Maui Real Estate Agent & Branch Manager
Sell. Lead. Thrive with Midway Vacations.
Are you a licensed real estate agent with strong leadership skills and a passion for Hawaii’s vacation rental and real estate market? Midway Vacations is expanding on Maui, and we’re looking for a motivated Real Estate Agent who will also serve as the Maui Branch Manager. This is a unique opportunity to take on a dual role—growing your real estate career while managing local operations in a thriving market.
About Midway Vacations:
Midway Vacations is a premier vacation rental management and real estate sales company with offices on Oahu and Maui. We currently manage 175 vacation rental units, including 15 on Maui, and are rapidly expanding. Our Maui office is located in a prime location at Kamaole Shopping Center in South Maui, just steps from the beach.
About the Role:
As Real Estate Agent & Branch Manager, you will:
Represent buyers and sellers in real estate transactions across Maui
Serve as the exclusive sales agent for Midway’s Maui branch—no internal competition
Lead and support a small, high-performing local team
Grow real estate sales and assist in expanding the vacation rental portfolio
Build strong relationships with owners, buyers, and local industry partners
Oversee office operations and coordinate with the Oahu headquarters
Stay up to date on Maui’s short-term rental regulations and real estate trends
Compensation & Benefits:
$4,000/month base salary + commission on closed sales
Exclusive sales role for the Maui branch with strong commission potential
Full-time position with complete benefits package, including:
Health insurance
Dental insurance
401(k) plan
Paid time off (PTO)
Access to a high-quality and growing database of investor leads and vacation rental owners
Full support from our marketing, reservations, and operations teams
Office located in a high-visibility, high-traffic area near Kamaole Beach
Long-term growth potential within a fast-expanding company
Ideal Candidate:
Active Hawaii Real Estate Salesperson License
2+ years of experience in real estate sales; leadership or management experience is a plus
Knowledge of Maui’s real estate market and vacation rental industry
Excellent communication, negotiation, and client service skills
Entrepreneurial, organized, and results-driven
Ready to grow your real estate career and lead our Maui branch?
Apply today and become part of the Midway Vacations success story.