| Winter Garden to Worthington (Ohio) | 802.32 mi (1,291.21 km) |
| Winter Garden to Wright (Florida) | 330.62 mi (532.08 km) |
| Winter Garden to Wyandanch (New York) | 963.48 mi (1,550.58 km) |
| Winter Garden to Wyandotte (Michigan) | 948.48 mi (1,526.43 km) |
| Winter Garden to Wylie (Texas) | 937.34 mi (1,508.50 km) |
| Winter Garden to Wyndham (Virginia) | 672.76 mi (1,082.71 km) |
| Winter Garden to Wyoming (Michigan) | 1,017.50 mi (1,637.51 km) |
| Winter Garden to Wyomissing (Pennsylvania) | 874.89 mi (1,408.00 km) |
| Winter Garden to Xenia (Ohio) | 781.27 mi (1,257.32 km) |
| Winter Garden to Yakima (Washington) | 2,436.05 mi (3,920.44 km) |
| Winter Garden to Yankton (South Dakota) | 1,325.06 mi (2,132.48 km) |
| Winter Garden to Yauco (Puerto Rico) | 1,181.96 mi (1,902.18 km) |
| Winter Garden to Yazoo City (Mississippi) | 602.22 mi (969.17 km) |
| Winter Garden to Yeadon (Pennsylvania) | 865.80 mi (1,393.37 km) |
| Winter Garden to Yelm (Washington) | 2,537.13 mi (4,083.11 km) |
