Herein, a kind of dual acid‐sensitive nanoparticles based on monomethoxy poly(ethylene glycol)‐imine‐β‐cyclodextrin is constructed by a facile phenylboronic acid‐cross‐linked way. The data of dynamic light scattering and transmission electron microscope reveal the cross‐linked nanoparticles have improved stability. The cross‐linked nanoparticles could easily self‐assemble and load the anticancer drug at neutral pH condition. However, when the drug‐loaded nanoparticles are delivered to extracellular tumor sites (pH ≈6.8), the surface of the nanoparticles would be amino positively charged and easily internalized by tumor cell due to the cleavage of the acid‐labile benzoic–imine. Subsequently, with the acidity in subcellular compartments significantly increasing (such as the endosome pH ≈5.3), the loaded drug would fast release from the endocytosis carriers due to the hydrolysis of boronate ester. These features suggest that these dual acid‐sensitive cross‐linked nanoparticles not only possess excellent biocompatibility but also can efficiently load and deliver anticancer drug into tumor cells to enhance the inhibition of cellular proliferation, outlining a favorable platform as drug carriers.