From property shares to coveted rentals on Airbnb Luxe, consider this your guide to locking in the perfect vacation rental.
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A rental villa on the island of Kea, in Greece
Villa Lianne, on the Greek island of Kea, is available to rent through In Residence.
| Credit: PIETER BRUNDYN/COURTESY OF IN RESIDENCE

The seven-bedroom retreat with a private pool sits just steps from the Atlantic Ocean and the Sea Pines Beach Club on Hilton Head Island, South Carolina. A double-height living room and massive kitchen with a marble-topped island give a sense of drama; bunk beds and a basement playroom complete with billiard table make the home perfect for families. And the 4,800-square-foot villa lists for just $680,000.

If it sounds too good to be true, well, it is — sort of. The Red Cardinal, as the property is known, is an offering from Pacaso, which sells vacation-property shares (as little as one-eighth) across the United States and in Spain. So while you can buy your dream escape on Hilton Head for less than a million bucks, you'll have to share it with seven other families who are, like most of us, in desperate need of some downtime.

Pacaso represents the newest — and perhaps most significant — step in the evolution of the vacation-rental business, which has undergone massive change in recent years. As more travelers seek out larger spaces, more privacy, and the blissful sense of freedom that comes with booking a whole home instead of a hotel room, gone are the drab Saturday-to-Saturday rentals of yore. They've been replaced by luxurious retreats with white-glove service and high-end finishes, now out there for anyone seeking an escape, whether they're buying or just renting for a long weekend.

Views from vacation rental homes in France
August's fractional membership options include properties in Chamonix (left) and Provence (right), France.
| Credit: Courtesy of August

And escape is indeed what many travelers are after. According to a Travel + Leisure survey of 369 parents with kids under age 18, rest and relaxation was the primary motivation for taking a trip this year. A close second: reconnecting with loved ones.

"After the past couple of years, travelers have really learned to appreciate slowing down and are living more in the moment," says Rossella Beaugié, of the villa agency the Thinking Traveller. The firm, which she cofounded with her husband, Huw, specializes in rentals on European islands, including Corsica, Mallorca, Mykonos, and Sicily. It recently acquired White Key Villas, the Greek luxury rental brokerage, adding dozens more estates to the company's portfolio.

"Greece is ideal for travelers looking to take it easy, as many of the islands have a slow-living mentality, hidden beaches and walking paths, and secluded villas," Beaugié notes. She says in-demand islands include Tínos, Hydra, Páros, and Syros, "all of which have their own personality."

A guest room in a former monastery in Croatia
Lopud 1483, a former Franciscan monastery in Croatia, is available to rent through In Residence.
| Credit: PIETER BRUNDYN/COURTESY OF IN RESIDENCE

Travelers are also turning to vacation rentals because they typically offer more amenities than a standard-issue hotel room. One recent study by the design studio Gensler found that vacationers rank in-unit kitchens as one of the most coveted features in a place to stay, outranking other pandemic-era must-haves like windows that open and in-room work spaces.

Flexible cancellation policies are equally in demand. "Consumers are looking for the same ease and consistency from rentals that they get from large hospitality brands," says Brian Egan, the CEO of Evolve, a vacation-rental platform. "Expectations have significantly changed during the past two years," Egan adds, noting that five-star customer support is no longer optional.

Tom Ito, Gensler's global hospitality lead, echoes this point: "Hosted rentals can be attractive to some travelers as they can provide the additional level of service, making a stay go from good to great and, in some cases, even exceptional."

Vacation Rentals 2.0: The Agencies to Know

If You're Looking to Cast a Wide Net

Well-known platforms such as Airbnb have zillions of listings, so whittling down the options is a must. Find the best using Airbnb Luxe, where fees include the services of a dedicated trip planner, who can arrange extras like a private chef. Homes & Villas by Marriott International has a growing roster of rentals around the world that promise hotel-caliber amenities and services, including professional cleaning, plus the option to pay with Bonvoy points.

If You Need Next-level Service

Evolve vets every one of the 16,000-plus homes listed on its site and offers 24/7 support in the event something goes wrong. You can also look to advisors, like those on the T+L A-List; they often keep a black book of vacation homes. Zachary Rabinor of Journey Mexico (info@journeymexico.com), for example, often recommends Villa Escondida, a four-bedroom hideaway in Oaxaca. France expert Philip Haslett of Kairos Travel (philip@kairos-travel.com) favors the Lily of the Valley hotel's Villa Pool Suite, a private three-bedroom property less than a mile from the beaches of the Côte d'Azur.

If You Want to Get Close to Nature

WorldMark by Wyndham, recently launched a hiking concierge program. It gives guests who book an apartment-style suite at one of five WorldMark properties near national parks, including Yellowstone and Yosemite, free access to written guides from outdoor-adventure expert Ash Nudd.

The Roellia Villa, in Porto Heli, Greece
The Thinking Traveller portfolio includes the Roellia Villa, in Porto Heli, Greece.
| Credit: Courtesy of The Thinking Traveller

If You Want to Feel Like a Local

In Residence by Pieter Brundyn got its start in Cape Town, but in recent years the portfolio has expanded to include more than 200 villas around the world, including destinations like the Caribbean and Greece. The agency's accommodations are often privately owned primary or secondary homes—as opposed to those used only as rentals—so they have a truly residential feel.

If You're Ready to Put Down Roots

Pacaso offers ownership shares of enviable properties in places like the Florida Keys and Maui, plus ski towns across the American West. Prefer to invest without getting locked into just one place? London-based August is another fractional ownership company. Its customers can buy bundled shares of five holiday homes in different parts of Europe. "We wanted to give the opportunity to own multiple homes," says Mélie Dunod, August's cofounder and CEO. "We then manage all of the properties, and you access the homes whenever you want through our booking system." Inspirato, which offers a private portfolio of homes to members of its Inspirato Club, launched its own real estate arm in 2021. Those who buy through Inspirato Real Estate can list rental properties with the company while also reserving dates for their own use.

A version of this story first appeared in the May 2022 issue of Travel + Leisure under the headline Why Vacation Homes Are Hotter Than Ever.