Vacation Specialist

Better Talent; Fort Myers Beach (FL); On-site; USD 28,000 - 30,000; Full time

Benefits offered by this job

Paid time off

Bonus opportunities

Competitive wages

Job summary

Coastal Vacation Properties in Fort Myers Beach is seeking an energetic Vacation Specialist to join our Guest Services team. You will be the primary contact for guests and property owners throughout the reservation lifecycle, ensuring accuracy, prompt communication, and smooth arrival readiness.

The role collaborates with Housekeeping, Quality Control, and Operations to resolve issues and maintain high service standards.

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.

Responsibilities

• 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.
• 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 inquiries across all booking channels within required response time.
• Assist guests with booking questions, property recommendations, and special requests to convert inquiries into reservations.
• Monitor and manage guest reviews across platforms and share with owners.
• Create Work Orders for guest-reported issues and update guests until resolved.

Skills

Vacation rental experience

Tech-savvy

Multitasking

Attention to detail

Team player

Customer service

Tools

Streamline VRS

Asana

Microsoft Teams

OTA platforms

Job description

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.

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 elevate 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.

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