Owner Relations Manager

Company Overview

Founded in 2015, My Perfect Stays is the largest vacation rental management company on the island of Maui, managing over 450 luxury vacation homes and condos with a team of more than 50 local hospitality professionals.

Our mission is simple: provide the perfect stay for every guest and complete peace of mind for every homeowner.

We believe exceptional hospitality comes from great people. Our team works together to deliver thoughtful service, clear communication, and consistently high standards for every property we manage.

Guests enjoy:

• Detailed arrival instructions
• Independent inspections after every clean
• Welcome gifts upon arrival
• Live check-in calls to ensure satisfaction
• Local recommendations from our Maui-based team

Our team is local, responsive, and available 24/7, ensuring every stay and every home is cared for with attention and pride.

Position Summary

The Owner Relations Manager serves as the primary point of contact between property owners and My Perfect Stays.

In this role, you will manage a portfolio of approximately 60 homes and homeowners, ensuring properties operate smoothly, owners remain informed, and homes continue performing at their best.

You’ll collaborate closely with departments across the company including housekeeping, maintenance, accounting, and revenue management to ensure issues are addressed quickly and owners receive exceptional service.

This is a relationship-driven operations role ideal for someone who enjoys communication, problem-solving, and working in a fast-moving hospitality environment.

📍 Please note: Applicants must live on Maui. We are hiring 2 candidates, one will work in Kahana office, and the other in the Kihei office. This is not a remote position.

What You'll Do

• Serve as the primary contact for assigned homeowners

• Maintain proactive and consistent communication with owners

• Coordinate across departments to support property operations

• Manage owner requests, property needs, and operational tasks

• Review monthly owner statements and address discrepancies

• Participate in weekly team meetings focused on operations and training

• Attend bi-monthly revenue meetings to support property performance

• Help identify opportunities to improve guest experience and property results

What We're Looking For

• Must currently live on Maui, Hawaii (ideally near Kihei or Kahana)

• 1+ year experience in hospitality, vacation rentals, property management, or customer service

• Strong written and verbal communication skills

• Organized and comfortable managing multiple priorities

• Positive, team-oriented mindset

• Ability to work independently and follow through on tasks

• Comfortable using business software and learning new systems

Preferred but not required

• Experience with Streamline, Breezeway, or property management software

• Experience in short-term rentals or hospitality operations

• Bachelor’s degree

Compensation, Benefits, & Schedule

Annual Salary - $70,000 - $75,000

Benefits

• Health insurance (includes vision)

• Retirement benefits including a 6% match

• Paid time off for vacation days after 1 year of employment

• 10% off vacation rentals apart of My Perfect Stays' parent company, Monarch Collective

• After training is completed, Hybrid working model of 3 days in office, 2 days at home is optional.

Schedule

• Full Time, Monday-Friday 9am-5pm

• 📍 Please note: Applicants must live on Maui. We are hiring 2 candidates, one will work in Kahana office, and the other in the Kihei office. This is not a remote position.