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Villa Paraiso Vacation Rentals

Property Manager

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What they do

A Property Manager manages operations for an apartment building or complex. Recruits and screens tenants for apartments, collects rents and security deposits, responds to requests or complaints from tenants, supervises maintenance and repairs; oversees payment of bills, insurance, taxes and recordkeeping. Manages property and services on behalf of a community association, for properties such as condominiums or cooperatives. Collects fees or dues, responds to requests or complaints, supervises maintenance, oversees work done by contractors, and provides accounting of income and expenses. May also assist owners or a board of directors with regulatory compliance or compliance with community association rules. Manages the operation of commercial or residential properties. Oversees the collection of rents and payment of bills, taxes and insurance for properties, and provides property owners with reports on finances and the status of properties. Directs leasing operations, or equipment and machinery rentals, for a company or business. Determines charges and prepares rental or lease agreements; supervises inventory, equipment maintenance and recordkeeping for leasing operations.

$71,656 / year median in Florida

+15% projected growth

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Job Description

Description:
Villa Paraiso Vacation Rentals manages ~20 luxury vacation homes in Marathon and Key Colony Beach. We're hiring an experienced property manager or realtor to take over our owner relationships and property-care standard, then grow the portfolio. You report directly to the founder and run your book like the business it is. This is not a coordinator seat.
You own outcomes end-to-end:
the owner who calls with a problem, the home that has to be guest-ready, the referral that becomes your next signed property.
WHAT YOU'LL OWN
  • Owner relationships — single point of contact for homeowners: monthly statements, payouts, revenue conversations, calm and fast problem-solving. Success looks like near-zero owner churn and owners referring their friends.
  • Property care & inspections — run inspections, catch wear and damage early, coordinate cleaning and maintenance, verify every turnover. You catch issues, not the guest.
  • Operations & quality — own guest-readiness and escalations across the Keys. Keep listings, pricing inputs, and calendars accurate in Guesty, PriceLabs, and Breezeway.
  • Growth — sign new owners, turn happy owners into referrals, onboard new homes end-to-end.
YOUR FIRST 90 DAYS
Days 1-30: meet every owner, walk every home, master the stack. Days 31-60: inspection cadence live, escalations flow through you, first owner wins on the board. Days 61-90: first new owner signed or referral pipeline built — you're running the book independently.
REQUIREMENTS
  • 3+ years in property management, vacation rentals, hospitality, or real estate with real client-relationship or closing experience
  • Live in the Florida Keys (Marathon / Middle Keys) with a reliable vehicle
  • Strong, calm communicator, obsessive about details
  • Comfortable with technology — you'll run an AI-native operations stack
  • On-call flexibility for genuine emergencies — you set your hours, but owners and guests come first
NICE TO HAVE
  • Active Florida real estate license
  • Existing Keys owner or realtor network
  • Guesty, Airbnb, VRBO, or Breezeway experience
  • A book of owners you could bring with you
COMPENSATION
  • Guaranteed base retainer: $40,000
  • 50,000/year, paid monthly
  • Uncapped new-owner commission with accelerators and a signing bonus for each owner you personally bring
  • Recurring management-revenue participation on every home you sign, every month it stays
  • Equity stake in the company you're helping build
  • On-target earnings $75K
  • 120K+, uncapped 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.
Screener questions (Indeed's screening step): 1. Do you currently live in the Florida Keys, or are you able to relocate before starting? →
Deal-breaker:
Yes 2. How many years of property management, hospitality, or real estate client experience do you have? →
Minimum:
3 3. Do you hold an active Florida real estate license? → Not a deal-breaker
Pay:
From $75,000.00 per year
Benefits:
401(k) 401(k) matching Dental insurance Flexible schedule Health insurance Life insurance Paid time off Professional development assistance Vision insurance
Work Location:
Hybrid remote in Marathon, FL