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The poor water solubility of rebamipide was enhanced by the mixed micelles of transglycosylated stevia (Stevia-G) and trimethylammonium chloride with varying carbon chain length (C n TAC, n = 14, 16, and 18). Fluorometry, isothermal titration calorimetry (ITC) and dynamic light scattering techniques examined the aggregation properties of Stevia-G and C n TAC. Synergism was found between Stevia-G and C n TAC using the approaches of Clint and Rubingh. The negative interaction parameter (average β m = −4.17, −5.47, and −7.07) and excess free energy (average ΔG° ex = −2.47, −3.06, and −3.88 kJ mol–1) increased with increasing chain length of C n TAC. The negative B 1 values by the Maeda approach suggested that chain–chain interactions contribute to the formation of a mixed micelle. The solubilization of rebamipide in the mixed micelle was evaluated in the term of the molar solubilization ratio (MSR) and partition coefficient (K m). The K m from the Stevia-G/C16TAC system was highest at a low mole fraction of C n TAC (0.2–0.6). In conclusion, the solubilization of rebamipide was more favorable between Stevia-G and C16TAC, although the stability of the mixed micelle was enhanced by an increase in hydrophobicity of the longer chain lengths used in C n TAC.