Dielectric elastomers are progressively emerging as one of the best-performing classes of electroactive polymers for electromechanical transduction. They are used for actuation devices driven by the so-called Maxwell stress effect. At present, the need for high-driving electric fields limits the use of these transduction materials in some areas of potential application, especially in the case of biomedical disciplines. A reduction of the driving fields may be achieved with new elastomers offering intrinsically superior electromechanical properties. So far, most attempts in this direction have been focused on the development of composites between elastomer matrixes and high-permittivity ceramic fillers, yielding limited results. In this work, a different approach was adopted for increasing the electromechanical response of a common type of dielectric elastomer. The technique consisted in blending, rather than loading, the elastomer (poly(dimethylsiloxane)) with a highly polarizable conjugated polymer (undoped poly(3-hexylthiophene)). The resulting material was characterised by dielectric spectroscopy, scanning electron microscopy, tensile mechanical analysis, and electromechanical transduction tests. Very low percentages (1–6 wt %) of poly(3-hexylthiophene) yielded both an increase of the relative dielectric permittivity and an unexpected reduction of the tensile elastic modulus. Both these factors synergetically contributed to a remarkable increase of the electromechanical response, which reached a maximum at 1 wt % content of conjugated polymer. Estimations based on a simple linear model were compared with the experimental electromechanical data and a good agreement was found up to 1 wt %. This approach may lead to the development of new types of materials suitable for several types of applications requiring elastomers with improved electromechanical properties.