© AirBNB
Amy Farley

Peer-to-peer rental behemoth Airbnb has announced that Cuban properties are now available to book on its website. The more than 1,000 listings, nearly half of which are in Havana, come as the United States and Cuba work to normalize relations and—eventually—bring more travelers to the country. Since the island lacks a significant hotel infrastructure, making Cuba’s extensive network of casas particulares, or guesthouses, available to a wider audience is a big step toward realizing this goal. 

These licensed guesthouses were originally established as part of an effort by the Cuban government in the 1990s to accommodate visitors and allow for a small measure of private entrepreneurship following the demise of the Soviet Union. They are, at heart, exactly the model that Airbnb was originally founded upon: private rooms in well-kept homes. And their now-experienced hosts are a natural fit for the site. As Kay Kühne, Regional Director for Airbnb in Latin America, explains, “The culture of private homestays is mainstream in Cuba.” 

Getting these properties onto Airbnb, however, was something of a logistical feat for the site. It had to work out complicated payment arrangements for hosts in a country where cash is king. (Travelers will continue to pay as they normally do through Airbnb.) And it had to provide a workaround for hosts without Internet access, which is extremely limited on the island, by finding them partners to help manage their listings.

As with all Cuba-related travel announcements, this one comes with a caveat: these rentals are only available to licensed U.S. travelers. Which means if you’re planning to book, you'll have to certify that your trip meets one of the 12 categories currently permitted by the U.S. Office of Foreign Assets Control, including educational travel, profession research, and people-to-people trips. (Of course, whether or not you’ll ever need to show this paperwork to anyone is another story; rules surrounding travel to Cuba remain a little fuzzy and no one seems to be asking for anything more than a signed affidavit.) It’s also worth noting that without any commercial flights from the U.S., you’ll either have to book with a charter company, such as Cuba Travel Services (an arm of Sun Country Airlines), or an established tour operator, such as GeoEx or Insight Cuba, who have been leading trips to Cuba for years.  

Amy Farley is the News Editor of Travel + Leisure.

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