Ablative procedures of the head and neck often result in substantial defects that require large-volume tissue transfer for restoration of form and function. Multiple simultaneous free flaps may be required for complex defects, but these procedures are often avoided because of the perception of an increase in associated surgical complications and morbidity. We present our experience with the use of simultaneous multiple free flaps as compared with single free flaps (SFFs) for head and neck reconstruction. Thirty-seven patients with a history of head and neck malignancy underwent SFF reconstruction, and 21 patients underwent double free flap (DFF) reconstruction. Statistical analysis was conducted comparing demographics, comorbidities, etiology of disease, and surgical outcomes between the 2 patient groups. Operative time and length of hospital stay were both significantly longer in the DFF group versus the SFF group. Despite significantly higher rates of preoperative radiation, osteoradionecrosis, and operation for secondary malignancy in DFF group, no significant differences in flap survival, partial flap loss, recipient site complications, or donor site complications were found. Overall flap-related reoperation rates were low, as were total flap losses. There were 10 complications (24%) that required reoperation in the DFF group, and 1 total flap loss (2.4%), on per-flap basis. There were 10 complications (27%) that required reoperation in the SFF group and 3 total flap losses (8.1%). Per-flap incidence of donor site morbidity in the DFF group was significantly lower than that in the SFF group (23.8% vs 56.8%, respectively, P = 0.011). The use of multiple free flaps for reconstruction of major head and neck tissue defects is sometimes necessary to achieve adequate reconstructive results. These procedures have no significant associated increase in overall flap-related complications. Our findings suggest that donor site morbidity can be minimized in double-flap reconstructions by thoughtful flap selection.