An application made for this job — a tailored resume and cover letter that speak straight to the posting.
First Chair Destinations is seeking a Property Caretaker to support a portfolio of vacation rental homes. You will handle owner and guest relations, maintenance, and housekeeping, with cross-functional teamwork across the company.
The role involves light maintenance, inspections, and responding to guest concerns. Schedule ranges from 20 to 30 hours weekly, with potential weekend/holiday shifts and travel between properties within the region.
We offer exceptional vacation homes across the countries most celebrated ski towns and coastal retreats. Each property is carefully selected, locally managed, and held to an uncompromising standard of care. We live and work in the communities we serve, which means every stay comes with generous local knowledge, genuine hospitality, and the confidence that what you booked is exactly what you’ll find.
We’re proud to offer a competitive benefits package designed to support our employees both at work and beyond. Benefits and eligibility may vary by position and are subject to change. Full plan details and terms will be provided during onboarding.
Health, Dental & Vision Insurance
401(k) with Company Match
Paid Time Off (PTO)& Holidays (non-exempt employees)
Paid Flexible Time Off & Holidays (exempt employees only)
Paid Sick Leave
Benefits are subject to the terms and conditions of the applicable plan documents, which govern in the event of any discrepancy. The Company reserves the right to modify, suspend, or terminate benefit plans and programs at any time.
About This Job
The Property Caretaker supports an assigned portfolio of vacation rental properties with responsibilities including all aspects of property management, including owner and guest relations, maintenance, and housekeeping. Supports cross-functionally across the team.
Compensation + Schedule
Essential Job Functions
Skills + Qualifications
Workplace Environment + Physical Requirements
This job description does not identify every requirement of the position. First Chair may change position requirements, responsibilities, and work environment at any time with or without notice.
Some positions may require that you drive a personal vehicle and/or company vehicle for work purposes. Employees who are required to drive a personal vehicle must have reliable transportation, a valid driver’s license, and be at least 18 years of age. Employees who are required to drive a company vehicle must have a valid driver’s license, be at least 21 years of age, and have been a licensed driver for no less than 3 years.
An offer of employment for this role will be contingent upon the successful completion a background check.