Vacation Rental Guest Specialist

Location: Remote

Schedule: Evening Shift | 4 PM – 12 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 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.

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
  
  

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.