Property Caretaker
$25 - $26 per hourFirst Chair Destinations
Job Description
Job Description
A Little Bit About Us
We offer exceptional vacation homes across the country's 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.
BenefitsWe'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
- $25 - $26 / HR less payroll deductions and all required withholdings
- Up to $100 monthly car allowance for eligible employees
- 30 - 40 hours per week
- Schedule: Varies weekly
- Weekends and holidays may be required
Essential Job Functions
- Assists in the daily operations of the assigned portfolio of homes. Identify areas for improvement, assisting managers in process enhancements to drive efficiency and quality outcomes.
- Support the team with escalated guest and homeowner concerns by responding to emails, calls and tickets.
- Perform light home maintenance (light bulbs, fix door hinges, unclog a toilet, etc).
- Conduct regular inspections prior to guest and owner arrivals.
- Works to resolve guest and homeowner concerns by responding to emails, calls and tickets. Partners with the management team on escalated issues.
- Partners and assists your Business Development Representative and management team when new units join the portfolio.
- Supports cross-functionally across the team as needed.
- Other duties as assigned because every day is different in hospitality!
Skills + Qualifications
- Experience working in hotel, hospitality, vacation or similar industry is highly preferred.
- Minimum 1 year experience in housekeeping, maintenance or similar role.
- Excellent time management skills with the ability to change activity frequently and cope with interruptions.
- Strong attention to detail.
- Tech-savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms.
- This role involves frequent travel between worksites, so reliable personal transportation is essential.
- Dependable and prepared. Showing up on time and ready to go is key to creating great stays for our guests and peace of mind for our homeowners.
- Must be dependable, self-motivated, and able to work independently while contributing positively to a collaborative team environment.
- Comfortable talking to people—online or in person—and being able to share information in a way that's clear, thoughtful, and represents the company in a positive way always.
Workplace Environment + Physical Requirements
- Work may take place indoors or outdoors, in a variety of settings including private homes, resorts, offices, and laundry facilities — often in varying weather conditions.
- We're in hospitality and our schedules can change based on guest and homeowner needs. Shifts may include early mornings, evenings, weekends, and holidays. We require flexibility to support this.
- Reliable transportation required.
- Regular travel within the locally assigned market and / or region.
- Ability to move freely (balancing, climbing, crawling, driving, squatting, standing, stooping, walking, bending, pushing, pulling, reaching, and repetitive hand/finger motions) and lift up to a maximum of fifty (50) pounds without assistance.
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 of a background check.
- Job Title Retail Sales and Service Technician (SST) Job Category Retail Position Summary The retail Sales and Service Technician (SST) is a unique hybrid role for stores and is intended as a key pipeline for future career-growth within Firestone Complete ...SuggestedDaily paidTemporary workLocal areaFlexible hours
- HARDY INDUSTRIES is looking for skilled technicians to join their team in Wilmington, Vermont. This position involves a variety of technical tasks including OS installations, structured cabling, and telecom work in different environments such as retail and medical. Applicants...SuggestedFlexible hours
- Benefits: Flexible schedule Opportunity for advancement Profit sharing This Is Not Your Average Tech Job Are you a hands‑on I.T. or Telecom professional looking for something beyond the desk? AMG Tech Support is seeking skilled, driven technicians to support our growing...SuggestedHourly payFor contractorsImmediate startFlexible hours
- Note : This is an educational program, not a job. Successful completion of the program does not guarantee employment but will equip you with valuable skills for the healthcare job market. Looking to start a rewarding career path in the healthcare industry? Use Dreambound...SuggestedFlexible hours
$20 - $23 per hour
Childrens Center Attendant Date: Jul 14, 2026 Location: West Dover, VT, US Company: Mount Snow Shift Type: Winter Seasonal 2026/2027 Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it's your first-time seeing snow or you were born ...SuggestedFull timePart timeSeasonal workLocal areaShift work- Assistant Manager As a Dunkin' franchisee, we are committed to our employees as much as we are committed to our customers. We value hardworking and enthusiastic employees and we make it a priority to ensure their success. The Assistant Manager will be responsible...
- DESCRIPTION As a Dunkin' franchisee, we are committed to our employees as much as we are committed to our customers. We value hardworking and enthusiastic employees and we make it a priority to ensure their success. The Assistant Manager will be responsible for...
