To improve the mechanical properties of hydroxyapatite (HA)/waterborne polyurethane (WBPU) composites, the hydroxyl group of HA was modified by urethane reactions: the hydroxyl groups of HA were reacted with aliphatic or cyclic diisocyanate, and then the modified HAs were extended by adding polyol and/or ${varepsilon}$-caprolactone. Composites were prepared by the prepolymer process method: the modified HA was directly pured into the urethane reaction of isocyanate and polyol. The properties of modified HA/WBPU composites were investigated by thermogravimetric analysis, tensile strength, and water resistance. The results showed that the reactivity of aliphatic diisocyanate to the hydroxy group of HA was faster than that of cyclic one. Comparing to those of pure HA/WBPU composite films, the thermal stability, water resistance, and mechanical properties of the modified composite films increased with a degree of modification of HA.