Discover a Home Away From Home in These Stunning Private Villa Rentals

Alex Yandell

Move in for a while to these totally private villa rentals fit for the whole clan.

Everybody has one: that familiar notion of home, where they feel most like themselves, at ease and unreserved. These days, that comforting place can exist in many locales, as more travelers and their families take up new residence for weeks—even months—in search of a satisfying (and secure) change of scenery. We’ve rounded up the top properties for every mood or style, whether your ideal version of home is a St. Bart’s beach villa, a Malibu mountaintop lair, or a historic Hawaiian hideaway.

Related: Have the Entire Hotel to Yourself This Holiday Season With These 12 Luxe Buyout Package

The Hipster Hideaway Made for Instagram

From left: Dining on the lawn at Haiku House Maui; The estate’s swimming pool. Michelle Mishina-Kunz

There are no tropical design clichés at Haiku House Maui. No tribal patterns or wicker—not a single tiki torch—yet the nine-suite Maui plantation house for 20 is without a doubt Hawaiian. The North Shore estate’s white balustrades and wraparound lanai date back to 1860, and the banyan and coconut trees spread throughout its 20 acres are even older (they’re best viewed from the pool terrace). Inside is light and bright, with original koa-wood floors and the occasional bit of Hawaiiana (a vintage schooner model, shell leis). Few private villas on the island are as stylish or spacious, and even fewer offer such a true sense of place. Pick pineapples and papayas in the organic garden, cook dinner in a traditional imu pit oven, learn to play the ukulele, and, yes, you can even have a private luau. $6,500 per night.

Your Very Own Villa Portfolio

Destination clubs have nothing in common with the dodgy time-shares of the past. Villa-rental programs like those pioneered by Exclusive Resorts and Inspirato give clients access to vacation homes all over the globe—a villa in Tuscany, a beach pad in Cabo, a penthouse in New York City—through memberships that reserve a specific number of nights per year, depending on size, location, and demand.

Both clubs offer guests concierge services, hotel-style amenities, and curated experiences during their stays. Tweaking the model for a new generation of travelers, meanwhile, is Thirdhome, which operates like a VIP Airbnb program, with members entering their own vetted homes into an exclusive pool in order to access thousands of other luxury properties in sought-after locations around the world.

Because Everybody Loves a Beach House

Views of St. Bart’s from Villa Vue de Rêve’s pool terrace. Courtesy Cuvée

There’s no place like paradise: nothing to do but swim and sun and stroll on the shore—and when you’ve got the keys to the sandcastle, you don’t have to share it with another soul. In St. Bart’s, Villa Vue de Rêve ($45,000 per week) is the kind of extravagant retreat that tricks you into thinking you own the whole island. The five-bedroom property hovers over Baie de St.-Jean on a hilltop with a pool terrace that gives its 12 guests little reason to leave—not even for dinner at Eden Rock resort, which offers many of its services directly in the home. In Puerto Rico, the five-bedroom Su Casa ($15,000 per night) at Dorado Beach, a Ritz-Carlton Reserve, is a modern hacienda with a past. The former estate of pilot Clara Livingston was last year re-envisioned by Champalimaud Design, adding a chic pastel color palette and murals by local artist Sofia Maldonado to the original 1920s architecture and Livingston’s own antiques. And while no man is an island, guests of Baoase Luxury Resort’s Isla Kiniw (price available upon request) can bask in the solitude of a castaway stay all on their own. The villa is on a private speck of land off the coast of Curaçao and includes four bedrooms, a pool, a marina (speedboat included), and a helipad.

Come for the Wine, Stay for the Winemaking

In the south of France, luxury villas are about as hard to come by as a glass of rosé, but La Verrière is the rare holiday home where you won’t just sip the good stuff— you’ll get to play winemaker. The ninth-century estate sits at the heart of Chêne Bleu, a celebrated southern Rhône château known for its Syrah and Grenache blends. The former priory has been renovated to include a swimming pool, a cinema, a gym, and seven bedrooms for up to 18 guests, who should find themselves feeling quite at home at the winery too. A stay at the estate includes the opportunity to join resident vintners in tastings, blending sessions, and, during harvest, pruning the vines and pressing the grapes. From $24,100 per week. 

Related: How to Drink Your Way Through the Best French Wine Regions

Make It a Town-and-Country Double

Farleigh Wallop

Hit the city, then head for the hills on a proper English getaway that satisfies everyone. In London, stay at the palatial Templeton House (from $19,000 per night) for more space and privacy than any Mayfair hotel could offer. The 234-year-old Georgian mansion in Roehampton was once the home of Winston Churchill; now the eight-suite estate comes with plenty of excuses to stay holed up for days, with a gym and spa, indoor pool, wine cellar and tasting room, and two-acre garden. Then it’s a jaunt to Hampshire, for a sporting stay at the 11-bedroom Farleigh Wallop (from $170,590 per week) a 15th-century country retreat where you can live like the earls, lords, ladies, and queens who stayed there in generations past. Its 4,000 acres and grand quarters are as much for the boating-fishing-clay-pigeon-shooting sort as they are for massage-cocktails-and-a-stroll-through-the-gardens types.

The Ski Chalet That’s All About That Après

One of eight bedrooms at Chalet Alice. Courtesy Four Seasons

There are few better places to be during ski season than atop France’s snowy Mont d’Arbois—unless you’re the very fortunate resident of Chalet Alice. The eight-bedroom Megève estate, part of Four Seasons Private Retreats, has all the look of a classic Alps chalet (the snow-covered eaves, the roaring fireplace, the wood panels everywhere) plus the fashionable interiors of designer Pierre-Yves Rochon (an eclectic collection of art and antiques, vibrant pops of color). The mountain may be just minutes away, but between Alice’s après salon, personal chef, and private spa and hammam, you might just have to stay behind for a run or two. From $11,815 per night.

Like a Night at the Museum...

The Malibu art villa. Courtesy Marriot

...except this art collection comes with a helipad, a private chef, and an infinity pool. Subtle this modern Malibu villa is not: The six-bedroom hilltop home is brimming with treasures, from the cinema with original seats from Hollywood’s Grauman’s Chinese Theatre to the psychedelic lounge crammed with neon art and objects. But what lies beyond the home’s retractable glass walls might be even more impressive: 20 private acres backed by the majestic Santa Monica Mountains. From $20,885 per night.