Trends of 15 extreme and non‐extreme daily rainfall indices for Mexico and the southern United States are analyzed for the extended boreal winter (November–March) and summer (June–October) during 1981–2010. The analysis includes gridded observations (CHIRPS and Livneh), reanalyses (ERA5, ERA‐Interim, MERRA2, and CFSR), the regional climate model RegCM4.7 (forced by ERA‐Interim), and four general circulation models (GCMs) from the CMIP5 (HadGEM2‐ES, CNRM‐CM5, MPI‐ESM‐MR, and GFDL‐ESM2M). The domain is divided into 13 regions with similar seasonal rainfall patterns according to the k‐means algorithm applied to CHIRPS monthly precipitation, as a reference. Gridded observations and reanalyses (O&R) show similar regional annual cycles and metrics of precipitation. The two observational data sets show the largest differences in the magnitude of some indices in the wettest region (southeastern Mexico) and in the monsoon. During summer, O&R show positive significant trends in extreme rainfall indices in regions commonly affected by tropical cyclones (southern Baja California Peninsula, northeastern Mexico, and the southeastern United States), while negative significant trends of seasonal accumulation of rainfall are seen in the Mediterranean Californias and the Sonoran Desert region. There is an agreement among most data sets that the frequency and intensity of extreme winter precipitation indices have declined in northwest Mexico and the southwestern United States, but trends are not statistically significant, while southeastern Mexico shows significant increases in 5‐days accumulation (rx5d). ERA5 followed by MERRA2 show the best performance. RegCM4.7 reproduces the annual cycle of precipitation in most of the regions and captures the main trend signals especially in winter, but it has difficulties in reproducing the summer interannual variability of few indices. The GCMs tend to overestimate (underestimate) the annual cycle of precipitation and the median values of extreme indices in the driest (wettest) regions. They are not able to capture the regional trends of the indices.