Reservations & Guest Services Specialist (Vacation Rentals)

Location & Employment Details

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

About the Company

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.

About the Role

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.

Key Responsibilities

Guest Communication & Support

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

Reservations & Booking Management

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

Payments & Administrative Support

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

Systems & Quality

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

Required Qualifications

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

Preferred Qualifications

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

Ideal Candidate Profile

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

Why Join Us

You'll join an established, growing company in a destination industry, working with a team that takes guest experience seriously. This is a stable, full-time, long-term remote opportunity with real ownership over the guest relationship — and the chance to grow as our reservations operation scales.

Reservations & Guest Services Specialist (Vacation Rentals) - 20123