Property Manager

Property Manager

Dwell Vacations by Casago

Hilton Head Island, SC

Job Description

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 trustand we need strong leadership to take us to the next level.

Position Summary

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.

What You'll Do

• 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

Required Qualifications

• 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

Compensation & Benefits

Annual Salary

$55,000 - $70,000

Bonus

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.

Benefits

• 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