Hilton Head Island, January 26, 2026
Hilton Head Island welcomes a significant investment from StayTerra into Vacation Homes of Hilton Head (VHHH), showcasing the island’s thriving luxury rental market. This partnership highlights the local economy’s growth, driven by innovative entrepreneurs. StayTerra’s involvement aims to enhance guest experiences and operational efficiency, reinforcing Hilton Head’s position as a leader in hospitality. With a growing demand for vacation rentals and substantial economic impacts from the tourism sector, this investment signals a positive outlook for the local business landscape.
Hilton Head Island Welcomes Strategic Investment in Luxury Rentals
Private Sector Innovation Fuels Continued Growth in Island’s Thriving Tourism Economy
Hilton Head Island continues to demonstrate its appeal as a premier destination, drawing strategic investment that underscores the vitality of its local economy and the robust entrepreneurial spirit thriving within its borders. The recent announcement of StayTerra’s investment in Vacation Homes of Hilton Head (VHHH) marks a significant moment for the island’s luxury tourism sector, highlighting how private enterprise and thoughtful capital deployment can enhance existing successes and contribute to broader Hilton Head economic growth.
This collaboration is more than just a business transaction; it represents a vote of confidence in the sustained allure of Hilton Head and the dedication of local businesses to provide exceptional experiences. Such investments are crucial for reinforcing the island’s position as a leader in hospitality, driven by the innovative endeavors of South Carolina SC entrepreneurs who consistently adapt and excel in a competitive market.
A Partnership Bolstering Local Excellence
StayTerra, a platform comprising leading vacation rental brands across America, has announced a strategic investment in Vacation Homes of Hilton Head (VHHH). StayTerra, established in 2024, focuses on delivering premier property management services for owners and elevated experiences for guests in sought-after destinations. The platform is committed to outstanding customer service, integrity, thoughtfulness, and hospitality.
Vacation Homes of Hilton Head, founded in 2008 by Hilton Head natives Chris and Jacquelyn Sankowski, has established itself as a leading luxury property management company on the island. VHHH is known for blending exclusivity and elegance across its portfolio, emphasizing memorable experiences for guests. The company offers a range of services including concierge assistance, private pools, pet-friendly accommodations, and keyless entry, all designed to provide a seamless and refined coastal living experience.
Driving Enhanced Guest Experiences and Operational Efficiency
The investment by StayTerra in Vacation Homes of Hilton Head is expected to bolster Hilton Head’s thriving tourism sector. This strategic move aims to enhance service offerings and leverage technological advancements, ensuring continued growth in the competitive short-term rental market. For VHHH, integrating with the StayTerra platform is anticipated to foster additional growth by providing access to capital, advanced technology, and enhanced operational support, all while preserving its distinct brand identity and local operational expertise.
This type of strategic partnership showcases how larger entities can invest in and empower successful Hilton Head small business, allowing them to thrive and contribute more substantially to the Beaufort County economy. It also signals confidence in the growth of the luxury vacation rental market, potentially enhancing revenue and market share for properties under VHHH’s management.
Hilton Head’s Robust Vacation Rental Market
The demand for vacation rentals on Hilton Head Island has surged, driven by a growing preference for private, family-friendly accommodations over traditional hotels. Hilton Head’s thriving tourist economy and its ability to attract a diverse population of travelers contribute to its high-speed growth and clear income potential for short-term rental properties.
Within South Carolina, Hilton Head ranks among the metropolitan regions with the largest annual impacts from short-term rental markets. These rentals contribute substantially to South Carolina entrepreneurs and property owners, generating an estimated $1.8 billion in revenue annually across the state, a figure that has more than doubled since 2018. The overall annual economic impact of short-term rentals in South Carolina is estimated at $4.2 billion, supporting over 50,000 jobs and more than $1.4 billion in labor income for South Carolinians.
Market Strengths and Future Outlook
Hilton Head Island boasts an impressive average occupancy rate of 60%, which surpasses the U.S. average of 58%. This indicates strong demand for rentals. Furthermore, Hilton Head Island visitors plan well in advance, with an average booking lead time of 122 days, significantly longer than the U.S. average of 55 days.
The island’s real estate market demonstrates consistent property value appreciation, with median home prices rising by 9.9% in 2025. This stability is supported by Hilton Head’s deliberate approach to development, which maintains tight control over new construction. This focus on conserving the island’s natural boundaries contributes to long-term scarcity, a key factor in property value resilience.
In 2024 alone, Hilton Head Island generated $2.8 billion in tourism revenue from 2.8 million visitors, and 160 new businesses opened. This sustained economic activity underscores the dynamic environment that attracts investments like StayTerra’s, further fueling the local economy.
A Bright Future for Hilton Head SC Business
The investment by StayTerra in Vacation Homes of Hilton Head exemplifies the power of private capital to uplift and expand successful local enterprises. It reflects a positive outlook for Hilton Head SC business and its burgeoning luxury tourism sector. As the island continues to attract visitors seeking high-quality experiences, partnerships such as this are vital for fostering innovation, maintaining high standards, and ensuring the long-term prosperity of the Beaufort County economy.
We encourage residents and visitors alike to continue supporting our local businesses and remain engaged in the exciting economic developments shaping Hilton Head’s future.
Frequently Asked Questions
What company recently invested in Vacation Homes of Hilton Head?
StayTerra, a platform of premier vacation rental brands across America, recently invested in Vacation Homes of Hilton Head (VHHH).
Who founded Vacation Homes of Hilton Head?
Vacation Homes of Hilton Head was founded in 2008 by Hilton Head natives Chris and Jacquelyn Sankowski.
What is the economic impact of short-term rentals in South Carolina?
The overall annual economic impact of short-term rentals in South Carolina is estimated at $4.2 billion, supporting over 50,000 jobs and more than $1.4 billion in labor income for South Carolinians.
What is the average occupancy rate for vacation rentals on Hilton Head Island?
Hilton Head Island boasts an average occupancy rate of 60%, which surpasses the U.S. average of 58%.
What services does Vacation Homes of Hilton Head provide?
Vacation Homes of Hilton Head provides concierge services, private pools, pet-friendly stays, and keyless entry.
Key Features of StayTerra’s Investment in Vacation Homes of Hilton Head
| Feature | Description |
|---|---|
| Investing Entity | StayTerra, a platform of premier vacation rental brands across America. |
| Acquired Entity | Vacation Homes of Hilton Head (VHHH), a luxury property management company. |
| VHHH Founding | Founded in 2008 by Hilton Head natives Chris and Jacquelyn Sankowski. |
| Investment Goal | Strategic expansion of StayTerra’s coastal portfolio, boosting Hilton Head’s tourism appeal. |
| Expected Benefits | Enhanced service offerings, leveraged technological advancements, local economic growth. |
| Hilton Head Occupancy Rate | 60%, surpassing the U.S. average of 58%. |
| SC Short-Term Rental Economic Impact | Estimated $4.2 billion annually, supporting over 50,000 jobs. |
Deeper Dive: News & Info About This Topic
HERE Resources
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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.
