| Winter Springs to Oskaloosa (Iowa) | 1,080.71 mi (1,739.23 km) |
| Winter Springs to Oswego (Illinois) | 981.62 mi (1,579.77 km) |
| Winter Springs to Oswego (New York) | 1,053.72 mi (1,695.80 km) |
| Winter Springs to Otsego (Minnesota) | 1,329.32 mi (2,139.33 km) |
| Winter Springs to Ottawa (Illinois) | 973.03 mi (1,565.93 km) |
| Winter Springs to Ottawa (Kansas) | 1,054.51 mi (1,697.07 km) |
| Winter Springs to Ottumwa (Iowa) | 1,058.85 mi (1,704.06 km) |
| Winter Springs to Overland (Missouri) | 865.97 mi (1,393.65 km) |
| Winter Springs to Overland Park (Kansas) | 1,041.89 mi (1,676.76 km) |
| Winter Springs to Overlea (Maryland) | 785.87 mi (1,264.73 km) |
| Winter Springs to Oviedo (Florida) | 5.47 mi (8.81 km) |
| Winter Springs to Owasso (Oklahoma) | 996.16 mi (1,603.16 km) |
| Winter Springs to Owatonna (Minnesota) | 1,251.99 mi (2,014.88 km) |
| Winter Springs to Owensboro (Kentucky) | 711.50 mi (1,145.05 km) |
| Winter Springs to Owings Mills (Maryland) | 783.68 mi (1,261.21 km) |
