Acetylacetonato‐platina[6]‐ and ‐platina[7]helicenes have been prepared from 2‐pyridyl‐substituted benzophenanthrene ligands by following a two‐step cycloplatination reaction. The photophysical properties (UV‐visible absorption and emission behavior) and chiroptical properties (circular dichroism and molar rotation) of the resolved enantiomers have been measured. These metallahelicenes constitute a novel family of easily accessible helicene derivatives that exhibit large and tuneable chiroptical properties that can be rationalized theoretically and compared to the parent [6]‐ and [7]carbohelicenes. Furthermore, they are red phosphors at room temperature and their large chiroptical properties can be modulated by oxidation of the metal center to PtIV. Hetero‐ and homochiral diastereomeric bis(metallahelicene)s that possess a rare PtIIIPtIII scaffold bridged by benzoato ligands have also been prepared. It is shown that the heterochiral (P,M)‐bis(PtIII–[6]helicene) 9 a1 can isomerize into the homochiral (P,P)‐ and (M,M)‐bis(PtIII–[6]helicene) 9 a2. Spectral assignments and an analysis of the optical rotation of these systems were made with the help of time‐dependent density functional theory. The calculations highlight the contributions of the metal centers to the chiroptical properties. For 9 a1 and 9 a2, σ–π conjugation between the helicenes and the PtPt moiety may contribute strongly to the optical rotation and electronic circular dichroism.