Travel & Tourism

With investment, Hilton Head luxury vacation rentals poised for growth

The Bradley Circle beachfront area of Hilton Head Island as photographed on July 17, 2025. A Hilton Head vacation rental company, which has properties in Bradley Circle, is now part of a luxury vacation rental platform.
The Bradley Circle beachfront area of Hilton Head Island as photographed on July 17, 2025. A Hilton Head vacation rental company, which has properties in Bradley Circle, is now part of a luxury vacation rental platform. dmartin@islandpacket.com

A New York-based vacation rental platform has invested in a Hilton Head luxury rentals company, a move that signals the travel industry’s confidence in the island as a vacation destination.

StayTerra, a platform of premier vacation rental brands in top U.S. travel destinations, said this month that it invested in Vacation Homes of Hilton Head, a luxury property management company founded in 2008 by Chris and Jacquelyn Sankowski.

Vacation Homes of Hilton Head manages 60 properties on the island, ranging from three to 10 bedrooms in Burkes Beach, Singleton Beach, Folly Field Beach, Forest Beach and Palmetto Dunes.

The investment represents StayTerra’s first foray into the southeastern Atlantic coast. The platform also features property management companies offering vacations in tourism hotspots like Florida’s gulf coast and Colorado’s Rocky Mountains.

The partnership is the “next phase” for Vacation Homes of Hilton Head, the Sankowskis said in a statement. It will “generate more value” for the company’s property owners, they said, as well as guests who come back to the area year after year.

“We are confident that VHHH is in great hands as part of the StayTerra collection, and we look forward to continuing to work together to promote the brand for years to come,” they said.

Hilton Head a top beach destination for families

It made sense for StayTerra to invest in a Hilton Head company, because the island is one of the country’s top 10 beach destinations for families, said Mary Lynn Clark, the company’s CEO.

Vacation Homes of Hilton Head is one of the top luxury property management companies on the island, she said, which makes the company a good fit for StayTerra’s portfolio.

“We are excited to expand into the southeastern Atlantic coast and look forward to growing VHHH to new heights, while preserving its ‘comfort meets coastal charm’ brand identity,” Clark said.

Hilton Head saw 2.8 million visitors in 2024.

Hotel and villa occupancy was 55% in 2024, 59% in 2023, 54% in 2022, nearly 60% in 2021 and about 48% in 2020. In 2019, the year before the covid pandemic, occupancy was 51.4%, according to the Hilton Head Island-Bluffton Chamber of Commerce.

Collections of tourism-generated taxes on the island increased from $25.6 million in fiscal year 2019 to $44.2 million in fiscal year 2023, data show.

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Laura Finaldi
The Island Packet
Laura Finaldi is an award-winning reporter and editor whose career has taken her everywhere from manufacturing companies in Massachusetts to dairy farms in rural Florida. Before joining the Island Packet in 2025, she was an editor at Homes.com in Richmond, Virginia and covered retail and tourism in Sarasota, Florida for five years. She has been published in the Worcester Business Journal, the Richmonder, Virginia Business, the Boston Globe and USA Today. 
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