Mario Otero Acosta was studying tourism and hospitality at the University of Havana when President Obama announced that he would ease  restrictions on travel to Cuba in January 2015. It was perfect timing; after graduating that year, Otero began leading tour groups catering to the new flood of American tourists. But he had his sights set on a bigger venture: renovating his father’s run-down apartment and listing it on Airbnb. He ended up launching the listing in 2018, charging $30–-$50 a night for guests to stay at the centrally located home in the Centro Habana neighborhood.

“[Airbnb] totally changed the game,” Otero told Rest of World. Before, finding accomodation in Cuba as a tourist often consisted of asking a cab driver if they had a friend who knew of an open guest room, a decades-old arrangement known as casas particulares in Cuba. “Everything was really primitive.” 

With Airbnb, renters and tourists interfaced seamlessly, spurring a wave of new entrepreneurs like Otero. By 2019, Cubans were making almost $50 million annually and hosting almost 750,000 guests a year. Airbnb had over 35,000 listings — almost twice the amount of casas particulares that had operated independently before it launched in Cuba. And Airbnb did not waste the press opportunity, with CEO Brian Chesky going on a promotional tour touting the company’s explosive growth in the island.  

But operating guesthouses using a U.S.-based company in Cuba is still a challenge. The U.S. still maintains restrictions on remittances and payment services operating in Cuba, crucial for the hospitality and travel industries. As a result, both Airbnb and Cuban hosts operate in a tenuous gray zone, of which the company finally admitted to falling afoul last week. The U.S. Department of the Treasury announced it was levying a fine of just over $90,000 against Airbnb for allegations that the company had violated sanctions related to non-authorized transactions that happened on its payments platform. Airbnb did not immediately reply to a request for comment.

For a company worth over $100 billion, the fine was pocket change. But it underscored the precarity faced by Cuban hosts.

“Being a host in Cuba is five times more difficult than being an Airbnb host in any other part of the world because of the lack of technology, because of the lack of flexibility, and because of the lack of connection,” said Otero. 

Lindiana Murphy told Rest of World that she and her husband were two of the first Cubans to put their apartment on Airbnb. When the company launched in Cuba, there were an estimated 20,000 casas particulares in operation; 4,000 of them quickly signed up for the platform.

Back then, Murphy told Rest of World, almost nobody had consistent internet access, so it was a struggle to maintain their profile. Even so, Murphy says they viewed their role as essential for new tourists coming in, especially from the United States, and helping them understand the country’s idiosyncrasies.


Under the Obama administration’s expanded policies, U.S. travelers could visit the island under a category called “people-to-people,” meaning they had to demonstrate that they were interacting with Cuban people and having cultural exchanges — not just visiting a beach on a cruise ship. U.S. tourism to the island exploded in the second half of the 2010s, rising from 160,000 visitors in 2015 to almost 640,000 in 2018, representing around 15% of all tourists. 

Murphy’s business evolved alongside the rise of American tourists. She rents two properties and also hosts two “experiences,” cultural activities bookable through Airbnb’s site. In one of these people-to-people-compliant experiences, guests are provided breakfast, while Murphy spins her favorite vinyl records from both before and after the Cuban Revolution.

But Murphy says that the byzantine restrictions created by the ongoing embargo make it particularly difficult to run her Airbnb. 

U.S. payment services are banned from operating in Cuba. To pay hosts, the company uses an intermediary — a Miami-based agency called Va-Cuba — that exchanges U.S. dollars and Euros for Cuban pesos. Murphy told Rest of World that through VaCuba, hosts receive only 50 Cuban pesos per dollar, rather than the accepted exchange on the street of roughly 80 pesos per dollar. 

With annual inflation at roughly 70%, she can hardly keep up with the costs of running her business. “If we raise the prices as hosts, that’s going to affect the decisions of our clients,” she said. 

To get a better exchange rate, some hosts ask friends in the United States to accept payments on their behalf and then bring them U.S. dollars when they come to Cuba. One Cuban host told Rest of World that after Airbnb discovered his Va-Cuba workaround, he received warnings from Airbnb threatening to cancel his account if he didn’t change his payment method. Other Cubans with dual citizenship are able to open bank accounts in different countries to receive payment.

Guests also face a variety of smaller inconveniences using Airbnb that, hosts say, add up. As a U.S.-based company, Airbnb treats all tourists as Americans, likely to avoid further violations. Cubans are used to creating ingenious hacks to bypass restrictions, from using VPNs to access the internet to finding different ways to receive payments, but visitors are not accustomed to the constant headaches.  

Otero told Rest of World that all Airbnb users who are reserving a stay on the island have to select why they’re traveling to Cuba under the U.S.-permitted rationales, such as people-to-people. 

Because payment services are restricted in Cuba, visitors can’t reserve new bookings while they’re on the island, and guests can find themselves stranded if their accommodation falls through.

AP Photo/Desmond Boylan

Beyond the technical challenges, hosts have had to battle the pervasive perception, especially among Americans while former-President Trump was in office, that Cuba is closed off. Under the last administration, restrictions did tighten again, although travel to the island was still possible. The growth in U.S. visitors under Trump slowed in 2017 and 2018, dropping substantially in 2019. Tom Popper, an expert on Cuban tourism from 82° West Consultants, a firm focused on business entry to Cuba, told Rest of World that the Trump administration’s policy change signaled to U.S. travelers that “Obama opened [Cuba] up, Trump shut it off, even though that wasn’t the case.”

Covid exacerbated the situation, with Cuba closing its borders to travelers for nearly the entire pandemic. Despite the complexity of operating on the platform, numerous hosts told Rest of World that Airbnb created economic opportunities for Cubans to create new income streams and open their homes and lives to foreign visitors. Still, the onus of a policy change lingers over even the best-performing hosts. One told Rest of World, “we can only pray for a sane [U.S.] government.”