| Winter Garden to Oskaloosa (Iowa) | 1,078.50 mi (1,735.67 km) |
| Winter Garden to Oswego (Illinois) | 983.83 mi (1,583.32 km) |
| Winter Garden to Oswego (New York) | 1,068.25 mi (1,719.18 km) |
| Winter Garden to Otsego (Minnesota) | 1,329.44 mi (2,139.53 km) |
| Winter Garden to Ottawa (Illinois) | 974.48 mi (1,568.28 km) |
| Winter Garden to Ottawa (Kansas) | 1,047.53 mi (1,685.84 km) |
| Winter Garden to Ottumwa (Iowa) | 1,056.58 mi (1,700.40 km) |
| Winter Garden to Overland (Missouri) | 863.30 mi (1,389.35 km) |
| Winter Garden to Overland Park (Kansas) | 1,035.63 mi (1,666.69 km) |
| Winter Garden to Overlea (Maryland) | 802.02 mi (1,290.72 km) |
| Winter Garden to Oviedo (Florida) | 26.10 mi (42.00 km) |
| Winter Garden to Owasso (Oklahoma) | 986.10 mi (1,586.98 km) |
| Winter Garden to Owatonna (Minnesota) | 1,251.58 mi (2,014.23 km) |
| Winter Garden to Owensboro (Kentucky) | 711.95 mi (1,145.77 km) |
| Winter Garden to Owings Mills (Maryland) | 799.54 mi (1,286.73 km) |
