Short Term Rentals Jobs in Orlando, FL (NOW HIRING)

Weekend-Focused | Remote, US-Based | Experienced Required

iTrip Sarasota & Venice are seeking an experienced Vacation Rental Guest Services Representative to support guest communications, reservations, and weekend operations for a growing vacation rental management company.

This part-time role is primarily focused on Saturday and Sunday coverage, when guest activity is at its highest. Weekends often include check-ins, checkouts, last-minute questions, access issues, maintenance coordination, housekeeping follow-up, and urgent guest support.

This is not an entry-level customer service position. The right candidate will bring direct experience in vacation rentals, short-term rentals, boutique hospitality, or a similar guest-facing operations role. They will be confident communicating with guests, making sound decisions, staying calm under pressure, and supporting the guest experience while the local team is active in the field.

The ideal candidate has worked in a fast-paced hospitality or guest services environment and understands that weekends are when responsiveness, judgment, and attention to detail matter most.

You are calm, organized, and dependable. You do not need to be micromanaged and can assess a situation, ask the right questions, use good judgment, and communicate clearly with both guests and internal teams.

You enjoy helping people, but you also understand the operational side of hospitality. You know how to balance guest satisfaction, company policies, owner expectations, and real-world property logistics.

• Serve as a primary point of contact for guests via phone, text, email, Airbnb, Vrbo, Booking.com, direct booking channels, and other booking platforms.

• Respond promptly, professionally, and warmly to guest questions before, during, and after their stay.

• Assist guests with check-in instructions, property access, parking information, Wi-Fi, house rules, local recommendations, and general stay-related questions.

• Handle weekend guest issues with urgency, empathy, and sound judgment.

• De-escalate frustrated guests when needed and help turn challenging situations into positive outcomes.

• Support guests during common weekend issues such as lockouts, access code problems, maintenance concerns, cleanliness complaints, missing items, noise concerns, or property-related questions.

• Determine when an issue can be resolved directly and when it needs to be escalated to local operations, maintenance, housekeeping, or management.

• Communicate clearly with the field team so issues are handled quickly and accurately.

• Document guest issues, actions taken, and follow-up needs for the weekday team.

• Assist with reservation questions, booking inquiries, changes, cancellations, extensions, and last-minute stay requests.

• Help guests understand property options, availability, pricing, policies, and booking requirements.

• Review reservation details for accuracy, including guest counts, arrival dates, special requests, access details, and property-specific notes.

• Support a smooth check-in and check-out experience by verifying important pre-arrival details.

• Create and update maintenance or housekeeping work orders in company software systems.

• Coordinate with housekeeping, inspections, and maintenance teams on weekend turnover or guest-related issues.

• Set, review, or verify door lock codes for upcoming reservations.

• Log notes, guest issues, vendor invoices, and property updates accurately in the appropriate systems.

• Help identify recurring issues or process gaps that should be reviewed by management.

• Help maintain a high-quality guest experience that supports strong reviews and repeat bookings.

• Monitor guest sentiment and flag potential review risks early.

• Summarize recurring guest feedback or operational issues for the weekday team.

• Represent the company in a professional, calm, and hospitality-minded way at all times.

• 1+ years minimum of direct experience in vacation rentals or short-term rentals mandatory

• Hands-on experience communicating with guests through Airbnb, Vrbo, Booking.com, direct booking websites, or similar online travel platforms required.

• Prior experience handling guest communication by phone, text, email, and platform messaging.

• Familiarity with property management software, reservation systems, guest messaging platforms, or similar hospitality operations tools.

• Comfortable supporting weekend guest issues such as lockouts, access code problems, maintenance concerns, cleanliness complaints, late arrivals, and urgent guest questions.

• Ability to coordinate with housekeeping, maintenance, inspections, or other field operations teams to resolve guest and property issues.

• Exceptional written and verbal English communication skills.

• Strong judgment and ability to de-escalate frustrated guests professionally.

• Comfortable working independently during weekend coverage without constant supervision.

• Strong attention to detail and ability to document issues, guest notes, reservation updates, and follow-up items accurately.

• Reliable availability to work Saturdays and Sundays.

• Experience with smart lock systems, work order systems, and automated guest messaging tools.

• Experience supporting remote teams in a fast-moving hospitality or operations environment.

• Familiarity with coastal vacation rental markets or drive-to leisure destinations.

• Experience with Streamline, Guesty, Hostfully, Escapia, Track, OwnerRez, LiveRez, or similar vacation rental property management systems.

Hourly: $18-$24

Part-Time: Up to 4 days per week

Required availability:

• Saturday

• Sunday

Potential additional days:

• Monday

• Tuesday

• Friday

Exact hours may vary based on business needs, seasonality, and guest volume. Weekend availability is required and should be considered the core responsibility of this role.

Remote, US-based.