| Winter Garden to Sunset (Florida) | 210.35 mi (338.52 km) |
| Winter Garden to Superior (Colorado) | 1,551.90 mi (2,497.55 km) |
| Winter Garden to Superior (Wisconsin) | 1,376.31 mi (2,214.96 km) |
| Winter Garden to Surprise (Arizona) | 1,852.27 mi (2,980.94 km) |
| Winter Garden to Susanville (California) | 2,346.43 mi (3,776.22 km) |
| Winter Garden to Sussex (Wisconsin) | 1,073.46 mi (1,727.57 km) |
| Winter Garden to Suwanee (Georgia) | 407.59 mi (655.95 km) |
| Winter Garden to Swansea (Illinois) | 842.66 mi (1,356.13 km) |
| Winter Garden to Sweetwater (Florida) | 205.16 mi (330.17 km) |
| Winter Garden to Sweetwater (Texas) | 1,150.59 mi (1,851.70 km) |
| Winter Garden to Sycamore (Illinois) | 1,010.90 mi (1,626.89 km) |
| Winter Garden to Sylacauga (Alabama) | 423.10 mi (680.92 km) |
| Winter Garden to Sylvania (Ohio) | 917.53 mi (1,476.62 km) |
| Winter Garden to Syosset (New York) | 963.64 mi (1,550.82 km) |
| Winter Garden to Syracuse (New York) | 1,046.71 mi (1,684.52 km) |
