Property Caretaker​/Lead Inspector

Property Caretaker / Lead Inspector – Launch Your Property Management Career

Panhandle Getaways @ Calypso Towers Resort
Location: Panama City Beach, FL |
Full-Time | On-Site (must live locally or relocate)

Panhandle Getaways is one of the Top 50 vacation rental management companies in the world
, managing 900+ luxury short-term rentals across the Florida Panhandle. At Calypso Towers
, one of our flagship beachfront resorts, we deliver 5‑star guest experiences and protect owner assets through obsessive attention to detail.

This is a high‑visibility, hands‑on operations role built for someone hungry to learn the vacation rental business from the ground up and grow within property management.

You’ll work side‑by‑side with the General Manager of Calypso Towers
, owning quality control and operations for 100+ beachfront units. This is an excellent opportunity for someone who enjoys hands‑on property work and wants to grow professionally within the property management field.

• Perform detailed pre‑arrival, post‑departure, and owner inspections (you’ll become an expert at spotting issues others miss)

• Create and track work orders
  , coordinate vendors, and ensure every repair is completed correctly and on time

• Partner daily with housekeeping, maintenance, and front‑desk teams to keep everything running smoothly

• Proactively catch small problems before they become negative reviews or owner complaints

• Use our tech stack (mobile inspection app, Teams, task system) to document everything with photos and notes

• Physical Requirements: Walk multiple units/floors daily, lift up to 30 lbs, bend/kneel/stoop for inspections, stand/walk for extended periods, and work indoors/outdoors as needed

• 1–3 years in hospitality, property maintenance, housekeeping supervision, or customer‑facing roles (or a rock‑solid work ethic and quick learning ability if you’re newer)

• Insane attention to detail — you notice the crooked picture frame, the scuff mark, the slightly burnt‑out bulb

• Organized, dependable, and follow through like your life depends on it

• Great communicator (text, phone, in‑person) with teams and vendors

• Tech‑savvy and comfortable on phones/tablets

• Flexible schedule —
  weekends and occasional evenings are part of resort life

• Positive, coachable attitude and a genuine desire to build a career in property management

• Competitive hourly pay with regular performance raises

• Full benefits:
  health, dental, vision

• Generous 401(k) match

• Paid time off + holidays

• Work literally steps from the Gulf of Mexico at one of PCB’s premier resorts

• Real mentorship from seasoned pros in the vacation rental space

• A genuinely fun and supportive team that is constantly improving while celebrating the wins

If you’re reliable, detail‑obsessed, and ready to turn your hustle into a real career in vacation rental management, we want to hear from you.

Apply today!