The Ultimate Guide to Booking the Perfect Vacation Home Rental

From property shares to coveted rentals on Airbnb Luxe, consider this your guide to locking in the perfect vacation rental.

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 a massive kitchen with a marble-topped island give a sense of drama. Bunk beds and a basement playroom, complete with a billiard table, make the home perfect for families. This 4,800-square-foot villa is available for an enticing price of just $680,000.

If it sounds too good to be true, well, it is — sort of. The property, known as the Red Cardinal, is an offering from Pacaso, which sells vacation-property shares (as little as one-eighth) across the United States and in Spain. 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, like most of us, are in desperate need of some downtime.

Pacaso represents a significant step in the evolution of the vacation-rental business, which has undergone dramatic changes in recent years. Travellers increasingly seek 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 They’ve been replaced by luxurious retreats with white-glove service and high-end finishes, available for anyone seeking an escape, whether buying or renting for a long weekend.

Moreover, the desire for escape is what many travelers are after. According to a recent survey, rest and relaxation was the primary motivation for taking trips this year.

“After the past couple of years, travelers have truly learned to appreciate slowing down and living more in the moment,” says Rossella Beaugié, of the villa agency the Thinking Traveller. This firm specializes in rentals on European islands, including Corsica, Mallorca, Mykonos, and Sicily, and has expanded its portfolio through the acquisition of White Key Villas.

“Greece is ideal for travelers looking to unwind, as many of the islands embody a slow-living mentality, featuring hidden beaches, walking paths, and secluded villas,” Beaugié notes. In-demand islands such as Tínos, Hydra, Pára, and Syros offer distinct local personality.

Furthermore, travelers are turning to vacation rentals because they typically offer more amenities than standard hotel rooms. Recent research by Gensler revealed that in-unit kitchens are among the most coveted features for vacationers, surpassing even other pandemic-era necessities like windows that open and in-room workspaces.

Flexible cancellation policies are also increasingly in demand. “Consumers are looking for the same ease and consistency from rentals that they expect from large hospitality brands,” states Brian Egan, the CEO of Evolve. “Expectations have changed significantly over the past two years,” he adds, noting that high-quality customer support is now essential.

Tom Ito, Gensler’s global hospitality lead, supports this sentiment: “Hosted rentals can be appealing to travelers as they provide an enhanced level of service, elevating a stay from good to exceptional.”

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Vacation Rentals 2.0: The Agencies to Know

If You’re Looking to Cast a Wide Net

Well-known platforms like Airbnb offer countless listings, making it essential to narrow down your options. Use Airbnb Luxe for curated offerings that include dedicated trip planners who can arrange additional services such as a private chef. Homes & Villas by Marriott International also has an expanding list of rentals worldwide, ensuring hotel-quality amenities and services along with professional cleaning options.

If You Need Next-level Service

Evolve thoroughly vets every one of the 16,000+ homes listed on its site and provides 24/7 support in case of any issues. Additionally, you can consult with advisors, like those on the iBestTravel A-List, who often maintain a collection of exclusive vacation homes. Zachary Rabinor of Journey Mexico frequently suggests Villa Escondida, a four-bedroom hideaway in Oaxaca. France specialist Philip Haslett of Kairos Travel often recommends the Villa Pool Suite at the Lily of the Valley hotel, a three-bedroom property conveniently located less than a mile from the beaches of the Côte d’Azur.

If You Want to Get Close to Nature

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

If You Want to Feel Like a Local

In Residence by Pieter Brundyn began in Cape Town but has expanded its portfolio to over 200 villas worldwide, including locations in the Caribbean and Greece. Many of the accommodations are privately owned homes, contributing to a true residential experience.

If You’re Ready to Put Down Roots

Pacaso offers ownership shares of desirable properties in locations such as the Florida Keys and Maui, as well as ski towns in the American West. For those looking to invest without anchoring to just one destination, London-based August offers another fractional ownership opportunity. Its customers can buy bundled shares of multiple holiday homes situated in different European locations. “We wanted to provide the option to own several homes,” says Mélie Dunod, August’s cofounder and CEO. “We manage all the properties, and you can access them whenever you like through our booking system.” Inspirato launched its real estate arm in 2021, providing customers the ability to list rental properties while reserving dates for their own use.

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