| Winter Haven to Oskaloosa (Iowa) | 1,106.31 mi (1,780.44 km) |
| Winter Haven to Oswego (Illinois) | 1,015.96 mi (1,635.03 km) |
| Winter Haven to Oswego (New York) | 1,105.34 mi (1,778.88 km) |
| Winter Haven to Otsego (Minnesota) | 1,359.59 mi (2,188.04 km) |
| Winter Haven to Ottawa (Illinois) | 1,005.98 mi (1,618.97 km) |
| Winter Haven to Ottawa (Kansas) | 1,069.39 mi (1,721.02 km) |
| Winter Haven to Ottumwa (Iowa) | 1,084.34 mi (1,745.07 km) |
| Winter Haven to Overland (Missouri) | 890.74 mi (1,433.51 km) |
| Winter Haven to Overland Park (Kansas) | 1,058.49 mi (1,703.48 km) |
| Winter Haven to Overlea (Maryland) | 838.67 mi (1,349.71 km) |
| Winter Haven to Oviedo (Florida) | 54.51 mi (87.73 km) |
| Winter Haven to Owasso (Oklahoma) | 1,003.30 mi (1,614.65 km) |
| Winter Haven to Owatonna (Minnesota) | 1,281.22 mi (2,061.93 km) |
| Winter Haven to Owensboro (Kentucky) | 742.70 mi (1,195.26 km) |
| Winter Haven to Owings Mills (Maryland) | 836.30 mi (1,345.89 km) |
