) and Group B (67 patients; LSC alone). The primary endpoint was evaluated using the Patient Global Impression of Improvement (PGI-I), the Pelvic Organ Prolapse Distress Inventory-6 (POPDI-6), the Pelvic Floor Impact Questionnaire-7 (PFIQ-7), the Female Sexual Distress Scale (FSDS), the Pelvic Organ Prolapse/Urinary Incontinence Sexual Questionnaire (PISQ-12), and the EuroQol (EQ-5D). The secondary endpoint was studied using the POP-Q study and an intra-, peri-, and post-operative complications assessment. Two-year follow-up data were analyzed for the study. Results: At 2 years, all women showed a statistically significant amelioration of their symptoms on the QoL questionnaires. We found a statistical difference in favor of posterior plication in terms of the PGI-I successful outcome rate (Group A versus B: 85.3% versus 67.1%), FSDS (median 11 versus 21), and PISQ-12 (median 89 versus 62) (p < 0.05 for all comparisons). A significant improvement of all EQ-5D values was observed from baseline to 2-year follow-up, and only for the “pain/discomfort” domains did we observe a significant improvement in LSC plus LPP patients versus LSC alone (p < 0.05). LSC plus LPP women showed, at 2 years, a significant amelioration of their Ap and GH POP-Q points. We observed no statistical differences in terms of intra-post-operative complications or anatomic failure rate between groups. Conclusions: Our LPP approach to LSC appears to be a safe, feasible, and effective treatment for advanced pelvic organ prolapse with a significant impact on the patient’s general health and sexual quality of life. Adding laparoscopic posterior vaginal plication to “two-meshes” sacral colpopexy is recommended in patients with apical/anterior prolapse and concomitant severe posterior colpocele. This surgical approach, in addition to improving the anatomical results of these patients, is associated with a significant improvement in sexual and quality of life indexes.