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Remote Short Term Rental Manager Jobs in Chicago, IL

PriceLabs

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Chicago, IL · Remote

About PriceLabs PriceLabs is a revenue management solution for the short-term rental and ... In 2025, we scaled to; * 600K+ listings * 160+ integrations * 300+ globally remote team * 70K ...

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 ... We are a remote-first organisation and accept work from home as the norm. PriceLabs is an equal ...

Pentice

Head of Guest Experience

Chicago, IL · Remote

... short-term rental operator. We turn long-term luxury rentals into exceptional short-term stays, delivering hotel-grade quality to guests while helping property managers unlock the top-line potential ...

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

Remote Short Term Rental Manager information

See Chicago, IL salary details

$24.7K

$58.7K

$106.1K

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

As of Aug 14, 2026, the average yearly pay for remote 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.

How does a remote short term rental manager effectively handle guest issues and property emergencies from a distance?

As a Remote Short Term Rental Manager, handling guest issues and property emergencies requires strong communication skills and a reliable network of local service providers. Managers typically use property management software, messaging apps, and smart home technology to monitor properties and respond quickly to concerns. Establishing relationships with trusted cleaners, maintenance professionals, and emergency contacts in each location is essential for prompt resolution of issues. Proactive communication with guests and clear instructions for self-check-in or troubleshooting can prevent many common problems.

What is a remote short term rental manager?

A Remote Short Term Rental Manager is a professional who oversees and manages vacation or short-term rental properties from a remote location, rather than being physically present on-site. Their responsibilities typically include communicating with guests, coordinating cleaning and maintenance, managing bookings and listings on platforms like Airbnb or VRBO, handling guest issues, and ensuring a smooth rental experience. They use digital tools to monitor property performance, automate processes, and maintain high occupancy rates. This role is ideal for individuals who are organized, tech-savvy, and skilled in customer service.

What are the key skills and qualifications needed to thrive as a remote short term rental manager?

To thrive as a Remote Short Term Rental Manager, you need experience in property management, knowledge of local regulations, and strong organizational skills, often supported by a background in hospitality or real estate. Familiarity with property management software (like Guesty or Hostaway), booking platforms (such as Airbnb and Booking.com), and digital communication tools is essential. Outstanding customer service, problem-solving ability, and attention to detail help you deliver excellent guest experiences remotely. These skills ensure efficient operations, maximize occupancy and revenue, and maintain guest satisfaction from a distance.

What is the difference between Remote Short Term Rental Manager vs Vacation Rental Coordinator?

AspectRemote Short Term Rental ManagerVacation Rental Coordinator
CredentialsExperience in property management, hospitality, or real estate; certifications like CAM or CPM beneficialCustomer service experience, hospitality background, basic property knowledge
Work EnvironmentRemote, managing multiple properties, coordinating bookings and maintenanceOn-site or remote, assisting with guest check-ins, cleaning schedules, and reservations
Industry UsageUsed across property management companies, online rental platformsCommon in hospitality and vacation rental companies

The Remote Short Term Rental Manager oversees multiple rental properties remotely, focusing on management, bookings, and maintenance. In contrast, the Vacation Rental Coordinator typically handles guest interactions and operational tasks, often on-site or remotely. Both roles require hospitality knowledge but differ in scope and responsibilities.

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

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

What job categories do people searching Remote Short Term Rental Manager jobs in Chicago, IL look for?

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

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

Cities near Chicago, IL with the most Remote Short Term Rental Manager job openings:

Remote Short Term Rental Manager jobs near you

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

Priwils

Chicago, IL • On-site, Remote

Full-time

Re-posted 27 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 [email protected]). 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 [email protected]

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