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.
My Perfect Stays is seeking a warm and detail-oriented Reservations Agent to join our team in Kihei. In this role, you'll be the welcoming voice and helpful guide for guests planning their Maui vacation experience. You'll coordinate reservation inquiries across multiple channels, ensure booking accuracy, and work closely with our internal teams to create smooth and memorable stays for our guests. This position is ideal for someone who thrives on building connections, solving problems with care, and supporting others through a seamless booking journey from first inquiry to confirmed reservation.
Manage inbound reservation inquiries across phone, email, and online channels
Assist prospective guests with availability, pricing, policies, and booking details
Accurately enter, update, confirm, modify, and cancel reservations in booking systems
Process payments and maintain organized guest records and administrative files
Coordinate with internal teams to ensure a smooth and accurate booking experience
Resolve special requests and booking issues in alignment with company policies
Recommend additional services and upsell opportunities when appropriate
Support general administrative tasks using Microsoft Word, Excel, and related systems
Must currently live on Maui, Hawaii
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, professional, team-oriented mindset
Ability to work independently and follow through on tasks
Comfortable using business software and learning new systems
$25 - $30
Telecommuting options
Workplace perks such as recreation activities, food and coffee, and flexible work schedules
Office space in either Kihei or Kahana
10% off vacation rentals apart of My Perfect Stays' parent company, Monarch Collective
Hybrid, part-time role. Weekends required. 9am-5pm