Reservation Specialist

HOA Talent • Hollywood, FL

2d • Onsite

About The Position

StaySouth Vacation Homes is hiring a Reservation Specialist for its on-site Hollywood, Florida team. StaySouth is a locally owned vacation rental management company serving Miami-Dade, Broward, and Palm Beach counties and is part of the Casago network.

This revenue-generating role owns booking opportunities from the initial inquiry through confirmed reservation. The specialist matches guests with appropriate homes, addresses objections, asks for the booking, and hands off accurate reservations to the Guest Experience team. The role requires persistent, guest-focused follow-up and attention to the revenue impact of missed inquiries.

Requirements

• At least 2 years of experience in reservations, hospitality sales, vacation rentals, travel sales, or a comparable inbound sales role.
• Proven track record of converting inquiries into bookings or sales.
• Experience with a reservation system, property management system, or CRM.
• Comfort quoting rates and explaining fees, payment schedules, and cancellation policies.
• Ability to manage high inquiry volume with strong accuracy.
• Availability for scheduled weekend, holiday, and evening coverage.

Nice To Haves

• Vacation rental or short-term rental reservation experience.
• Experience with Guesty or another vacation rental property management system, such as Hostaway, Track, Streamline, or Escapia.
• Familiarity with Airbnb, Vrbo, and Booking.com booking workflows.
• Bilingual English/Spanish ability.
• Familiarity with the South Florida vacation rental market.
• Group, extended-stay, or travel-agent booking experience.

Responsibilities

• Respond promptly to inbound inquiries by phone, text, email, website, and online travel agency channels, including Airbnb, Vrbo, and Booking.com.
• Qualify guest needs, recommend suitable properties or alternatives, prepare accurate quotes, and follow up through reservation close.
• Grow direct bookings through staysouth.co, repeat guests, referrals, and corporate, group, extended-stay, and travel-agent inquiries.
• Create and maintain accurate reservations in Guesty, including dates, occupancy, rates, fees, taxes, deposits, and booking source.
• Collect guest payments through GuestyPay, follow up on failed or overdue balances, and coordinate discrepancies with Accounting.
• Process date changes, extensions, and cancellations according to policy, and work to retain bookings when guests want to cancel.
• Follow guest verification and screening procedures and escalate suspicious or noncompliant reservations.
• Coordinate special requests and reservation changes with Guest Experience and Operations using Breezeway.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed