This article describes the synthesis of functional pressure sensitive adhesives (PSA) derived from plant oils and highlights how the viscoelastic and adhesion properties can be tailored by incorporation of the cereal based monomer 1,4:3,6-dianhydro-D-glucitol (isosorbide). At first, the synthesis of carboxylic acid terminated polyesters from bulk polycondensation of dimerized fatty acids with several diols such as diner fatty diol, butanediol or isosorbide is described The resulting polymers were then fully characterized, before being cured with epoxidized plant oils to form viscoelastic bioelastomers with tunable stickiness degrees. The role of isosorbide in the rheological and adhesion profiles of the glues was investigated and discussed These renewable coatings combined the intrinsic flexibility of lipids with the polarity of sugars and demonstrate interesting performances. This article exemplifies that in soft materials such as PSA, isosorbide can play multiple roles such as adjusting the glass transition temperature, modulating the viscoelastic spectrum, and tuning the interfacial properties of the glue, and this gives a new twist to this promising renewable monomer that, up to now, has mostly been incorporated in rigid polymeric systems.