Senior Vacation Specialist
Coastal Vacation Properties
Posted May 28, 2026
Job Description
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 are seeking an experienced, motivated Senior Vacation Specialist to support our growing reservations department. This is a hybrid role combining reservation specialist responsibilities with leadership development opportunities.
The ideal candidate is highly organized, guest-focused, and experienced in vacation rental or hospitality operations. This role will begin with a primary focus on reservations and guest service, allowing the candidate to become fully familiar with our systems, portfolio, and operational procedures. As experience and familiarity with our operations grow, the position will gradually expand to include leadership responsibilities within the department.
Our team is committed to maintaining the highest level of service and professionalism, and we’re looking for someone who can lead by example while supporting both guests and fellow team members.
Key Responsibilities
Reservation Specialist Duties
Manage reservations, including payments, documentation, check-in instructions, and guest communication
Respond to guest inquiries across all booking channels (direct, Airbnb, Vrbo, and other OTAs)
Answer incoming phone calls and emails from guests and property owners
Assist guests with booking questions, stay requests, and issue resolution
Monitor and respond to guest reviews
Coordinate with housekeeping, operations, and quality control regarding reservation updates or guest concerns
Assist with onboarding and setup of new rental properties
Leadership & Department Oversight (assumed after training and operational familiarity)
Train and mentor Vacation Specialist team members on systems, policies, and procedures
Manage all HOA/Condo paperwork submittal
Monitor team performance, productivity, and guest communication quality
Manage department coverage
Conduct one-on-one check-ins and assist with performance evaluations
Provide coaching on call handling and guest service standards
Assist with handling escalated guest concerns, refund requests, and disputes
Review reservation correspondence to ensure accuracy and professionalism
Maintain reservation procedures and identify opportunities to improve workflow efficiency
Help create and maintain Standard Operating Procedures (SOPs) for reservation processes
Monitor booking accuracy and assist in resolving issues such as double bookings or guest relocations
Reporting & Performance Monitoring
Track weekly booking performance
Monitor call volume, response times, and inquiry conversion
Review guest disputes and refund requests
Identify booking errors and ensure proper documentation and notes are maintained
Required Qualifications
1+ years minimum previous experience in vacation rentals, hospitality, or property management
Experience with reservation systems (Streamline PMS preferred)
Strong leadership, communication, and problem-solving skills
Highly organized with strong attention to detail
Ability to multitask and adapt in a fast-paced environment
Tech-savvy and comfortable learning new systems and software
Team-oriented with a positive, professional attitude
Ability to work Monday–Friday with occasional on-call or weekend coverage
Preferred Qualifications
Bilingual preferred but not required
Compensation, Benefits, & Schedule
Hourly Salary
21-22
Benefits
Paid time off such as PTO, sick days, and vacation days
Schedule
Monday-Friday, On-call shifts as needed