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Confidence votes 173K. There are three kinds of answers: ones that are mostly right, ones that are mostly wrong, and those that once were right but now are wrong. The three largest islands are Cuba, Hispaniola, and Jamaica.Cuba and Hispaniola, along with Puerto Rico, form the northern border of the Caribbean. Hispaniola is occupied by two countries, Haiti and the Dominican Republic.onfidence votes 173K. There are three kinds of answers: ones that are mostly right, ones that are mostly wrong, and those that once were right but now are wrong. The three largest islands are Cuba, Hispaniola, and Jamaica.
Hispaniola. Hispaniola is the second largest Caribbean island, and it is home to two different countries. The Dominican Republic (godominicanrepublic.com) is the larger of this island's two countries, with an area of 18,792 square miles.Spanish is the official language of the Dominican Republic.he Bahamas. At 5,359 square miles in area, the 700-island chain of the Bahamas (bahamas.com) is larger than Puerto Rico and Jamaica; however, these islands are in the Atlantic Ocean, not the Caribbean Sea. Cubaâs location blocks this chain's access to the waters of the Caribbean.