Hilton Head, SC, January 21, 2026
StayTerra’s recent investment in Vacation Homes of Hilton Head showcases the island’s economic dynamism and tourism appeal. This partnership aims to enhance local businesses and foster substantial growth in Hilton Head’s vacation rental market. Founded by natives in 2008, Vacation Homes of Hilton Head combines luxury with exceptional customer care. This collaboration between a national platform and local excellence highlights the potential for innovation and private investment in driving the region’s economy forward.
Hilton Head, SC
Private Investment Fuels Hilton Head’s Vacation Rental Market Growth
A recent strategic investment by StayTerra into Vacation Homes of Hilton Head highlights the enduring appeal and economic dynamism of our island’s thriving tourism sector. This collaboration underscores the power of entrepreneurial innovation and private capital in enhancing local businesses and contributing to the broader Beaufort County economy.
The move by StayTerra, a national platform of premier vacation rental brands, to invest in a locally founded and operated company like Vacation Homes of Hilton Head exemplifies how targeted private sector engagement can bolster regional strengths. It speaks to the vision of local entrepreneurs and the attractiveness of Hilton Head Island as a destination for sustained economic growth and quality hospitality experiences.
StayTerra Recognizes Local Excellence
On January 21, 2026, StayTerra announced its investment in Vacation Homes of Hilton Head (VHHH), a leading luxury property management brand nestled right here on Hilton Head Island, South Carolina. StayTerra, established in 2024, is recognized as a platform comprising premier vacation rental brands across America, dedicated to delivering top-tier property management for owners and exceptional experiences for guests. This investment expands StayTerra’s reach into the attractive Hilton Head market, which is celebrated as a significant vacation rental hub and a top 10 beach destination for families in the U.S..
Vacation Homes of Hilton Head: A Local Success Story
Founded in 2008 by Hilton Head natives Chris and Jacquelyn Sankowski, Vacation Homes of Hilton Head has built a solid reputation for blending exclusivity and elegance within its portfolio of luxury vacation rental homes on the Island. The company is known for its meticulous property care, superior revenue generation, and a dedicated round-the-clock local team, supported by tech-enabled pricing and management tools. VHHH also offers a family-friendly vacation experience, providing exceptional customer care, comprehensive concierge services, and exclusive free, curated local activities through its Southern Hospitality Pass. This commitment to service and quality has firmly established VHHH as a cornerstone of the Hilton Head SC business landscape.
Strategic Growth and Expanded Horizons
The partnership positions Vacation Homes of Hilton Head for substantial growth, benefiting from StayTerra’s advanced technological and customer service capabilities, an experienced leadership team, and significant growth capital. StayTerra’s existing portfolio includes successful brands such as Cape & Coast and Prime Vacations along Florida’s gulf coastline, as well as Moving Mountains in the Colorado Rockies, demonstrating a proven model for enhancing vacation rental operations. Backed by leading investment firms Garnett Station Partners and Bessemer Venture Partners, StayTerra’s strategic approach seeks to empower local brands while leveraging broader market expertise.
Hilton Head’s Enduring Appeal and Economic Impact
Hilton Head Island continues to be a magnet for visitors and investors alike. The island has been recognized as the #1 Island in the Continental U.S. by Travel + Leisure. With more than three million vacation visitors annually, a figure that has consistently grown since 2021, the market demonstrates robust demand, characterized by a high summer season and strong shoulder seasons. This consistent visitor influx directly supports countless Hilton Head small business ventures, from restaurants and retail to local activity providers, driving significant Hilton Head economic growth. Investments like StayTerra’s validate the economic vibrancy of the region and create new opportunities for South Carolina SC entrepreneurs.
A Positive Outlook for Local Business and Tourism
This investment marks a positive development for Hilton Head’s tourism industry and the local economy. It showcases how collaboration between established national platforms and strong local businesses can lead to mutual growth and enhanced service offerings for visitors. Such partnerships, driven by private enterprise and innovation, often bring new resources and efficiencies, contributing to the overall prosperity and competitive edge of destinations like Hilton Head Island.
