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Vacation Rental Property Management Jobs in Wisconsin

Real Property Management Lakeshore

Be Seen First

Leasing Agent and Office Administrator

Oshkosh, WI · On-site

$38K - $42K/yr

Responsibilities also include completing daily property and showing reports, assisting the Property Manager with marketing available properties, processing rental applications, and supporting the day ...

Real Property Management Lakeshore

Be Seen First

Leasing Agent and Office Administrator

Oshkosh, WI · On-site

$38K - $42K/yr

Responsibilities also include completing daily property and showing reports, assisting the Property Manager with marketing available properties, processing rental applications, and supporting the day ...

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All JobsVacation Rental Property Management JobsVacation Rental Property Management Jobs in Wisconsin

Vacation Rental Property Management information

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$13

$22

$33

How much do vacation rental property management jobs pay per hour?

As of Aug 22, 2026, the average hourly pay for vacation rental property management in Wisconsin is $22.28, according to ZipRecruiter salary data. Most workers in this role earn between $17.69 and $25.00 per hour, depending on experience, location, and employer.

What does a vacation rental property manager do?

A Vacation Rental Property Manager oversees short-term rental properties, handling tasks like guest communication, bookings, cleaning, maintenance, and pricing strategies. They ensure a smooth guest experience while maximizing the owner's revenue. Responsibilities may also include marketing the property, managing listings on platforms like Airbnb and Vrbo, and coordinating with service providers. Their goal is to keep the property well-maintained and generate positive reviews for repeat bookings.

What are the key skills and qualifications needed to thrive in vacation rental property management, and why are they important?

To excel in Vacation Rental Property Management, you need a solid understanding of property operations, hospitality basics, and local regulations, along with experience in customer service or real estate. Familiarity with property management software (such as Guesty or Hostaway), online booking platforms (like Airbnb, Vrbo), and a valid real estate or property management license (when required) are highly beneficial. Strong organizational skills, attention to detail, excellent communication, and the ability to resolve issues swiftly are crucial soft skills in this role. These competencies are essential for maintaining high occupancy rates, ensuring guest satisfaction, and optimizing property performance in a competitive rental market.

What are some common challenges faced in vacation rental property management roles?

Vacation rental property managers often face challenges such as coordinating last-minute maintenance, addressing urgent guest requests, and managing reservations across multiple platforms to avoid double bookings. Balancing owner expectations with guest satisfaction can require excellent communication and quick problem-solving skills. Staying updated on local short-term rental regulations and handling seasonal fluctuations in demand are also key aspects of the job. Successful managers thrive by being proactive, detail-oriented, and adaptable to changing circumstances, making these challenges rewarding opportunities to enhance service quality.

How much do vacation rental property managers make?

Vacation rental property managers typically earn between $40,000 and $70,000 annually, depending on experience, location, and the size of the property portfolio. Some managers earn additional income through commissions or performance bonuses, especially when managing multiple properties or high-end rentals.

What are the most commonly searched types of Vacation Rental Property Management jobs in Wisconsin?

The most popular types of Vacation Rental Property Management jobs in Wisconsin are:

What are popular job titles related to Vacation Rental Property Management jobs in Wisconsin?

For Vacation Rental Property Management jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Vacation Rental Property Management jobs in Wisconsin look for?

The top searched job categories for Vacation Rental Property Management jobs in Wisconsin are:

Vacation Rental Property Management jobs near you
Infographic showing various Vacation Rental Property Management job openings in Wisconsin as of August 2026, with employment types broken down into 38% Full Time, and 62% Part Time. Highlights an 100% In-person job distribution, with an average salary of $46,341 per year, or $22.3 per hour.

Property Caretaker

VRM Wisconsin OpCo LLC

Wisconsin Dells, WI • On-site

$18 - $21/hr

Full-time

Posted 28 days ago

Job description

Description:

About The Company

VueStay Vacations by Casago hosts premier stays across top vacation destinations in the United States. With local experts in every market and the backing of a trusted national network, we provide a seamless, well-supported experience so guests can book with confidence and enjoy more relaxing trips! We partner with homeowners to oversee everything from guest experience and on-the-ground property care, while maximizing our homes' performance and providing owners peace of mind.

We expertly manage over 4500 homes across 8 states, offering a variety of "Vues" for our guests' stay. When you join VueStay Vacations, you're not just taking a job—you're becoming part of a company that values your contributions, invests in your growth, and gives you the opportunity to make a real impact on the homeowners and guests we serve every day.


About This Job

The Property Caretaker supports an assigned portfolio of vacation rental properties with responsibilities including all aspects of property management, including owner and guest relations, maintenance, and housekeeping. Supports cross-functionally across the team.


Compensation

$18-21/hr plus $100 monthly auto reimbursement


Essential Job Functions

  • Assists in the daily operations of the assigned portfolio of homes. Identify areas for improvement, assisting managers in process enhancements to drive efficiency and quality outcomes.
  • Support the team with escalated guest and homeowner concerns by responding to emails, calls and tickets.
  • Perform light home maintenance (light bulbs, fix door hinges, unclog a toilet, etc).
  • Conduct regular inspections prior to guest and owner arrivals.
  • Works to resolve guest and homeowner concerns by responding to emails, calls and tickets. Partners with the management team on escalated issues.
  • Partners and assists your Business Development Representative and management team when new units join the portfolio.
  • Supports cross-functionally across the team as needed.
  • Other duties as assigned because every day is different in hospitality!
Requirements:

Skills + Qualifications

  • Experience working in hotel, hospitality, vacation or similar industry is highly preferred.
  • Minimum 1 year experience in housekeeping, maintenance or similar role.
  • Excellent time management skills with the ability to change activity frequently and cope with interruptions.
  • Strong attention to detail.
  • Tech-savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms.
  • This role involves frequent travel between worksites, so reliable personal transportation is essential.
  • Dependable and prepared. Showing up on time and ready to go is key to creating great stays for our guests and peace of mind for our homeowners.
  • Must be dependable, self-motivated, and able to work independently while contributing positively to a collaborative team environment.
  • Comfortable talking to people—online or in person—and being able to share information in a way that’s clear, thoughtful, and represents the company in a positive way always.


Workplace Environment + Physical Requirements

  • Work may take place indoors or outdoors, in a variety of settings including private homes, resorts, offices, and laundry facilities — often in varying weather conditions.
  • We’re in hospitality and our schedules can change based on guest and homeowner needs. Shifts may include early mornings, evenings, weekends, and holidays. We require flexibility to support this.
  • Reliable transportation required.
  • Regular travel within the locally assigned market and / or region.
  • Ability to move freely (balancing, climbing, crawling, driving, squatting, standing, stooping, walking, bending, pushing, pulling, reaching, and repetitive hand/finger motions) and lift up to a maximum of fifty (50) pounds without assistance.


Special Note

This job description does not identify every requirement of the position. Casago may change position requirements, responsibilities, and work environment at any time with or without notice

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