Background: In adults with chronic heart failure (HF; defined as people with previously diagnosed left ventricular dysfunction) telemonitoring randomized controlled trials (RCTs) failed to consistently demonstrate improved clinical outcomes. We aimed to examine if patient and HF characteristics are associated with device preferences and use. Methods: Using a cross-sectional, multicenter, international design, ambulatory and hospitalized adults with HF in Ohio, California, and Denmark viewed a six-minute video of telemonitoring configurations (tablet, smart phone, and key fob) and completed questionnaires. Comparative analyses were performed and when significant, pairwise comparisons were performed using Bonferroni-adjusted significance levels. Results: Of 206 participants, 48.2% preferred smart phones for telemonitoring, especially when traveling (54.8%), with new/worsening symptoms (50%), for everyday use (50%), and connecting with doctors (48.5%). Participants preferred two-way communication and a screen with words over voice or number pads. Of device purposes, allowing for nurse communication ranked highest, followed by maintaining overall health. Very few patient and HF factors were associated with device preferences. Patients with higher health literacy (p = 0.007), previous/current device use history (p = 0.008), higher education level (p = 0.035), and married/cohabitating status (p = 0.023) had higher perceptions of ease of using devices. Those who were asymptomatic or had mild HF had higher self-confidence for health devices (p = 0.024) and non-white patients perceived devices as more useful (p = 0.033). Conclusion: Telemonitoring use may be enhanced by simple plug-and-play type devices, two-way communication, and features that meet patients’ personal learning and use needs.