The 10 Best Hotels in Puerto Rico

There’s history to be found at Hotel El Convento. The original building, built in the 1600s as Americas’ first nunnery, was torn down and rebuilt in 1854—yet much of the ambiance remains, from handmade Andalusian tiles to mahogany beamed ceilings and one-off antiques, including every wood-carved bed in the 58 guest rooms. Its outdoor spaces prove equally as beautiful: the rooftop has its own hot tub and wading pool with views of the city, while its inner courtyard, bursting with palm trees and bougainvillea, is the place to be during happy hour for complimentary pre-dinner cocktails and hors d’oeuvres.

La Concha made a splash on the Condado beach scene when it first debuted in 1958, with its midcentury modern interiors and eye-catching poolside restaurant housed in the shape of a giant seashell. After a $220 million revamp by Renaissance Hotels for its 50th anniversary, the hotel is even more of an architecture-lover’s dream: think streamlined guest rooms awash in hues of seafoam green and beige, while the white marble lobby features an entire wall of glass that lets in the light from the beach. After a dip in one of its three pools (we recommend the adults-only infinity number), freshen up for the buzzy restaurant and bar scene that draws urbanites after dark.

Despite being just a half-hour drive outside San Juan, this St. Regis is a true oasis. A former coconut plantation just outside El Yunque National Forest is now home to 139 rooms spread out among a smattering of low-rise buildings, all done up with colonial-style furnishings like cherry furniture, beamed ceilings, and rattan fans. Expect the usual luxury trappings of a St. Regis stay, like a 10,000-square-foot Remède Spa, Robert Trent Jones Jr. golf course, and excellent restaurants including a Jean-George Vongerichten menu of Puerto Rican classics at Fern, which faces the beach. An added touch: the property’s own private bird sanctuary, where you can learn to spot exotic species before a marine biologist-led tour along the surrounding nature trails.

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Low-key Dorado Beach, once an exclusive northern coast escape for the likes of Elizabeth Taylor and Amelia Earhart, is now one of Puerto Rico’s buzziest resort towns, all thanks to the debut of Dorado Beach, a Ritz-Carlton Reserve. The resort sets a new bar for luxury hotels in the country, where check-in is replaced with private ambassadors that show you directly to your room (some have multiple bedrooms and private plunge pools), a Twenties-era plantation house has been restored as a stunning five-bedroom villa, and José Andrés’ Mi Casa restaurant combines the best of Spanish and local cuisine. If the spa, which sprawls across 22 buildings over five acres of primordial rain forest, isn’t enough to lure you here, the powdery three-mile coastline surely will.

This 22-room island retreat, the debut hotel from music exec Simon Saeyertz, is far more like a seasoned hotelier’s passion project than a first-run try. Its most striking feature is its curvaceous concrete façade, whose carved louvers create intricate shadows that dance across the inner hallways as the sun arcs across the sky. Interiors are all about 1950s Tropical Modernism—geometric tiled floors, purposely unfinished plaster walls, striped throws, terraces with impressive views of Vieques and the sea—while the social scene is no-fuss and laid-back. After a morning spent sleeping in, be sure to carve out some time between the beach and the rooftop plunge pool to taste some of chef José Enrique’s famous dishes (bacon and egg empanadas; seafood soup) at the second floor’s bar and restaurant.

Old meets new at this historic Spanish Revival property on San Juan’s popular Condado Beach, which was painstakingly restored in 2014 to redeliver the elegance and grandeur it once embodied in the early 20th century. Details like the original iron staircase in the lobby to red velvet settes and a new-build cigar bar transport you back to the hotel’s heyday, while the 319 rooms upstairs are more timeless and modern, with tufted headboards, dark-wood furniture, and a soothingly neutral palette of taupe and cream. An infinity pool and upscale restaurants are more expected amenities, but unlike many of San Juan’s historic properties (we’re looking at you, El Convento), this one grants direct access to the beach.

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The Olive manages to feel down-home yet luxurious—a winning combination that lures romantics seeking the best of both worlds. The owner, an avid traveler, has amassed a global collection of French, Italian, Moroccan, and Spanish pieces that comes together beautifully: think all-glass bathrooms, distressed wood walls, and wrought-iron chandeliers and lamps that add charm to the 15 cozy (if compact) guest rooms. All come with terraces, some of which look out towards the Condado Lagoon. The beach is two blocks away, but that’s okay: the real scene is found on the rooftop terrace, where a bar-café keeps conversations flowing.

Just steps away from the Olive Boutique lies its sister property, O:LV Fifty Five, an opulent adults-only stay that ups the ante with a sleek, designer-inspired aesthetic. Its sumptuous suites are stocked with film noir–esque artwork, floor-to-ceiling headboards, black-and-white marble floors, and turquoise and purple furnishings, while a bi-level rooftop with an infinity pool fuels the decidedly grown-up atmosphere. And then there's the food scene at Raya, steered by local celeb chef Mario Pagan—highlights include spiced adobo kurobuta ribs, wasabi grilled cheese, and Japanese whiskey infused cocktails.

If the beach is what you're after, look no further than the InterContinental San Juan, set on two miles of manicured shoreline in Isla Verde. The 16-story stay offers well-appointed guest rooms with modern furnishings and sweeping views, but the beachfront terrace and lagoon-style swimming pool (with a swim-up bar!) are where you'll likely spend most of your time. After a morning under the sun, schedule an ocean-inspired massage at the 10,000-square-foot Akua Spa, where you can request a private outdoor treatment room overlooking the sea.

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Is Royal Isabela the most romantic clifftop hotel in the Caribbean? You can definitely make a case for it: the property spreads out over some 426 tropical acres facing the Atlantic in northwestern Puerto Rico, where just 20 casitas make guests feel like they own the place. Living spaces are big and breezy and feel more like actual homes with their separate living rooms and private decks with plunge pools. The golf course is one of the Caribbean’s best: its 18 holes stretch out over three miles of forest, farmland, and clifftop and feature some of the most epic sea views in the game; the same vistas can be found at the open-air Croquet Bar and farm-to-table restaurant, which sources ingredients from its own gardens as well as local farms.