Top 5 Celebrities' Winter Vacation Spots...

Here’s where to find Brad and Angelina, Jay-Z and Beyoncé, Jerry Seinfeld, Fergie, and other A-list celebrities in the wintertime.

Question: If you’re Jennifer Lopez (the ninth-richest woman in entertainment with a net worth of $110 million), you have a $350 million fragrance and fashion empire, and your husband just bought ownership in the Miami Dolphins, where do you spend your winter vacations?
Answer: Anywhere you damn well please, of course. But for JLo, “winter getaway” has sometimes meant heading to the Mexican resort Las Ventanas, in Los Cabos.
It’s not surprising why: the luxurious Las Ventanas has the perfect formula for any traveler looking to escape a dreary winter. There’s a long, crowdless, milky-white beach that stretches for miles; giant suites with private Jacuzzis on big balconies overlooking the sea; and Mini Cooper convertibles and fully loaded Kindles to borrow.
But what really draws JLo (and fellow superstars like Leonardo DiCaprio, Charlize Theron, Adam Sandler, Fergie, Arnold Schwarzenegger, and Brad Pitt) is that the resort is private and remote. It doesn’t even have a sign. And when it comes to a getaway, “the number one thing celebrities look for is seclusion and privacy—places out of the reach of the paparazzi,” says noted wedding planner Mindy Weiss, who has organized nuptials for Jessica Simpson, Gwen Stefani, and Adam Sandler. Privacy at Las Ventanas begins at check-in, where there’s not even a desk. It’s handled in rooms so stars can come and go without being noticed.
Privacy is essential in cold-weather destinations, too, and part of Aspen’s appeal is that celebrities can just blend in—especially at places like the Little Nell. Right at the base of Aspen Mountain, the resort has been a celebrity hot spot for two decades, attracting the likes of Mariah Carey and Kate Hudson, who can mix in with minimal rubbernecking. “The celebrities really don’t stand out,” says Carol Hooper, the Little Nell’s head concierge, who has seen her share of A-listers eating burgers and going unnoticed during après ski, like any other guest. “They hang out in the lobby; they have lunch in the restaurants. They feel very comfortable here,” she says.
Another important element for stars: hotels that can handle any request. At the fashionable Setai in South Beach, which has played host to celebrities like Bono, Jay-Z, Beyoncé, and Leonardo DiCaprio, there’s a dedicated team of sales managers whose sole responsibility is to look after famous guests and be in touch with assistants and publicists. It’s one-stop shopping for anything the celebrity needs.
That person proved helpful a couple years ago, when an A-lister asked if one of the bedrooms could be converted into an exercise studio. No problem. And could the hotel bring a giant exercise ball? Done. And could that exercise ball be pink? Of course. The world’s best hotels get a lot of odd requests (see our story on outrageous concierge requests) but do their best to take care of their clientele—especially big names who are hibernating there for the winter.

Setai, South Beach, Miami

Wintertime Guests: Gisele and Tom Brady, Jay-Z, Beyonce, Leonardo DiCaprio, Bono.
Why They Like It: This South Beach hotel merges Zen Asian aesthetics with Art Deco chic (a nod to its South Beach setting). Antique bricks from Shanghai fill the lobby, which spills into an alfresco courtyard with soaring columns, pergolas, and ponds. Of course, celebrities flock to the 40th floor, four-bedroom, $30,000-a-night penthouse suite with a private rooftop infinity pool, Steinway piano, and two large Jacuzzi tubs encased in coral.
Celebrity Scoop: Hidden inside the hotel is a 2,500-square-foot ocean-view recording studio designed by Lenny Kravitz. Beyonce, Timbaland, and Mary J. Blige have laid tracks there.

Round Hill Hotels and Villas, Montego Bay, Jamaica

Wintertime Guests: Emma Thompson, Gabrielle Union, Ewan McGregor, Lance Armstrong, Michelle Williams, Nicole Miller, Mena Suvari, Patrick Dempsey, Shaggy, Russell Simmons, Sigourney Weaver, Paul McCartney.
Why They Like It: In the movie How Stella Got Her Groove Back, Stella found her mojo at Round Hill; many celebrities come here to do the same. Picture villas with horizon pools, mahogany beds, vaulted ceilings, wicker furnishings, and alfresco living rooms with sweeping ocean views. Each separately owned cottage has its master’s personality.
Celebrity Scoop: Owners include Ralph Lauren, Jamaican track star Merlene Ottey, and (at one point) Betsey Johnson. Every Christmas when he was married to Linda, Paul McCartney booked a master villa—maid, gardener, and cook included.

Parrot Cay, Turks and Caicos

Wintertime Guests: Demi Moore and Ashton Kutcher, Bruce Willis, Alex Rodriguez, Jerry and Jessica Seinfeld, Ben Affleck, Jennifer Garner.
Why They Like It: There are no cars on the 1,000-acre private isle; guests get around via golf cart. Airy rooms have whitewashed interiors, teak furnishings, four-poster beds, and terracotta floors, and there’s a one-mile-long white sand beach. And since the hotel can be reached only by boat, it offers celebrities a respite from the paparazzi.
Celebrity Scoop: Ben Affleck and Jennifer Garner married in the sand and then honeymooned on the property. Jerry and Jessica Seinfeld honeymooned here, too. Last December, Alex Rodriguez, Demi Moore, Ashton Kutcher, Bruce Willis, and Donna Karan rang in the New Year on the island.

Courtesy of Fairmont Chateau Whistler

Fairmont Chateau Whistler, Whistler, BC

Wintertime Guests: Heidi Klum and Seal, Justin Timberlake, Queen Latifah.
Why They Like It: Set at the base of Blackcomb Mountain, this 550-room luxury hotel offers ski-in, ski-out access along with (of course) great mountain views.

Celebrity Scoop: Queen Latifah likes to kick back at the resort’s Mallard Lounge. And in December 2004, the resort arranged for Seal and Heidi Klum to fly via helicopter to the top of a 14,000-foot glacier, reported People Magazine. When they arrived, he proposed in an igloo built just for the moment.