We consider analytical, numerical, and experimental approaches developed to describe the mechanical contact between a rigid indenter and an elastic half-space coated with an elastic layer. Numerical simulations of the indentation process were performed using the recently generalized boundary element method (BEM). Analytical approximation of the dependence of contact stiffness on the indenter diameter was used to verify the results of BEM simulations. Adhesive contacts of hard indenters of different shapes with soft rubber layers have been experimentally studied using specially designed laboratory equipment. The comparison of the results from all three implemented methods shows good agreement of the obtained data, thus supporting the generalized BEM simulation technique developed for the JKR limit of very small range of action of adhesive forces. It was shown that the half-space approximation is asymptotical at high ratios of layer thickness h to cylindrical indenter diameter D; however, it is very slowly. Thus, at the ratio h/D = 3.22, the half-space approximation leads to 20% lower contact stiffness compared with that obtained for finite thickness using both an experiment and simulation.