| The Villages to Seymour (Indiana) | 728.95 mi (1,173.13 km) |
| The Villages to Seymour (Tennessee) | 492.93 mi (793.29 km) |
| The Villages to Shady Hills (Florida) | 48.32 mi (77.76 km) |
| The Villages to Shafter (California) | 2,209.29 mi (3,555.51 km) |
| The Villages to Shaker Heights (Ohio) | 868.92 mi (1,398.40 km) |
| The Villages to Shakopee (Minnesota) | 1,264.37 mi (2,034.81 km) |
| The Villages to Sharon (Pennsylvania) | 856.07 mi (1,377.72 km) |
| The Villages to Sharonville (Ohio) | 730.27 mi (1,175.25 km) |
| The Villages to Shasta Lake (California) | 2,407.41 mi (3,874.35 km) |
| The Villages to Shawnee (Kansas) | 1,011.85 mi (1,628.41 km) |
| The Villages to Shawnee (Oklahoma) | 981.55 mi (1,579.65 km) |
| The Villages to Sheboygan (Wisconsin) | 1,073.11 mi (1,727.01 km) |
| The Villages to Shelby (North Carolina) | 442.06 mi (711.43 km) |
| The Villages to Shelbyville (Indiana) | 765.63 mi (1,232.16 km) |
| The Villages to Shelbyville (Kentucky) | 669.19 mi (1,076.96 km) |
