1

Vacation Rental Assistant Jobs in Illinois (NOW HIRING)

Will assist in scanning of all rental equipment during delivery and return processes as well as ... Vacation: 40 hours of vacation after 1 year of full-time employment * Sick: 40 hours of sick after ...

Will assist in scanning of all rental equipment during delivery and return processes as well as ... Vacation: 40 hours of vacation after 1 year of full-time employment * Sick: 40 hours of sick after ...

Searching for a hotel or rental using Hotel Database/Rental Websites/Internet/Direct Connect ... Robust PTO offerings including: select major holidays, vacation, sick, personal, & volunteer time

Searching for a hotel or rental using Hotel Database/Rental Websites/Internet/Direct Connect ... Robust PTO offerings including: select major holidays, vacation, sick, personal, & volunteer time

Searching for a hotel or rental using Hotel Database/Rental Websites/Internet/Direct Connect ... Robust PTO offerings including: select major holidays, vacation, sick, personal, & volunteer time

... Assist in orienting, training, assigning, and checking of work • Adherence to EHS protocol at all ... Paid vacation days, up to 15 days; paid sick days, up to 5 days; paid personal leave, up to 5 days ...

CNA

Saint Elmo, IL

$17.50 - $24/hr

Paid Vacation, Sick and Holidays * Daily Pay - Access your earnings when you need them * Voluntary ... Travel, hotels & rental cars * Fitness memberships * Groceries & dining * Theme parks, events ...

Assistant Property Manager

Geneva, IL · On-site

$18 - $24.75/hr

Assistant Property Manager We are looking for a motivated and experienced Assistant Property ... Paid vacation, sick, and holiday time. * Employee rental discounts. * Paid new parent leave. * A ...

Assistant Property Manager

Geneva, IL

$18 - $24.75/hr

Assistant Property Manager We are looking for a motivated and experienced Assistant Property ... Paid vacation, sick, and holiday time. * Employee rental discounts. * Paid new parent leave. * A ...

Herc Employee Career Portal Founded in 1965, Herc Rentals is one of the leading equipment rental ... Holidays, Vacations, Sick Days) Paid parental leave. Military leave & support for those in the ...

As the Assistant Property Manager, you'll ensure that each resident and employee experience is in ... Apartment Rental Discounts The Perks: * Vacation Reimbursement after 1 year of employment * Company ...

Parts Assistant

Joliet, IL · On-site

$18.99 - $26.11/hr

Sunbelt Rentals strives to be the customer's first choice in the equipment rental industry. From ... vacation days depending on years of service * 5 sick days * 6 holidays * 2 half day holidays * 2 ...

Parts Assistant

Morris, IL · On-site

$18.99 - $26.11/hr

Sunbelt Rentals strives to be the customer's first choice in the equipment rental industry. From ... vacation days depending on years of service * 5 sick days * 6 holidays * 2 half day holidays * 2 ...

Assistant Branch Manager

Chicago, IL · On-site

$65K - $70K/yr

Herc Employee Career Portal Founded in 1965, Herc Rentals is one of the leading equipment rental ... Holidays, Vacations, Sick Days) Paid parental leave. Military leave & support for those in the ...

Showing results 21-40

Vacation Rental Assistant information

What does a vacation rental assistant do?

A Vacation Rental Assistant supports property owners or managers by handling day-to-day tasks related to vacation rental properties. Their duties often include communicating with guests, coordinating check-ins and check-outs, managing bookings, and overseeing cleaning and maintenance schedules. This role ensures guests have a smooth experience and that the property is well-maintained. Vacation Rental Assistants may also help with marketing the property and responding to guest inquiries promptly.

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

To thrive as a Vacation Rental Assistant, you need strong organizational skills, attention to detail, and experience in hospitality or property management. Familiarity with property management systems (PMS), online booking platforms like Airbnb or VRBO, and basic maintenance tools are often required. Excellent communication, customer service orientation, and problem-solving abilities help you stand out in this role. These skills ensure smooth operations, satisfied guests, and positive reviews, which are crucial for business success in the vacation rental industry.

