Short Term Rental Hospitality Operations Assistant

Short-Term Rental Operations & Guest Experience VA

We’re hiring a proactive, hospitality-minded Virtual Assistant to support the operations of a growing short-term rental portfolio. This role goes beyond simple guest messaging, we’re looking for someone who is solution-oriented, operationally sharp, and able to help keep the business running smoothly in real time.

You’ll assist with guest communication, issue resolution, turnover coordination, vacancy monitoring, and OTA listing optimization. This job will also entail cold calling apartment complexes, property managers, and owners of properties.

Responsibilities:

* Guest Communication & Support

- Monitor and respond to guest messages quickly and professionally
- Assist guests with check-in instructions, parking & general stay support
- Handle guest concerns calmly and professionally while finding fast solutions
- Escalate urgent situations appropriately when necessary
- Assist with after-hours guest support coverage during scheduled shifts

* Operations Coordination

- Coordinate with cleaners, maintenance personnel, and teammates to resolve operational issues quickly
- Create, track, and follow up on maintenance work orders
- Troubleshoot active property issues and help drive solutions in real time
- Monitor same-day turnovers and upcoming arrivals
- Ensure units are guest-ready before check-ins

* Revenue & Listing Management

- Monitor vacancies daily inside the property management system
- Identify open gaps in the calendar and communicate opportunities
- Adjust OTA listings daily to help improve visibility and booking performance
- Support optimization efforts across OTA platforms like Airbnb, VRBO and ----------

Cold Calling:

- Prospect landlords and property owners through high-volume outbound calls to identify owners open to long-term rental agreements for short-term rental subletting opportunities.
- Pitch the arbitrage model clearly by educating property owners on how the arrangement works, addressing concerns around wear-and-tear, liability, and consistent rent payments
- Qualify properties and negotiate terms by assessing location, unit type, and owner flexibility to secure favorable lease agreements that support profitable short-term rental operations????????????????

Schedule / Coverage Needs

We are primarily seeking coverage during:

1 hr unpaid lunch

Tuesday (11am CST - 8PM CST)
Wednesday (10am CST -4PM CST)
Thursday (10am CST -4PM CST)
Friday/ Saturday (3PM CST - 1AM CST)
Sunday (930AM CST -230PM CST)

Schedule flexibility is important depending on occupancy and operational needs.

Ideal Candidate

* Strong problem-solving and communication skills
* Hospitality, hotel, Airbnb, or property management experience preferred
*cold calling experience held to KPIs
* Comfortable multitasking
* Highly organized with strong follow-through
* Able to make judgment calls and take initiative
* Strong written English skills
* Reliable internet and work setup
* Able to coordinate teammates and moving parts efficiently

Preferred Experience

* Hospitable or similar PMS software
* OTA platforms like Airbnb, ---------- , or Vrbo
* Guest communication workflows
* Maintenance coordination or dispatching
* Calendar and vacancy management
* STR operations or hotel operations
* Cold calling to close real estate deals

To Apply

Please send:

* Resume
* Hourly rate
* Relevant STR/hospitality experience
* Available working hours in CST
* Internet speed screenshot
* Short intro video (preferred)

We’re looking for someone dependable, fast-moving, and solutions-focused who can become a key part of our operations team long term.