Eight molecules, four peptides (SPs) and four lipopeptides (LPs) derived by rational design from surfactin, a well‐known secreted biosurfactant from Bacillus subtilis, were produced employing Fmoc‐based solid‐phase synthesis. These new peptides were tested to evaluate their potential biosurfactant and biological activities, aiming at possible applications in industrial, biological, pharmaceutical, and medical use. Five molecules (SP1, SP2, SP4, LP5, and LP8) presented potential for medical uses, mainly due to their drug delivery properties as suggested by their synergistic activity with the antibiotic vancomycin against Staphylococcus aureus. All synthetic peptides showed low toxicity against Vero cell cultures, in assays of hemolysis, and in different cytotoxicity assays. In addition, we found that three peptides (SP1, LP6, and LP7) had potential technological and industrial use because of their emulsifying capacity, low toxicity, and ability to physically stabilize solutions. These novel molecules retained some properties of the parental molecule (surfactin, which was originally obtained through nonribosomal synthesis in Bacillus subtilis) but have the advantage of being linear peptides, which can be produced at large scales through the use of conventional heterologous protein expression protocols. We synthesized eight novel linear peptides derived from surfactin using classical Fmoc‐based solid‐phase synthesis method for their production. All of the peptides had surface tension reduction activity, and several of them facilitated the delivery of the antibiotic vancomycin, exhibiting synergism with its action against a virulent strain of S aureus (MU50). Cytotoxicity was evaluated through different assays; the promising results indicated that all of the peptides were poorly cytotoxic and that only one (LP8) had considerable hemolytic activity.