Background: The COVID-19 pandemic has affected dentists globally, both financially and mentally. This study aimed to determine the knowledge, attitude, and practices of dentists in Caribbean countries during the COVID-19 pandemic. Methods: A non-probability sample was obtained from dentists in more than ten different Caribbean countries. They were invited to complete a self-reported questionnaire, which was conducted from December 2020 to March 2021. Ethics approval was sought and an exemption was received from the UWI ethics committee. Results: One hundred and fifty-two dentists responded. More than one-third (38.8%) were in the >35–45 age group, and 58.6% were females. Most (84.9%) were general dentists and 75% were stressed by the COVID-19 situation with 80.9% being affected financially. The majority, 94.7%, believed that the highest risk of transmission of COVID-19 was via aerosol-generating procedures and 87.5% were worried about contracting it clinically. The majority (69.1%) were willing to receive the vaccine, the main reason reported for vaccine hesitancy was due to the possible side effects (35.3%). Most (75%) consumed alcohol. When the locus of control was determined, 54.6% felt they were in control of protecting themselves while 52% felt that external factors controlled their lives. Conclusions: The findings suggest that most dentists in the Caribbean were knowledgeable about COVID-19 and followed current guidelines in their practice and were willing to receive the vaccine.