Background: Pregnant and breastfeeding women received unclear recommendations regarding COVID-19 vaccination at the beginning of the pandemic, as they were not included in the initial clinical trials. This systematic review aims to provide an update regarding COVID-19 vaccines during pregnancy and breastfeeding. Methods: The systematic review was carried out through a literature search in Medline/Pubmed. Studies were selected if they included information regarding COVID-19 vaccination during pregnancy and breastfeeding. The PRISMA guidelines for systematic reviews were followed. Results: A total of 33 studies were included. The main adverse effect is pain at the injection site, as in the general population. Adverse effects are more frequent after the second dose, being slightly more frequent after the Moderna vaccine. COVID-19 vaccination reduces the risk of severe COVID-19 in pregnant women. Additionally, COVID-19 vaccination induces artificial active immunogenicity in the mother and natural passive immunogenicity in the child. Breastmilk straddles both immediate antibody-mediated and long-lived cellular-mediated immune protection. Regarding neonatal benefits, vaccination is associated with a larger and more stable Immunoglobulin G response, while COVID-19 Infection is associated with a rapid and long-lasting Immunoglobulin A response. Conclusions: COVID-19 vaccines are not only suggested but strongly recommended for pregnant and breastfeeding populations to protect mothers and newborns.