Founded in 2015, My Perfect Stays is the largest vacation rental management company on the island of Maui, managing over 450 properties with a team of more than 50 employees.
At My Perfect Stays, our goal is to provide the perfect property at the perfect price for every guest. We focus on thoughtful service and clear communication to ensure each stay is comfortable, seamless, and memorable.
Guests receive detailed arrival instructions, independent inspections after every clean, a welcome gift, a live check-in call to confirm satisfaction, and a personal call at departure. Based on Maui, our team is available 24/7 to assist with any questions or needs.
As Maui locals, we’re happy to share recommendations on restaurants, activities, and favorite local spots to help guests experience the island like a resident.
What truly sets My Perfect Stays apart is our team. With more than 50 years of combined business experience, our leadership believes that a strong team creates a great company.
My Perfect Stays is seeking a detail-oriented and self-driven Onboarding Field Agent to join our team in Lahaina, HI. This role is ideal for someone who enjoys working independently and takes pride in getting every detail right. You’ll prepare newly acquired vacation rental homes for their first guests: coordinating inventory, completing staging setups, and verifying that each space meets our quality and presentation standards.
In this position, you’ll move between properties, follow established onboarding processes, and ensure every home is fully functional, stocked, and ready for a seamless guest experience. Strong organization, reliability, and the ability to stay focused while working autonomously are essential, along with the physical capability to handle hands-on setup tasks.
Conduct detailed inventory of new units including furniture, appliances, kitchenware, and décor.
Set up and stage units according to company standards for guest readiness and professional photography.
Unstage units following photography sessions as needed.
Ensure all spaces are organized, functional, and guest-ready, with thoughtful placement of furnishings and items.
Safely move and lift furniture or equipment up to 50 lbs.
Adapt to flexible schedules, including weekdays, weekends, and occasional travel between West and South Maui.
Must be able to provide images to support task accuracy and completion via our property management software from your personal cell phone.
Must live in Maui, Hawaii
Ability to lift and move up to 50 lbs safely.
Comfortable working independently and managing tasks across multiple properties.
Valid driver's license for travel between properties.
Flexible availability to support varying schedules and occasional travel.
Hourly, $28 - $31
Workplace perks such as recreation activities, food and coffee, and flexible work schedules
20-40 hours, 5 days a week.