Private Property Caretaker Jobs (NOW HIRING)

At Heavenly Vacations by Casago, we believe the best vacations begin with local expertise and genuine hospitality. Proudly serving the Hawaiian Islands, our team is passionate about creating exceptional experiences for both homeowners and guests through personalized service, trusted relationships, and an unwavering commitment to excellence. As local experts, we understand that every home, every owner, and every guest is unique, and we take pride in delivering thoughtful, attentive care at every step.

Our culture is rooted in the spirit of aloha, where integrity, respect, stewardship, and service guide everything we do. We believe in treating every property as if it were our own, building lasting relationships through trust and transparency, and working together to create memorable experiences that keep guests returning year after year. Backed by the resources of the trusted Casago network while maintaining our local ownership and personalized approach, Heavenly Vacations offers the opportunity to build a rewarding career with a team that is passionate about hospitality, community, and making a meaningful difference every day.

We're seeking a skilled and hands-on Property Caretaker to maintain our beautiful Big Island property. This role is perfect for someone who takes pride in their craftsmanship and enjoys working independently while creating and maintaining exceptional environments. As our Property Caretaker, you'll use your practical expertise and attention to detail to ensure our property remains in pristine condition, tackling diverse maintenance tasks with precision and care while adapting to the unique needs of this island location.

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. 

• 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!

• Minimum 1 year experience required in housekeeping, maintenance or property inspection role required

• Experience working in hotel, hospitality, vacation or similar industry is highly preferred.

• 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.

• 1 Week Paid Vacation after 1 Year, 2 Weeks Paid Thereafter

• Single Payer Health insurance paid for by company

• Dental insurance

• Vision insurance

• Optional Supplemental Insurance

• 401K

• Opportunity to participate in Professional and Life Educational Seminars

• Employee recognition programs