| Winter Haven to Isabela (Puerto Rico) | 1,138.63 mi (1,832.45 km) |
| Winter Haven to Iselin (New Jersey) | 963.71 mi (1,550.94 km) |
| Winter Haven to Isla Vista (California) | 2,284.14 mi (3,675.97 km) |
| Winter Haven to Issaquah (Washington) | 2,542.78 mi (4,092.20 km) |
| Winter Haven to Ithaca (New York) | 1,038.89 mi (1,671.93 km) |
| Winter Haven to Ives Estates (Florida) | 169.63 mi (272.99 km) |
| Winter Haven to Jackson (Michigan) | 994.92 mi (1,601.18 km) |
| Winter Haven to Jackson (Mississippi) | 588.70 mi (947.42 km) |
| Winter Haven to Jackson (Missouri) | 794.64 mi (1,278.86 km) |
| Winter Haven to Jackson (Tennessee) | 673.46 mi (1,083.82 km) |
| Winter Haven to Jackson (Wyoming) | 1,933.43 mi (3,111.55 km) |
| Winter Haven to Jacksonville (Alabama) | 466.96 mi (751.49 km) |
| Winter Haven to Jacksonville (Arkansas) | 775.82 mi (1,248.57 km) |
| Winter Haven to Jacksonville (Florida) | 160.33 mi (258.03 km) |
| Winter Haven to Jacksonville (Illinois) | 944.89 mi (1,520.65 km) |
