Dwell Vacations is the largest vacation rental management company on Hilton Head Island, with an established presence in Edisto Beach and expansion underway into Charleston and Myrtle Beach. We combine strong local execution with national backing and are building a best-in-class operation focused on transparency, performance, and owner trust. We’re looking for strong leadership to help take us to the next level.. We are building a best-in-class operation focused on transparency, performance, and owner trust—and we need strong leadership to take us to the next level.
This is a hands-on, high-impact role at the center of our homeowner and guest experience.
You’ll act as a trusted partner to homeowners, helping them understand their property performance while finding ways to elevate their investment. At the same time, you’ll be in the field ensuring homes are guest‑ready, issues are solved quickly, and standards are consistently exceeded.
One moment you might be reviewing performance metrics with a homeowner… The next, you’re troubleshooting a maintenance issue or helping a guest enjoy their stay.
If you thrive in a role where no two days are the same, this is the opportunity for you.
Lead day‑to‑day operations for a portfolio of vacation homes
Build strong, trust‑based relationships with homeowners
Provide recommendations to improve property performance, condition, and revenue
Conduct property inspections to ensure homes are guest‑ready
Respond to escalated guest and homeowner concerns with urgency and professionalism
Troubleshoot and resolve basic maintenance issues in real time
Maintain deep knowledge of each home in your portfolio
Monitor key performance metrics (guest experience, property condition, operations)
Partner with onboarding and field teams to bring new homes online successfully
Collaborate with team members to deliver a seamless experience
Jump in wherever needed, because hospitality is never one‑size‑fits‑all
Experience in hospitality, vacation rentals, hotels, or a related field
3+ years in operations or field‑based support roles
Hands‑on experience with property upkeep, housekeeping, or maintenance
Strong communication and relationship‑building skills
A proactive, solutions‑driven mindset
Comfort using technology (mobile apps, systems, and tools)
Ability to work independently while staying connected to a team
Reliable transportation and willingness to travel locally
$55,000 - $70,000
The position will also be eligible for a performance-based bonus program tied to key operational metrics, including homeowner satisfaction, guest reviews, responsiveness, and other measurable performance indicators that this individual will have the ability to directly impact.
Paid time off such as PTO, sick days, and vacation days
Health, Dental, and Vision insurance
Life insurance
Retirement benefits or accounts
Healthcare spending or reimbursement accounts, such as HSAs, FSAs, and HRAs
Long term and Short term disability insurance
Tuition reimbursement
Childcare benefits
Relocation assistance