Reservations & Guest Services Specialist (Vacation Rentals) - 20123

• Employment Type: Full-time / IC
• Location: Remote 
• Schedule: Full overlap with U.S. Central Time business hours (operation runs 9:00 AM–5:00 PM CST
• Reports to: Reservations Manager

We are a rapidly growing, U.S.-based vacation rental management company along Florida's Gulf Coast, managing 500+ professionally maintained homes and condos across the Emerald Coast and beyond — including Panama City Beach, 30A, Destin, Okaloosa Island, Navarre Beach, Anna Maria Island, and Longboat Key.

We operate on a book-direct model and pride ourselves on a seamless guest experience backed by responsive, local support. Backed by an established parent organization, we are scaling our reservations and guest-support function to keep pace with rising demand across our two regional operations.

This role exists for two reasons: we recently lost a member of our reservations team, and our guest call volume has grown faster than our current staff can comfortably handle. We're looking for one to two sharp, dependable specialists to become the front line for our guests.

You will be the voice guests hear when they call with questions, the person who turns an inquiry into a confirmed booking, and the steady hand that keeps reservation details, payments, and correspondence accurate. This is a high-touch, customer-facing seat in a fast-moving hospitality business — the kind of role where strong communication and follow-through directly shape the guest experience and protect our reputation.

You'll work inside our proprietary property management system (modeled closely on Escapia), so comfort learning and operating in a CRM-style platform is essential.

• Answer a high volume of inbound calls and respond to guest inquiries promptly and professionally
• Serve as the first point of contact for questions about properties, bookings, policies, and amenities
• Handle guest requests and escalations with patience, ownership, and sound judgment
• Send timely, accurate correspondence to guests throughout the booking and stay lifecycle

• Manage reservations from inquiry through confirmation within the property management system
• Maintain accurate, up-to-date booking and guest records
• Coordinate details across the reservations workflow to ensure a smooth guest experience

• Process and enter guest payments accurately
• Complete administrative tasks tied to reservations and guest accounts
• Flag discrepancies or issues to the appropriate internal team

• Operate confidently within our proprietary PMS and adopt new tools quickly
• Follow established processes while identifying small ways to work more efficiently
• Keep documentation clean so teammates can pick up any account without friction

• 2+ years in customer service, guest services, reservations, or a phone-based support role
• Excellent spoken and written English with a clear, professional, customer-ready phone presence
• Demonstrated comfort learning and working inside CRM or reservation/booking software
• Strong attention to detail, especially with bookings, payments, and records
• Reliable home-office setup: stable high-speed internet, quiet environment, and a quality headset
• Ability to work full U.S. Central Time business hours, including weekend rotation

• Experience in vacation rentals, property management, hospitality, or travel
• Hands-on experience with a property management system — Escapia experience is a strong plus — or platforms such as Streamline, Track, Guesty, or Hostaway
• Experience handling guest escalations or de-escalating frustrated callers
• Experience processing payments or working with billing/accounts

You are:

• A warm, confident communicator who genuinely enjoys helping people over the phone
• Highly organized and detail-oriented, even on a busy, fast-paced day
• Tech-savvy and quick to learn new systems without hand-holding
• Calm and solutions-focused when a guest is frustrated or a problem needs sorting out
• Dependable and self-managed in a remote setting, with strong follow-through
• Comfortable owning repetitive, detail-heavy work without losing accuracy or care