Airbnb is so brand-new in Cuba that my hosts in the hot, sleepy, charming fishing town of Cojimar on the outer edge of Havana aren’t sure how the rental dollars I’ve paid as their very first guest are going to make it into their pockets.

“OK, we know you’re here,” says Marco, the Austrian-born son-in-law of Candy, the owner of the house I’m renting in, steps from the waters of the Straits of Florida and its salty breezes. “We thought, ‘Let the customer come and see what happens.’” Cojimar is, perhaps, not all that ready for visitors either. The sky is a striking blue, dotted with clouds, and there are palm-frond umbrellas on the waterfront. And like its neighbor Key West to the north, this is a place obsessed with Hemingway; the writer kept his fishing boat in Cojimar, near where a metal head-and-shoulders bust of him now stands. But there is little in the way of tourist amenities beyond the sun that Marco estimate blazes overhead 300 days a year, and that waterfront is dotted with trash.

That said, Marco, Candy and her daughter Lauren, a pianist who met Marco while performing in Abu Dhabi do know some things. They know, for example, that Airbnb will take a 5 percent cut of the $45 a night I have already paid through the San Francisco-based online peer-to-peer room rental company. But how will that money actually make it to them in a country with so little in the way of modern commercial infrastructure? That part is still a mystery. “Who,” jokes Marco, “will knock on the door and give us money?”

As we sit and talk as rhumba music floats over Cojimar, somebody knocks on the door. I catch myself thinking that perhaps, who knows, maybe this is someone with their money. Then I think that’s ridiculous; the heat has gotten to my brain. Then I think that’s possible again. I’ve been in Havana — Cuba’s capital of two million on the country’s northwestern shore — only long enough to know that I’m nearly completely confounded by the city.

I’m not the first to feel that way. This city has always been at the heart of the United States’ contested relationship with Cuba, its role as a Mob playground overrun with casinos and soaked with decadent nightlife a particular affront to Fidel Castro-led revolutionaries. In the five and a half decades since the socialist takeover, Havana’s cosmopolitanism, if crumbling, has remained a point of pride for Cuba. The micro-enterprise that keeps its streets humming is legendary. Given all this, perhaps I shouldn’t be so surprised that this city might be the most hospitable place on earth to Airbnb. In fact, Cuba, in some ways, thought of Airbnb years before Airbnb thought of Cuba.

Though Airbnb is worth an estimated $10 billion now and operates in 34,000 cities around the planet with some 1.2 million listings, the company began in just 2008, as a way for a few friends in San Francisco to make rent by throwing down air mattresses in their living room. But Cuba’s network of casas particulares, or licensed private room rentals, which Airbnb tapped into to get up and running, dates back even a decade before that, to the late 1990s. Casas are much like Airbnb without the Internet.

And they are so much now a part of Cuba’s urban life that the blue anchor symbol that marks their doorways are featured prominently in the street art sold along Paseo de Pardo, the promenade that runs down to the water from Habana Vieja, or Old Havana — where I’ll also stay, in a $90-a-night two-bed Airbnb rental hosted by a couple named Raul and Monica. Other cities around the world, from New York to Amsterdam, have fought about allowing in Airbnb, over concerns ranging from doing away with affordable housing to violating existent tenants’ rights. But Havana? Havana was primed for Airbnb.

Perhaps for that reason, the Cuban government, according to Airbnb, has worked cooperatively with the startup since it sent teams to meet with Cuban hosts soon after President Obama moved to relax 60-year-old restrictions on trade and travel in December. (The Cuban government did not respond to comment for this article.) “Airbnb has had productive conversations with the Cuban government and the company has informed them about its plans,” says an Airbnb spokesperson. “They see the benefits of allowing American travelers to more efficiently tap into the casas particulares system.”

When I get back home in the U.S., I ask someone with the company how my hosts in Cojimar will get their money.

Cuba’s banking options are changing quickly she says, and they’ll change more as the United States works to open up relations, even should Congress not choose to completely do away with the U.S. embargo on that country. But at the moment, hosts with functioning bank accounts can choose to have those funds deposited into them electronically through a newly legal payment exchange. Those without a bank account can opt to be paid in a variety of others ways, through third-party providers in Cuba.

