In this paper, strain-controlled non-proportional creep-fatigue tests under three non-proportional loading paths were performed for type 304 stainless steel. The strain holding period at the peak axial or peak shear strains was introduced to investigate the effect of the holding position on the creep damage accumulation. Compared with the other non-proportional loading paths, the circle loading path generated the most detrimental effect on the material life. In addition, the introduction of the holding period reduced the material life, in which axial holding resulted in a greater creep damage than that of the shear holding. A post-examination method through the electron backscattered diffraction (EBSD) observations was conducted to reveal the damage mechanisms under various loading paths. The variations of six EBSD-based disorientation parameters showed the significant effect of the loading path and holding position on the damage mechanisms. Subsequently, a multiaxial damage factor (MDF)-involved strain energy density exhaustion (SEDE) model and a non-proportional energy parameter (NPEP)-involved Ostergren model were collaborated to provide a precise prediction within a factor of 1.5 for non-proportional creep-fatigue life distributions.