A rigid diol with a cyclic acetal structure was synthesized by facile acetalation of fructose-based 5-hydroxymethyl furfural (HMF) and partly bio-based di-trimethylolpropane (di-TMP). This diol (Monomer T) was copolymerized with potentially bio-based flexible polytetrahydrofuran and diisocyanates to prepare thermoplastic poly(cycloacetal-urethane)s. A modified one-step solution polymerization protocol resulted in relatively high molecular weights (Mn ∼ 41.5-98.9 kDa). All the obtained poly(cycloacetal-urethane)s were amorphous with tuneable glass transition temperatures up to 104 °C. Thermogravimetric analysis indicated that these polymers were thermally stable up to 253 °C and had a relatively high pyrolysis char residue, which may indicate potential inherent flame resistance. Melt rheology measurements were performed to determine a suitable processing window between 165-186 °C, after which the polymer was successfully melt-spun into ∼150 meters of homogeneous fibres at 185 °C. The resulting fibres could be readily hydrolysed under acidic conditions, resulting in partial recovery of the original chemical building blocks.