ZipRecruiter

Log In

1

Vacation Rental Property Inspector Jobs in Chicago, IL

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 ... Performs periodic property inspections and completes site audit forms. Recommends and/or approves ...

Colliers

Property Assistant

Rosemont, IL · On-site

$23.11 - $29.15/hr

From managing service contracts and tracking bid packages, to completing property inspections and ... Employees will also receive 10 days of sick leave and a minimum of 15-days vacation annually.

Colliers

Property Assistant

Rosemont, IL · On-site

$23.11 - $29.15/hr

From managing service contracts and tracking bid packages, to completing property inspections and ... Employees will also receive 10 days of sick leave and a minimum of 15-days vacation annually.

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 ... Performs periodic property inspections and completes site audit forms. Recommends and/or approves ...

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 ... Performs periodic property inspections and completes site audit forms. Recommends and/or approves ...

Colliers

Property Assistant

Rosemont, IL · On-site

$23.11 - $29.15/hr

From managing service contracts and tracking bid packages, to completing property inspections and ... Employees will also receive 10 days of sick leave and a minimum of 15-days vacation annually.

S2 Residential

Property Manager

Villa Park, IL · On-site

$85K/yr

Property Name: How you'll make an impact: * Drive sales, measurably increase revenue, improve ... Apartment Rental Discounts The Perks: * Vacation Reimbursement * Company-sponsored events & team ...

S2 Residential

Property Manager

Villa Park, IL

$85K/yr

Property Name: How you'll make an impact: * Drive sales, measurably increase revenue, improve ... Apartment Rental Discounts The Perks: * Vacation Reimbursement * Company-sponsored events & team ...

Inland Group

Commercial Property Manager

Oak Brook, IL · On-site

$98 - $124/hr

Conduct regular property inspections to ensure assets are maintained to the highest standards ... Vacation Time, Nine Paid Holidays, Three floating holidays per year * Sick time * Company-paid life ...

previous pagenext page

Showing results 21-40

All JobsVacation Rental Property Inspector JobsVacation Rental Property Inspector Jobs in Chicago, IL

Vacation Rental Property Inspector information

See Chicago, IL salary details

$29.4K

$51.2K

$77.8K

How much do vacation rental property inspector jobs pay per year?

As of Aug 24, 2026, the average yearly pay for vacation rental property inspector in Chicago, IL is $51,180.00, according to ZipRecruiter salary data. Most workers in this role earn between $40,200.00 and $59,200.00 per year, depending on experience, location, and employer.

What does a vacation rental property inspector do?

A Vacation Rental Property Inspector ensures that vacation rental properties meet cleanliness, safety, and maintenance standards before guests arrive. They conduct detailed inspections, check for damages, verify that amenities are in working order, and report any issues to the property management team. Their role helps maintain high-quality guest experiences and ensures compliance with company or regulatory standards. This job requires attention to detail, organizational skills, and a keen eye for spotting potential maintenance concerns.

What does a typical workday look like for a vacation rental property inspector?

A typical day for a Vacation Rental Property Inspector involves traveling between properties to conduct thorough inspections before guest arrivals and after departures. Inspectors check for cleanliness, safety hazards, maintenance needs, and inventory compliance, recording findings using mobile inspection apps or checklists. They frequently coordinate with cleaning crews, maintenance staff, and property managers to ensure standards are met and resolve any issues promptly. While much of the work is independent, regular communication with team members and quick problem-solving are essential to maintain smooth property operations.

What are the key skills and qualifications needed to thrive as a vacation rental property inspector, and why are they important?

To excel as a Vacation Rental Property Inspector, you need a keen eye for detail, knowledge of property standards, and experience in real estate or hospitality inspection. Familiarity with digital inspection tools, property management software, and possibly certification in property inspection adds value. Strong communication, organizational skills, and the ability to work independently help inspectors manage schedules and interact professionally with property owners and cleaning teams. These capabilities are crucial for ensuring properties meet quality expectations, remain compliant with regulations, and provide a positive guest experience.

What are popular job titles related to Vacation Rental Property Inspector jobs in Chicago, IL?

For Vacation Rental Property Inspector jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Vacation Rental Property Inspector jobs in Chicago, IL look for?

The top searched job categories for Vacation Rental Property Inspector jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Vacation Rental Property Inspector jobs?

Cities near Chicago, IL with the most Vacation Rental Property Inspector job openings:

Vacation Rental Property Inspector jobs near you
Infographic showing various Vacation Rental Property Inspector job openings in Chicago, IL as of August 2026, with employment types broken down into 75% Full Time, and 25% Contract. Highlights an 100% In-person job distribution, with an average salary of $51,180 per year, or $24.6 per hour.

