One of the ways companies seeking their competitive advantage and gaining revenue from their products is by using a freemium model, where both a free and paid version of the service exist within the platform. This study aims to examine the factors that affects customer’s loyalty intention (continuance intention and intention to purchase premium plan) on a freemium streaming service, specifically in music and movie category. From previous research, we identified the influencing factors, namely satisfaction; user characteristics (free mentality and personal innovativeness); relational characteristics (brand familiarity, interpersonal relationship); and marketplace characteristics (value for money, relative advantage, switching cost, and alternative attractiveness). This quantitative cross-sectional study collected data from 978 eligible respondents using self-administered online questionnaire distributed through social media. After confirming that all variables are valid and reliable, we analyze the data and test the hypotheses using structural equation modeling. The results show that satisfaction, brand familiarity, interpersonal relationships, and switching cost significantly affect both continuance intention and intention to purchase, while free mentality and personal innovativeness only significantly affect intention to purchase. Value for money and relative advantage also significantly affect intention to purchase. This study provides insight to companies in online streaming freemium business on how to increase loyalty intentions from their existing customers. © 2021, The Author(s), under exclusive license to Springer Nature Singapore Pte Ltd.