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Seasonal Short Term Rentals Jobs in Chicago, IL (NOW HIRING)

Walmart

Seasonal Team Associate

Bloomingdale, IL · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Walmart

Seasonal Team Associate

Hammond, IN · On-site

$15 - $28/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Walmart

Seasonal Team Associate

Lake Zurich, IL · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Walmart

Seasonal Team Associate

Saint Charles, IL · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Walmart

Seasonal Team Associate

Addison, IL · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Sunbelt Rentals

Union Yard Associate

Joliet, IL · On-site

$15 - $19.50/hr

Sunbelt Rentals strives to be the customer's first choice in the equipment rental industry. From ... Short-term and long-term disability * Accident, Life and Travel insurance, as well as flexible ...

Sunbelt Rentals

Union Yard Associate

Joliet, IL

$14.50 - $19/hr

Sunbelt Rentals strives to be the customer's first choice in the equipment rental industry. From ... Short-term and long-term disability * Accident, Life and Travel insurance, as well as flexible ...

Walmart

Seasonal Team Associate

Vernon Hills, IL · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Walmart

Seasonal Team Associate

Valparaiso, IN · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

New

Walmart

Seasonal Team Associate

Hodgkins, IL · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Sunbelt Rentals

Equipment Rental Associate

Carol Stream, IL · On-site

$23.52 - $27.93/hr

Sunbelt Rentals strives to be the customer's first choice in the equipment rental industry. From ... Short-term and long-term disability * Accident, Life and Travel insurance, as well as flexible ...

Walmart

Seasonal Team Associate

Richton Park, IL · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Walmart

Seasonal Team Associate

Joliet, IL · On-site

$16 - $29/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

Walmart

Seasonal Team Associate

Crestwood, IL · On-site

$17 - $30/hr

When major holidays hit, seasonal associates are prepared! Requires product knowledge, problem ... Other benefits include short-term and long-term disability, company discounts, Military Leave Pay ...

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Seasonal Short Term Rentals information

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How much do seasonal short term rentals jobs pay per hour?

As of Sep 6, 2026, the average hourly pay for seasonal short term rentals in Chicago, IL is $16.51, according to ZipRecruiter salary data. Most workers in this role earn between $15.10 and $17.84 per hour, depending on experience, location, and employer.

What are seasonal short term rentals?

Seasonal short term rentals are properties that are leased out to tenants for brief periods, typically ranging from a few days to several months, and are most often available during peak vacation or holiday seasons. These rentals are popular in tourist destinations and provide an alternative to hotels, offering amenities like kitchens and private living spaces. Property owners often use platforms like Airbnb or VRBO to list their seasonal rentals, catering to travelers looking for flexibility and comfort. Regulations and requirements for operating such rentals can vary widely depending on the location, so it's important for both owners and renters to research local laws.

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

To thrive as a Seasonal Short-Term Rental Manager, you need strong organizational skills, attention to detail, and knowledge of property management, often supported by experience in hospitality or real estate. Familiarity with booking platforms like Airbnb or Vrbo, property management software, and local rental regulations is typically required. Excellent communication, problem-solving abilities, and customer service skills help you effectively address guest needs and coordinate with service providers. These skills ensure smooth operations, high guest satisfaction, and compliance with regulations during peak rental seasons.

What are some common challenges faced when managing seasonal short term rentals, and how can they be addressed?

Managing seasonal short term rentals often involves handling fluctuations in guest demand, which can lead to periods of high intensity and downtime. During peak seasons, quick turnovers and maintaining property standards become crucial, requiring excellent time management and coordination with cleaning and maintenance teams. Off-season periods may involve strategizing marketing efforts to attract bookings and performing property upgrades. Building strong relationships with local service providers and using property management software can help streamline operations and reduce stress during busy times.

What is the difference between Seasonal Short Term Rentals vs Property Manager?

AspectSeasonal Short Term RentalsProperty Manager
CredentialsNone required, but knowledge of local regulations helpsReal estate or property management certifications often preferred
Work EnvironmentIndividual or small team managing short-term rentals, often remotelyOversees multiple properties, may work on-site or remotely
Employer & IndustryHospitality, real estate, vacation rental platformsReal estate firms, property management companies

Seasonal Short Term Rentals involve managing or hosting short-term rental properties, focusing on guest experience and property upkeep. Property Managers oversee multiple rental units, handling maintenance, tenant relations, and operational tasks. While both roles require knowledge of local regulations and customer service skills, Property Managers typically have more formal credentials and broader responsibilities across multiple properties.

What are the most commonly searched types of Short Term Rentals jobs in Chicago, IL?

The most popular types of Short Term Rentals jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Seasonal Short Term Rentals jobs?

Cities near Chicago, IL with the most Seasonal Short Term Rentals job openings:

Seasonal Short Term Rentals jobs near you

Residential Cleaner (Part-Time)

Honey Bee Cleaning Services Llc

Oak Lawn, IL • On-site

$16 - $18/hr

Part-time

Re-posted 15 days ago

Job description

Honey Bee Cleaning Service is a boutique cleaning service company servicing the Chicagoland area. We clean common areas of apartment buildings, apartments, short term rentals, houses and occasionally events. As a growing company we thrive on commitment and opportunities to grow. Learn the importance of property maintenance and how to possibly grow a company opening up a branch of your own.

Cleaner Job Responsibilities:

  • Responsible for all basic cleaning in and around residences, office buildings or large residential buildings.

  • Cleans floors and rooms: including dust mopping, damp mopping, sweeping, vacuuming, dusting, picking up larger objects off the floor, cleaning baseboards and spot cleaning glass and windows.

  • Cleans restrooms, including restocking (upon request), emptying trash, cleaning and sanitizing fixtures, cleaning mirrors, spot cleaning partition doors and walls, sweeping and mopping tile floors, and cleaning toilets and urinals.

  • Vacuums, empties trash, and replaces liners.

  • Sets up, stocks, and maintains cleaning equipment and supplies.

  • Post construction cleaning.

  • Sometimes required to move furniture.

  • Assist in haul away and/or property clean outs.

  • Comfortable cleaning outside with picking up trash, raking/blowing leaves, cleaning around dumpsters, occasionally handling garbage.

  • Monitors and maintains sanitation and organization of assigned areas.

  • Transports dirty linens to the correct area to be cleaned and restocks areas with clean linens.

  • Must be ok with handling hazardous waste and performing deep cleanings.

  • Assists other departments when needed to ensure optimum service to guests.

  • Performs additional duties as needed.

Work Hours & Benefits: This position is Part-Time. Hours Varies. Additional work may be picked up. After 60 days a gas stipend is available.

Cleaner Qualifications / Skills:

  • Positive attitude

  • Strong Attention to detail

  • Excellent communication and organizational skills

  • Strong interpersonal and problem-solving abilities

  • Highly responsible & reliable

  • Ability to work cohesively as part of a team

  • Timeliness

  • Cleanliness

Additional Qualifications:

  • Phone with strong cellular data for clocking in/out and uploading before and after photos/videos.

  • Reliable transportation with adequate space to carry cleaning supplies.

Education, Experience, and Licensing Requirements:

  • High school diploma, GED, or equivalent

  • Previous cleaning experience a plus

  • Valid driver’s license

To become apart of our awesome team, click the apply button now!

Company Description

Honey Bee Cleaning Service is a boutique cleaning service company servicing the Chicagoland area. We are a property manager's best friend. We maintain their interior of their buildings, the grounds and assist with unit cleanings. As a growing company we thrive on commitment and opportunities to grow. Learn the importance of property maintenance and how to grow a company to take on bigger projects.