Background and Objectives: Surgical management of local recurrence of soft tissue sarcomas (STS) is still challenging. In this article, we report on multiple flap reconstructions for multiple local recurrences of STS. Their feasibility will be validated by examining clinical cases. Materials and Methods: Patients who underwent multiple flap reconstructions for multiple local recurrences of STS between April 1997 and October 2021 were included in this retrospective study. Patient demographics, tumor characteristics, surgical characteristics, and postoperative complications were examined. Results: Twenty operations of eight patients were identified. The location of the defects was the back in two, the buttock in two, the groin in two, and the lower extremities in two. The average total number of wide resections was 4.0 and the average total number of flap reconstructions was 2.5. The average follow-up period was 109.4 months. The average size of the defect was 102.4 cm2 and the average flap size was 15.7 × 10.8 cm. The histological diagnoses were malignant fibrous histocytoma (MFH) in eight operations, osteosarcoma in two operations, myxoid liposarcoma in two operations, undifferentiated pleomorphic sarcoma (UPS) in six operations, and myxofibrosarcoma (MFS) in one operation. Of twelve subsequent operations, the resection of the previously transferred flap was performed in six operations (50%). The occurrence of take back, flap complications, and donor-site complications in the primary operation group was 25%, 25%, and 12.5%, respectively. The occurrence of take back, flap complications, and donor-site complications in the second and subsequent operation group was 0%, 0%, and 16.7%, respectively. Conclusions: Multiple operations including wide resections followed by flap reconstructions for multiple local recurrences are feasible. Reconstructive surgeons should choose the options of the flaps considering the future local recurrence for tumors with a high risk of recurrence.