Location: Remote
Schedule: Evening Shift | 3 PM – 12 AM EST (45 hrs/week)
Compensation: $850/month
Who We Are
At UPKEY Rentals, we’re redefining what it means to feel “at home” while away. Based in Gainesville, Florida, we manage a growing portfolio of thoughtfully designed vacation homes that prioritize comfort, style, and hospitality in every detail. Whether hosting a traveling nurse, a Gator football fan, or a family exploring Florida’s freshwater springs, we deliver more than a stay — we create memorable, elevated guest experiences.
As one of the top-rated short-term rental operators in the region, we are known for our quality, care, and commitment to excellence. We're a small, nimble, and passionate team with big ambitions. If you're someone who thrives in an environment where you can make a real impact and grow alongside the business, keep reading.
The Role
We’re looking for a Vacation Rental Guest Specialist who thrives on making people feel cared for. You’ll be the friendly, reliable voice behind our guest communications — from pre-booking to checkout. You'll handle inquiries, resolve issues quickly, coordinate with field teams, and ensure each guest enjoys a seamless, memorable stay. This is a fast-paced, remote role ideal for someone with excellent written communication, STR (short-term rental) experience, and a knack for solving problems calmly and professionally. This role also includes the opportunity for pay increases based on performance at quarterly reviews
Responsibilities - What You'll Do
Be the first point of contact for guests via Airbnb, Vrbo, Booking.com, and direct bookings
Respond to messages quickly (within 10 minutes during your shift) with warmth, clarity, and professionalism
Troubleshoot real-time guest issues — Wi-Fi, lockouts, appliance questions, etc.
De-escalate complaints and offer proactive, thoughtful solutions
Coordinate with cleaners, maintenance, and vendors to resolve concerns quickly
Manage reservations and automate messaging across our property management platforms
Process guest charges, refunds, and folio adjustments as needed
Assist in compiling incident reports and documentation for insurance claims
Keep detailed records of all communications and issue resolutions
Flag high-risk reviews and help us improve continuously
Attend regular team meetings
Qualifications - What We’re Looking For
3+ years in a Short-Term Rental management company virtual assistant role
Familiar with platforms like Airbnb, Vrbo, Booking.com, and property management software (Guesty preferred)
Proficient in Google Workspace (Docs, Sheets, Gmail, Calendar) and team tools like Loom, Slack, Notion, and Google Meet
Exceptional written and verbal English — friendly, clear, and professional
Proven track record of delivering excellent guest experiences and resolving problems under pressure
Organized, detail-oriented, and able to juggle multiple tasks at once
Self-motivated with strong time management skills
Fast, reliable internet (50+ Mbps) and a quiet, professional home workspace
Willing to work evenings, weekends, and holidays as needed
Bonus Points:
Previous experience working with U.S.-based clients or companies
Management experience or worked in a Leadership role
Familiar with PMS automation logic and creating automations
Competency in OTA Listing Optimization
Opportunity for pay increases based on performance at quarterly reviews
Why Join Upkey?
Join a small, tight-knit, high-performing team
Make a real impact in a company passionate about hospitality
Flexible, remote work
Opportunity to grow with a fast-scaling business
Apply now and help us deliver the kind of hospitality that makes people feel truly at home — wherever they are.