10 Coolest Retro Hotels

Located on Montego Bay, this old-world Caribbean getaway has been a clubhouse for the Hollywood jet set since the 1950s. The open-air cocktail bar pays homage to its bold-faced guests with black-and-white photos of everyone from Bing Crosby to Paul McCartney and Michael Douglas sunbathing on the private beach. Stay in Villa 12, where Oscar Hammerstein first penned the Sound of Music (after meeting a vacationing Maria von Trapp) or in Villa 11 where Stella Got Her Groove Back. Or make like JFK and Jackie and honeymoon in Villa 10. Ralph Lauren has long owned Cottage 26, and in 2004 lent his timeless decorating skills to renovating the hotel’s historic Pineapple House. The mahogany four-poster beds, plantation-style chairs and whitewashed ceilings lend a modern elegance that feels at once effortless and classic. Jackie-O would be proud.

Built in 1912 before there was even a city named Beverly Hills, this pink palace has been as much of a celebrity in Hollywood as the stars that hole up here. Early A-listers Charlie Chaplin, Gloria Swanson, Buster Keaton and Will Rogers gave way to the hard-partying Rat Pack (bottoms up Frank Sinatra and Dean Martin). It’s frequently served as a movie set--in the 1950’s for Gregory Peck and Lauren Bacall’s Designing Woman—and as a love nest (cuddle up John and Yoko). Frequenting this hotel became a family matter for the Taylors: Francis Lenn Taylor opened an art gallery in the hotel’s lower level, and his daughter Elizabeth Taylor stayed in the bungalows with six of her eight husbands. Her standing room service order with Richard Burton (husband five)? Two bottles of vodka with breakfast and another two with lunch.

A trip to Palm Springs is a study in midcentury modernism, and the Jonathan Adler-designed Parker is the perfect contemporary expression of the aesthetic. Built in 1959 as California’s first Holiday Inn and purchased by cowboy singer Gene Autry, this 144-room hotel was given a $27 million facelift by Adler in 2003. The hotel has had its share of tabloid-worthy scandal (Robert Downey Junior got arrested here partying a little too hard), but it’s far from a boozy crash pad. That’s thanks to the killer Adler aesthetic, a whimsical mix of shaggy Moroccan rugs, cheeky needlepoint pillows, lacquered four-poster beds and retro wall hangings. The vintage “Drugs" sign in the lobby, though, still winks at the hotel’s party past.

Every old hotel has its secrets. But this southern grande dame has some doozies, like a massive 112,544-square-foot Cold War bunker built by President Dwight D. Eisenhower 720 feet below ground. For over 30 years, high-society bankers, industrialists, and kings unknowingly slept above the concealed bunker until it was decommissioned in the 1990s. What’s no secret? Design icon Dorothy Draper’s legendary Hollywood Regency interiors, an over-the-top riot of bold florals and plaids, checkerboard floors and spiral staircases.

Built in 1940 for $250,000 and designed by the legendary L. Murray Dixon, this paragon of Deco décor has since been passed down through some of the biggest names in hotel history, including Andre Balazs for his renovation in 2000 and Tommy Hilfiger, who plans to turn it into an exclusive private club and hotel starting in 2015. Both hoteliers were romanced by the storied resort’s history–during World War II, it was converted into barracks, and it soon after became a kosher hotel with the ballroom used as a synagogue. A stay here feels a bit like a trip to the 1940s, with interiors dressed in pink lounge chairs, vintage tables and gorgeous terrazzo floors. But the real star is that curvaceous, graphic pool, which has hosted everything from Esther Williams swimming routines to Chanel’s cruise collection show, where Karl Lagerfeld & Co. constructed a runway atop its scalloped border. The Raleigh itself is a lot like that pool: cool, pretty and a place to be seen.

The Breakers is proof that you can’t keep a good hotel down. Opened in 1896, this Floridian landmark burned to the ground twice, devastating the Rockefellers, Vanderbilts and Astors that vacationed in its hallowed halls. After the 1925 conflagration, the hotel brought in 75 artisans from Italy to paint the 200-foot long ceilings in the main lobby, and countless others to create a stately palace modeled on Florence’s Villa Medici. It remains today a stunning example of grand Floridian architecture with miles of stately gardens, graceful arches and Florentine fountains, and a thoroughly modern oceanfront spread with four new pools, luxe bungalows and a St. Tropez-inspired bar for today’s scions of industry.

Nothing feels more throwback than summer camp, and Runschmeyer’s channels that carefree summer vibe to a T. The 1950s camp got a seriously cool-kid upgrade in 2012. The inspiration? Dirty Dancing meets Jacques Cousteau. Think macramé, Moroccan rugs and wicker peacock headboards in the no-frills guestrooms and ping pong, sand pits and teepees outside. Purchase a retro canteen from the general store, take a spin around Montauk on a vintage-style cruiser and then head back to the mess hall-style restaurant for clam pizza and lobster rolls.

A paragon of midcentury tropicalia, this urban beach resort in San Juan’s tony Condado neighborhood fell on hard times. Abandoned and left to rot in the 1990s, the once glam Puerto Rican icon was nearly demolished. Thankfully the architectural community and Renaissance Hotels swept in, bringing on architect José R. Marchand and designer Jorge Rosselló to restore it to its former glory. The pair opened up the lobby, creating a soothing sea of marble, low-slung white sofas and an undulating ceiling that opens onto a lush al fresco lounge and terraced pool. They also restored original architect Mario Salvatori’s famous shell shaped restaurant, which appears to float on the water at the back of hotel.

The Maritime appears to sail majestically through New York, the porthole-like windows of its ocean liner façade overlooking the Meatpacking District. Once the home of the National Maritime Union, the swinging 60s building was designed by New Orleans architect Albert Ledner. Nightlife and hotel big guns Sean K. MacPherson and Eric Goode took over in 2003, decorating the funky lobby in buttery leather and a rich palette of navy and hunter green. The retro ocean-liner feel is complemented by the blue and white striped mod cabanas on the outdoor patio.

A burst of color against the sandy backdrop of the Arizona desert, The Saguaro Hotel channels the swinging 60s with its modernist lines and trippy Technicolor palette. Architects Peter Stamberg and Paul Aferiat transformed the property—formerly a Mondrian—from its staid white block design into a colorful 194-room oasis with outdoor fireplaces and a funky botanical spa. We dig the throwback beach cruiser bikes and the bumping pool scene where DJs spin and waiters ferry fresh fruit margaritas to pretty people on daybeds. Just goes to show that old school is new again.