Milk vending machines (MVMs) are growing in popularity in Kenya and worldwide. Milk vending machines dispense varying quantities of locally sourced, pasteurized milk. The Kenya Dairy Board has a regulatory framework, but surveillance is weak because of several factors. Milk vending machines' milk is not routinely screened for antibiotics, thereby increasing potential for antibiotic misuse. To investigate, a total of 80 milk samples from four commercial providers (N = 25), street vendors (N = 21), and three MVMs (N = 34) were collected and screened in Eldoret, Kenya. Antibiotic residue surveillance occurred during December 2016 and January 2017 using Idexx SNAP® tests for tetracyclines, sulfamethazine, beta-lactams, and gentamicin. Overall, 24% of MVM samples and 24% of street vendor samples were presumably positive for at least one antibiotic. No commercial samples were positive. Research into cost-effective screening methods and increased monitoring by food safety agencies are needed to uphold hazard analysis and critical control point for improving antibiotic stewardship throughout the Kenyan private dairy industry.