| The Villages to Orangeburg (South Carolina) | 323.94 mi (521.34 km) |
| The Villages to Orangevale (California) | 2,332.23 mi (3,753.36 km) |
| The Villages to Orchards (Washington) | 2,476.81 mi (3,986.04 km) |
| The Villages to Orcutt (California) | 2,277.98 mi (3,666.06 km) |
| The Villages to Oregon (Ohio) | 884.59 mi (1,423.60 km) |
| The Villages to Oregon (Wisconsin) | 1,052.53 mi (1,693.88 km) |
| The Villages to Oregon City (Oregon) | 2,474.16 mi (3,981.77 km) |
| The Villages to Orem (Utah) | 1,852.32 mi (2,981.03 km) |
| The Villages to Orinda (California) | 2,380.30 mi (3,830.72 km) |
| The Villages to Orland Park (Illinois) | 937.62 mi (1,508.95 km) |
| The Villages to Orlando (Florida) | 49.26 mi (79.28 km) |
| The Villages to Ormond Beach (Florida) | 60.12 mi (96.76 km) |
| The Villages to Oro Valley (Arizona) | 1,734.54 mi (2,791.47 km) |
| The Villages to Oroville (California) | 2,355.69 mi (3,791.11 km) |
| The Villages to Oshkosh (Wisconsin) | 1,105.71 mi (1,779.46 km) |
