The existing model for calculating the settlements of group piles is based on the principle of superposition, which fails to calculate the interaction between piles more comprehensively and to take into consideration the influence of slip between pile and soil. In this paper, the interaction between group piles is analyzed from a novel perspective. It is assumed that the interaction between piles is a dynamic equilibrium process, i.e., additional shear forces and additional displacements are continuously transferred between piles until a state of equilibrium is reached. On this basis, we propose a new model for calculating the settlements of group piles considering pile–soil slip. First, a calculation method for pile–side resistance is developed considering the influence of slip. Based on experience with the pile–soil interface, pile–side soils can be categorized as near–pile soil and far–pile soil, and different load–transfer models are applied to describe their mechanical states. By equating pile–side soils into a nonlinear spring and connecting them in series to determine the overall equivalent stiffness considering the effect of pile–soil slip, the pile–side resistance under different loading conditions can be accurately determined. Secondly, equilibrium analysis of the pile unit is carried out when the equilibrium condition is reached, and the stiffness matrix for load transfer is derived. Therefore, in this paper, the interaction between piles is concentrated in this matrix, which makes the proposed model for pile settlement calculation clearer and more concise. Compared with measured data, the proposed method can capture the main features of the load–settlement behavior of group piles.