Best San Juan Hotels

One of the island's biggest and best, El San Juan offers unparalleled luxury. Swim up to one of their many tiki bars in the huge pool, or lounge on a chaise on their private beach (where you can order lunch and have it brought to you, if you like). The interior is awash in glowing chandeliers, plush blue and gold velvet chairs, lots of mahogany and Art Deco touches like large fish carved into the main columns. The casino is straight out of a James Bond movie, with good-looking people and maybe a villain or two playing for high stakes. Guestrooms are surprisingly modern, given the colonial feel to the main building, with an all-white motif, and sliding glass doors onto private balconies. 

Instantly recognizable by its beautiful lemon-yellow facade with tiny balconettes in front of each window, Cervantes Chateau is a stunner. The 17th-century Spanish building has 12 rooms spread through six floors, each one more opulent than the next. Its boutique design is courtesy of Puerto Rican Nono Maldonado, who preserved its colonial grandeur. Inside it's like a French chateau (hence the name), but with all the modern amenities you could want sprinkled about. Free continental breakfast in the on-site Panza restaurant, which also does room service until well past midnight.

A stunning old structure dating back to the Conquistador era, El Convento is a renovated Carmelite nunnery. Its inner courtyard is a multi-story atrium filled with plants and flowers, and a charming old espresso bar. Rooms above all lead onto balconies that overlook the atrium, which is tiled in old Spanish flagstones. Each room is adorned in aged wood beams, with carved chairs and velvet curtains worth of a Spanish grandee. Two very large suitesl—the former rooms of the Carmelite nuns in charge of the monastery—are also available. Its on-site bar, El Picoteo, is a great place to grab a drink and tapas (Spanish finger food).

A sleek and modern boutique hotel, The Water Club is aptly named. A sheet of water runs down a wall near its entrance, and it's rooftop bar is often bathed in the light Puerto Rican rains (that doesn't stop people from dancing). The rooms are big and airy, with gauzy white curtains wafting in the breeze and light blue lights lending the space a futuristic atmosphere. Along with the rooftop bar there's a rooftop pool that allows you to sit in the balmy air and gaze down the long, curving beach.

In the center of Old San Juan, this mid-range, rather drab hotel is right around the corner from the Nuyorican Cafe, and just steps from the dining hotspots of Calle Fortaleza. There's nothing wrong with Hotel Milano that some updating wouldn't fix. The rooms, especially in the lower floors, are a bit dark because they get no light, and the usually one window in each room is blocked by the air conditioning. It's clean and a step up from the budget options clustered around San Juan, with sturdier beds, more modern showers and thicker walls.

Close to the beach and in an area with several high-end hotels, this small inn doesn't offer much, but does the best with what it has. That amounts to small rooms with basic beds and air conditioning, and little else. The hallways are open to the elements, so during the frequent island rains you will see pooling water, but it's quickly cleared away.  The Isla Verde beach is a short walk away, across a highway. To get there you have to use a pedestrian bridge. Avoid crossing that bridge late at night, and it's wise to stay off the beach after the sun goes down.

Check in to an art-filled, renovated mansion at Da House, where the staircases are grand, the ceilings have crown-molding and the railings are wrought-iron. Da House strikes a minimalist tone, the better to show off the fine lines of its old, grand dame of a building. Rooms are so spare as to be almost Spartan, but there's something refreshing about waking up in a white room, in a big white bed, with the bright morning light spilling in from the balcony. The downstairs common rooms look almost museum-worthy, thanks to the many different artworks carefully placed about.

A hippie, funky little B&B just a few steps from the white sands of Playa del Condado, this Casa is a favorite among European travelers. Rooms are decked out with air conditioners, tropical rainbow-colored bedspreads and tile floors, with TVs in small dressers and wooden wardrobes. The real beauty is outside though: Casa del Caribe has a lovely wrap-around veranda, dripping with green plants, where you can grab your morning coffee and complimentary breakfast. Best of all is proximity to the beach.