Background Human Immunodeficiency Virus self-test (HIVST) refers to a process where a person collects his or her own specimen (blood or oral), performs a test and interprets the results. The interpretation of results can either be done in private or through support of a trusted partner. Self-test should be seen as screening and confirmatory tests are typically strongly encouraged. Study objective To determine facilitating factors for HIVST acceptability and uptake among men who have sex with men (MSM). Methods A cross-sectional exploratory study design, targeting MSM in Nairobi was used. Adult men (aged 18–60 years) who reported to be actively engaging in anal or oral sex with men were eligible for the study. Purposive sampling was used to identify the sites where data was collected, snowballing technique was then employed to reach the respondents. Data was collected between July 2018 and June 2019. A total of 391 MSM respondent were recruited of whom 345 MSM completed the questionnaires. The missing data was handled through the listwise approach that omits those cases with the missing data and analyze the remaining data. We also excluded responses with inconsistencies in all confirmatory questions in the questionnaire. Results Two-thirds (64.0%) of the participants were aged 18–24 years with 13.4% being married to women and 40.2% having tertiary level of education. Majority, 72.7% were unemployed and two-thirds (64.0%) of participants were young (18–24 years) and self reported as male sex workers (58.8). There were significant associations between willingness to undertake HIV self-tests and frequency of HIV testing as well as with previous knowledge about self-testing. Habitual HIV testers were more likely to have used the HIVST kit than the non-habitual testers. Willingness to undertake confirmatory test within one month of self-testing was associated with acceptability of HIVST. Most of the MSM preferred blood sample self-test kits as compared to oral self-test kits, believing that blood test will be more accurate than oral self-test. Other factors associated with HIVST included consistent use of protection regardless of HIV status, preference of “treatment buddies”. High costs of the self-test kits and inadequate knowledge on the use of HIV self-test kits were the main hindrances to HIVST uptake. Conclusions This study has showed that age, habitual testing, self-care/partner care, as well as confirmatory testing and immediate introduction into care if found sero-positive were associated with the use of HIVST kit. This study contributes to the pool of knowledge of the characteristics of MSM that would adopt and embrace HIVST, and demonstrates that these MSM are self and partner care aware and conscious. The challenge however remains on how to encourage those that are not self/partner care aware to embrace HIV testing and particularly HIVST as routine practices. Future studies may need to explore potential motivators to self-testing among the young, elder MSM generations and the MSM with higher economic status in Kenya.