Purpose: Choroidal coloboma (CC) eyes are associated with a high risk of retinal detachment (RD), which are challenging to repair. Methods: We retrospectively evaluated medical records of 30 patients with CC associated with RD who underwent pars plana vitrectomy at our tertiary care center. Data recorded were age, CC and RD morphology, breaks, resurgeries performed, and final outcome. Results: Patients’ ages ranged from 2 to 49 years. CC was present in 53 of 60 eyes (88%), with 41 of 60 eyes (68.3%) associated with iris coloboma. RD was present in 36 of 53 CC eyes (67.9%), with 10 of 53 (18.9%) having bilateral RD. Thirty-one eyes with RD underwent 23-gauge pars plana vitrectomy. Colobomatous region breaks were detected in 5 of 31 eyes (16.1%), peripheral breaks only in 12 of 31 (38.7%), and both types in 3 of 31 eyes (9.7%). Silicone oil endotamponade was used in 29 of 31 eyes (93.5%) and perfluoropropane (C3F8) in 2 of 31 eyes (6.45%). Median postoperative follow-up duration was 31.5 months. Fourteen of 31 eyes (45.2%) developed redetachment requiring resurgery, with 50% developing within 6 months. Eighteen of 31 eyes (58.1%) maintained retinal attachment at last follow-up without endotamponade, whereas the rest were oil filled. Final visual outcome between macula-involved and macula-spared CC eyes was not significantly different; however, best visual acuity achieved any time during follow-up was significantly better in macula-spared eyes. Conclusions: RD surgery in CC eyes has a risk of frequent redetachments and subnormal gain of vision over the long term, especially in colobomas involving the macula. Endolaser in 360° peripheries in addition to barrage of the margin of the coloboma may be considered to help maintain the attached retina.