| Pleasantville to Olympia (Washington) | 2,451.96 mi (3,946.04 km) |
| Pleasantville to Olympia Heights (Florida) | 1,002.63 mi (1,613.58 km) |
| Pleasantville to Omaha (Nebraska) | 1,138.80 mi (1,832.72 km) |
| Pleasantville to On Top of the World Designated Place (Florida) | 836.94 mi (1,346.92 km) |
| Pleasantville to Onalaska (Wisconsin) | 914.20 mi (1,471.26 km) |
| Pleasantville to Oneida (New York) | 261.59 mi (420.99 km) |
| Pleasantville to Oneonta (New York) | 213.71 mi (343.94 km) |
| Pleasantville to Ontario (California) | 2,392.18 mi (3,849.85 km) |
| Pleasantville to Ontario (Oregon) | 2,188.81 mi (3,522.56 km) |
| Pleasantville to Opa-locka (Florida) | 989.48 mi (1,592.41 km) |
| Pleasantville to Opelika (Alabama) | 763.50 mi (1,228.74 km) |
| Pleasantville to Opelousas (Louisiana) | 1,164.92 mi (1,874.75 km) |
| Pleasantville to Orange (California) | 2,409.70 mi (3,878.04 km) |
| Pleasantville to Orange (Texas) | 1,262.25 mi (2,031.40 km) |
| Pleasantville to Orange City (Florida) | 818.93 mi (1,317.95 km) |
