Puerto Rico has more than 130 hotels, which is a lot to choose from. But there are some that stand out for their history, unique location, authentic vibe, luxury experience — and some with a combination of all of the above. These are the Puerto Rico hotels and resorts that draw us back to the Island of Enchantment time and again, whether it feels like visiting an old friend or experiencing a new property for the first time.

Dorado Beach, A Ritz-Carlton Reserve, Dorado

This is the crown jewel of Puerto Rican hospitality, an ultra-luxe resort that delivers the promise of transcendent luxury in the newly-resurgent Dorado Beach, one of the hottest destinations in the hemisphere since the pandemic. People who know luxury destinations like Little Dix Bay in the British Virgin Islands and the former Caneel Bay on St. John won’t be surprised to know that this is another classic property founded by Laurance Rockefeller, who had a knack for building on perfect beaches and the foresight to buy up and keep wild lots of pristine land around his hotels.

The Fairmont El San Juan Hotel

The Fairmont’s newest addition is a collectin of 13 luxe Banyan Bungalows, named for the 300-year-old Banyan tree on the property. Set apart from the main hotel building, the bungalows feature spacious showers with dual shower heads and private patios. Key amenities include a beach club and freeform pool deck facing Isla Verde Beach, an elegant casino, a cabaret channeling the spirit of a 1950s speakeasy, and a lively nightclub.

O:Live Boutique Hotel, San Juan

The rooftop bar at this boutique hotel overlooking the Condado lagoon is a not-so-secret gathering place for stylish locals and informed tourists, and guest suites at O:Live (“oh, live” or “olive,” as you please), even those without views, feel like sanctuaries, and larger accommodations stand out with amenities like ornate tubs sheltered by slatted pergolas. The Sage lobby restaurant steakhouse by celebrity chef Mario Pagan extends the hotel’s warm, rustic atmosphere into a sophisticated Italian steakhouse.

The Hotel Rumbao, San Juan

The Sheraton Old San Juan was a solid if unspectacular property; Now it’s the Rumbao, a reinvention of the Sheraton property and part of Marriott’s Tribute Portfolio, retainining its predecessor’s unique location near the Old San Juan cruise port. The old city is right at the doorstep of this freshly renovated hotel, as are the shops, bars and restaurants comprising The Landing.

Don Rafa Boutique Hotel & Residences, San Juan

A former family home in San Juan’s Miramar district debuted in 2023 as a 39-room boutique hotel with a midcentury vibe and a collector’s eye for vibrant local artwork, which is displayed throughout the property’s public spaces. Canvas, the rooftop restaurant, nods to the creative decor as well as a menu that paints outside the lines, dipping into a palette of Puerto Rican and international influences.

Wyndham Palmas Beach & Golf Resort, Palmas del Mar

This property has gone through several iterations over the years, but its newest one seems like a keeper, following a “dramatic” renovation. There’s a lot to do here, too: when not strolling or sunning on Trova Beach, guests can hike through a forest of Pterocarpus trees, tennis or pickle ball, ride a horse on the beach — the activity list is extensive for a resort of this size. But the biggest story at the Wyndham Palmas is the golf: a pair of courses designed by Rees Jones and Gary Player, respectively.

The Caribe Hilton, San Juan

It’s said that the bar at the Caribe Hilton was where the first pina colada cocktail was shaken up (although a competing version of history has its birthplace at the must-visit Barrachina in Old San Juan) Originally a hand-blended drink — the frozen version came later — the Pina colada is still served, in several variations, at the hotel’s lobby-located Caribar. The Caribe Hilton manages to keep touch with its mid-century elegance while still presenting as a fresh, modern resort, making it a truly iconic address for a San Juan stay.

The El Conquistador, Fajardo

The “El Con” has a legendary name and a location to match. This is a big resort, and getting bigger: currently with 368 rooms, the resort will grow back to its original size of 750 rooms once fully recovered from damage from 2017’s Hurricane Maria. Hotels this expansive can be overwhelming, but the El Con has something of a pressure-relief valve in the form of a private offshore oasis, the 100-acre Palomino Island, which has sandy beaches, water sports activities, and its own restaurant. Activities abound, from golf and tennis to a water park and spa.

Villa Montaña Beach Resort, Aguadilla

With just 76 rooms on 35 acres of beachfront property, Villa Montaña is a boutique hotel with individually designed and decorated guest quarters in a part of Puerto Rico less frequently visited by tourists. Walking and hiking paths weave through the surrounding jungle, there’s horseback riding on the beach and snorkeling offshore, and golf is available at the nearby Royal Isabela and Punta Borinquen courses. The rustic, alfresco Eclipse restaurant is one of the top culinary spots on Puerto Rico’s west coast.

The Hotel El Convento, San Juan

Location, location location: it doesn’t get any better than this hotel located in a former convent in the heart of Old San Juan. A stay here is to literally weave yourself into the tapestry of the city’s history: the yellow, Spanish Colonial building has been a fixture on San Juan’s cobblestone streets for  more than 370 years. The 81 guest rooms are located in galleries surrounding a peaceful interior courtyard; modern amenities include a rooftop pool and exclusive beach club for guests.