A phenyliodine(III) diacetate-promoted/1,1,1,3,3,3-hexafluoroisopropanol-controlled dearomative spirocyclization of phenolic ketones was reported, providing two libraries of structurally interesting scaffolds, spirocyclohexadienonic ketals and their acetoxylated counterparts, in moderate to excellent yields under mild conditions. Control experiments unravel that the reaction proceeds through a spirocyclohexadienone-oxocarbenium cation species. In addition, an in situ-generated hypervalent iodine(III)-catalyzed version, as well as the late-stage transformation of products via conjugate additions, was also realized.