| The Villages to Olympia (Washington) | 2,516.92 mi (4,050.59 km) |
| The Villages to Olympia Heights (Florida) | 241.89 mi (389.29 km) |
| The Villages to Omaha (Nebraska) | 1,163.79 mi (1,872.94 km) |
| The Villages to On Top of the World Designated Place (Florida) | 22.80 mi (36.69 km) |
| The Villages to Onalaska (Wisconsin) | 1,153.55 mi (1,856.46 km) |
| The Villages to Oneida (New York) | 1,040.39 mi (1,674.34 km) |
| The Villages to Oneonta (New York) | 1,012.81 mi (1,629.96 km) |
| The Villages to Ontario (California) | 2,117.91 mi (3,408.45 km) |
| The Villages to Ontario (Oregon) | 2,184.20 mi (3,515.14 km) |
| The Villages to Opa-locka (Florida) | 233.18 mi (375.27 km) |
| The Villages to Opelika (Alabama) | 328.37 mi (528.47 km) |
| The Villages to Opelousas (Louisiana) | 615.71 mi (990.88 km) |
| The Villages to Orange (California) | 2,130.40 mi (3,428.55 km) |
| The Villages to Orange (Texas) | 712.50 mi (1,146.65 km) |
| The Villages to Orange City (Florida) | 42.43 mi (68.28 km) |
