Background/Objectives: The objective of this research was to analyze the experiences and factors associated with perinatal grief in mothers in the urban context of Santa Cruz de la Sierra, Bolivia. Methods: The sample consisted of seven mothers who experienced a loss during pregnancy up to the second month after the baby's birth, occurring between 2015 and 2020 in the city of Santa Cruz de la Sierra. The mean age of the mothers was 34.86 years (SD = 3.13), and they belonged to middle or upper-middle socioeconomic levels. Data were collected through semi-structured interviews and analyzed using descriptive qualitative analysis. Results: The identified characteristics of perinatal grief were sadness, anger, guilt, emotional numbness, social isolation, and anxiety. Factors contributing to grief processing included support from the partner and family, when they accommodated and respected the mother's needs. Factors hindering the grieving process included social and cultural environments that often silence and minimize the loss, a history of previous losses, the desire to be pregnant, and the mother's life expectations and projects focused on motherhood. Conclusions: In conclusion, this research suggests that perinatal losses in the Bolivian context may be influenced by factors such as knowledge of the cause of death, previous loss experiences, and their emotional effects. The limitations of the study include the lack of diversity in participants' educational and socioeconomic backgrounds and the restriction of the sample to an urban area in Bolivia. Emotional interventions to support these bereaved mothers in those complex moments should be integrated in the Bolivian healthcare system.