Vacation Rental Reservations Specialist

Position Summary

We are seeking a friendly, detail-oriented, and customer-focused Vacation Rental Reservations Specialist to support our guest services and booking operations. This role is ideal for someone who thrives in a fast-paced, remote environment while maintaining strong attention to detail and responsiveness. You will be the first point of contact for guests—managing inquiries, processing reservations, and ensuring a seamless experience from initial booking through arrival.

In addition to guest communication, this role plays an important part in updating and optimizing property listings, assisting with special projects, and driving repeat bookings through post‑stay follow‑ups. Success in this position comes from balancing excellent communication with organization, efficiency, and a proactive approach to improving both guest experience and listing performance.

• Respond promptly to guest inquiries via phone, email, and platforms like Airbnb, Vrbo, and
• Provide accurate information on property details, availability, pricing, amenities, and local attractions
• Process reservations, modifications, and cancellations in line with company policies
• Send check‑in instructions, arrival details, and pre‑stay communications
• Handle guest questions, concerns, and special requests with professionalism and efficiency

• Update and maintain property listings across all booking platforms
• Ensure accuracy of descriptions, amenities, photos, and pricing notes
• Optimize titles and content to improve listing performance and conversions
• Assist with seasonal updates, promotions, and listing enhancements

• Assist with special projects such as onboarding new properties, system updates, and process improvements
• Collaborate with internal teams to ensure listings and systems reflect real‑time availability and updates
• Maintain organized records of guest communication, bookings, and payments

• Conduct post‑stay follow‑ups to gather feedback, encourage reviews, and promote repeat bookings
• Build relationships with past guests and identify opportunities to convert them into returning customers
• Help enhance the overall guest journey from booking to departure

• 1+ year experience in hospitality, reservations, or customer service (preferred)
• Strong written and verbal communication skills
• High attention to detail and strong organizational abilities
• Ability to multitask and prioritize in a fast‑paced environment
• Tech‑savvy and comfortable learning new systems
• Experience with STR platforms such as Streamline PMS, Breezeway, or similar systems preferred
• Customer service mindset with a proactive and problem‑solving attitude
• Flexible availability, including evenings and weekends as needed

• Based in the Orlando area (a plus for local knowledge and occasional support needs)
• Bilingual skills are a plus

• Paid time off such as PTO, sick days, and vacation days

• 5 days per week, rotating weekends, remote