The behavior of different polymerizable surfactants was investigated in order to improve the water resistance of pressure sensitive adhesives (PSAs) based on acrylic acid (AA) and n-butyl acrylate (n-BA). Differences in the adhesion properties were found according to the chemical structure and the critical micelle concentration of the polymerizable surfactant, especially when compared to the non-polymerizable reference surfactant (Dowfax 2A1). The polymerizable surfactants with a branched structure resulted in more gel content and higher glass transition temperature in the adhesive. In general, the peel resistance and tack properties decreased with the use of polymerizable surfactants in the PSA formula. However, increased shear resistance was observed with respect to the PSA adhesive synthesized with the reference surfactant. Furthermore, the adhesives made with higher molecular weight polymerizable surfactants resulted in higher shear elastic modulus, shear strength and deformation energy than the rest of PSA adhesives. On the other hand, as expected, all the polymerizable surfactants studied contributed to improved water resistance of the PSA compared to the reference PSA prepared with a conventional surfactant. The covalent bond formed between the polymer and the surfactant limited the migration of the surfactant towards the air-film interface thus reducing the formation of water entry pathways. The polymerizable surfactants with linear molecular structure showed the best water resistance performance.