To analyze the load-settlement response of tapered pile and tapered pile group, a hyperbolic model and a bilinear hardening model were incorporated in the proposed approach. Based on the two proposed models, considering the concordant displacement and property of multilayered soil, an iterative program was developed to calculate the settlement of the tapered single pile. A finite difference program was employed to analyze the interaction between two piles. Then considering the boundary condition and the proposed interaction between piles, the iterative program was proposed for the settlement prediction of tapered pile groups under rigid and soft pile caps. Finally, the pile settlement and the pile group settlement predicted by the iterative programs were compared with the load-settlement response of three well-instrumented tests. The results demonstrate the validity of the simplified calculation method adopted in the prediction of load-settlement response of the tapered pile and tapered pile group.