| Winter Springs to Orangeburg (South Carolina) | 332.77 mi (535.55 km) |
| Winter Springs to Orangevale (California) | 2,377.67 mi (3,826.48 km) |
| Winter Springs to Orchards (Washington) | 2,519.89 mi (4,055.37 km) |
| Winter Springs to Orcutt (California) | 2,323.91 mi (3,739.98 km) |
| Winter Springs to Oregon (Ohio) | 903.89 mi (1,454.66 km) |
| Winter Springs to Oregon (Wisconsin) | 1,082.43 mi (1,742.00 km) |
| Winter Springs to Oregon City (Oregon) | 2,517.40 mi (4,051.36 km) |
| Winter Springs to Orem (Utah) | 1,896.86 mi (3,052.71 km) |
| Winter Springs to Orinda (California) | 2,425.90 mi (3,904.11 km) |
| Winter Springs to Orland Park (Illinois) | 966.37 mi (1,555.23 km) |
| Winter Springs to Orlando (Florida) | 15.17 mi (24.41 km) |
| Winter Springs to Ormond Beach (Florida) | 43.34 mi (69.75 km) |
| Winter Springs to Oro Valley (Arizona) | 1,780.42 mi (2,865.31 km) |
| Winter Springs to Oroville (California) | 2,400.94 mi (3,863.94 km) |
| Winter Springs to Oshkosh (Wisconsin) | 1,133.32 mi (1,823.90 km) |
