As American hotel companies make their first forays into the Cuban market after a nearly 60-year absence, they're finding that Airbnb is already firmly established on the island. It's usually the other way around—with hotels entrenched and the home-sharing site as the upstart. But ever since President Obama began easing travel restrictions to Cuba in December 2014, hotels have had to deal with government regulations, construction delays, and infastructure challenges. Airbnb, on the other hand, didn't have to construct any buildings and could rely on a network of already licensed homeowners, thanks to a program the Cuban government started in the 1990s to help residents earn extra income by renting rooms in their homes.
Since moving into Cuba in April 2015, Airbnb has expanded from an initial 1,000 listings to more than 4,000—making Cuba the fastest-growing market in Airbnb's history.