$25.25 per hour
Salary: $25.25/Hourly Company Summary EchoStar is reimagining the future of connectivity. Our business reach spans satellite television service, live-streaming and on-demand programming, smart home installation services, mobile plans and products. Today, our ...Hourly payLocal areaFlexible hoursAfternoon shift$50k - $65k
Description: Stewart's Shops is a fast growing convenience store chain in New York and Vermont with friendly store associates and great customers! We are looking for Manager Trainees to join our fast track training program in our shops. Our Manager Trainees work closely...Full timeTraineeshipFlexible hours- Peckham Industries Crusher Plant Maintenance Operator Please wait while the page is processing... chevron_left Back to Job Postings Crusher Plant Maintenance Operator Apply Now Share via Email Print Position Title: Crusher Plant Maintenance Operator...Full timeLocal area
$20 - $23 per hour
Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it’s your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors while building lifelong connections...Full timePart timeSeasonal workWork at officeLocal areaImmediate startShift work$20 - $23 per hour
Childrens Center Attendant Date: Jul 14, 2026 Location: West Dover, VT, US Company: Mount Snow Shift Type: Winter Seasonal 2026/2027 Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it's your first-time seeing snow or you were born on the...Full timePart timeSeasonal workLocal areaShift work$17 - $18 per hour
Part-time Shop Partner Stewart's Shops is a fast-growing convenience store chain in New York, Vermont and New Hampshire with friendly store associates and great customers! We are looking for part-time shop partners with flexible schedules to provide excellent customer...Full timePart timeFlexible hoursWeekend workDay shiftAfternoon shift$22 per hour
...Housing Availability: No Job Responsibilities: ~ Clean guest units, offices, and common areas (including restrooms) at the property ensuring adherence to Vail Resorts quality, health, and safety standards ~ Replenish amenities in areas including, but not limited...Full timePart timeSeasonal workLocal areaFlexible hoursShift workNight shiftWeekend work$20 per hour
Activities Attendant Date: Jul 14, 2026 Location: West Dover, VT, US Company: Mount Snow Shift Type: Winter Seasonal 2026/2027 Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it's your first-time seeing snow or you were born on the...Full timePart timeSeasonal workLocal areaFlexible hoursShift work- Deli Clerk As a Deli Clerk, your day is centered around preparing fresh food and creating a welcoming experience for customers. You're often the first stop for something ready to enjoy, helping customers choose from deli meats, cheeses, hot foods, and prepared items...Weekly payFlexible hoursWeekend workAfternoon shiftEarly shift
- DESCRIPTION Why Dunkin'? America runs on Dunkin', and so do our teams! We're seeking motivated, energetic, and reliable individuals to join our team as Shift Managers . This is your opportunity to lead the way - ignite teams, wow guests, and level up your career...Flexible hoursShift workAfternoon shiftEarly shift
- Job Title: Senior Software Developer Location: Client US DE Wilmington Years of Experience: 7 10 Years Job Summary: We are seeking a highly skilled Senior Software Developer with a strong background in AWS Administration to join our dynamic team. The ideal ...
- DESCRIPTION As a Dunkin' franchisee, we are committed to our employees as much as we are committed to our customers. We value hardworking and enthusiastic employees and we make it a priority to ensure their success. The Restaurant Manager will always maintain a...
- Restaurant Manager As a Dunkin' franchisee, we are committed to our employees as much as we are committed to our customers. We value hardworking and enthusiastic employees and we make it a priority to ensure their success. The Restaurant Manager will always maintain...
$20 per hour
Job Description Job Description Garde Manger for Award-Winning Restaurant Location: Southern Vermont (Ski Region) Position: Garde Manger (Cold Station / Pantry Chef) - Cross-training available Compensation: $20.00 / hour (Plus end-of-season bonus potential...Extra incomePart timeLocal areaShift workNight shiftWeekend workAfternoon shift- Why Dunkin’? America runs on Dunkin’, and so do our teams! We’re seeking motivated, energetic, and reliable individuals to join our team as Shift Managers . This is your opportunity to lead the way - ignite teams, wow guests, and level up your career! Perks & Benefits: ...Flexible hoursShift workAfternoon shiftEarly shift
- About the Role and Job: Job Title Service Management Lead Location: Wilmington, DE Model: Onsite Job Type : Full time/ Contract Job Summary: This job posting is for an existing, active vacancy and We are currently looking for ITIL Process...Full timeContract workWork at office
$22 - $26.88 per hour
Job Description Job Description Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it’s your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors...Full timePart timeSeasonal workLocal areaShift workAfternoon shift- Description: Why join UCS? Since 1958, United Counseling Service (UCS) has been dedicated to providing exceptional care and support to individuals and families in our community. Through a wide range of programs, services, and educational opportunities, we strive to...Hourly payTemporary workWork at office
- Join Our Team as a Food and Beverage Manager at The Hermitage ClubThe Hermitage Club at Haystack Mountain is seeking an experienced, service-driven senior Food and Beverage Manager to lead all food and beverage operations for our private, member-owned resort community. ...Full timeSeasonal workShift workNight shiftWeekend work
$20 - $30 per hour
...Little Bit About Us We offer exceptional vacation homes across the country's 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...Hourly payLocal areaFlexible hoursAfternoon shiftEarly shift$69k
Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely, serving clients by providing guidance and protection solutions...Remote workWork from homeFlexible hours$55k - $65k
...What You Bring: Minimum of 5 years of prior experience in the insurance industry, specifically within Personal Lines An active Property & Casualty License A strong sense of integrity, professionalism, and reliability A team-oriented mindset paired with high self‑motivation...Temporary workInternshipLocal areaRemote workFlexible hours$27 - $32.14 per hour
Create Your Experience of a Lifetime! Come work and play in the mountains! Whether it’s your first-time seeing snow or you were born on the slopes, joining our team means discovering (or re-discovering!) a passion for the outdoors while building lifelong connections...Hourly payFull timeSeasonal workLocal areaShift workDay shift
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Property Caretaker. Be the first to apply!




