| Winter Springs to Olympia (Washington) | 2,559.38 mi (4,118.93 km) |
| Winter Springs to Olympia Heights (Florida) | 212.70 mi (342.30 km) |
| Winter Springs to Omaha (Nebraska) | 1,202.88 mi (1,935.86 km) |
| Winter Springs to On Top of the World Designated Place (Florida) | 67.89 mi (109.26 km) |
| Winter Springs to Onalaska (Wisconsin) | 1,184.97 mi (1,907.03 km) |
| Winter Springs to Oneida (New York) | 1,041.85 mi (1,676.70 km) |
| Winter Springs to Oneonta (New York) | 1,012.28 mi (1,629.11 km) |
| Winter Springs to Ontario (California) | 2,163.86 mi (3,482.40 km) |
| Winter Springs to Ontario (Oregon) | 2,227.57 mi (3,584.93 km) |
| Winter Springs to Opa-locka (Florida) | 202.54 mi (325.96 km) |
| Winter Springs to Opelika (Alabama) | 367.19 mi (590.93 km) |
| Winter Springs to Opelousas (Louisiana) | 661.45 mi (1,064.50 km) |
| Winter Springs to Orange (California) | 2,176.35 mi (3,502.50 km) |
| Winter Springs to Orange (Texas) | 757.92 mi (1,219.76 km) |
| Winter Springs to Orange City (Florida) | 17.02 mi (27.40 km) |
