Background: Oblique lateral interbody fusion (OLIF) at lumbosacral junction is typically performed on the central window between the bifurcations of iliac vessels. However, the central window of lumbosacral transitional vertebrae (LSTVs) is usually obstructed by the iliocaval venous structures. We aimed to describe the vascular anatomy and surgical approach in OLIF at LSTVs compared with those in OLIF at typical L5-S1 junction. Methods: Sixty-eight consecutive patients who underwent OLIF at lumbosacral junction were included. Of these, 31 patients had LSTVs and 37 patients had typical L5-S1 junction. The position of the iliocaval junction and the configuration of the left common iliac vein were compared using the preoperative CT and MR images of the lumbar spine. The surgical approach and intraoperative vascular findings were analyzed. Results: Almost 70% of LSTVs had the iliocaval junction at low or very low position. Mobilization of left common iliac vein for central window was potentially difficult in almost 74% of OLIF at LSTVs while it was not required or was potentially easy in almost 80% of OLIF at typical L5-S1. Vascular injury was identified in 2 (6.5%) patients with OLIF at LSTVs and in 3 (8.1%) patients with OLIF at typical L5-S1 junction (P = 0.904). Conclusions: In our series, OLIF at LSTVs was performed through lateral window in 93.5% of the cases. Preoperative evaluation of the iliocaval junction using CT/MR of lumbar spine was reliable and valid in the determination of OLIF approach at lumbosacral junction.