This is not a coordinator seat. We are looking for a seasoned, hungry operator – a property manager or realtor – to take over our owner relationships and property-care standard, then grow the book.
You report directly to the founder and run your book like the business it is.
The opportunity
~20
home portfolio
Run owner relationships, property care, guest-readiness, and growth with a direct line to the founder.
Be the single point of contact for owners: monthly statements, payouts, revenue conversations, and calm, fast problem-solving.
Working when: owner churn is near zero and owners refer their friends.
02
Property care & inspections
Treat every home like your own. Run inspections, catch wear and damage early, coordinate cleaning and maintenance, and verify every turn.
Working when: homes are guest-ready every time – you catch issues, not the guest.
03
Operations & quality
Own guest-readiness and resolve escalations across the Keys. Keep listings, pricing inputs, and calendars accurate on Guesty, PriceLabs, and Breezeway.
Working when: issues resolve fast and 5-star reviews stay the norm.
04
Growth
Sign new owners, turn happy owners into referrals, and onboard new homes end-to-end. Represent Villa Paraiso like it is your own company.
Working when: your book grows steadily and pays you more every month.
The runway
Your first 90 days
Days 1-30
Take the reins
Meet every owner, walk every home, and master the stack. Owners feel the handoff was seamless.
Days 31-60
Own the standard
Inspection cadence is live, escalations flow through you, and the first owner wins are on the board.
Days 61-90
Grow the book
Your first new owner is signed or the referral pipeline is built – you are running the book independently.
Required
What you bring
3+ years in property management, vacation rentals, hospitality, or real estate with real client-relationship or closing experience.
You live in the Florida Keys (Marathon / Middle Keys) with a reliable vehicle.
A strong, calm communicator who is obsessive about details.
Comfortable with technology – you will run an AI-native stack.
Available 24/7 for what matters – you set your hours, but owners and guests come first.
Nice to have
Your unfair advantage
Active Florida real-estate license.
An existing Keys owner or realtor network.
Guesty, Airbnb, VRBO, or Breezeway experience.
A book of owners you could bring with you.
How you are paid
$75,000-$120,000+ on-target. Uncapped.
Guaranteed base retainer: $40,000-$50,000/year, paid monthly.
New-owner commission: uncapped, with accelerators and a signing bonus for each owner you personally bring.
Book residual: recurring management-revenue participation on every home you sign, every month it stays.
Equity: a real ownership stake in the company you are helping build.
Why this is not a normal job
Own your book and your schedule.
Work directly with the founder.
Share in the growth you create.
Use AI-native tools to remove busywork.
Live and work on the water in the Florida Keys.
Immediate start
Apply for this role
Share your details, experience, and resume below. We review every application for this role.
Villa Paraiso Vacation Rentals considers applicants without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other status protected by law.
Just need your email
We'll email you a one-tap link. No password, no account to set up.
