Job DescriptionNOTE: Applicants who reach out to us via messages will be reviewed for consideration first! Referrals are a plus.
About Us:
We are a boutique vacation rental management company primarily based in Chicago. We don’t just offer beds to sleep in; we curate well-designed and guest focused homes. Our reputation is built on providing a "White Glove" service, hence, clean, well-maintained spaces are the heart of what we do. We manage over 40 homes, and we treat this business and our team like family. We don’t have corporate red tape or distant managers. We are a close-knit group deeply aligned on one simple goal: providing an experience that is nothing short of excellent. We're currently looking for a Housekeeping Associate—someone hands-on, detail-oriented, and motivated to grow. This role is ideal for someone with solid cleaning experience who's also interested in learning the ins and outs of property management. If you're great with people, a quick learner, consistent and most importantly- share our vision, we'd love for you to reach out.
About the Role:
This is a working lead position. You’ll be cleaning properties yourself, especially at the start, but also helping to train and manage a small team of cleaners as we grow. You'll work closely with our property management team to ensure all homes are spotless, stocked, and ready for guests or residents. We’re also looking for someone who can eventually grow into a client-facing role—handling guest issues, overseeing turnovers, and possibly moving up to a Property Manager position.
What We Offer:- Competitive hourly pay based on experience (~$20-$25/hour)A guaranteed opportunity for growth into a property management or operations role (provided certain criteria are met)
- Paid time off
- Quarterly Performance bonuses
- Flexible scheduling, however, some weekends and holidays might be required.
- What We’re Looking For1–2 years of cleaning experience (short-term rental or hotel experience a plus).Leadership potential — someone who takes initiative and can eventually supervise others.
- Great attention to detail — you notice the little things.
- Strong communication and basic tech skills (we use apps for scheduling and property checklists).A people-person — friendly, respectful, and professional if/when interacting with guests or clients.
- Must have reliable transportation (properties are located around Chicago).Ability to lift up to 30 lbs and be on your feet for extended periods.
- Most importantly, someone who is consistent.
- Bonus If You Have:
- Experience with short-term rentals (Airbnb, etc.).Basic handyman or light maintenance skills.
- Bilingual (especially Spanish/English) is a plus.