And if all else fails? If all else fails, Airbnb says, someone will knock on a Cuban host’s door and just hand him his money.

Getting Back on to the Global Network

The exchange between me and my Havana hosts actually begins about five days before I set foot in Cuba. I sit down at my desk in Washington, D.C. and, a little nervously, fire up Airbnb. For various scheduling reasons, I don’t have a lot of time to plan my trip, and much of the prep is spent making sure that I, as a journalist, am coloring between the lines when it comes to U.S. rules on travel to Cuba under the embargo. So I have to find some place decent and safe to stay in Havana, a city that has for so long been off-limits to most Americans.

Luckily, I have a cheat: JB and Bree, a French couple living in Manhattan who had rented a different room, also in Old Havana, from my future hosts, Raul and Monica. JB had posted, in translation, of that apartment: “The room was cool and calm in a bustling neighborhood on the outskirts of Old Havana. The best neighborhood in the capital. Room spotless private bathroom. Excellent breakfast with plenty of tropical fruits.”

Good enough for me. I click to reserve my rooms. Nearly instantly, my requests pop up some 1,100 miles away, in Havana.

Five days later, I arrive in Havana, for so long a city of mystery. Ishmael, Raul’s brother-in-law, picks me up at the airport, something we had pre-arranged via Airbnb’s messaging service.

The rental is spare but comfortable, what I imagine a middle-class apartment in Moscow might be like, save for the scorching heat ameliorated by a much welcome pair of in-room air conditioners. When the temperature breaks late in the day, there’s a small balcony to use, set off from the living room by slatted doors. I sit out there, listening to roosters make their noises and pet birds, kept in cages outside next-door apartments, chirp. Kids play soccer down on the street. On the balcony across from mine, a man in white gym shorts, a black tank top and gold chains leans on a wood railing as a boy, maybe two, plays with a ball near his feet. The man watches the street life go by. Later, as I retreat into the apartment, I’ll wonder why so much of the street noise seems to be filtering in, until I realize that the small pantry off the kitchen is missing much of its exterior wall.

When Ishmael dropped me off, I’d been met by Raul and Monica. We share a fragrant coffee and chat. I ask Monica if it’s strange that I, an American, am here. She tilts her head. It’s strange, she says, that you haven’t been. Raul and Monica rent out rooms across Havana as a business, and they have played host to plenty of Canadians, Europeans and other visitors. And missing wall aside, this apartment is a desirable one. It’s blocks from La Floridita, supposedly a favorite Hemingway haunt, where bartenders use tweezers to place tiny straws into frozen daiquiris while outside, the streets, torn up with deep gouges, are full with strolling Cubans.

Monica and Raul hand over the keys, an image of the ubiquitous Che Guevara on the keychain. There’s a cold Ciego Montero soda in the fridge, Monica says. She points out the good places to eat, the best sights to see. She does, though, have one small warning. If someone offers to take you to the festival de salsa, just say “No, gracias,” and walk away, she says. “No está un festival de salsa,” she says, shaking her head.

Over the next few days, I’ll find that most Habaneros simply politely ignore me. But, when I am, later, walking down Havana’s famed Malecón walkway along water, both dripping with sweat and cooled by the ocean winds, and a man approaches and offers to take me to a festival de rhumba, I beam and say, “Ah, no, gracias!,” thrilled with how adaptable my local knowledge, shared with me by my Airbnb hosts, has proven to be. He seems startled with how happy I am to reject his hustle.

It’s one of Cuba’s many ironies that the communist Castro government long ago set the conditions that let Airbnb get up and running so quickly. In the late 1990s, facing a dire economic situation brought on in part by the collapse of the Soviet Union, Cuba entered what is euphemistically called its “special period.” In a bid to help average Cubans find some way to survive, Castro created a regulatory framework for the casas particulares network, to allow citizens to tap the value in one of the few assets they might still have, their homes. While casas come with their own strict rules including restrictions that bar Cubans from staying in many of them, these state-sanctioned B&Bs offer visitors from abroad a personable alternative to no-frills hostels or grander historic hotels, like the Hotel Nacional de Cuba, a sweeping seaside estate built in the 1930s by New York City architects where the mojitos are cold and, in a food-deprived country, the cheese sandwiches are, if not tasty — Cuban food en situ generally lacks spicing beyond salt and pepper, and perhaps a little garlic — abundant.

