The Havanese itself developed uniquely in Cuba, either as the result of said Spanish sailors, or as is often believed by native Cubans, as gifts from Italian traders to open the doors of wealthy houses to their goods. The "Little Dog from Havana" even traveled back to Europe where it found brief favour in the late 19th century as a circus and trick dog and a court companion.

As part of the Cuban Revolution, many trappings of aristocracy were culled, including the pretty but useless fluffy family dogs of the wealthy land owners of Cuba! Even though many upper class Cubans fled to the United States, few were able to bring their dogs, nor did they have the inclination to breed them. Indeed, when Americans became interested in this rare and charming dog in the 1970s, the gene pool available in the US was only 11 animals.

With dedicated breeding, as well as the acquisition of some new dogs of type internationally, the Havanese has made a huge comeback, with recognition by many major kennel clubs and one of the fastest growing registration of new dogs in the AKC (+42% in 2004). They have also suffered from a certain level of trendiness due to rarity, good temperament, and publicity by such famous owners as Barbara Walters.