Acute urine retention is the most common urologic emergency, and it usually presents with abdominal pain and an inability to pass urine. The distended bladder in urine retention can be enormously large, raising the intra-abdominal pressure and compressing the iliac veins draining the lower limbs and pelvis. Many cases have been reported to have deep vein thrombosis (DVT)-like features with urine retention that resolves with bladder decompression. In rare cases, urine retention can lead to DVT, particularly in young patients. We report a case of a young female patient with a huge distended bladder who devolved extensive venous thrombosis bilaterally. The report sheds light on this unusual complication of acute urine retention and reviews the existing literature on the topic.