Vacation Rental Reservations Specialist

Company Overview

White Rose Villas is a professionally licensed property management company serving Central Florida’s most sought-after vacation communities, with offices based in Kissimmee, Florida and the United Kingdom. We are proud to bring a global perspective while delivering a personalized, high-quality experience to both our guests and homeowners.

Our team is made up of experienced, dedicated professionals with a strong understanding of every aspect of the vacation rental industry—from guest services and reservations to property care and owner relations. We place a strong emphasis on attention to detail and are constantly developing new services and processes that set us apart from our competitors.

We operate seven days a week, providing prompt, reliable, and efficient service, and we take pride in creating exceptional experiences for everyone we serve.

Why You’ll Love Working With Us

At White Rose Villas, you’re not just another employee—you’re part of a supportive, close-knit team that values communication, collaboration, and a positive work environment.

We are a growing company that is always evolving, which means your ideas matter. You’ll have the opportunity to contribute, grow, and be part of improving how we serve our guests and homeowners every day.

Our work is fast-paced and dynamic—no two days are the same. If you enjoy problem-solving, helping people, and being part of a team that takes pride in delivering great service, you’ll

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.

Key Responsibilities

Guest Communication & Reservations

• Respond promptly to guest inquiries via phone, email, and platforms like Airbnb, Vrbo, and Booking.com

• 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

Listing Management & Optimization

• 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

Project & Operational Support

• 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

Guest Experience & Retention

• 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

Required Qualifications

• 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

Preferred Qualifications

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

• Bilingual skills are a plus

Compensation, Benefits, & Schedule

Hourly Salary$18 - $23 (1099 Contractor)

Benefits

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

Schedule

• 5 days per week, rotating weekends, remote