| Winter Garden to Olympia (Washington) | 2,551.24 mi (4,105.83 km) |
| Winter Garden to Olympia Heights (Florida) | 209.51 mi (337.17 km) |
| Winter Garden to Omaha (Nebraska) | 1,198.14 mi (1,928.22 km) |
| Winter Garden to On Top of the World Designated Place (Florida) | 57.10 mi (91.90 km) |
| Winter Garden to Onalaska (Wisconsin) | 1,185.99 mi (1,908.67 km) |
| Winter Garden to Oneida (New York) | 1,057.14 mi (1,701.30 km) |
| Winter Garden to Oneonta (New York) | 1,028.24 mi (1,654.80 km) |
| Winter Garden to Ontario (California) | 2,148.52 mi (3,457.71 km) |
| Winter Garden to Ontario (Oregon) | 2,218.32 mi (3,570.03 km) |
| Winter Garden to Opa-locka (Florida) | 200.31 mi (322.37 km) |
| Winter Garden to Opelika (Alabama) | 362.61 mi (583.57 km) |
| Winter Garden to Opelousas (Louisiana) | 644.76 mi (1,037.64 km) |
| Winter Garden to Orange (California) | 2,160.89 mi (3,477.61 km) |
| Winter Garden to Orange (Texas) | 740.42 mi (1,191.59 km) |
| Winter Garden to Orange City (Florida) | 32.95 mi (53.03 km) |
