Vacation Rental Management Assistant

Job Title: Vacation Rental Management Assistant
Compensation: $4 – $5 per hour (Based on Experience) + Eligibility for an Annual Bonus
Job Type: Full-Time Only
Location: Remote
Start Date: ASAP
Hours/Week: 40–60, depending on the season

About Us:

We are a growing vacation rental management company committed to delivering high-quality service to both guests and homeowners. We use modern systems and tools to streamline our operations and ensure each property is well cared for. We’re looking for a reliable and detail-oriented Vacation Rental Management Assistant to support our day-to-day operations and help us deliver an excellent guest experience.

This is a full-time position designed for someone looking for stable, long-term (multi-year) remote work with the possibility of promotions and raises — and also includes the opportunity to earn an annual performance-based bonus at the end of each year.

What You’ll Be Doing:

• Monitoring and responding to guest communications, including overnight messages
• Assisting with the onboarding of new properties into our systems
• Coordinating and dispatching vendors for cleaning, maintenance, and repairs
• Reviewing and organizing property photos and quality reports in Breezeway
• Managing and updating inventory checklists
• Placing and tracking orders for supplies
• Entering and organizing property-related expenses for reporting and billing
• Performing general data entry tasks
• Supporting social media efforts by scheduling and posting property content

Who We’re Looking For:

We’re looking for someone who’s not just seeking a job—but a long-term role where they can grow professionally, earn promotions, and secure pay increases over time. This is a great opportunity for someone who values consistency, is self-motivated, and takes pride in being reliable and organized.

The ideal candidate will also have:

• Strong written and spoken English skills
• Experience in vacation rentals or hospitality (preferred but not required)
• Comfort using tools like Breezeway, Notion, Microsoft Excel, and Guesty (or willingness to learn)
• High attention to detail and strong organizational skills
• Reliable availability on weekends
• A focused and disciplined approach to working remotely

Tech Requirements:

• A dependable computer and fast, stable internet connection
• Willingness to use time-tracking and remote monitoring software during scheduled work hours
• Ability to commit to a full-time schedule without other job or freelance obligations during work hours

To demonstrate that you’ve read this job post carefully, please write "I am a detail oriented person" in the last field of the application form. This helps us identify applicants who follow instructions closely and are interested in the role.

Why This Role:
• Long-term, stable remote position
• Supportive training and onboarding
• Performance-based promotions and pay increases
• Annual bonus opportunity
• Work-from-home flexibility with clear structure and expectations

What You Need to Know:
• This is a full-time position (40+ hours/week)—we’re looking for someone ready to fully commit to our company
• Weekend availability is required as part of a rotating schedule
• Remote activity monitoring software is required during scheduled hours
• Outside freelance or employment during work hours is not permitted, to ensure full focus on this role

We provide the structure, support, and training to help you succeed—and we’re looking for someone who’s equally invested in growing with us.

How to Apply:

If this sounds like the kind of long-term role you’ve been searching for, we’d love to hear from you.
Please apply using the link below to apply:

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Applications will only be accepted through the form linked above. Please do not email or message directly outside of the form.