Old San Juan to Condado: The 11 Best Hotels in San Juan, Puerto Rico
San Juan is where history, style, and the sea converge in one of the Caribbean’s most vibrant cities—and one of its best places to stay. From the iconic pastel buildings of Old San Juan to the golden beaches of Condado and Isla Verde, the Puerto Rican capital is packed with charm, culture, and energy. It’s more than just a gateway to the island—it’s a destination in its own right.
And when it comes to hotels in San Juan, Puerto Rico, the options are as diverse as the city itself. Whether you’re looking for a luxury escape, a romantic boutique hotel tucked inside a centuries-old building, or a beachfront resort with all the amenities, there’s something here for every kind of traveler. Think rooftop pools with ocean views, art-driven interiors, and sleek new brands that blend island cool with urban sophistication.
From legendary landmarks to stylish newcomers, these are the 11 best hotels in San Juan right now— across a range of categories and price points, from intimate inns to iconic resorts to brand-name favorites.
OLV: Fifty Five
This is where modern San Juan style lives. Tucked into the heart of Condado, The 26-room OLV: Fifty Five is part hotel, part gallery, part rooftop party—always with a design-forward, adults-only energy. The rooftop pool is the signature draw, with skyline views and DJ-backed nights. But the real magic is in the details: moody lighting, velvet textures, and oversized soaking tubs in the suites. I loved this place the first time I checked in, and now I love it even more. It’s number one because it exemplifies the new San Juan: hip, sophisticated, cool and unforgettable. It’s locally owned, locally designed and world-class.
Staying here is like sleeping inside history—except it’s wrapped in luxury. This former Carmelite convent in Old San Juan is now a boutique stunner, with Spanish Colonial architecture, a peaceful courtyard, and rooms that feel both classic and contemporary. You’re steps from the Cathedral and blue cobblestone streets, but El Convento is its own oasis: quiet, refined, and unmistakably Puerto Rican. Tip? Have a Ron del Barrilito at the courtyard bar. Then have another.
One of the Caribbean’s most romantic stays. With just 15 rooms, O:live feels intimate from the moment you walk in. The design channels Mediterranean luxury with Caribbean flair—think freestanding tubs, wood beam ceilings, and leather trunk mini-bars. The rooftop bar and plunge pool deliver one of the best sunset views in the city. It’s indulgent, yes—but never showy. Tip? Enjoy a dinner at the rooftop bar, the place that ushered in the new era of San Juan hospitality when the team of Loisse Herger and Fernando Davila opened it back in 2012. I’d argue they’re the top hoteliers on the whole island right now — and that shows, with three hotels on this list.
A landmark reborn. Built in 1919, the Vanderbilt is the grand dame of Condado—restored to full glory with marble floors, oceanfront pools, and butler-serviced suites. The vibe is old-world glamour meets modern resort, with fine dining at 1919 and champagne service at the beach club. It’s where you go when you want full-on San Juan luxury with a splash of Gatsby. The rooms aren’t huge (particularly the standard ones) but that’s the price you pay when you go for old-school, historic hospitality. And the build quality, service and F&B more than make up for that. Tip? Check out the hidden-away AVO Lounge just off the main lobby. This is San Juan’s premier luxury option.
This is where the party lives. Nestled on Isla Verde Beach, this icon blends nightlife energy with resort polish. You’ve got a legendary lobby bar, a buzzing pool scene, and four pools—including cabana-lined showstoppers. Rooms are sleek and beachy, while villas bring extra privacy. Whether it’s a weekend escape or a big celebration, El San Juan always feels alive. Tip? This is the best casino in Puerto Rico, so if it’s gaming you’re after, this is the spot.
San Juan Marriott Resort & Stellaris Casino
Big resort energy, right in Condado. This Marriott delivers the full resort experience: direct beach access, a waterslide-equipped pool, a 24-hour casino, and lots of family-friendly fun. Rooms have been stylishly updated, many with balconies overlooking the sea. It’s the best of both worlds—steps from restaurants and nightlife, but still fully self-contained. Tip? Get out and explore Condado — it’s a walkable, fun neighborhood with the capitals’ best shopping and a leafy, residential vibe.
A hidden gem in Old San Juan, this adults-only boutique stay feels like a well-kept secret. Set in a 19th-century building, it balances historic charm with modern finishes. The rooftop pool is a knockout, with panoramic views of the old city and San Juan Bay. Downstairs, you’re right in the middle of it all, from museums to mojitos. Palacio Provincial is chic, calm, and perfectly placed.
La Concha Renaissance San Juan Resort
This is where you go when you want to feel the pulse of Condado—bold, bright, and always moving. La Concha is a mid-century masterpiece reborn for the modern traveler: sleek lines, swaying palms, and a soundtrack of crashing waves. You check in and step straight into the scene—three shimmering oceanfront pools, beachside cabanas, and nights that begin with cocktails at the iconic open-air lobby and stretch late into the energy of the 24-hour casino. The 478 rooms are cool and contemporary, many with ocean views that frame the city’s tropical edge. It’s part style, part nostalgia, and all San Juan. Tip? Dine at the newest Caribbean restaurant by multiple-Michelin-starred-Chef Michael White.
The apocryphal birthplace of the piña colada and still one of Puerto Rico’s flagship resorts. Sprawled across a peninsula with its own beach, this Hilton mixes retro charm with resort reliability. The pools are big, the grounds are lush — including the hidden-away tropical garden, replete with swans — and the dining spans everything from sushi to steaks. A recent renovation brought new polish to this San Juan classic—but it’s always been iconic. Tip? This is the best hotel for families in the whole city, with all of the amenities you’re looking for and things that, let’s be honest, you always want when you’re traveling kids (Starbucks, we’re looking at you).
The younger, bolder sibling of O:live. Aire is all curves, textures, and rooftop moments. It’s adults-only, ultra-stylish, and unapologetically bold, with a design that fuses avant-garde with Mediterranean sensuality. The rooftop infinity pool and jungle bar are made for golden-hour lounging. It’s a hotel for the creatively inclined—and those who never skip golden hour. Our tip? Go for a room with an ocean-view plunge pool high above the beach in Isla Verde, San Juan’s most beachy neighborhood.
Old San Juan’s coolest new address (it opened in 2024). Hotel Rumbao takes over a prime corner of the historic district and infuses it with bold modern energy. It’s art-forward, musically inspired, and tailor-made for travelers who want heritage with an edge. The rooms are sleek and sunlit, the rooftop pool and lounge overlook centuries-old architecture, and the vibe is distinctly local—but fresh. You’re steps from tapas bars, boutiques, and the buzz of the old city, but Rumbao adds something new: a rhythm all its own. Tip? This location is pretty hard to beat and that alone makes it one of our best hotels in San Juan Puerto Rico.
Where to Stay in San Juan
Whether you’re here for the historic plazas or the pool parties, San Juan delivers a spectrum of hotel experiences—from heritage-laced hideaways to pulse-quickening rooftop escapes. This list of the best hotels in San Juan, Puerto Rico is your guide to our favorites, whether you want romance, history, design, or pure Caribbean luxury.
Guy Britton is the managing editor of Caribbean Journal. With more than four decades of experience traveling the Caribbean, he is one of the world's foremost experts covering the region.
