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Short Term Rental Manager Jobs in Chicago, IL (NOW HIRING)

RWE

Short-term Congestion Trader

Chicago, IL · On-site

$125K - $175K/yr

The US congestion trading desk at RWE manages the long- and short-term congestion exposure of our existing renewables portfolio. Our trading activities are focused around various ISOs across the US ...

RWE

Short-term Congestion Trader

Chicago, IL

$125K - $175K/yr

The US congestion trading desk at RWE manages the long- and short-term congestion exposure of our existing renewables portfolio. Our trading activities are focused around various ISOs across the US ...

Landing

Task Force Manager

Chicago, IL · On-site

$70K - $75K/yr

As a Task Force Manager, you will deploy into Landing markets across the US -- wherever the ... If you've run a hotel, a short-term rental portfolio, or a high-volume hospitality operation, you ...

Landing

Task Force Manager

Chicago, IL · On-site

$70K - $75K/yr

As a Task Force Manager, you will deploy into Landing markets across the US - wherever the business ... If you've run a hotel, a short-term rental portfolio, or a high-volume hospitality operation, you ...

Indie Campers

Rental Operations Supervisor

Chicago, IL · On-site

$24/hr

We offer a comprehensive and expanding array of road trip possibilities: short-term RV rentals ... Booking activities control, manage stock, local suppliers and cleaning services; * Handle ...

Indie Campers

Rental Operations Supervisor

Chicago, IL · On-site

$24/hr

We offer a comprehensive and expanding array of road trip possibilities: short-term RV rentals ... Booking activities control, manage stock, local suppliers and cleaning services; * Handle ...

Indie Campers

Rental Operations Supervisor

Chicago, IL · On-site

$24/hr

We offer a comprehensive and expanding array of road trip possibilities: short-term RV rentals ... Booking activities control, manage stock, local suppliers and cleaning services; * Handle ...

PriceLabs

Senior, Market Insights (Remote)

Chicago, IL · Remote

$109K - $124K/yr

PriceLabs is a revenue management solution for the short-term rental and hospitality industry, founded in 2014 and headquartered in Chicago, IL. Our platform helps individual hosts and hospitality ...

Beyond

Business Development Representative

Chicago, IL · On-site +1

Beyond powers the business of short-term rentals with a best-in-class Revenue Management System ... the vacation rental market So what can you expect after you apply? Your application will be ...

PriceLabs

You pick the title

Chicago, IL · Remote

About PriceLabs PriceLabs is a revenue management solution for the short-term rental and hospitality industry, founded in 2014 and headquartered in Chicago, IL. Our platform helps individual hosts ...

Goldbelt

Customer Service Representative II

Chicago, IL · On-site

$19.23 - $28.85/hr

... Fleet Management Federal customers under the GSA Short-Term Rental (STR) Program. The Customer Service Representative II provides intermediate-level support and independently handles moderately ...

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Showing results 1-20

All JobsShort Term Rental JobsShort Term Rental Manager JobsShort Term Rental Manager Jobs in Chicago, IL

Short Term Rental Manager information

See Chicago, IL salary details

$24.7K

$58.7K

$106.1K

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

As of Aug 7, 2026, the average yearly pay for short term rental manager in Chicago, IL is $58,703.00, according to ZipRecruiter salary data. Most workers in this role earn between $46,400.00 and $64,900.00 per year, depending on experience, location, and employer.

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

AspectShort Term Rental ManagerProperty Manager
CredentialsExperience in hospitality, rental platforms, and customer serviceReal estate licensing or property management certifications often preferred
Work EnvironmentFocus on short-term rentals, vacation properties, and hospitality servicesManage long-term residential or commercial properties
Employer & IndustryVacation rental companies, Airbnb hosts, property management firmsReal estate agencies, property management companies, landlords

While both roles involve managing rental properties, a Short Term Rental Manager specializes in short-term, vacation, or hospitality rentals, focusing on guest experience and platform management. A Property Manager typically oversees long-term residential or commercial properties, handling tenant relations, maintenance, and lease agreements. The roles share some credentials and work environments but differ mainly in rental duration and industry focus.

What are the key skills and qualifications needed to thrive as a short term rental manager, and why are they important?

To thrive as a Short Term Rental Manager, you need expertise in property management, hospitality, and local rental regulations, often supported by experience or relevant certifications. Familiarity with property management software, online booking platforms like Airbnb or VRBO, and dynamic pricing tools is essential. Strong interpersonal skills, problem-solving abilities, and attention to detail help you deliver excellent guest experiences and handle operational challenges. These skills ensure high occupancy rates, positive reviews, and compliance with regulations in a competitive short-term rental market.

What does a short term rental manager do?

A Short Term Rental Manager oversees the daily operations of properties that are rented out for short periods, such as through platforms like Airbnb or Vrbo. Their responsibilities typically include managing bookings, communicating with guests, coordinating cleaning and maintenance, ensuring compliance with local regulations, and optimizing rental income. They also handle guest check-ins and check-outs, resolve issues that may arise, and may be involved in marketing the property to attract more bookings. Essentially, they ensure that the rental property operates smoothly and profitably while providing a positive experience for guests.

What are some common challenges faced by short term rental managers, and how can they be addressed?

Short Term Rental Managers often encounter challenges such as managing last-minute bookings, handling guest issues promptly, and ensuring consistent property cleanliness across multiple locations. Effective communication with both guests and cleaning staff, implementing reliable booking and property management software, and establishing clear protocols for maintenance and emergencies are key to overcoming these hurdles. Building strong relationships with local vendors and staying up-to-date with regulations also greatly contribute to smoother operations and guest satisfaction.
What are popular job titles related to Short Term Rental Manager jobs in Chicago, IL? For Short Term Rental Manager jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Short Term Rental Manager jobs in Chicago, IL look for? The top searched job categories for Short Term Rental Manager jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Short Term Rental Manager jobs? Cities near Chicago, IL with the most Short Term Rental Manager job openings:
Short Term Rental Manager jobs near you
Infographic showing various Short Term Rental Manager job openings in Chicago, IL as of August 2026, with employment types broken down into 67% Full Time, and 33% Part Time. Highlights an 82% In-person, and 18% Remote job distribution, with an average salary of $58,703 per year, or $28.2 per hour.

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

Priwils, Inc

Chicago, IL • Remote

Full-time

Re-posted 18 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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