Reservation Specialist

Reservation Specialist – Vacation Rentals
$40,000 - 45,000/year + commission
Hollywood, FL - On-Site

About StaySouth Vacation Homes

StaySouth is a locally owned vacation rental management company serving Miami-Dade, Broward, and Palm Beach counties. As part of the Casago network, we pair professional hospitality management and modern technology with deep local expertise for guests and homeowners.

The Role

This is a revenue-generating role, not an order-taking one. You'll own every booking opportunity from first inquiry through confirmed reservation: matching guests to the right home, handling objections, asking for the booking, and handing off a clean, accurate reservation to our Guest Experience team. We want someone who is persistent without being pushy and knows every missed inquiry is lost revenue.

What You'll Do

• Respond quickly to inbound inquiries by phone, text, email, website, and OTA channels (Airbnb, Vrbo, Booking.com)
• Qualify guest needs, recommend the right property or alternative, prepare accurate quotes, and follow up until the reservation closes
• 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 per 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 (Breezeway)

What We're Looking For (Required)

• 2+ years in reservations, hospitality sales, vacation rentals, travel sales, or a comparable inbound sales role
• Proven track record 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 Have

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