What are some common challenges faced by vacation rental assistants, and how can they be managed effectively?

Vacation Rental Assistants often juggle multiple responsibilities, such as coordinating guest check-ins, handling last-minute maintenance requests, and ensuring properties are cleaned and ready on time. One of the main challenges is managing unexpected issues, like scheduling conflicts or guest concerns, while maintaining a positive guest experience. Staying organized, communicating clearly with property owners and cleaning staff, and using property management tools can help streamline daily tasks and reduce stress. Building strong relationships with vendors and having backup plans in place also contribute to smoother operations.

What is the difference between Vacation Rental Assistant vs Property Manager?

AspectVacation Rental AssistantProperty Manager
CredentialsBasic customer service, hospitality, or administrative skillsReal estate or property management certifications often preferred
Work EnvironmentAssists with daily rental operations, guest communication, and bookingsOversees entire property, handles maintenance, leasing, and tenant relations
Employer & IndustryVacation rental companies, hospitality industryReal estate firms, property management companies

While both roles involve managing rental properties, a Vacation Rental Assistant primarily supports daily operations and guest interactions, whereas a Property Manager oversees the entire property, including maintenance and tenant relations. The assistant role is more focused on hospitality tasks, making it ideal for those starting in the industry or seeking administrative experience.

What are the most commonly searched types of Vacation Rental jobs in Illinois?

The most popular types of Vacation Rental jobs in Illinois are:

What are popular job titles related to Vacation Rental Assistant jobs in Illinois?

For Vacation Rental Assistant jobs in Illinois, the most frequently searched job titles are:

What cities in Illinois are hiring for Vacation Rental Assistant jobs?

Cities in Illinois with the most Vacation Rental Assistant job openings:

Infographic showing various Vacation Rental Assistant job openings in Illinois as of August 2026, with employment types broken down into 56% Full Time, and 44% Part Time. Highlights an 100% In-person job distribution.

Regional Sales Manager- Global Rental Sales- Sports Illustrated Resorts

Travel + Leisure Co.

Chicago, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 20 days ago


Travel + Leisure Co. rating

7.5

Company rating: 7.5 out of 10

Travel + Leisure Co.

Based on 25 frontline employees who took The Breakroom Quiz

7.8

Company rating compared to similar companies: 7.8 out of 10

Travel agencies average

Based on 157 frontline employees who took The Breakroom Quiz

The best things about working at Travel + Leisure Co.

  • 94%

    94% say their managers don’t change their shifts at short notice

    say their managers don’t change their shifts at short notice

  • 94%

    94% say their health insurance is affordable

    say their health insurance is affordable

  • 77%

    77% say they have respectful managers

    say they have respectful managers

Featured by Travel + Leisure Co., based on 25 Breakroom Quiz responses from their frontline employees


