Travel

The Caribbean is Calling

By Mark Ellwood and Nick Remsen

A mountaintop perch with an aerial view

Toucan Hill in Mustique offers unrivaled luxurious seclusion—and views.

Planning ahead for a winter getaway in the sun? Yes, we are too. To help lighten the lift, we’ve selected three of the most extraordinary villas to rent in the ultimate winter playland, the Caribbean. From a family home on the region’s quirkiest, most exclusive island to a non-stop party pad that’s perfect for a jet-set group, here are three perfect Caribbean villas, each of them anchored by someone who transforms them beyond mere brick and mortar.

A pool with a scenic view

A pool with a view that can’t be beat at Toucan Hill.

TOUCAN HILL, MUSTIQUE

If you were never really into the quiet luxury trend, then consider a getaway to Toucan Hill, a luxurious, Moroccan-style five-bedroom home perched high above Britannia Bay in Mustique.

Inspired by the Alhambra in Spain, the estate is a perfumed daydream of domes, arches, tiled courtyards, and pavilions that gleam at high noon and shimmer in the sunset light. Toucan Hill has 360-degree views from its mountaintop position, with all of Mustique’s gilded emerald slopes and glittering pools unfurling beneath it. The island, of course, is well known to and a closely guarded semi-secret among the jetset (particularly the who’s-who of the UK), and has hosted countless celebrities and royalty, including Princess Margaret, whose home, “Les Jolies Eaux,” was given to her in 1959 as a wedding gift; current residents include Tommy Hilfiger, Kelly Ripa, and Mick Jagger, among others.

Even in a place with just over 100 villas, Toucan Hill is notable on this most rarified of islands. It was built by businesswoman and philanthropist Tatiana Copeland as a hideaway aerie for her and her husband, Gerret; they’re among the few remaining proprietors who can remember Mustique’s early days firsthand. “It is a very special haven for people who seek luxury and security,” says Copeland.

An outdoor candlelit dining table for two with a view of the Caribbean

Toucan Hill’s Moroccan-inspired opulence.

Inside Toucan Hill’s five large main bedrooms, the interiors are tropically inclined but not overbearingly so, with touches of Moroccan lanterns, fauna prints, and jewel tones. Each, too, has its own porch to sit and read or have a glass of wine in the tradewinds. But the common areas are the real standouts; there’s a grand central living room with U-shaped sofas, which gives way to a columned veranda and an infinity pool with not million- but perhaps billion-dollar views. Copeland is not precious about it all, though: whether on the couch, waterside, or anywhere in between, she reflects that the entire point is to “put your feet up” and soak it all in. —Nick Remsen

A villa with seating and view of St Barths water and sunset

The epitome of inside-out living at Unik Villa in St Barths; photo by Laurent Benoit.

UNIK VILLA, ST BARTHS

Anne Dentel is the doyenne of doing it just right, that Goldilocks approach to luxury hospitality— equal parts attention and privacy. With her shock of bleach-blonde hair, omnipresent dog, and Champagne-bubble laugh, she’s renowned around St Barths, running the villa rental program that operates under the auspices of the Eden Rock hotel. It offers a range of homes dotted around the island, which come bundled with services from the hotel.

You’ll have the connections of the concierge there, not to mention chefs to prep meals, all of whom were trained under Jean-Georges Vongerichten; if you want to spend the afternoon on Eden Beach, you’re more than welcome. Pick of this season’s options is undeniably the aptly named Unik Villa, which sits on 10 acres; the 10-bedroom property, designed by the prankish French polymath Philippe Starck, is more like a small boutique hotel.

Unik Villa has two pools, including a 65-foot infinity pool, fitness center, home theater, an immersive surround sound system, and spectacular views over St Jean Beach. Most importantly, it comes with the ultimate amenity: Dentel herself, whose reputation unlocks even the hardest-to-open doors around the island.

A pool pavilion with seating and brown wicker furniture

The pool pavilion at Laughing Waters.

LAUGHING WATERS, BARBADOS

Sandy Lane Estate, on the Platinum Coast of Barbados, is a benchmark for luxury in the region. That world-class hotel sits on the western reaches of the island nation, perched on some of the best beaches in the world, and has long been a magnet for celebrities, from Aristotle Onassis to Tiger Woods; the famously seclusion-seeking Greta Garbo would check in under the pseudonym “Harriet Brown.”

A pool shot in evening light with a view of a hotel courtyard

Inside-out living at its finest at Laughing Waters.

Next to the hotel is Laughing Waters, an enclave of equally top-tier villas located on a four-acre property from the 1960s that was recently reimagined by London-based interior designer Emma Pearson. Expect 32,000 square feet of living space across 12 bedrooms, housed in three buildings—the pick of them, of course, are in the Great House, which is also where you’ll find the cinema, gym, dining room, and home bar. Rent here and you’ve got access not only to Sandy Lane Estate’s Beach Club and other hotel amenities, but also the Tom Fazio–designed Green Monkey golf course. Even better, a portion of your rental fee at Laughing Waters is donated to the local Barbados Children’s Trust, which serves to uplift the local community.


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A look into our “Vacationland.” From a striking, hotel-inspired check-in and champagne greeters to signature bites from the Shops’ restaurants, it was a night full of decadence. We mingled over martinis at Whitman’s Bar and danced al fresco at The Collins Club with DJ Sets by @isaaclikes_ and a headlining musical performance from the legendary @chakakhan . This is 60.
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