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Vacation Rental Management Jobs in Hawaii (NOW HIRING)

General Manager

Lihue, HI ยท On-site

$100 - $140/hr

A leading vacation rental management company is seeking an experienced General Manager to oversee all aspects of its local operation on Kauai . This executive leadership role offers full ...

Full-Time Property Inspector

Lahaina, HI ยท On-site

$25 - $28/hr

Company Overview Founded in 2015, My Perfect Stays is the largest vacation rental management company on the island of Maui, managing over 450 luxury vacation homes and condos with a team of more than ...

Maintenance Technician

Lahaina, HI ยท On-site

$28 - $35/hr

Company Overview Founded in 2015, My Perfect Stays is the largest vacation rental management company on the island of Maui, managing over 450 luxury vacation homes and condos with a team of more than ...

Assistant Manager

Kihei, HI ยท On-site

$22.50/hr

Yes Company Opened in 2017, we now have the largest selection of vacation rental equipment on Maui ... Assisting Management with HR - recruiting, training, ongoing coaching, and motivation of employees.

Assistant Manager

Kihei, HI ยท On-site

$22.50/hr

Yes Company Opened in 2017, we now have the largest selection of vacation rental equipment on Maui ... Assisting Management with HR - recruiting, training, ongoing coaching, and motivation of employees.

Regional Supervisor

Honolulu, HI ยท On-site

$20 - $22/hr

... vacation rental cleaning , delivering spotless results and healthier environments. Clearview Services , based in Florida, was created to bridge the gap between remote property management and on-the ...

Equipment Rental Specialist

Lahaina, HI ยท On-site

$23.52 - $27.93/hr

Develop skills for career growth through an outside sales or operational management career track ... vacation days depending on years of service * 5 sick days * 6 holidays * 2 half day holidays * 2 ...

Develop skills for career growth through an outside sales or operational management career track ... vacation days depending on years of service * 5 sick days * 6 holidays * 2 half day holidays * 2 ...

Equipment Rental Specialist

Lahaina, HI ยท On-site

$23.52 - $27.93/hr

Develop skills for career growth through an outside sales or operational management career track ... vacation days depending on years of service * 5 sick days * 6 holidays * 2 half day holidays * 2 ...

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 ...

About This Job As a Maintenance Technician, you'll travel between multiple vacation rental ... Be available and willing to assist your colleagues and management team and provide cross-coverage ...

Reservation Manager

Kihei, HI ยท On-site

$78K - $85K/yr

Strong time management, organization and prioritization skills with comfort in being self-directed, following up and meeting deadlines. * Desire previous condo or vacation rental experience.

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Showing results 1-20

Vacation Rental Management information

See Hawaii salary details

$24.9K

$59.2K

$107K

How much do vacation rental management jobs pay per year?

As of Aug 11, 2026, the average yearly pay for vacation rental management in Hawaii is $59,205.00, according to ZipRecruiter salary data. Most workers in this role earn between $46,800.00 and $65,500.00 per year, depending on experience, location, and employer.

What is the difference between Vacation Rental Management vs Property Management?

AspectVacation Rental ManagementProperty Management
CredentialsExperience in hospitality, rental lawsReal estate licensing, landlord laws
Work EnvironmentShort-term rentals, customer service focusLong-term rentals, maintenance focus
Employer & IndustryVacation rental platforms, hospitality companiesReal estate firms, property owners

Vacation Rental Management primarily focuses on short-term rental properties, guest services, and hospitality, while Property Management handles long-term leases, maintenance, and landlord relations. Both roles require knowledge of rental laws but differ in their daily operations and customer interactions.

What is vacation rental management?

Vacation rental management involves overseeing short-term rental properties, such as homes or apartments, that are leased to guests for vacations or temporary stays. Managers handle tasks like marketing the property, communicating with guests, coordinating cleaning and maintenance, setting pricing, and ensuring compliance with local regulations. Many property owners hire vacation rental managers or companies to maximize their rental income and provide a seamless experience for guests. Effective management can lead to higher occupancy rates, positive reviews, and increased profitability.

What are some common challenges faced in vacation rental management, and how can they be addressed?

