Background and Objectives: Diabetes is linked to a higher risk of urinary tract infections (UTIs) in women, often leading to recurrent antibiotic treatments. Frequent antibiotic use for UTIs can contribute to antimicrobial resistance (AMR), a critical public health threat that increases treatment failure. This study investigated the prevalence of AMR and its associated factors among women with UTIs, comparing those with and without diabetes. Results: The study population had a mean age of 52 years (SD = 23) for the women without diabetes and 68 years (SD = 14) for those with diabetes. Resistance was highest for cefazolin and levofloxacin in the Access and Watch antibiotic groups, while ciprofloxacin was the most frequently prescribed antibiotic. AMR prevalence was 35.7% among the women with diabetes and 21.3% among those without. After adjustment, AMR was significantly associated with both uncomplicated diabetes (OR 1.14, 95% CI 1.08–1.21) and complicated diabetes (OR 1.54, 95% CI 1.45–1.64), as well as with higher numbers of prescribed antibiotics (OR 277.39, 95% CI 253.79–303.17). Methods: Using a cross-sectional cohort from the Physionet database, we analyzed data on 116,902 female participants treated for UTIs, including their antibiotic exposure, diabetes status, comorbidities, and hospital admission details. Antimicrobials were classified per the WHO’s AWaRe criteria. The primary outcome was AMR identified in urine cultures, and the association with diabetes status was evaluated using multivariable logistic regression. Conclusions: Our findings highlight the need for focused antimicrobial stewardship in women with diabetes to reduce the AMR rates in this vulnerable group.