Best Luxury Hotels in San Juan, Puerto Rico

The Condado Vanderbilt Hotel is located directly on the beach, in San Juan’s vibrant Condado district. Early 20th-century antiques are ubiquitous throughout, and the hotel plays up its historic setting with handsome restaurants and lounges that exude a turn-of-the-century ambience, though the infinity-edge pool, innovative spa, and high-tech meeting spaces keep things contemporary. The 319 guest rooms are timelessly attractive, with dark-wood furniture and stone-topped bathroom vanities.

Marriott’s top-tier hotel in San Juan is an easy five-minute drive from the airport along Isla Verde beach. The 416 rooms and suites are contemporary and upscale, if a tad generic, and most are without balconies. Most guests spend their time on the sand, or at the lively outdoor pool where attentive service is a focus. Just watch out for the super-pricey cocktails. In the evenings, the lobby bar is the place for small plates and pre-dinner cocktails before dressed-up guests (and some locals) make their way to their reserved tables at on-site restaurants BLT Steak and Il Mulino. The hotel attracts a mix of post-cruise goers, conference attendees, and leisure guests on long weekend getaways. Wi-Fi, tennis, and a fitness center is free, unless you count the 18 percent luxury resort fee added to the bill.

There is nothing quite like European-style El Convento in Old San Juan. It was a convent for 252 years, and today it's the neighborhood's principal upscale hotel, offering 58 elegant rooms and suites filled with Spanish antique treasures and modern amenities. Its history is present everywhere, from the exposed wood beams to the 350-year-old Nispero tree rising high above the romantic courtyard. A nightly wine and cheese reception takes place on the terrace, allowing guests (mostly couples) to mingle while overlooking views of San Juan Bay. The main restaurant offers al fresco fine dining in the courtyard; other features include the beautiful sun terrace and small outdoor pool. Service is a priority here, and it shows.

The Caribe Hilton is a San Juan original. In 1949, it was the first Hilton to be erected outside of the continental United States, and since then it's hosted plenty of celebrities and dignitaries. History aside, the 910-room Caribe Hilton is massive and lively -- an upscale destination for cruisers, group tours, retirees, families, conference-goers, honeymooners, and partiers. The hotel's 17 acres include bird-filled tropical gardens, multiple restaurants, a lively bar, and gorgeous pools. The manmade beach isn't the best, and can be packed, but rooms are modern and comfy, with Hilton's excellent beds, and many have furnished balconies with ocean views.

The highlights of this 402-room Isla Verde resort are the large, low-key beach and the inviting pool, which has Jacuzzis, a rock grotto area with waterfalls, and a swim-up bar. Rooms are chain-like but pleasant enough, with clean white linens, light blue accent walls, and basic shower/tub combos, though there are some signs of wear (the bathroom fixtures in particular could use updating). There are some decent restaurants and bars within walking distance, and Old San Juan is just a short drive away.

This big, reliable (and yes, predictable) Sheraton hotel across from Puerto Rico’s Convention Center opened in 2009 as the prototype for the revitalized Starwood brand, and offers 503 modern rooms. Rooms have tub/shower combos, modern amenities, and well-lit work desks; extensive event space includes the largest ballroom in San Juan. A handful of restaurants and bars are available and there are even fewer noteworthy options within walking distance -- though it doesn’t take long to taxi to Old San Juan or Condado for more choices (or the beach). It's geared toward business travelers, but those with free time can hit the fourth-floor infinity pool and sun deck with views of the bay. Guests of the Sheraton Club Rooms get access to free breakfast and snacks in the Club Lounge. Wi-Fi is free but parking comes with a daily fee.

The upscale, 15-room Olive Boutique Hotel is an inviting Condado hotel with a rustic-chic ambience and a vibe that feels laid-back and high-end at the same time. Rooms are modern and stylish, and include thoughtful details like daily fresh cookies and premium toiletries. Outdoor terraces in all rooms are a major bonus -- they have vibrant Spanish tiling and luxe modern furniture, and some feature Condado Lagoon views. The beach is just two blocks away, and the hotel has a swish rooftop bar and lounge with a plunge pool, plus excellent on-site dining at Sage Steak Loft.

Situated right on the beach in Condado, the Marriott Resort & Casino is a step above some other hotels in the neighborhood: The grounds and the hotel -- including the pools, the tennis courts, and the spa -- are well-kept, and the upscale rooms feature warm colors, flat-screen TVs, and large bathrooms with granite vanities. Though there is a casino on-site, the hotel also caters to families, with amenities such as a game room, laundry facilities, and a pool with a waterslide. But some have complained of hearing noise from the casino in the rooms on the lower floors, and fees for extras such as Wi-Fi and beach chairs are annoying.

The vibe at the 382-room El San Juan Hotel & Casino is that of a fun and relaxed party. The property features a lively lobby, a sprawling free-form pool with a swim-up bar, and a location right on white-sand Isla Verde Beach. Rooms are stylish and beach-y, with white bedding and furniture, light wood, and tropical accents. The bathrooms are modern, too, but aren't exactly spotless or spacious. Just make sure you're happy staying put: There's not much to do nearby, and Old San Juan is at cab ride away.

Owned by the same couple for decades, the historic Gallery Inn is run like an informal bed-and-breakfast -- guests are greeted by name, much of what the restaurant serves is grown in the garden, and no two rooms are the same (though they do share lots of Spanish-style charm). Also like a bed-and-breakfast, the hotel lacks amenities such as TVs and a fitness center. The property's main draws include the convenient Old San Juan location, ocean views from the wine deck, and the artsy, laid-back feel. The innkeepers are both artists, and it's evident they put thought into every detail of the restoration -- expect beautiful old-world details like brick floors, wood-beam ceilings, rugs, sculptures, and antique knickknacks.