Assistant Property Manager

Bridge33 Capital

Chicago, IL • On-site

$58K - $70K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted yesterday

Job description

JOIN OUR TEAM
Bridge33 Capital is a rapidly growing, vertically integrated real estate private equity firm specializing in open-air retail real estate. Poised to launch its next fund-a pivotal milestone-the Company remains dedicated to driving value at every stage of the investment lifecycle.
We are seeking a COMMERCIAL REAL ESTATE ASSISTANT PROPERTY MANAGER, who is looking to learn and grow into a Commercial Real Estate Property Manager and beyond! This role is 4 days/week in-person, and 1 day/week work from home, based in our downtown Chicago office. Come make your mark as an integral part of Bridge33 Capital!
MISSION
We build relationships and create value where others don't.
KEY PRINCIPLES
We're Better Together We're Here to Serve We crush our egos, and we have empathy for teammates We stay positive We embrace accountability, and we champion results.
ESSENTIAL RESPONSIBILITIES
  • Supports the Property Manager in managing all aspects of property management functions for Bridge33 assets. Including, but not limited to, tenant and vendor relationships, lease obligations, construction management of tenant improvements, and rental collections for the assets.
  • Responds to tenant needs with a sense of urgency, ensuring any issues or repairs are addressed and resolved promptly and in a cost-effective manner.
  • Ensures services are provided in compliance with company policies, procedures, regulations, and contractual obligations and standards.
  • Performs periodic property inspections and completes site audit forms. Recommends and/or approves alterations, maintenance, and reconditioning as necessary.
  • Bids, secures and administers service agreements with vendors and suppliers while achieving the best value for the asset. Requires tactful negotiation skills. Achieves cost savings without sacrificing services is an ongoing goal.

• Resolves maintenance issues, administration of property improvements and oversight of existing conditions to achieve the long-term preservation of the shopping center.
  • Coordinates tenant move-ins and move-outs, and "walk-through" spaces with tenants and manages tenant improvement projects, including oversight of tenant's general contractor's work.
  • Prepares and delivers timely, accurate and complete asset updates and reports as required.
  • Develops and controls annual budgets for operating expenses and rent rolls. Forecasts management plans and reviews/audits monthly rent roll report and monthly account receivable (A/R) aging report, explaining variances.
  • Assists with creating tenant lease abstracts and manages all critical dates and actions for the Property Manager's direction and approval when required.
  • Assesses risks and implements facility preparation, assessment, and recovery strategies, as part of business continuity program during and after normal business hours.
  • Collects rent and pays expenses in compliance with lease terms. Prepares all required legal notices. Recommends and coordinates legal action as necessary.
  • Collaborate with Property Manager to develop and manage strong tenant retention by cultivating deep tenant relationships.
  • Maintains strong business relationships with property vendors.
  • Proactively manages tenant relations to keep a pulse on the asset and the overall market.
  • Develops new business relationships through membership participation in professional industry/trade and civic organizations.
  • Responds 24 hours, 7 days per week to any tenant issue or property emergency.
  • Performs other duties as assigned.

Requirements
  • Minimum of 2 years' experience or training in commercial real estate.
  • Ability to analyze and interpret financial reports, budgets, contracts and similar documents necessary to manage and operate a shopping center.
  • Demonstrate sound verbal and written communication skills.
  • Ability to adapt to a dynamic work environment.
  • Knowledge of lease financial terms and principles, including rent calculations, operating expense management and reconciliations. Ability to calculate intermediate figures such as percentages, discounts, and/or commissions. Conducts basic financial analysis.
  • Ability to make decisions based on real estate business practices and procedures as well as company policies to achieve set results and deadlines. Responsible for setting own project deadlines when necessary.

Benefits
  • Fast paced and dynamic work environment, including frequent interaction with the senior management team.
  • Generous paid time off policy.
  • Company sponsored medical, dental and vision insurance.
  • Company paid life insurance.
  • Company paid short- and long-term disability insurance.
  • Paid parental leave.
  • 401k plan with Company match.
  • 11 paid holidays.

The annual base salary range for this role is $58,000 - $70,000 and the role is eligible for an annual discretionary bonus.
Bridge33 provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, age, sex, national origin, disability status, genetic information, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. Bridge33 is committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. To request reasonable accommodation, please contact our Human Resources department at hr.requests@bridge33capital.com.

Apply