And as more Americans take advantage of their newfound freedom to travel to Cuba, making licensed casas easily available via the Internet solves one of the communist government’s most immediate problems: an underdeveloped tourism infrastructure.

Richard Feinberg is a professor of political economy at the University of California at San Diego with a focus on Latin America. At a recent event on Cuban economics at the Brookings Institution in Washington, D.C., he detailed the challenges: “Can Cuba put together enough beds? Can it overcome the shortage of rooms, as well as the other services required for a good and healthy tourism sector?” Airbnb is one way for Cuba to quickly absorb more tourist dollars while still keeping a grip on travel to the country, all with little upfront investment.

Ted Piccone, a senior fellow in the Latin America Initiative at the Brookings Institution, has called Airbnb a perfect example of how a U.S. company can do business in Cuba while adding weight to a policy approach of “empowering the Cuban people and allowing them to develop their own economic activities.”

After saying goodbye to Raul and Monica, still a bit disoriented by finding myself so quickly in Cuba, I wander over to one of Havana’s historic neo-colonial hotels, the Iberostar Parque Central at the center of Habana Vieja. The guidebooks say it offers Internet access from the state-run telecom ETECSA for about six dollars an hour via scratch-off code cards. I go in for a fix.

The Internet, it turns out, is closed. You can only buy passes ocho a ocho, a desk clerk explains. So I sit at the bar and order a cold Cristal lager and listen to a masterful band play “Oye Como Va,” followed by “Yesterday.” The bartenders are polite but icy themselves. After only a few songs I find myself wanting to head out back into Havana’s maddening, sweaty, absorbing streets. There are, of course, other Americans like me, and many others who would never choose to stay in a place like the Hotel Nacional or the Iberostar, and now, through Airbnb, they have other options.

Many options. Airbnb launched in Havana with more than a thousand places to stay. The number grows every day.

Sharing, Cuban Style

If Airbnb is having a good run of things in Cuba, does that mean that other so-called “sharing economy” companies will follow? Some indicators suggest that they could: Cuba has a robust informal economy already, and it doesn’t take too much to imagine that Cubans, given an opportunity to make what they’re already doing easier and far more profitable, would jump on it.

There are plenty of fairly obvious ways that tech-enabled “sharing” could work for Cubans — swapping tools for fixing up all those classic American cars, pooling labor as they go about fixing their historic architecture, sharing car rides or trading garden-grown sustenance. But there are still major structural impediments.

Airbnb is often something you use, like I did, while sitting at your desk or on your couch. But services like Lyft, Instacart and TaskRabbit took off in the United States in part because of an exploding population of digitally banked people walking around with constant broadband access in their pockets. At present, though, Cubans don’t have either the broadband or the credit access to enable the instant online exchanges these platforms demand in the rest of the world. The government, led by Raúl Castro, brother of Fidel, has lately said that it wants a more connected Cuba. But whether it has the interest or ability to make that anything more than rhetoric is something on which many are keeping a close eye. Cuba’s Interests Section in D.C., which represents the country in the United States, did not respond to a request for comment. By all accounts, they’re struggling to keep up with the flood of attention suddenly being paid to their island.

The interest is not likely to die down anytime soon. Augusto Maxwell is a Miami attorney with the firm Akerman. He helped Airbnb figure out its options in Cuba. The process, he says, was wonderful; he called it working with “an incredibly talented, intelligent group of young people who see the world in quite a different way.” And the model they’d come up with several years back — let just about anyone list just about any room on their open, largely DIY platform — was “tailor-made for this opportunity,” says Maxwell. They can flesh out their vision of a connected world (“Belong Anywhere,” is a current slogan) without putting too much on the line. “It doesn’t,” Maxwell notes, “require them to build anything on the island.” The same proposition applies to other cloud-based “sharing” companies, pointing to the possibility that it will be this class of nimble startups that is best positioned to take advantage of American capitalism’s leap into Cuba.

