| Winter Springs to Oakleaf Plantation (Florida) | 107.73 mi (173.38 km) |
| Winter Springs to Oakley (California) | 2,399.99 mi (3,862.41 km) |
| Winter Springs to Oakton (Virginia) | 740.45 mi (1,191.64 km) |
| Winter Springs to Oakville (Missouri) | 851.11 mi (1,369.73 km) |
| Winter Springs to Oatfield (Oregon) | 2,518.56 mi (4,053.23 km) |
| Winter Springs to Ocala (Florida) | 63.08 mi (101.51 km) |
| Winter Springs to Ocean Acres (New Jersey) | 861.15 mi (1,385.89 km) |
| Winter Springs to Ocean City (New Jersey) | 824.15 mi (1,326.35 km) |
| Winter Springs to Ocean Pines (Maryland) | 756.56 mi (1,217.57 km) |
| Winter Springs to Ocean Pointe (Hawaii) | 4,753.36 mi (7,649.80 km) |
| Winter Springs to Ocean Springs (Mississippi) | 467.00 mi (751.56 km) |
| Winter Springs to Oceanside (California) | 2,147.54 mi (3,456.13 km) |
| Winter Springs to Oceanside (New York) | 931.39 mi (1,498.93 km) |
| Winter Springs to Ocoee (Florida) | 17.64 mi (28.39 km) |
| Winter Springs to Oconomowoc (Wisconsin) | 1,073.59 mi (1,727.78 km) |
