The Hotel Inglaterra has been one of the best places to stay in Havana since it opened in 1875. Its colonial façade and bright neon signage fit right in with the nearby capitol building and Gran Teatro, and its guest book includes such famous names as Cuban national hero José Martí.

There’s just one catch: The property is stuck in time, just like the rest of Cuba. You’ll have to pay $312 a night for what looks like a Holiday Inn, albeit one with pretty terracotta-tiled floors. 

In the six months since independent travel from the U.S. was officially whitelisted, tour operators have introduced itineraries and major airlines (such as American and Jet Blue) have scheduled their first flights into Havana. By the end of the year, the Inglaterra will be rechristened as part of Starwood’s Luxury Collection, becoming the company’s second hotel after a Four Points by Sheraton opened earlier this year.

But when it comes to hotels in Cuba, there’s almost always a catch, just as there is at the Inglaterra—and that problem isn't likely to go away soon.

Just ask Leo Ghitis, owner of one of Costa Rica’s most luxurious hotels, Nayara Springs. When he was approached to open a property in Havana, he took the first flight out. “I received a tremendously warm welcome,” he said about his meetings with the minister of tourism and top government officials. “But even after getting the red carpet treatment, I had to decide to postpone my plans,” he said, citing major infrastructural limitations.

That doesn't necessarily mean you have to settle for mediocre accommodations should you choose to visit. Despite the island's many challenges, comfortable and beautiful options do exist if you know where to look. And if you play your cards just right, a five-star trip to Cuba can be well within reach.

Don’t Go It Alone
Just because you can buy a plane ticket and fly to Havana with your significant other doesn’t mean it’s the best place for a spontaneous getaway.

“Many of the larger reputable hotels in Havana are reserving their rooms only for big group trips of 40 to 60 travelers,” said Melissa Biggs Bradley, founder and chief executive officer of Indagare, a members-only travel company that has been coordinating trips to Cuba since 2011. The reason, she says, is that they “prefer to sell a few big blocks of rooms instead of one-off reservations,” which results in little availability for independent travels.

There are other benefits to going with a group, aside from having an organizer who can help you navigate all the required paperwork. Bradley advises DIY travelers that bookings made on many hotel websites can get bumped or cancelled by the tourism authority—often without warning. Plus, she says photos can be misleading; a perfectly nice-looking hotel may be subject to frequent water shut-offs or power outages. (Those who aren’t members of Bradley’s organization can book luxury trips via Ker & Downey and Cazenove + Loyd.)

If you’re dead set on going without a group, book through Cuba Travel Network, which guarantees all its reservations by selling rooms from preassigned blocks. But plan on booking at least three months ahead.