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Weekend Short Term Rental Property Manager Jobs in Chicago, IL

We service condo, townhome, and homeowner associations, and provide rental management services to ... Front loaded PTO + personal time * 401k - Company match up to 4% * Long and short term disability ...

We service condo, townhome, and homeowner associations, and provide rental management services to ... Front loaded PTO + personal time * 401k - Company match up to 4% * Long and short term disability ...

Property Manager

Chicago, IL ยท On-site

$70K - $75K/yr

We service condo, townhome, and homeowner associations, and provide rental management services to ... Front loaded PTO + personal time * 401k - Company match up to 4% * Long and short term disability ...

Property Manager

Chicago, IL ยท On-site

$70K - $75K/yr

We service condo, townhome, and homeowner associations, and provide rental management services to ... Front loaded PTO + personal time * 401k - Company match up to 4% * Long and short term disability ...

Support leasing activities, renewals, and rental agreements. * Manage reservation calendars and list updates for short-term rentals. * Process invoices, track payments, and maintain accurate property ...

Assistant Property Manager

North Chicago, IL ยท On-site

$50K - $60K/yr

Support leasing activities, renewals, and rental agreements. * Manage reservation calendars and list updates for short-term rentals. * Process invoices, track payments, and maintain accurate property ...

Role & Responsibilities -- Work in a pod team structure managing, leasing and maintaining a portfolio of residential rental properties -- Maintain rental listings for the pod's portfolio of managed ...

Role & Responsibilities -- Work in a pod team structure managing, leasing and maintaining a portfolio of residential rental properties -- Maintain rental listings for the pod's portfolio of managed ...

Role & Responsibilities -- Work in a pod team structure managing, leasing and maintaining a portfolio of residential rental properties -- Maintain rental listings for the pod's portfolio of managed ...

Ability to work flexible hours, including some overtime, weekends, and holidays. * High School ... Employee rental discounts. * Paid new parent leave. * A supportive and inclusive company culture.

Ability to work flexible hours, including some overtime, weekends, and holidays. * High School ... Employee rental discounts. * Paid new parent leave. * A supportive and inclusive company culture.

Ability to work flexible hours, including some overtime, weekends, and holidays. * High School ... Employee rental discounts. * Paid new parent leave. * A supportive and inclusive company culture.

Task Force Manager

Chicago, IL ยท On-site

$70K - $75K/yr

If you've run a hotel, a short-term rental portfolio, or a high-volume hospitality operation, you ... Liaison with property management teams to resolve maintenance requests, address member concerns ...

Task Force Manager

Chicago, IL ยท On-site

$70K - $75K/yr

If you've run a hotel, a short-term rental portfolio, or a high-volume hospitality operation, you ... Liaison with property management teams to resolve maintenance requests, address member concerns ...

... rental assistance administrators and referral sources required for unit mix compliance. * Ensure ... Availability to respond to emergency work hours during evenings or weekends. Education & Experience

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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 6, 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.

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:
What job categories do people searching Weekend Short Term Rental Property Manager jobs in Chicago, IL look for? 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? Cities near Chicago, IL with the most Weekend Short Term Rental Property Manager job openings:

Customer Service Team Lead (Short-Term Rental (STR) Program)

Priwils, Inc

Chicago, IL โ€ข Remote

Full-time

Re-posted 17 days ago


Job description

 Overview: The STR Customer Service Team Lead provides direct oversight of daily customer service operations supporting the GSA Short-Term Rental (STR) Program. The Team Lead supervises Customer Service Representatives (CSR I, CSR-II; and CSR–III), ensures compliance with program policies and contractual performance standards, and serves as the primary escalation authority for complex federal user and vendor inquiries.
 
Minimum Qualifications
  • Bachelor’s degree preferred; extensive relevant professional experience may be substituted in lieu of formal education.
  • This is a Remote (work from home) position.
  • 7-10 years of experience in customer service, logistics operations, or call center environments, with demonstrated supervisory or team leadership experience.
  • Demonstrated ability to manage operational performance metrics.
  • Proficiency in Microsoft Office, particularly Excel.
  • Proficiency in Adobe Acrobat.
  • Experience navigating the following federal systems: SAM.gov and FPDS.gov.
  • Strong written and verbal communication skills.
  • Demonstrated ability to manage high call volumes and dynamic program changes.
  • Experience working with rental car, fleet, or equipment rental agencies required.
  • Advanced communication, leadership, and problem resolution skills
Responsibilities
  • The Team Lead supervises Customer Service Representatives (CSR I, CSR-II; and CSR–III), ensures compliance with program policies and contractual performance standards, and serves as the primary escalation authority for complex federal user and vendor inquiries.
  • Operate a national customer support center that responds to telephone, e-mail, and other electronic communication requests (emails or other electronic “Chat” platforms) from Federal STR customers.
  • Perform routine tasks which require knowledge of GSA Fleet and STR procedures and rules. Provide simple vehicle leasing and rental information and appropriate information sheets and forms to current and potential fleet customers regarding services available, the procedures to follow, and where to obtain additional program information.
  • Respond to customer inquiries and assist with customer requests on a wide variety of available vehicles and/or equipment; familiarity with industry terminology and offerings as well as vehicle/equipment specifications needed.
  • Assist with records management in areas such as assembling/creating routing and archiving contract files on Google Drive, WebSTR or comparable electronic data storage system (e.g. Electronic Data Management System (EDMS))
  • Create reports using government databases and query tools such as but not limited to MySQL Workbench.
  • Provide upon request a listing of available vehicles/equipment with ceiling pricing and assist the customer with related factors such as length of trip, freight/passenger requirements, vehicle or equipment pickup/delivery and fuel card use.
  • Maintain and update fleet management information systems and ensure data integrity across all fleet management platforms.
 

We will never send communications through any other domain, including @Priwilscareers.com, @gmail.com or@yahoo.com). We will never request payment from you, nor will we send payment to you, prior to your start date. If you have been asked to send or receive any payment, or if you have any doubt about whether you have been contacted by a Priwils employee, please contact us at jobs@Priwils.com

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