We encourage our readers to continue supporting local businesses and stay informed about the evolving economic landscape of Hilton Head Island, which remains a testament to entrepreneurial spirit and strategic investment.
Frequently Asked Questions (FAQ)
- What company announced an investment in Vacation Homes of Hilton Head?
- StayTerra announced an investment in Vacation Homes of Hilton Head (VHHH) on January 21, 2026.
- When was Vacation Homes of Hilton Head founded?
- Vacation Homes of Hilton Head was founded in 2008 by Chris and Jacquelyn Sankowski.
- What services does Vacation Homes of Hilton Head offer?
- Vacation Homes of Hilton Head offers meticulous property care, superior revenue generation, a round-the-clock local team, and tech-enabled pricing and management tools. They also provide a family-friendly vacation experience with customer care, concierge services, and free curated local activities through their Southern Hospitality Pass.
- What is StayTerra?
- StayTerra is a platform comprising premier vacation rental brands in top destinations across America, committed to providing best-in-class property management for owners and seamless, elevated experiences for guests. It was established in 2024.
- What are the benefits for Vacation Homes of Hilton Head from this investment?
- The investment positions Vacation Homes of Hilton Head for outsized growth, supported by StayTerra’s advanced technological and customer service capabilities, experienced leadership team, and growth capital.
- How many vacation visitors does Hilton Head boast each year?
- Hilton Head boasts more than three million vacation visitors each year, consistently increasing since 2021.
- Which firms back StayTerra?
- StayTerra is backed by Garnett Station Partners and Bessemer Venture Partners.
Key Features of the StayTerra Investment in Vacation Homes of Hilton Head
| Feature | Description | Scope |
|---|---|---|
| Investing Company | StayTerra, a platform of premier vacation rental brands. | Nationwide |
| Invested Company | Vacation Homes of Hilton Head (VHHH), a luxury property management brand. | Hilton Head Island, South Carolina |
| Announcement Date | January 21, 2026. | Local |
| VHHH Founding Year | 2008, by Chris and Jacquelyn Sankowski. | Local |
| VHHH Services | Meticulous property care, superior revenue generation, local team, tech-enabled tools, concierge, and Southern Hospitality Pass. | Local |
| StayTerra’s Backing | Garnett Station Partners and Bessemer Venture Partners. | Nationwide |
| Hilton Head Tourism | More than three million vacation visitors annually, consistently increasing since 2021. | Local |
| Hilton Head Ranking | Ranked as the #1 Island in the Continental U.S. by Travel + Leisure. | Nationwide |
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Author: STAFF HERE HILTON HEAD
The HILTON HEAD STAFF WRITER represents the experienced team at HEREHiltonHead.com, your go-to source for actionable local news and information in Hilton Head Island, Beaufort County, and beyond. Specializing in "news you can use," we cover essential topics like product reviews for personal and business needs, local business directories, politics, real estate trends, neighborhood insights, and state news affecting the area—with deep expertise drawn from years of dedicated reporting and strong community input, including local press releases and business updates. We deliver top reporting on high-value events such as the RBC Heritage golf tournament, Hilton Head Island Wine & Food Festival, and the Gullah Celebration. Our coverage extends to key organizations like the Hilton Head Island-Bluffton Chamber of Commerce and Community Foundation of the Lowcountry, plus leading businesses in tourism and hospitality that power the local economy such as Sea Pines Resort and Sonesta Resort Hilton Head Island. As part of the broader HERE network, including HEREAiken.com, HEREBeaufort.com, HEREChapin.com, HERECharleston.com, HEREClinton.com, HEREColumbia.com, HEREGeorgetown.com, HEREGreenwood.com, HEREGreenville.com, HEREHiltonHead.com, HEREIrmo.com, HEREMyrtleBeach.com, HERENewberry.com, HERERockHill.com, and HERESpartanburg.com, we provide comprehensive, credible insights into South Carolina's dynamic landscape.
