I live in Puerto Rico and have stayed in San Juan's most beautiful hotels. Here are my top 10, from beachfront resorts to quirky inns.
Visitors might instantly recognize La Concha Resort, located right on Condado Beach, from its iconic seashell structure. Named "Perla," meaning "pearl," it's a stunning architectural structure that served as a wedding venue during the pandemic and will soon return to being a restaurant.
The hotel is a Marriott Bonvoy property and has three pools on-site, including an adults-only pool. There's also a lively bar in the lobby with a casino attached for those seeking a vibrant nightlife. I recommend opting for an ocean-view room — leave your balcony door ajar and sleep to the sound of lapping waves.
The Caribe Hilton is one of two places that claim to have invented the piña colada, the other being Barrachina, a restaurant in Old San Juan. The only way to know for sure is to taste both for yourself.
While you have a drink in hand, head to the Caribe Hilton's secluded, buoy-enclosed stretch of beach, complete with cabana rentals and a floating platform. The hotel offers a variety of brightly lit rooms and suites, many with balconies and ocean views, and it's easy to book a room here with Hilton Honors points.
Barack and Michelle Obama once stayed at this boutique hotel on a hill in Old San Juan. There are only 27 rooms, each with lavish and distinct decorations. There are no TVs in the rooms as the hotel maintains its historic aesthetic with details like canopies and four-posted beds, beautifully renovated and curated by Jan D'Esopo, the owner and caretaker. Her artwork adorns the space and she often mingles with guests throughout the premises with a pink parrot accompanying her.
The on-site Cannon Club restaurant and Venetian-style piano bar features live music, a full bar, and tapas. They host events like a candlelight concert series, and the guests can enjoy the soundtracks of visiting musicians throughout the common spaces of the hotel.
Located in Condado and overlooking the lagoon, the O:LV Fifty Five is a luxury, modern hotel with one of the most Instagrammable rooftops in the city. It has a two-tiered pool and jacuzzi, and the guest rooms feature sleek marble bathrooms with rain showers.
As an adults-only property, they offer customized experiences from romantic dinners in private suites to floating champagne decks on the lagoon. Dining options include ARYA, a posh eatery and bar with a Rolls Royce transformed into a DJ Booth, and Raya, a Caribbean-Asian restaurant with a menu that Mario Pagán, a renowned local chef, personally customized. Reservations are a must.
Adorned with dreamcatchers throughout, this award-winning hotel has strong Bohemian vibes. Located a block away from the ocean and enmeshed in lush greenery, the DREAMCATCHER by DW is a tranquil oasis in the middle of a busy city. They have yoga on the beach or under the stars, and select rooms have outdoor showers.
As a vegan hotel, they serve plant-based breakfast and brunch with organic and locally sourced ingredients. They also have a communal pescetarian kitchen and a fridge in every room for those who want to prepare their own meals.
A celebrity favorite, the Condado Vanderbilt is a five-star, high-end hotel that's been a staple in San Juan for over 100 years. It's located on the oceanfront and has stylish suites with luxurious touches, from personal ice-maker machines to 300-thread count sheets.
The hotel is home to 1919, an exclusive restaurant by Juan José Cuevas, a Michelin-starred chef, that's one of Puerto Rico's most coveted fine-dining experiences — it requires you to be in formal wear. They also have a more casual Mexican eatery called Tacos & Tequila, launched in partnership with Tequila Patrón.
Preferred Hotels & Resorts, the same hotel group that runs El Convento, a convent-turned-famously-romantic hotel in Old San Juan, opened the adults-only Hotel Palacio Provincial around the corner in January 2021. Featuring Juliette balconies, courtyards, and a glass-enclosed library, this hotel blends old-world charm with modern sophistication.
The rooms feature intriguing architectural details like wooden beams, and there's a rooftop pool. As the first new hotel to open in Old San Juan in decades, it marks a new, upward direction for travel and tourism on the island.
About the Author
Ricky Díaz
Aventura, Florida and Dorado, Puerto Rico.
Hollywood Real Estate Investments LLC founded in Florida in 2004.
Commercial real estate broker in New York City for 6 years.
Financial Advisor - 15 years (1989 - 2004) Merrill Lynch and Smith Barney.
Education- BA- University of Georgia -MBA- Inter- American University of Puerto Rico-Metropolitan Campus.
Whether you're in the research phase at the beginning of your real estate search or you know exactly what you're looking for, you'll benefit from having a real estate professional by your side. I'd be honored to put my real estate experience to work for you.
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