One of the most common challenges in vacation rental management is balancing guest satisfaction with property maintenance and owner expectations. Managers often need to coordinate cleaning, repairs, and guest check-ins on tight schedules, especially during peak seasons. Effective communication, use of property management software, and building strong relationships with local vendors can help address these challenges. Additionally, handling last-minute booking changes and ensuring compliance with local regulations require strong organizational skills and adaptability.

What are the key skills and qualifications needed to thrive as a vacation rental manager?

To thrive as a Vacation Rental Manager, you need strong organizational skills, property management experience, and a solid understanding of hospitality practices, often backed by a relevant degree or professional certification. Familiarity with property management systems (PMS), online booking platforms like Airbnb or VRBO, and digital marketing tools is typically required. Exceptional customer service, problem-solving abilities, and effective communication are crucial soft skills for building guest satisfaction and quickly resolving issues. These skills are essential for maximizing occupancy, maintaining property standards, and ensuring repeat business in a competitive market.
What are popular job titles related to Vacation Rental Management jobs in Hawaii? For Vacation Rental Management jobs in Hawaii, the most frequently searched job titles are:
What job categories do people searching Vacation Rental Management jobs in Hawaii look for? The top searched job categories for Vacation Rental Management jobs in Hawaii are:
Infographic showing various Vacation Rental Management job openings in Hawaii as of August 2026, with employment types broken down into 66% Full Time, and 34% Part Time. Highlights an 94% In-person, and 6% Remote job distribution, with an average salary of $59,205 per year, or $28.5 per hour.

VACATION RENTAL - Property Caretaker

CRISTAL CLEAR CLEANING LLC

Honolulu, HI โ€ข On-site

Full-time

Posted 4 days ago


Job description

Benefits:
  • Competitive salary
  • Free uniforms
  • Opportunity for advancement
  • Training & development

Position: Property Caretaker – Vacation Rentals
Location: West Palm Beach, FL and Miami FL
Employment Type: Part-Time to Full Time
About the Role
We are seeking a reliable and detail-oriented Vacation Rental Property Caretaker to ensure our homes are always guest-ready, secure, and well-maintained. As the on-the-ground support for our vacation rentals, you will handle routine property upkeep, support guests when needed, and assist with smooth daily operations. This role is perfect for someone who takes pride in their work, enjoys hands-on tasks, and values delivering top-quality hospitality.
Key Responsibilities
Property Care & Maintenance

  • Conduct routine property inspections to ensure homes are secure, clean, and fully stocked.
  • Perform light maintenance and minor repairs (e.g., changing lightbulbs, etc).
  • Coordinate with trusted vendors for major repairs or specialized services.
  • Monitor and maintain inventory of supplies, replenishing as necessary.
Guest Readiness & Support

  • Prepare properties for guest arrivals, ensuring they are spotless, welcoming, and fully operational.
  • Inspect housekeeping work to maintain 5-star quality standards.
  • Respond promptly to on-site guest needs (lockouts, troubleshooting appliances, resolving small issues).
Operational Support

  • Communicate property conditions, maintenance needs, and guest feedback to the Operations Manager.
  • Follow established Standard Operating Procedures (SOPs) for consistency and efficiency.
  • Assist with compliance regarding safety, security, and local regulations.
Qualifications
  • Previous experience in hospitality, property care, facilities management, or maintenance preferred.
  • Strong attention to detail and pride in keeping properties in pristine condition.
  • Ability to troubleshoot basic issues (plumbing, electrical, appliances).
  • Self-motivated, reliable, and able to work independently.
  • Good communication skills with guests, vendors, and team members.
  • Flexibility to work evenings, weekends, and holidays as needed.
  • Valid driver’s license and reliable transportation required.
What We Offer
  • Competitive pay with room for advancement.
  • Discounts on stays at our properties.
  • A supportive and collaborative team environment.
  • The opportunity to work in beautiful properties while making a direct impact on guest satisfaction.
Requirements
  • Must send a 2 to 5-minute video introduction explaining why you are a good fit for the position (send video to both pamela@cristalclearcleaning.com and cristy@cristalclearcleaning.com)