Caribe Hilton (1 Calle San Geronimo, 787/721-0303, fax 787/725-8849, sjnhi_sales [at] hilton [dot] com, www.hiltoncaribbean.com, $319 s/d, $845 one-bedroom villa, $1,216 two-bedroom villa, includes 12 percent resort tax) is proof that all Hilton hotels are not all alike. This stunning display of modernist architecture and design is a beloved blast from the past, a reminder of a time when the Condado was an epicenter of glamour. Built in the late 1940s, the sprawling hotel features an enormous lobby awash in curved lines and modular shapes that merge elegantly with blond woods, polished steel, and thick glass. Be sure to gaze up at the ceiling, a stunning wooden structure that mimics the swooping shape of ocean waves.

There are seemingly countless bars, including a swim-up bar at the pool. The Caribe Hilton is one of two places in Puerto Rico (the other being Barranchina in Old San Juan) that claims to have invented the piña colada, so tourists often stop by to have one, whether they’re staying at the hotel or not. And don’t miss the hard-to-find Tropical Garden. Tucked away in a quiet corner is an oasis of lushly landscaped grounds built around a pond and gazebo where peacocks, geese, and black swans roam freely.

There are 814 units in the hotel and nine restaurants, including Morton’s the SteakHouse. There is also a spa and boutiques for shopping. Although the hotel is on the ocean, the only swimmable beach is a small public facility beside the hotel.

Condado Plaza Hotel & Casino (999 Ave. Ashford, 787/721-1000 or 866/316-8934, www.condadoplaza.com, $199–259 s/d, $329–459 suites, plus taxes and resort fees) is an interesting bookend to the 1940s-era modernism of the Caribe Hilton. The Condado Plaza Hotel is a 21st-century modernist’s dream with a minimalist aesthetic and a tastefully rendered nod to pop art sensibilities. The lobby is blindingly white with occasional touches of brilliant orange that draw the eye around the room, from the low-backed couches to the textured wooden wall treatments to the private nooks and crannies tucked behind beaded curtains. Modernist touches continue in the guest rooms, where billboard-size black-and-white photographs hang over the beds and the shower is a clear glass cube situated in the center of the spacious bathroom. The casino is open 24 hours a day, and there are multiple restaurants, including Tony Roma’s and the dramatic Strip House, a steakhouse done up in red and black and appointed with black-and-white photographs of 1950s-era burlesque dancers. There is also a fitness center, a business center, and two pools, one of which is filled with salt water.

La Concha Renaissance Resort (1077 Ave. Ashford, 787/721-85000, fax 240/724-7929, www.laconcharesort.com, $309–369 s/d, $549 one-bedroom suite, plus tax and fees) was built in 1958 and is another huge, shimmering modernist hotel on the Condado. It closed and lay dormant for years, but a recent renovation has returned it to its former glory and beyond. Amenities include multilevel swimming pools with waterfalls and a sandy beach with food and beverage service, two lounges, and four restaurants, including Perla, an upscale restaurant serving contemporary American cuisine heavy on seafood in a stunning clamshell-shaped space right on the beach.

The South Beach party crowd gravitates to The Water Club (2 Calle Tartak, 787/728-3666 or 888/265-6699, fax 787/728-3610, info [at] waterclubsanjuan [dot] com, www.waterclub.com, $179–399 s/d). The modern high-design boutique hotel offers super-luxurious accommodations for the young, trendy, and well-heeled crowd. The hotel’s 75 rooms come with air-conditioning, satellite TV, CD players, two-line telephones, data ports, high-speed Internet, minibars, in-room safes, and superior beds topped with down comforters. Water is the theme of this stark white and aqua property: Bubbles float in Lucite countertops at the reception desk, and water features abound. Liquid, the lobby bar, has a corrugated tin wall with a constant flow of water trickling over it. Wet, the rooftop bar, features stunning views of the city and huge leather couches and beds—yes, beds—that spill out around the pool. The restaurant, Tangerine, serves American Asian cuisine.