Vacation Rentals Are More Popular Than Ever — Here's How to Secure the Perfect One

This seven-bedroom getaway features a private pool and is just moments away from the Atlantic Ocean and the Sea Pines Beach Club on Hilton Head Island, South Carolina. With a dramatic double-height living room and a spacious kitchen boasting a marble-topped island, it’s perfect for families, complete with bunk beds and a basement playroom with a billiard table. This 4,800-square-foot villa is listed for only $680,000.

If it sounds almost too perfect, that's because it is — to an extent. Known as The Red Cardinal, this property is a listing from Pacaso, which offers shares in vacation homes (starting as low as one-eighth) across the United States and Spain. So while you can acquire your dream retreat on Hilton Head for under a million dollars, you’ll need to share it with seven other families who, like many of us, are eager for some relaxation.

Pacaso marks a pivotal advancement in the vacation rental industry, reflecting significant changes over recent years. With travelers increasingly desiring spacious, private accommodations and the liberating experience of renting entire homes instead of traditional hotel rooms, the once standard Saturday-to-Saturday rentals have been transformed. Now, luxurious getaways with top-notch service and exquisite finishes are accessible for anyone seeking a getaway, whether purchasing or simply renting for a short stay.

Many travelers are indeed seeking escape. A recent survey by Dinogo, which included 369 parents of children under 18, revealed that relaxation was the primary motivation for this year’s trips, closely followed by a desire to reconnect with family and friends.

"In the wake of recent years, travelers have come to truly value the art of slowing down and embracing the present moment," remarks Rossella Beaugié of the villa agency, Thinking Traveller. Co-founded with her husband Huw, the agency specializes in rentals across European islands like Corsica, Mallorca, Mykonos, and Sicily, and has recently expanded by acquiring White Key Villas, a luxury rental firm in Greece, adding numerous estates to their offerings.

"Greece is perfect for those seeking relaxation, as many islands embody a laid-back lifestyle, featuring hidden beaches, scenic walking paths, and tranquil villas," notes Beaugié. She highlights popular islands like Tínos, Hydra, Páros, and Syros, each with its own unique charm.

Vacation rentals are increasingly appealing to travelers because they often provide more amenities than typical hotel rooms. A recent study by design studio Gensler revealed that vacationers consider in-unit kitchens one of the most desired features, surpassing other pandemic-era essentials like operable windows and dedicated workspaces.

There is also a rising demand for flexible cancellation policies. "Consumers expect the same convenience and reliability from rentals as they do from major hotel brands," says Brian Egan, CEO of Evolve, a vacation rental platform. "Expectations have shifted significantly over the past two years," Egan continues, emphasizing that top-tier customer support is now a necessity.

Tom Ito, Gensler's global hospitality leader, emphasizes this notion: "Hosted rentals can appeal to certain travelers by offering an elevated level of service, transforming a good stay into a great one, and sometimes even an extraordinary experience."

Vacation Rentals 2.0: Key Agencies to Consider

For Those Seeking a Wide Selection

Popular platforms like Airbnb boast countless listings, making it essential to narrow down your choices. Discover the best options through Airbnb Luxe, which includes a dedicated trip planner to arrange services like private chefs. Additionally, Homes & Villas by Marriott International features an expanding selection of rentals worldwide, promising hotel-quality amenities and services, including professional cleaning and the option to pay with Bonvoy points.

For Enhanced Service Needs

Evolve thoroughly screens each of the over 16,000 homes listed on its platform and provides 24/7 support should any issues arise. You can also consult advisors, such as those on the T+L A-List, who often maintain a curated selection of vacation homes. For instance, Zachary Rabinor from Journey Mexico ([email protected]) frequently recommends Villa Escondida, a secluded four-bedroom retreat in Oaxaca. Similarly, French travel expert Philip Haslett of Kairos Travel ([email protected]) endorses the Villa Pool Suite at the Lily of the Valley hotel, a private three-bedroom accommodation located less than a mile from the Côte d'Azur beaches.

For Those Seeking a Connection to Nature

WorldMark by Wyndham has recently introduced a hiking concierge service, providing guests who book an apartment-style suite at one of five WorldMark locations near national parks, including Yellowstone and Yosemite, complimentary access to written guides from outdoor expert Ash Nudd.

For Those Who Want to Experience Local Living

In Residence by Pieter Brundyn began in Cape Town but has since grown to feature over 200 villas globally, including locations in the Caribbean and Greece. The agency's properties are typically privately owned primary or secondary homes, lending them an authentic residential ambiance rather than being purely rental units.

If You're Looking to Establish a Home Base

Pacaso offers fractional ownership in desirable properties located in the Florida Keys, Maui, and various ski towns across the American West. If you prefer flexibility without committing to a single location, London-based August allows customers to purchase shares in five holiday homes scattered across Europe. "Our goal was to provide the chance to own multiple homes," explains Mélie Dunod, August's cofounder and CEO. "We manage all properties, and you can access them whenever you like via our booking platform." Inspirato, which provides a private collection of homes for members of its Inspirato Club, also launched a real estate division in 2021. Buyers through Inspirato Real Estate can list their properties for rent while reserving dates for their personal use.

This article first appeared in the May 2022 issue of Dinogo titled Why Vacation Homes Are More Popular Than Ever.