Lead. Grow. Thrive with Midway Vacations.
Are you a motivated real estate professional with strong leadership skills and a passion for
Hawaii’s vacation rental and real estate market? Midway Vacations is expanding, and we’re
looking for a dynamic Broker-in-Charge to grow our Maui branch, oversee sales and property
management operations, and take our presence on the island to the next level.
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 units in
Maui, and are rapidly expanding. Our Maui branch is located in a prime location at Kamaole
Shopping Center in South Maui, just steps from the beach.
About the Role:
As Broker-in-Charge, you will be responsible for:
Growing real estate sales and lead generation across Maui
Overseeing and expanding the vacation rental property management portfolio
Leading and supporting a small, high-performing local team
Ensuring full compliance with Hawaii real estate laws and licensing requirements
Collaborating with the executive team to implement strategies for growth, visibility, and
brand excellence on Maui
Building strong relationships with clients, owners, agents, and industry partners
Compensation & Benefits:
$4,000/month fixed base salary + commission based on sales
Leadership position with long-term growth opportunity
Full support from our experienced marketing, reservations, and operations teams
Access to Midway’s established portfolio of investor clients and vacation rental owners
Office located in a high-visibility, high-traffic area near Kamaole Beach
Ideal Candidate:
Active Hawaii Real Estate Broker License (BIC eligible)
5+ years of experience in real estate sales, brokerage management, or property
management
Strong knowledge of short-term rental regulations and Maui’s real estate landscape
Leadership skills and an entrepreneurial spirit
Experience with vacation rentals or hospitality is a strong plus
A passion for delivering high-quality service to owners, buyers, and guests
Ready to take the lead and grow a top-tier real estate and vacation rental operation i
Maui?
Apply today and become part of the Midway Vacations success story.
Send an application here, and we will contact you quickly.