The osmotic dehydration (OD) of tomatoes in solutions of alternative sweeteners was investigated using Response Surface Methodology (RSM), while selected desirability functions were implemented in order to define the optimum process parameters (temperature/duration of osmotic treatment, osmotic solution composition and concentration). Mass exchange, color and texture were measured during the process. Changes in color occurred rapidly at the beginning of the process, while firmness was significantly increased, indicating that OD processing led to tomato texture improvement. Color and firmness changes were adequately modeled using a polynomial model. RSM coupled with desirability functions was applied to optimize OD procedure in terms of color retention and maximum solid gain, a requirement for candied products. A maximum desirability was obtained by incorporating oligofructose into the osmotic solution, at relatively short treatment times. Results were validated and sensory analysis was conducted at the optimized conditions to assess samples’ organoleptic acceptance.