| Winter Springs to Sunset (Florida) | 213.67 mi (343.86 km) |
| Winter Springs to Superior (Colorado) | 1,561.83 mi (2,513.52 km) |
| Winter Springs to Superior (Wisconsin) | 1,374.27 mi (2,211.67 km) |
| Winter Springs to Surprise (Arizona) | 1,867.77 mi (3,005.88 km) |
| Winter Springs to Susanville (California) | 2,358.25 mi (3,795.23 km) |
| Winter Springs to Sussex (Wisconsin) | 1,070.25 mi (1,722.40 km) |
| Winter Springs to Suwanee (Georgia) | 405.53 mi (652.64 km) |
| Winter Springs to Swansea (Illinois) | 845.07 mi (1,360.01 km) |
| Winter Springs to Sweetwater (Florida) | 208.46 mi (335.48 km) |
| Winter Springs to Sweetwater (Texas) | 1,166.28 mi (1,876.95 km) |
| Winter Springs to Sycamore (Illinois) | 1,008.84 mi (1,623.57 km) |
| Winter Springs to Sylacauga (Alabama) | 428.44 mi (689.51 km) |
| Winter Springs to Sylvania (Ohio) | 910.03 mi (1,464.56 km) |
| Winter Springs to Syosset (New York) | 945.86 mi (1,522.21 km) |
| Winter Springs to Syracuse (New York) | 1,031.78 mi (1,660.49 km) |
