From late December to early January, private jets touch down in the storied havens of Aspen and St. Bart’s perhaps more than any other time of the year. With each locale boasting legendary parties, pop-up clubs, and some of the most stunning natural topography on earth, it’s easy to see how reservations in these towns book up a year in advance. However, good things can still come to those who wait. Here, we’ve worked with leading villa rental agencies Wimco in St. Barth’s and Aspen Signature Properties in Aspen to give us their insider leads on amazing villas still available for the festive season. Need help with getting there? Private chefs and dinner reservations while you’re in residence? Each company can help with that too. Click. Book. Enjoy.
All prices are listed for the New Year’s Eve/holiday season.
Location: Flamands Beach
About: This newly built home features contemporary décor and more than 16,000 square feet of space spread out on three levels. Direct access to famed Flamands Beach—and the popular La Cabane restaurant—as well as a private pool, gym, home spa, and entertaining spaces make it a fantastic home base for enjoying the holiday season.
About: This hillside villa overlooking one of the island’s most tucked away beaches is named for the Sinatra song and features a grand piano in the living room, which also has a built-in bar, making it great for hosting parties. Two infinity pools, a home gym, retractable TVs, and an underground garage for 11 cars are just some of its knockout amenities.
About: This newly built three-level hillside home combines stunning views with contemporary furnishings. The infinity lap pool is located directly beyond the expansive living room with panel doors that open seamlessly to the outdoors, while an elevator makes accessing the home easy after late nights dancing in the clubs of Gustavia.
Location: Mont Jean
About: With Zen décor, tropical landscaping, palm trees, and a tranquil view of Tortue Island and Marigot Bay, it’s easy to see where this villa gets its name from. The refreshed interiors feature comfortable areas for lounging, while the outdoor areas are terraced to take in views and accommodate the 55-foot-long swimming pool.
Location: Lorient Beach
About: Located directly on the sand, this long-standing home has been recently renovated to become a modern beach lover’s haven. The quaint home with its beach-chic white décor opens directly onto the sand and has its own hot tub. The swimmable beach is known to appeal to surfers, while a nearby surf shack offers surf and paddle lessons and rentals.
Red Mountain Elegance
Location: Between Wright Road and Red Mountain Road, about 8 minutes from the Aspen Mountain Ski Resort.
About: Floor-to-ceiling windows frame views of the nearby mountains, including Aspen, Highlands, and Tiehack. The expansive common areas are perfect for entertaining and lounging, and the pair of master suites make the home ideal for groups and couples. A game room, media room, and wine cellar mean that not everyone has to be a skier to enjoy the trip.
Location: On Wildwood Lane, overlooking Independence Pass.
About: This new-to-market rental is completely bespoke to include a separate guest wing, guest apartment, playroom, gym, home theater, game room with pool table and bar, and outdoor living area. The cook’s kitchen is great for hosting parties, while the octagon-shaped dining room seats 14. Outside, the grounds feature ponds, waterfalls, a riverside trampoline, and a hammock.
Location: On North Monarch street, about a 10-min walk to the slopes.
About: Built in 1884, this traditional Victorian treasure has been completely transformed into a contemporary jewel with wide-plank ash floors, granite and marble counters, a chef’s kitchen, a media room, and a rooftop terrace with hot tub. Vaulted ceilings and natural light flood the top-level master suite, while the three additional guest bedrooms are located on the lower level.
West End Elegance
Location: On W Hallam Street, two blocks from Main Street and about 5 minutes from the ski mountain.
About: One of the few homes of this size in the coveted central neighborhood, the three-story, 4,488-square-foot residence is within walking distance of the downtown area and all of its sites and restaurants. The open floor plan, media room, and entertaining areas accommodate a range of guests, while the three fireplaces keep things cozy.
Location: On the Oregon Trail, near the base of the Tiehack Express.
About: A beautiful art collection, gourmet kitchen, direct ski access, and a large’s chef’s kitchen are just some of the standout amenities to this lovely home. A media room, dining room with wet bar, and master suite with his and hers bathrooms also make the experience of staying here convenient and special.