Herein, we report a novel iodine(III)-mediated intramolecular dearomative spirocyclization of indole derivatives to generate highly strained spirocyclobutyl, spirocyclopentyl, and spirocyclohexyl indolenines in moderate to good yields. A set of structurally novel, densely functionalized spiroindolenines with broad functional group compatibility was efficiently constructed in this way under mild reaction conditions. Moreover, the β-enamine ester as a versatile functional group in the product provides great convenience for the synthesis of bioactive compounds and related natural products.