My hosts in Cojimar tell me they are eager to have Airbnb-using arrivals from the U.S. While I find myself comforted having read their profiles before arriving, they tell me they felt the same. The old way — visitors arrived in Cuba and knocked on the doors of casas, or perhaps called a few days in advance but didn’t pay upfront — was a system “based on trust,” says Lauren, Candy’s daughter, and it didn’t always work out. “Sometimes you don’t even know where they’re coming from,” she says, and that can be especially unsettling when you’re renting your own home. More than that, adds Marco, “you can’t imagine how many people say they’re coming and don’t show up. If someone’s booked the room for two weeks, that really puts a hole in your budget.”

While Airbnb requires at least a tiny leap of faith, there is a payment guarantee built in: Guests are required to provide banking or credit card information so even if they don’t show, hosts get the money promised.

Moreover, Airbnb lets hosts like Candy take in a heftier profit. Casas generally run about 25 Cuban pesos, or about half what I’ve paid to stay in Cojimar and a third of what it costs me for my Habana Vieja apartment. Those prices are agreed to, and paid, in advance. In the past, says Marco, hostel-minded backpackers would arrive and offer, perhaps, just 15 pesos, and after you hand over the government’s licensing fee, that doesn’t leave much profit. Such visitors, says Candy, with a tilt of her head, are sometimes “not high quality.” She’s hopeful that Airbnb “gives the opportunity to increase the quality of the service,” perhaps competing with other casas by adding extra features. “Cubans didn’t have access to Americans,” says Lauren. Now, they’re at least beginning to.

But what extra services those new guests might want, hosts are just starting to sort out.

First, there is the issue of cultural translation. Cuba is uniquely unknown to Americans — and the local customs aren’t always clear. For starters, there are two currencies in Cuba. The Cuban Convertible Peso, or CUC or “kook,” used mostly by tourists, and the far less valuable Cuban Peso, or CUP, which is the daily money of most Cubans and which travelers might pick up as they shop in local markets and at kiosks. I admit to Ishmael, Raul’s brother-in-law, that I find the whole thing utterly perplexing, as he takes me — at a price of 10 CUCs — from Habana Vieja to Cojimar. (Raul and Monica’s rentals are a family affair. Ishmael offers driving services. Raul’s mother cleans.) He finds it perplexing too, Ishmael admits. The best thing to do, he suggests, laughing, is not to think about it too much. “One pocket for national money,” he says, gesturing to a leg of his cargo shorts, and then the other. “And one pocket for CUCs.”

What I come to understand about Cuban money comes mostly by the way of Candy, an economist, as well as from Marco, her son-in-law. I ask them to help me understand, and Marco begins by asking to see the money I have in my own pockets. All CUCs. “You’re fully a tourist,” jokes Marco. Candy gives a lesson. She pulls out bills of both types, and, as the ocean waves crash in the background, lays the two red-tinged notes side by side. For several minutes, she walks me through the history of the CUC, an attempt begun in 1992 by the Castro government to deal with its desire to exchange with the outside world without having to dirty its hands with the dreaded U.S. dollar.

Indeed, the Cuban government is, however invisibly, still involved in nearly every exchange of any value in the country. Visitors to casas particulares must hand over their passports and visas, and the details are recorded in a large paper ledger stamped with the blue anchor on its cover. The government takes its cut, as Airbnb acknowledges. “In accordance with OFAC regulations” — that is, of the U.S. Department of Treasury’s Office of Foreign Assets Control, “all our payments will be for licensed travel, and therefore are licensed transactions.” That is, the Cuban government isn’t being skirted simply because hosts and guests might now be connecting directly with one another via the Internet.

Candy, whose work in that same Cuban government’s economic development efforts has given her an intimate knowledge of the ins and outs of CUCs and CUPs, tolerates my confused questions on the topics for several long minutes. They bring me a Cristal beer to help ease the evident pain of this currency lesson.

“You don’t get this at the Hotel Nacional,” says Candy, with a laugh.

