Vacation Rental Guest Specialist

Location: Remote (LATAM preferred for time zone alignment)Schedule: Evening Shift | 4pm-12am EST (40 hrs/week)Compensation: $750–$850/monthWho We AreAt 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 RoleWe’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 DoBe the first point of contact for guests via Airbnb, Vrbo, Booking.com, and direct bookingsRespond to messages quickly (within 10 minutes during your shift) with warmth, clarity, and professionalismTroubleshoot real-time guest issues — Wi-Fi, lockouts, appliance questions, etc.De-escalate complaints and offer proactive, thoughtful solutionsCoordinate with cleaners, maintenance, and vendors to resolve concerns quicklyManage reservations and automate messaging across our property management platformsProcess guest charges, refunds, and folio adjustments as neededAssist in compiling incident reports and documentation for insurance claimsKeep detailed records of all communications and issue resolutionsFlag high-risk reviews and help us improve continuouslyAttend regular team meetingsQualifications - What We’re Looking For3+ years in a Short-Term Rental management company virtual assistant roleFamiliar 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 MeetExceptional written and verbal English — friendly, clear, and professionalProven track record of delivering excellent guest experiences and resolving problems under pressureOrganized, detail-oriented, and able to juggle multiple tasks at onceSelf-motivated with strong time management skillsFast, reliable internet (50+ Mbps) and a quiet, professional home workspaceWilling to work evenings, weekends, and holidays as neededBonus PointsPrevious experience working with U.S.-based clients or companiesManagement experience or worked in a Leadership roleFamiliar with PMS automation logic and creating automationsCompetency in OTA Listing OptimizationWhy Join Upkey?Join a small, tight-knit, high-performing teamMake a real impact in a company passionate about hospitalityFlexible, remote work from anywhere in LATAMOpportunity to grow with a fast-scaling businessApply now and help us deliver the kind of hospitality that makes people feel truly at home — wherever they are.