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Weekend Short Term Rental Property Manager Jobs in Chicago, IL

VOA Illinois

Assistant Property Manager-HMV

Chicago, IL · On-site

$19.30 - $23.16/hr

Affordable, high-quality rental properties and homeownership opportunities immediately surrounding ... This role manages daily operations, staff supervision, regulatory compliance, and resident ...

Inland Group

Commercial Property Manager

Oak Brook, IL · On-site

$98 - $124/hr

Manage the day-to-day financial and operational performance of assigned retail properties ... Company-paid short-term and long-term disability This position is eligible as an internal promotion ...

Bridge33 Capital

Assistant Property Manager

Chicago, IL · On-site

$58K - $70K/yr

... rental collections for the assets. * Responds to tenant needs with a sense of urgency, ensuring any ... Company paid short- and long-term disability insurance. * Paid parental leave. * 401k plan with ...

Bridge33 Capital

Assistant Property Manager

Chicago, IL

$58K - $70K/yr

... rental collections for the assets. * Responds to tenant needs with a sense of urgency, ensuring any ... Company paid short- and long-term disability insurance. * Paid parental leave. * 401k plan with ...

Bridge33 Capital

Assistant Property Manager

Chicago, IL · On-site

$58K - $70K/yr

... rental collections for the assets. * Responds to tenant needs with a sense of urgency, ensuring any ... Company paid short- and long-term disability insurance. * Paid parental leave. * 401k plan with ...

The Scion Group

Regional Property Manager

Chicago, IL · On-site +1

$80K - $108K/yr

The Regional Manager is a strategic leader who thrives in a fast-paced, agile, collegiate ... or to cover short term vacancies. * Ensures that all emergencies that happen at property are ...

The Scion Group

Regional Property Manager

Chicago, IL · On-site +1

$80K - $108K/yr

The Regional Manager is a strategic leader who thrives in a fast-paced, agile, collegiate ... or to cover short term vacancies. * Ensures that all emergencies that happen at property are ...

The Scion Group

Regional Property Manager

Chicago, IL · On-site +1

$80K - $108K/yr

The Regional Manager is a strategic leader who thrives in a fast-paced, agile, collegiate ... or to cover short term vacancies. * Ensures that all emergencies that happen at property are ...

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All JobsShort Term Rental Property JobsWeekend Short Term Rental Property Manager JobsWeekend Short Term Rental Property Manager Jobs in Chicago, IL

Weekend Short Term Rental Property Manager information

See Chicago, IL salary details

$28.8K

$60.1K

$99.4K

How much do weekend short term rental property manager jobs pay per year?

As of Aug 23, 2026, the average yearly pay for weekend short term rental property manager in Chicago, IL is $60,093.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,300.00 and $70,000.00 per year, depending on experience, location, and employer.

What is the difference between Weekend Short Term Rental Property Manager vs Vacation Rental Housekeeper?

AspectWeekend Short Term Rental Property ManagerVacation Rental Housekeeper
CredentialsProperty management certifications, leasing knowledgeCleaning certifications, hospitality training
Work EnvironmentOversees rental operations, guest interactionsPerforms cleaning and maintenance tasks
Employer & IndustryProperty management companies, rental platformsHospitality, vacation rental services
Search & Comparison IntentManaging rental properties, guest servicesCleaning, turnover, hospitality services

The Weekend Short Term Rental Property Manager focuses on overseeing rental operations, guest interactions, and property maintenance during weekends. In contrast, the Vacation Rental Housekeeper primarily handles cleaning and turnover tasks to prepare properties for guests. While both roles support short-term rentals, the property manager manages the overall guest experience and rental process, whereas the housekeeper ensures cleanliness and readiness of the property.

Do weekend short term rental property managers work on weekends?

Weekend short term rental property managers often work on weekends to oversee guest check-ins, handle maintenance issues, and ensure guest satisfaction. Their schedules can include weekend hours to accommodate guest needs and property operations.

What are popular job titles related to Weekend Short Term Rental Property Manager jobs in Chicago, IL?

For Weekend Short Term Rental Property Manager jobs in Chicago, IL, the most frequently searched job titles are:

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The top searched job categories for Weekend Short Term Rental Property Manager jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Weekend Short Term Rental Property Manager jobs?

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Weekend Short Term Rental Property Manager jobs near you

Property Manager - Polish Senior Living Community

HHDC

Chicago, IL

$60K - $63K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 4 days ago

Job description

Property ManagerPosition Summary

Under the direction of the Property Supervisor, the Property Manager is responsible for the overall day-to-day operations of CHA assigned properties. This position ensures the properties are well-managed, financially sound, properly maintained, and in compliance with all regulatory agencies, investors, and company policies.

The Property Manager provides leadership to onsite staff, oversees resident relations, coordinates with vendors and maintenance teams, and helps create a safe, supportive, and welcoming environment for residents.

Schedule & Compensation

Full-Time: 40 hours per week
Schedule: Monday – Friday; must be available on-call for property emergencies as needed.
Annual Salary: $60,000 – $63,000

Key Responsibilities
  • Oversee the daily operations of assigned properties.
  • Supervise, support, and provide direction to onsite staff.
  • Work closely with the Maintenance Supervisor to monitor work orders, repairs, unit turnovers, and preventive maintenance.
  • Conduct routine inspections of property grounds, common areas, vacant units, and completed maintenance work.
  • Ensure vacant units are prepared and ready for occupancy in a timely manner.
  • Assist with annual unit, site, and regulatory inspections.
  • Monitor property expenses and recommend repairs, replacements, and improvements within the approved budget.
  • Identify opportunities to improve operations and reduce unnecessary costs.
  • Ensure property emergencies are handled promptly and appropriate corporate staff are notified.
  • Oversee safety and security procedures.
  • Manage marketing, leasing, occupancy, and resident retention efforts.
  • Build positive relationships with residents and address concerns professionally.
  • Serve as a liaison between residents and community, public, and private agencies when needed.
  • Monitor financial reporting and property performance.
  • Ensure compliance with Fair Housing requirements and applicable affordable housing programs.
  • Manage vendor relationships and ensure contracted work is completed appropriately.
  • Perform other duties as assigned.
Minimum Qualifications
  • High school diploma or equivalent required; college degree in Business, Urban Planning, Real Estate, or a related field preferred.
  • Must be bilingual in English and Spanish.
  • Minimum of 5 years of property management experience, preferably within affordable housing, nonprofit housing, real estate development, construction, or property management.
  • Experience managing affordable housing programs such as Section 8 and/or public housing is required.
  • Knowledge of Fair Housing regulations.
  • Strong leadership, supervisory, organizational, and time-management skills.
  • Excellent customer service, interpersonal, written, and verbal communication skills.
  • Proficiency with Microsoft Office and experience with property management software preferred.
  • Strong attention to detail and basic mathematical skills.
  • Valid driver's license, vehicle, insurance, and good driving record.
Employee Benefits
  • Medical, Dental, and Vision Insurance
  • Paid Time Off (PTO)
  • Paid Vacation
  • Paid Holidays
  • 401(k) Retirement Plan
  • Short-Term and Long-Term Disability
  • Tuition Reimbursement
  • Employee Assistance Program, if applicable
  • Ongoing Training and Professional Development

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