Description
Location: Remote (LATAM preferred for time zone alignment)
Schedule: Evening Shift | 5 PM – 1 AM EST (40 hrs/week)
Compensation: $750–$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 Guest Experience 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.
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 guest communications or STR 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
Why Join Upkey?
- Join a small, tight-knit, high-performing team
- Make a real impact in a company passionate about hospitality
- Flexible, remote work from anywhere in LATAM
- 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.