Potentially tridentate, phosphine‐containing Schiff bases with P,N,O and P,N,P donor sets have been prepared from 2‐(diphenylphosphino)benzaldehyde, salicylaldehyde, 2‐aminophenol and 2‐((diphenylphosphino)phenyl)methylamine and reacted with (NEt4)2[Re(CO)3Br3] in methanol. Deprotonation and the formation of neutral [Re(CO)3(L)] complexes with tridentate coordination of the Schiff bases has been obtained for the salicylidene derivatives, while the potential P,N,P ligand L3 forms [Re(CO)3Br(L3)] with the Schiff base in a bidentate bonding mode. The formation of a cationic [Re(CO)3(L3)]+ complex with tripodal coordination of the organic ligand could be achieved by the addition of Ag(PF6) to the reaction mixture. The obtained rhenium(I) complexes were studied spectroscopically and by X‐ray diffraction.