During the coronavirus diseases 2019 (COVID-19) pandemic, the safety and efficacy of vaccination during pregnancy, particularly regarding the risk of preterm birth, have been a subject of concern. This systematic review aims to evaluate the impact of COVID-19 vaccination on preterm birth risk and to inform clinical practice and public health policies. Following PRISMA (Preferred Reporting Items for Systematic Reviews and Meta-Analyses) guidelines, a database search included PubMed, Embase, and Scopus, conducted up until October 2023. Inclusion criteria focused on studies that examined COVID-19 vaccination during pregnancy and its correlation with preterm birth, defined as a birth before 37 weeks of gestation. Six studies met these criteria, encompassing 35,612 patients. A quality assessment was performed using the Newcastle–Ottawa Scale and the Cochrane Collaboration’s tool, with the risk of bias evaluated via a funnel plot analysis and an Egger’s regression test. The studies demonstrated geographical diversity, mainly from Israel, Romania, and the United States, with a blend of prospective and retrospective designs. The patient cohort’s mean age was 31.2 years, with common comorbidities such as gestational diabetes and obesity affecting 9.85% of the total population. The vaccination types varied across the studies, with BNT162b2 being the most used. The results indicated a low heterogeneity among the included studies, evidenced by a Cochran’s Q statistic of 2.10 and an I2 statistic of 13%. The meta-analysis yielded a pooled odds ratio (OR) for a preterm birth risk post-vaccination of approximately 1.03 (95% CI: 0.82–1.30), suggesting no significant increase in preterm birth risk was associated with COVID-19 vaccination. Notable findings included a low preterm birth rate (as low as 0.6% and up to 6.1%) with minimal differences in neonatal outcomes, such as birth weight and APGAR (appearance, pulse, grimace, activity, and respiration) scores between vaccinated and unvaccinated groups. This study concludes that a COVID-19 vaccination during pregnancy does not significantly increase the risk of preterm birth. These findings are crucial for reassuring healthcare providers and pregnant women about the safety of COVID-19 vaccines and supporting their use in public health strategies during the pandemic.