| Winter Haven to Olympia (Washington) | 2,570.92 mi (4,137.49 km) |
| Winter Haven to Olympia Heights (Florida) | 178.99 mi (288.06 km) |
| Winter Haven to Omaha (Nebraska) | 1,222.89 mi (1,968.06 km) |
| Winter Haven to On Top of the World Designated Place (Florida) | 83.51 mi (134.40 km) |
| Winter Haven to Onalaska (Wisconsin) | 1,217.01 mi (1,958.59 km) |
| Winter Haven to Oneida (New York) | 1,094.08 mi (1,760.75 km) |
| Winter Haven to Oneonta (New York) | 1,064.97 mi (1,713.91 km) |
| Winter Haven to Ontario (California) | 2,154.94 mi (3,468.04 km) |
| Winter Haven to Ontario (Oregon) | 2,236.30 mi (3,598.98 km) |
| Winter Haven to Opa-locka (Florida) | 170.96 mi (275.14 km) |
| Winter Haven to Opelika (Alabama) | 388.82 mi (625.74 km) |
| Winter Haven to Opelousas (Louisiana) | 649.01 mi (1,044.47 km) |
| Winter Haven to Orange (California) | 2,167.01 mi (3,487.47 km) |
| Winter Haven to Orange (Texas) | 742.34 mi (1,194.69 km) |
| Winter Haven to Orange City (Florida) | 68.54 mi (110.30 km) |