Job description

We Put the World on Vacation
Travel + Leisure Co. is the world's leading vacation ownership and travel membership company, with a dynamic and growing portfolio of resort, travel club, and lifestyle travel brands. Our dedicated associates help the company achieve its mission to put the world on vacation. Innovation and growth keep our work interesting and fun. Every day is a chance to learn something new and turn vacation inspiration into exceptional experiences for millions of travelers worldwide.
This position manages the implementation of Rental Sales and Marketing for multiple sites in a specific region. Also responsible for maximizing rental usage to achieve budgeted room nights, revenue goals, forecasts, and implementing business plans. Position may have supervision responsibility of a Sales Coordinator(s). In certain locations, the individual may be responsible for the overall operations and performance of rental sales, whole owner relations, quality assurance and revenue management.
Essential Job Responsibilities
Responsibilities include, but are not limited to:
1. Responsibility #1
a. Account Sales and Management (60% time)
i. Meets and exceeds revenue goals by developing new accounts and growing current accounts.
ii. Maintains well-documented, accurate, organized and up-to-date file management system in order to service clients.
iii. Prospect new business opportunities within the transient, group and travel trade. This includes defining the market mix, pricing; direct sales campaigns, and identify marketing opportunities.
iv. Develop local travel industry / business relationships within each destination to understand market trends, competitors, and leading customer strategies.
v. Conduct presentations to call centers, attend key travel industry related organization meetings, site inspections, tradeshows and GSI.
vi. Ensure there is a positive working relationship between resort operations and sales team, including working cooperatively with each Resort Manager to update them on rental programs.
vii. Prepare written marketing plans by region to effectively manage sales plan.
viii. May monitor and direct Sales Assistant, provide, motivation, support, encouragement, and direction where applicable.
2. Responsibility #2
a. Yield Management (30% time)
i. Collaborates with Yield Team and / or utilizes yield management techniques to profitably negotiate room rates, function space, wholesale and OTA accounts as needed. Accountable to the performance and potential performance for each account.
ii. Weekly rental forecasting review and monthly explanation of results.
iii. Ongoing competitive rate analysis for existing and new resorts.
3. Responsibility #3
a. Product Knowledge (10% time)
i. Conducts research, surveys, personal investigation and studies market place and territory in order to effectively capitalize on the resorts
ii. Strengths and competitor's weaknesses and capabilities.
4. Other duties as assigned
Travel Requirements
25% travel required
Minimum Requirements and Qualifications
Education
• Bachelor's Degree
Training requirements
• None
Knowledge and skills
• Demonstrate effectiveness as an inspirational leader with strong written verbal communications, presentation and organization skills.
• Experienced in simplifying complex initiatives and integrating diverse perspectives into an operational plan; effectively gets teams working together in an integrated fashion toward a common goal
• Knowledge of Timeshare Industry
• Knowledge of Hotel Sales & Marketing
Technical Skills
• Proficient in Microsoft Word, Excel, PowerPoint, Delphi or other sales management systems, Micros Opera.
• Knowledge of Hotel Operation's Knowledge of RCC
• Knowledge of I Hotelier system
• Delphi, Opera Sales or other Catering sales applications
Job experience
• Manager or above level in sales and/or reservations center experience, with both generalist and specialized functions in hotel/vacation resort rental sales & marketing, operations and catering.
• 7-10 years hotel and or Timeshare Rental related experience in rental sales, catering and operations management, experience in hotel or related hospitality service industry, experience in budgeting and business planning.
• 3-5 years of experience in 3rd party tour operators & OTA's
Experience equivalent to the education requirement may be accepted in lieu of the education requirement.
How You'll Be Rewarded:
We offer a diverse range of comprehensive health and welfare benefits to associates who work 30 or more hours per week to meet your needs and support you throughout your career with us. Travel + Leisure Co. benefits include: Note: Temporary and/or seasonal associates are ineligible for Paid Time Off.
• Medical
• Dental
• Vision
• Flexible spending accounts
• Life and accident coverage
• Disability
• Depending on position, paid time off, parental leave and holidays (speak to your recruiter for additional information)
• Wish day paid time to volunteer at an approved organization of your choice
• 401k with employer match (subject to eligibility requirements, including tenure - speak to your recruiter for additional information)
• Legal and identity theft plan
• Voluntary income protection benefits
• Wellness program (subject to provider availability)
• Employee Assistance Program
Compensation
Generally starting at $95,000 - $120,000 per year. The actual salary of the candidate(s) selected for this role will be set based on a variety of factors, including but not limited to experience, education, skills, training, and work location.
Where Memories Start with You
Hospitality is at the heart of all we do at Travel + Leisure Co. Here, you'll find an inclusive environment where we deliver excellence and take time to have fun, celebrate together, and support one another. We're always looking ahead to what's next and how we can strengthen our business, its neighboring communities, and the customer experience. Join our global team and build a career where memories start with you.
We are an equal opportunity employer, and all applications will be considered for employment without attention to their membership in any protected class. If you require any reasonable accommodation to complete your application or any part of the recruiting process, please email your request to MyCareer@travelandleisure.com, including the title and location of the position for which you are applying.

Working at Travel + Leisure Co.

What to expect from working at Travel + Leisure Co.

From Travel + Leisure Co.


What Travel + Leisure Co. employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom