Soil water repellency (SWR) reduces the rates of wetting in dry soils and is known to interfere with water movement into as well as within the soils. The objective of this study was to investigate the hydrophysical characteristics of three water-repellent tropical exotic plantation forest soils in wet and dry seasons. The study sites were Eucalyptus grandis (EG), Pinus caribaea (PC), and Casuarina equisetifolia (CE) plantation forest soils located in the up-country intermediate zone (EG and PC), and low-country dry zone (CE). Field experiments were conducted to measure the infiltration rate, unsaturated hydraulic conductivity (k), water sorptivity (SW). Laboratory experiments were conducted to measure the potential SWR and water entry value (hwe). All three soils showed higher SWR in the dry season, where CE soils showed the highest. The EG soils showed the highest SWR in the wet season. Although SWR in all soils decreased with increasing depth in the wet season, only CE soils showed a significant decrease in SWR with soil depth in the dry season. Compared with the wet season, the k (–1 cm) was lower and hwe was higher in the dry season. However, SW did not show a significant difference between wet and dry seasons. Initial infiltration rate and k (–1 cm) showed a negative correlation with contact angle in all three soils. Soils showed positive linear correlations between k (–1 cm) and SW, and negative linear correlations between SW and hwe showing that surface water absorption is related to both subsurface unsaturated water flow and surface water entry pressure. It was clear that the water entry into soils and the subsurface water flow were hindered by the SWR. High water entry values in the dry season predict high potentials for intensified surface runoff and topsoil erosion. Future research will be required on the interactions between soil biology and soil properties such as pore structure that would influence water flow into and within soils.