Vacation Specialist

Company Overview

Coastal Vacation Properties is the Premier Vacation Property Management Company in Fort Myers Beach. A family-owned business, we've become successful by personalizing the needs of our clients. We offer competitive wages, bonus opportunities, and paid time off.

For over 25 years, we have managed preferred vacation rental homes of all sizes, from condos to large multi-family luxury beach homes. Our success is in prioritizing our guests' experience and working diligently to grow our vacation rental homeowners' businesses with professionalism, relationship building, and effective marketing.

Position Summary

We're seeking an energetic, detail-oriented Vacation Specialist (VSP) to join our Guest Services team in our Fort Myers Beach office. The VSP is the primary point of contact for guests and property owners throughout the reservation lifecycle, from first inquiry through check-out and post-stay feedback. You'll be responsible for the accuracy of every reservation, prompt and professional communication across all booking channels, daily arrival readiness, and resolving guest issues in coordination with Housekeeping, Quality Control, and Operations.

The ideal candidate is organized, with excellent interpersonal and communication skills. Previous experience in property management or hospitality is highly desired. Coastal Vacation Properties is committed to maintaining the highest level of quality and standards, and it is our team members who help us ensure this. Advancement opportunities are available for the right candidate.

Responsibilities

Reservation Management

• Maintain complete and accurate reservation records in Streamline, including guest details, payments, documentation, check-in instructions, and auto-responders.

• Process new bookings, modifications, and cancellations according to company rental and cancellation policies.

• Ensure all required reservation documentation is completed, including signed rental agreements, security deposits or damage waivers, and

• guest verification.

• Manage guest add-ons such as early check-ins, late check-outs, extended stays, and pet fees, coordinating with Housekeeping and Operations.

• Enter owner stays and blocks accurately and communicate them to the appropriate departments.

Guest & Owner Communication

• Answer incoming phone calls and emails from guests and property owners professionally and promptly.

• Return voicemails at the start of each shift and throughout the day.

• Respond to all inquiries across every booking channel, including direct, Airbnb, Vrbo, and other OTAs, within each platform's required response timeframe.

• Assist guests with booking questions, property recommendations, and special requests, working to convert inquiries into confirmed reservations.

• Acknowledge and follow up on all new CRM Leads daily.

Daily Arrival Readiness

• Confirm arriving guests have completed all arrival steps, received full arrival instructions, and have no outstanding balances.

• Monitor field team updates on unit readiness and proactively communicate any arrival delays to guests.

Guest Issue Resolution & Work Orders

• Assist guests with issues and requests during their stay, escalating urgent matters to a supervisor.

• Create Work Orders for guest-reported issues, assign them to the proper department, and keep guests updated until resolved.

Reviews, Coordination & Projects

• Monitor and manage guest reviews across all platforms, including responding to guests, sharing with owners, and adding reviews to the company website.

• Review guest surveys and escalate low scores to a supervisor.

• Communicate with Housekeeping, Quality Control, and Operations regarding reservation changes, add-ons, and guest issues.

Required Qualifications

• 1–2 years of experience in the vacation rental or hospitality industry

• Experience with Streamline VRS or similar software preferred.

• Tech-savvy, with the ability to quickly learn new software and systems (Streamline, Asana, Microsoft Teams, OTA platforms).

• Creative problem-solving skills and the ability to think quickly and effectively on your feet.

• Strong attention to detail and follow-through across multiple channels and priorities.

• Team player with a positive, professional mentality.

• Ability to multitask, prioritize, and adapt to changing daily business needs.

• Must work in the office on Saturdays and Sundays, plus assigned holidays.

Compensation & Benefits

• Pay: $20–$22/hour, based on experience

• Bonus: Bonus opportunities for securing direct bookings and for the highest production

• Benefits: Paid time off

Schedule & Other Notes

• Schedule: Part-time or full-time, depending on the candidate

• Location: In-person at our Fort Myers Beach office

• Weekend Availability: In-office attendance on both Saturdays and Sundays is mandatory

• Probationary Period: 90 days, followed by a discussion regarding a potential pay increase and long-term fit

• On-Call Coverage: After-hours on-call responsibilities will be added down the road, once the new hire has gained experience and is comfortable in the role