| The Villages to Oskaloosa (Iowa) | 1,044.71 mi (1,681.30 km) |
| The Villages to Oswego (Illinois) | 952.11 mi (1,532.27 km) |
| The Villages to Oswego (New York) | 1,050.11 mi (1,690.00 km) |
| The Villages to Otsego (Minnesota) | 1,296.54 mi (2,086.58 km) |
| The Villages to Ottawa (Illinois) | 942.32 mi (1,516.52 km) |
| The Villages to Ottawa (Kansas) | 1,013.09 mi (1,630.41 km) |
| The Villages to Ottumwa (Iowa) | 1,022.77 mi (1,646.00 km) |
| The Villages to Overland (Missouri) | 829.40 mi (1,334.79 km) |
| The Villages to Overland Park (Kansas) | 1,001.18 mi (1,611.24 km) |
| The Villages to Overlea (Maryland) | 787.17 mi (1,266.82 km) |
| The Villages to Oviedo (Florida) | 51.41 mi (82.74 km) |
| The Villages to Owasso (Oklahoma) | 952.19 mi (1,532.40 km) |
| The Villages to Owatonna (Minnesota) | 1,218.45 mi (1,960.90 km) |
| The Villages to Owensboro (Kentucky) | 679.32 mi (1,093.27 km) |
| The Villages to Owings Mills (Maryland) | 784.11 mi (1,261.90 km) |
