We present a comprehensive study on Higgs pair production in various archetypical extended Higgs sectors such as the real and the complex 2-Higgs-Doublet Model, the 2-Higgs-Doublet Model augmented by a real singlet field and the Next-to-Minimal Supersymmetric extension of the Standard Model. We take into account all relevant theoretical and experimental constraints, in particular the experimental limits on non-resonant and resonant Higgs pair production. We present the allowed cross sections for Standard Model (SM)-like Higgs pair production and the ranges of the SM-like Yukawa and trilinear Higgs self-coupling that are still compatible with the applied constraints. Furthermore, we give results for the pair production of a SM-like with a non-SM-like Higgs boson and for the production of a pair of non-SM-like Higgs bosons. We find that di-Higgs production in the models under investigation can exceed the SM rate substantially, not only in the non-resonance region but also due to resonant enhancement. We give several benchmarks with interesting features such as large cross sections, the possibility to test CP violation, Higgs-to-Higgs cascade decays or di-Higgs production beating single Higgs production. In all of our benchmark points, the next-to-leading order QCD corrections are included in the large top-mass limit. For these points, we found that, depending on the model and the Higgs pair final state, the corrections increase the leading order cross section by a factor of 1.79 to 2.24. We also discuss the relation between the description of Higgs pair production in an effective field theory approach and in the specific models investigated here.