Vacation Rental Caretaker & Guest Experience

First Chair Destinations; Dover (VT); On-site; USD 34,000 - 36,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

401(k) match

PTO & holidays

Flexible time off

Sick leave

Job summary

First Chair Destinations is seeking a Property Caretaker to manage a portfolio of vacation homes, handling owner and guest relations, maintenance, and housekeeping. You will support cross-functional teams to ensure every stay meets our high standards.

The role offers 30–40 hours per week with flexible scheduling, weekends/holidays, and travel between worksites. Experience in hospitality and reliable transportation are essential to deliver exceptional guest experiences.

Qualifications

• Experience in hotel, hospitality, vacation or similar industry preferred.
• Minimum 1 year experience in housekeeping, maintenance or similar role.
• Excellent time management and ability to adapt to interruptions.
• Comfort with using digital systems and mobile apps.
• Willingness to travel between worksites; reliable transportation essential.

Responsibilities

• Assist daily operations of assigned portfolio of homes and drive process improvements.
• Respond to guest and homeowner concerns by email, calls, tickets.
• Perform light home maintenance (bulbs, hinges, unclog a toilet).
• Conduct regular inspections before guest/owner arrivals.
• Collaborate with management on escalated issues and resolutions.
• Support cross-functionally when new units join the portfolio.
• Other duties as assigned in hospitality.

Skills

Hospitality experience

Time management

Attention to detail

Tech savvy

Strong communication

Reliable transportation

Independent worker

Customer service

Job description

First Chair Destinations is seeking a Property Caretaker to manage a portfolio of vacation homes, handling owner and guest relations, maintenance, and housekeeping. You will support cross-functional teams to ensure every stay meets our high standards.

The role offers 30–40 hours per week with flexible scheduling, weekends/holidays, and travel between worksites. Experience in hospitality and reliable transportation are essential to deliver exceptional guest experiences.