This 1949 landmark just outside Old San Juan has 814 rooms done up with contemporary Caribbean flair. The hotel is divided into three different wings, each offering similarly-sized-and-styled accommodations (the water-facing wing has the best views). Although the hotel mostly caters to business travelers, Caribe Hilton does have a number of resort perks, such as shorefront swimming pools, an Olas Spa and Fitness Center, and access to a secluded beach.

Expect to gasp upon entering the Conrad San Juan Condado Plaza. A $70 million renovation was completed in 2008—with the evident intention of transforming the hotel from a tattered casino-with-rooms into a tower of trendification. As far as the lobby goes, goal achieved: The front desk is a glowing bolt of frosted orange glass, lounge nooks are stuffed with amoebalike chairs in turquoise and red, the walls shimmer with textured plastic surfaces, exotic sharks prowl a wall-size fish tank. The whole first floor emits a late-night Miami vibe, with some authentic salsa touches. The 570 rooms keep the style going in various shades of deep red (in the ocean tower) and acid green (lagoon tower). Even the hallways are beautiful, with Japanese vases arranged on sleek lowboys. The only serious lapse is the mezzanine, where the restaurants remain mired in the 1980s: an Italian cafeteria reminiscent of a Cleveland airport and a Japanese noodle shop that overlooks a row of slot machines in the dowdy central casino. Luckily, new additions are helping to salvage the dining scene: Chef Wilo Benet has relocated his famous Pikayo restaurant here, and his new restaurant Varita in the lagoon tower is a fun, casual spin on Puerto Rican barbecue. There are two pools and a small beach, and the Condado location, about 15 minutes from Old San Juan, means plenty of options for sightseeing and activities. But what draws the clientele is the style—without the nonstop nightlife of similar properties like La Concha and El San Juan. If you like the mod look but not deep bass thumping through your walls at 3 am, you've found your hotel.—Leigh Newman

The El San Juan Hotel was designed to remind wealthy travelers of the pleasure palaces of Havana, and it's still turning heads. The mahogany-paneled lobby, with its red marble floors and centuries-old tapestries, no longer gets all the attention. Now the main attraction is the curvaceous pool that meanders past four-poster daybeds perfect for lounging, as well as air-conditioned cabanas that have nearly as many amenities as the guest rooms. A 2007 makeover also gave the 382 rooms a new look, their white-on-white scheme livened up with bursts of citrusy orange and lime, and playful Philippe Starck–style ghost chairs. We like the ultramodern furnishings, but if you're more traditional, opt for one of the oceanfront lanai rooms. These suites, in a separate building, have kept their plantation-style charm—a look that, like the old-school glamour of the lobby, plays nicely with the contemporary gloss of the white rooms and pool. The eight on-site restaurants also offer a little something for everyone, from sushi to Starbucks to Brother Jimmy's, a rooftop barbecue joint. But the real action is on the weekends, when the hotel's nightlife scene, including live salsa bands in the lobby and the pulsing in-house club Brava, never stops.

This place is for the birds—literally. You're greeted in the lobby by Campeche, a cockatoo who proffers a business card identifying him as the hotel's social director. And there are several other colorful creatures, from a blue hyacinth macaw named Mikey to a harlequin macaw named Pica (who might nip your ear if you're paying too much attention to another bird). One of the birds is usually on the shoulder of owner Jan D'Esopo, an artist who has filled the 300-year-old mansion with her cheerful watercolor paintings and massive bronze sculptures. D'Esopo is often hard at work in the adjoining art studio or the hotel's flower-filled courtyard. If she's not putting the finishing touches on a piece, she'll be happy to show you some of the 22 guest rooms, all of which have over-the-top touches like four-poster beds swathed in brocades and walls covered with trompe l'oeils. This is not a place for introverts: You'll undoubtedly get drawn into late-afternoon wine-and-cheese gatherings on the sunny terrace or a concert in the music room. There's no beach, so ask for a room with a view, as this is Old San Juan's only lodging facing the Atlantic Ocean.

One of the Historic Hotels of America, the Hotel El Convento is a thoroughly renovated 17th-century Carmelite convent. The small boutique hotel has 58 rooms and sits in the heart of Old San Juan. Rooms have preserved their period grandeur, with high ceilings, huge windows, Andalusian tile, and exposed mahogany beams. Guests who regret the distance from the beach can get a tropical fix in the rooftop pool. An elegant alternative to the sprawling, modern hotels of San Juan, El Convento is worth a visit even if you're staying elsewhere; come for breakfast or lunch in the courtyard, and then a stroll through its dramatic vaulted arcade.

This midcentury modern masterpiece presided over Condado's rise to tourism fame in the 1950s, and it's been the star of this beach strip ever since. Retro elements like the diamond-patterned facade and a restaurant inside a curving cement seashell feel at home among of-the-moment features like a multilevel pool, which transforms into an indoor-outdoor party platform when night falls. In the 483 guest rooms, low-slung furnishings pay homage to the past while feeling completely current, with the assistance of tech toys like iPod docks. Consider spending an extra $60 or so per night to upgrade to the suite tower (completed in 2010), where curvy blond-wood furniture is accented with pops of sea blue and you get a fully equipped kitchenette, ideal for hosting an after-party with new friends from La Concha's rowdy weekend scene. The crowd skews toward party people, but the great pool setup and kid-friendly restaurant also attract hip young families.—Updated by Colleen Clark

The luxurious Ritz-Carlton San Juan announces its grandeur with large lion statues spouting water into a courtyard pool. The other public spaces, and the 416 rooms, are suffused with Ritz-Carlton-esque touches: enormous flower arrangements, dark hardwood furniture, heavy drapes, and richly colored fabrics. None of it seems particularly Puerto Rican, and the whole thing teeters on fussy—especially in unpretentious San Juan—but it's saved by the overall feeling of hospitality and the genuine warmth of the staff. Cool scented towels and fresh fruit juice are always at hand, and if you need more than that, there are five dining options for you to choose from (including Caribbean outposts of New York's BLT Steak and Il Mulino). There's also a lively, swimmer-friendly beach, a busy casino, and a Club Level with 46 rooms and its own reception and concierge. On the downside, the ten-story building is only five minutes from the airport—great for catching some last rays before your flight, but not so good if your window faces the noisy runways. Ask for a room overlooking the Atlantic.—Peter J. Frank

Set on the beach in posh Isla Verde, this boutique hotel gets feverish press for its imaginative design elements—glass-enclosed waterfalls in the elevators, doors made of Murano glass, and photographs of pebbles instead of carpeting in the corridors. Wet, the rooftop lounge, has a DJ who spins all night. But if most reviews seem to focus on public spaces and nightlife rather than rooms and service, that's because the hotel does, too. The 78 rooms, all white and beige, have floor-to-ceiling windows that face the Atlantic. They are on the small side, and form certainly trumps function. (Good luck hanging a weekend's worth of clothes in the tiny wardrobe recess.) Service is leisurely to the point of nonexistent; the hotel solicits your "desires" (beverage preferences and such) on its Web site before your stay, but often forgets them once you arrive. It's all fun and chic, of course, and if all you care about is the beach and a place to party till the wee hours, it's probably the place for you.