Glycolipids have become an ecofriendly alternative to chemically obtained surfactants, mainly for the cosmetic, pharmaceutical, and food industries. However, the sustainable production of these compounds is still challenging, because: (i) water is a recognized inhibitor, (ii) multiphases make the use of cosolvent reaction medium necessary, and (iii) there are difficulties in finding a source for both starting materials. This study used sugars and lipids from peach palm fruit shells or model compounds as substrates to synthesize glycolipids on five different renewable deep eutectic solvents (Re-DES) alone or with a cosolvent system. Substrate conversions up to 24.84% (so far, the highest reported for this reaction on DES), showing (1) the non-precipitation of glucose in the solvent, (2) emulsification and (3) low viscosity (e.g., more favorable mass transfer) as the main limiting factors for these heterogeneous enzymatic processes. The resulting conversion was reached using a cosolvent system Re-DES:DMSO:t-butanol that was robust enough to allow conversions in the range 19–25%, using either model compounds or sugar and fatty acid extracts, with free or immobilized enzymes. Finally, the characterization of the in-house synthesized glycolipids by surface tension demonstrated their potential as biosurfactants, for instance, as an alternative to alcohol ethoxylates, industrially produced using less sustainable methods.