And that, in many ways, is Airbnb’s pitch to the world, distilled. The platform fosters human-to-human connections, whether that’s a currency lesson with Candy and her family or an entirely comfortable ride out to the beach with my host’s brother-in-law. “With over a million homes around the world, you’re never a stranger,” goes a television ad the company has been running of late. That’s true, the thinking goes, even if there’s an economic transaction that is inextricably the framework upon which those connections are based.

Candy and I, and Ishmael and I, have a seller-of-services, consumer-of-services relationship, for sure. But it’s difficult not to feel that we’re also kinda friends. At the very least, there is little opportunity for us to be strangers. My Airbnb profile is a gateway to everything else that is knowable about me that exists online. I ask about Lauren’s career in music. Candy tells me that she recently completed a master’s degree, online, from Boston University. “I went to BU,” I say. “I know,” says Candy.

And if it’s not living like a local, it can feel a lot like living with locals. As Candy and I talk on the roof deck once more, a black car pulls up on the grass plot that edges the beach.

(Like so many cars in Cuba, this one has an Apple logo stuck in its window. Should that company choose to follow Airbnb’s lead and attempt to plant a flag here, it will likely find itself getting a warm hug from the Cuban people. I ask one cab driver, a rather staid fellow, what’s with all the Apple stickers? At this, he laughs heartily. “Propaganda,” he says. In Cuba, as in Cupertino, the Apple logo is simply shorthand for being the best.)

As we watch a seeming family of three get out of the car, Candy explains that we’re about to see a ritual, an offering. The group climbs down below the rocks, and begins to fill and empty jugs and vases. Soon after they leave, another group pulls up, and does much the same thing. Without Candy, I wouldn’t have known what I was seeing here on the beach of Havana. I wouldn’t have even known to look.

But there are other more concrete amenities that Americans expect that Cuba’s lacking. Those include WiFi and hot water, says Marco, and there is little of either there. Access to the global network in Cuba has been measured at only about 5 percent. That’s one reason Obama made the trade of IT equipment a centerpiece of his first moves to open up Cuba.

“Americans can’t imagine what it means to be in the Third World,” says Marco. “Europeans are more used to it. East Germany was right next door.”

Cubans, in self-conception and what seems to be actual fact, are tinkerers, whether that’s keeping the ubiquitous 1950s American cars up and running or figuring out how to navigate the casas particulares system to make ends meet. Lauren, the pianist, has a particularly evocative phrase for it. “Cubans make something,” she says, rubbing her thumb, forefinger and ring finger together, “from dirt.”

Given the vast digital divide, Airbnb and its cloud-based peers would seem to be long shots for the island nation. What makes Airbnb viable for Cuba are a few simple but effective design hacks. Candy, like other better-off Cubans, has a mobile phone and, she explains, when I’d clicked on my laptop up in Washington, D.C., to make my reservation, she had gotten an alert on the phone, letting her know that she had 24 hours to confirm or turn away the booking. It’s a design trick that helps Airbnb route around Cuba’s Internet blackout. Resourceful Cubans, Candy and her family explain, are able to find a way to get online, if only for just a few minutes, if given a day.

Another adjustment: In Cuba, the company acknowledges, it also works with middlemen — professional property managers like Raul and Monica — far more than is the case in other cities around the globe. And they, too, are able to act as bridges between property owners and the Internet.

It’s a model that could be replicated by other companies and seems to have the potential to grow a great deal. But how exactly that growth happens will be critical, says Airbnb.

“We anticipate that Cuba could become one of Airbnb’s biggest markets in Latin America,” says a spokesperson. “But we are committed to taking a measured approach to building our community in Cuba. We want to ensure we’re making a positive impact for the Cuban people and supporting local Cuban entrepreneurs who are excited to share their country and culture with the world.”

Strange Bedfellows

All the joys of person-to-person cultural exchange on the shores of Cojimar still can’t hide the fact that the relationship between Cuba and the U.S. is still hugely fraught. As much as Airbnb might be a quick back door into the country, it also taps directly into one of the most contentious aspects of the Cuban-U.S. experience — aside from Cuba’s difficult record of locking up, or worse, those who differ with the government — and that’s housing.

