| Winter Garden to Waycross (Georgia) | 189.94 mi (305.68 km) |
| Winter Garden to Wayne (Michigan) | 954.30 mi (1,535.79 km) |
| Winter Garden to Waynesboro (Pennsylvania) | 807.60 mi (1,299.71 km) |
| Winter Garden to Waynesboro (Virginia) | 676.19 mi (1,088.23 km) |
| Winter Garden to Weatherford (Oklahoma) | 1,109.30 mi (1,785.25 km) |
| Winter Garden to Weatherford (Texas) | 1,003.35 mi (1,614.74 km) |
| Winter Garden to Webb City (Missouri) | 952.99 mi (1,533.69 km) |
| Winter Garden to Webster (Texas) | 819.24 mi (1,318.45 km) |
| Winter Garden to Webster Groves (Missouri) | 856.86 mi (1,378.98 km) |
| Winter Garden to Weddington (North Carolina) | 450.60 mi (725.16 km) |
| Winter Garden to Weigelstown (Pennsylvania) | 835.81 mi (1,345.11 km) |
| Winter Garden to Weirton (West Virginia) | 821.79 mi (1,322.55 km) |
| Winter Garden to Wekiwa Springs (Florida) | 15.00 mi (24.14 km) |
| Winter Garden to Welby (Colorado) | 1,539.93 mi (2,478.28 km) |
| Winter Garden to Wellington (Colorado) | 1,566.18 mi (2,520.53 km) |
