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We undertook a qualitative analysis informed by grounded theory to explore pregnancy intention and the barriers to contraceptive use as perceived by homeless women with children. Semi-structured interviews (n = 22) were performed in English and in Spanish. The dominant theme emerging from the interviews was a strong desire to avoid pregnancy while homeless. However, few women in our sample used contraception or accessed reproductive health care consistently. There were multiple barriers to using contraception and to accessing reproductive health care services that homeless women reported: (1) inability to prioritize health due to competing demands, (2) shelter-related obstacles and restrictive provider practices that impede access to reproductive health care services and the use of contraception, and (3) change in the power dynamics of sexual relationships while homeless, making women more vulnerable to sexual exploitation. Findings suggest a multifactorial approach is needed to help homeless women use contraception and access reproductive health services.