| Winter Garden to Odenton (Maryland) | 779.38 mi (1,254.28 km) |
| Winter Garden to Odessa (Texas) | 1,258.08 mi (2,024.69 km) |
| Winter Garden to Ogden (Utah) | 1,917.92 mi (3,086.59 km) |
| Winter Garden to Oildale (California) | 2,230.92 mi (3,590.33 km) |
| Winter Garden to Ojus (Florida) | 199.25 mi (320.66 km) |
| Winter Garden to Okemos (Michigan) | 991.15 mi (1,595.10 km) |
| Winter Garden to Oklahoma City (Oklahoma) | 1,046.33 mi (1,683.91 km) |
| Winter Garden to Okmulgee (Oklahoma) | 973.34 mi (1,566.44 km) |
| Winter Garden to Olathe (Kansas) | 1,040.99 mi (1,675.30 km) |
| Winter Garden to Old Jamestown (Missouri) | 868.30 mi (1,397.39 km) |
| Winter Garden to Oldsmar (Florida) | 73.59 mi (118.43 km) |
| Winter Garden to Olean (New York) | 952.18 mi (1,532.38 km) |
| Winter Garden to Olive Branch (Mississippi) | 656.51 mi (1,056.55 km) |
| Winter Garden to Olivehurst (California) | 2,385.29 mi (3,838.75 km) |
| Winter Garden to Olney (Maryland) | 777.05 mi (1,250.54 km) |