Havana’s big hotels, many of them built with money from the American mafia, had by the 1950s become glitzy gambling dens that were a particular affront to Cuban revolutionaries, perhaps chief among them the same Che Guevara who’s on the keychain handed to me by the quite clearly entrepreneurial Raul.

The Havana Hilton was long a city landmark before it was taken as something of a headquarters of the Cuban revolution; today, just about every hotel in Cuba includes the government as a partner. Some things have changed. The same lobby where khaki-clad revolutionaries made their plans, tourists sink into leather lounge chairs and dig into their email. But the hard feelings remain, as do those over the property, including houses, that was taken by the revolution in a breach that still rankles many Cuban-Americans, particularly those in a portion of the diaspora gathered in Miami. What, from the U.S., looked like an inexcusable violation of property rights was in many ways what drove the creation of the U.S. embargo on Cuba. And the wounds — economic and emotional — that still surround personal property in Cuba are ones that Airbnb will likely have to address if and when its presence takes real root in that country.

Already, Cubans aren’t containing themselves to Havana, notes Airbnb. The capital is home to only about 40 percent of the country’s listings. The rest are spread across more than 30 towns, from Santiago de Cuba near Guantánamo Bay, to Nueva Gerona on a tiny spit of land off Cuba’s southwest coast.

Even before Obama’s moves, Cubans had asked to list on Airbnb, says Maxwell, the Miami attorney who helped Airbnb get established in Cuba. As things changed, the lawyer says that his role was a bit like that of Morpheus in The Matrix, standing on rooftop and telling Neo that “free your mind” is key to making the leap to the next building. But Maxwell is a lawyer: He and colleagues did their due diligence in both Washington and Havana to make sure the open-minded company wasn’t going too far beyond what geopolitics would allow.

It wasn’t. Airbnb points out that it took about three years for the platform to reach the number of listings in the urban hotspots of San Francisco and Berlin that Havana listed in its first two months. And it took just another month and a half for that number to double. Airbnb’s existence in Cuba is growing in other directions as well — fleshing out in ways that suggest it might soon be the robust ecosystem that is flourishing in so many other cities around the world.

When I rented Raul and Monica’s apartment, there were no reviews on it. Now there are seven, each doing its part to reaffirm that this is a viable option for the traveler eager to explore Havana.

During a recent, packed U.S. Senate Foreign Relations hearing in Washington, Arizona Senator Jeff Flake called Airbnb’s presence in Cuba, “very significant,” saying that Cuban hosts “will benefit from visits by Americans and others.” Flake, who is perhaps Congress’ most vocal Republican advocating for normalizing relations, pointed out that Airbnb offers alternatives to government-run, government-partnered hotels means that “there’s less of a chance that money will flow to the government.”

Even Florida’s Marco Rubio, the Republican son of Cuban immigrants who is running for president and maybe Congress’ most adamant opponent of increasing ties with Castro’s Cuba, floated in that same hearing the possibility that Airbnb on the island might not be a bad thing. Rubio, like Flake, saw it as a way to route travelers — if there must be more of them — away from Cuban government-affiliated hotels and reduce the flow of American dollars to Castro.

Airbnb is itself eager to do what it can to be a bridge between the U.S. and Cuba in these complicated times. “Airbnb is supportive of any policies that promote meaningful interaction between ordinary American and Cuban citizens,” says the company spokesperson, “and help to create more opportunities for the Cuban people.”

What those opportunities turn into, on both sides of the water, will no doubt be dictated in part by politics, and likely years more of high-volume debate. But they will also likely be shaped by the human interactions that Cubans and Americans are beginning, after a 50-year break, to experience. Since Obama loosened some restrictions on those relationships, travel to Cuba by Americans without family ties there has more than tripled. And, notes Airbnb, their numbers show that Americans are beginning to open their eyes to Cuba in huge numbers. According to the company, searches originating from the U.S. for places to stay in the urban behemoths of Rio de Janeiro, Buenos Aires or Mexico City are already outnumbered by searches for places to call home, at least for a few days, in Cuba.