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Beach, Ski and Surf: Favorite Winter Escapes of the Hollywood A-List

Luxury Defined presents an international showcase of homes in glamorous, celebrity-endorsed resorts to escape or embrace the winter chill

The old adage “You can’t take it with you” has an exception among Hollywood’s superstars: “Yes, that’s true; but you can take it on vacation.” Herewith, Luxury Defined offers a collection of fabulous homes—beachfront villas, mountain chalets, and palatial private compounds—in posh, post-Oscar getaways habituated by the red carpet set. Even the place names evoke the lifestyles of the glitterati: Cabo San Lucas, St. Barths, Aspen, Telluride, Miami Beach, Marrakesh . . . If you’re rich and famous, the chances are you’ve already been there and fallen in love with these rarefied destinations. If you have yet to thank the Academy for your golden statuette, it’s time to start packing.

Contemporary Mountain Home in Aspen, Colorado

This chic contemporary home is in Aspen, the Rocky Mountain ski resort long favored by Hollywood A-listers, including Goldie Hawn and Jack Nicholson.

A 19th-century silver mining town turned chic ski resort, Aspen, Colorado, is a favorite winter playground of the A-list and the Forbes List. The Rocky Mountain town is revered for its arts and culture, fine shopping and dining, and the challenging slopes that rank it among the world’s top ski resorts.

This sophisticated open-concept home in Aspen’s West End combines airy, modern interiors with serene outdoor living spaces, including balconies, terraces, and tranquil wooded grounds. The heart of the three-level residence is a brand new, custom-designed kitchen with a wall of windows that face the lush rear garden. Family and friends are accommodated in style with six en suite bedrooms, including a stunning main-floor master suite and a top-floor guest suite, as well as a well-appointed family room that opens to the back patio and hot tub.

Cliffside Aerie in Cabo San Lucas, Mexico

During the Fifties, stars such as Bing Crosby, John Wayne, and Desi Arnaz would fly to Cabo to escape the Hollywood spotlight. Though much has changed in this once sleepy fishing village on the Sea of Cortez, the resort still attracts big-name stars due to its dazzling white beaches, luxury resorts, and championship golf courses.

With its serene white-sand beaches, luxury spa resorts, world-class golf and deep-sea fishing, and convenient location (just two hours’ flight from LAX), it’s easy to see why Cabo San Lucas on Mexico’s Baja Peninsula is a favorite escape for Hollywood’s A-list.

In this beautiful corner of the world, the aptly named Casa Ventana al Cielo (window to heaven), is a breathtaking residential aerie high above Cabo San Lucas. This 6,000-square-foot mountaintop home combines vast, open living spaces with lavish features including interior gardens, six luxurious bedrooms, and six and one half spa-like bathrooms. With commanding sea views from every vantage point, the home is an entertainer’s dream, with a casually chic decor, full furnishings, artisan finishes, and lavish touches including an elevator, gym, and infinity pool.

La Gorce Island Waterfront in Miami Beach, Florida

This tropical waterfront home enjoys a star-studded location on La Gorce Island, an ultra-exclusive island community in Miami Beach.

This unrivaled waterfront home has a prized location on La Gorce Island, an exclusive island enclave of Miami Beach. The beaches and nightlife of Miami make it a top celebrity hotspot and winter escape for supermodels, sports superstars, and music moguls alike.

This enchanting home on Biscayne Bay is the ultimate waterfront retreat. The main level comprises an eat-in kitchen, family room, formal living and dining rooms, as well as two bedrooms and two full and two half bathrooms. Four bedrooms upstairs include the lavish master suite with its wraparound terrace, en suite bathroom, enormous walk-in closet, and a sitting room/office. The amenities rival a luxury resort and include an elevator, gym, four-car garage, and a covered living area overlooking the pool, spa, dock, barbecue, and cabana bath, which is the perfect space to relax and enjoy the Miami Beach lifestyle.

Modernist Villa in Marrakesh, Morocco

Villa Askel is just 10 minutes from the heart of the Old City of Marrakesh, renowned for its medieval Medina (a UNESCO World Heritage site), labyrinthine passageways, bustling souks, and beautiful riads, made famous by celebrated artists, writers, and cultural figures.

The medieval citadel of Marrakesh has long been a cultural hotspot for the international jet set. In 1943, Winston Churchill visited what he called “the most lovely spot in the whole world.” And in the 1960s, on the heels of the “Marrakesh Express,” visits by The Beatles and Yves Saint Laurent cemented its place among the in crowd.

Just outside the Old City is Villa Askel, a stunning contemporary home designed by renowned Moroccan architect Imaad Rahmouni. The 10,763-square-foot villa is characterized by geometric forms and walls of glass that flood the interiors with natural light. The chic furnishings, sourced mostly from Bali, blend with exquisite Moroccan details. Each bedroom suite has its own fireplace and media space. The reception areas are grandly scaled, and include a vast living room, dining room, library, media space and bar. Adding to the splendor are indoor and outdoor pools, a gym, hammam, and a garden, a haven of tranquility featuring a Berber tent surrounded by an olive grove.

Tropical Haven in Petite Saline, St. Barthélemy

This Caribbean jewel is an enclave of unsurpassed privacy in St. Barthélemy. Located in the French West Indies, the island’s pristine white-sand beaches, gentle seas, French-Caribbean cuisine, and discreet atmosphere make it a top-ranking winter resort destination for the international glitterati.
This Caribbean jewel is an enclave of unsurpassed privacy in St. Barthélemy. Located in the French West Indies, the island’s pristine white-sand beaches, gentle seas, French-Caribbean cuisine, and discreet atmosphere make it a top-ranking winter resort destination for the international glitterati.

At just eight square miles, St. Barths is the smallest island in the French West Indies, but it has a stellar reputation among the international elite. The French Caribbean island is home to a who’s who of A-list actors and musicians, supermodels, and Russian oligarchs, attracted by its beautiful beaches and lagoons, luxury resorts and villas, fine dining, art galleries, and designer boutiques.

Villa RKK is an enclave of privacy and seclusion perched above the bay of Lorient on the island’s north shore. This unique luxury compound is composed of a main villa, two garden villas, and several ancillary dwellings. The residential areas connect to the grounds by stone pathways that meander through lush vegetation. The main house opens onto a spectacular infinity pool with sweeping views of the bay and ocean. The tropical gardens overflow with exotic flowers and trees. A two-bedroom gate lodge, garage, gym, and tennis court complete this serene tropical hideaway.

Mountain Village Ski Estate in Telluride, Colorado

This majestic mountain estate has direct access to the ski trails, the gondola, and all the amenities of the top-ranked US ski resort of Telluride—home to such stars as Tom Cruise, Kevin Costner, and Oprah Winfrey.

A Colorado mining boomtown until the 1890s, Telluride revived its fortunes in the ’60s and ’70s as a world-class ski resort, averaging 177 inches of snowfall a year. With its stay-small development ethos, Telluride has preserved its Old West architecture and village ambience, and drawn celebrities in droves.

Nestled on a wooded hillside overlooking the Mountain Village Core, this palatial mountain lodge boasts direct access to Telluride’s world-class pistes, close to village amenities and the gondola. The home’s bold stone and timber façade integrates perfectly with its setting. Inside, exquisite architectural elements include a two-story, circular staircase; cherrywood cabinetry and doors; and marble and flagstone floors. There are five bedrooms, including two master suites, eight bathrooms, a family room with wet bar and fireplace, a theater, an elevator, and a ski room opening to the trail.