Orlando is one of the most profitable short-term rental markets in the country, but it’s also one of the easiest places to lose money quietly.
Between Disney-driven seasonality, strict local regulations, HOA enforcement, and wildly different management models, choosing the wrong short-term rental manager can drain your ROI long before you realize it.
The problem isn’t a lack of options. It’s that most owners ask the wrong questions or stop at surface-level answers.Below are the 15 questions Orlando vacation rental owners actually need to ask before hiring a manager, plus exactly how to tell a green-flag answer from a red flag. If a company can’t answer these clearly, you already have your answer.
1. How Is Your Management Fee Calculated?
Why this matters:
Two managers charging “20%” can deliver wildly different results depending on how that fee is calculated.
🚩 Red Flag Answer:
“It’s just 20% pretty standard.”
(Unable or unwilling to explain gross vs. net revenue.)
✅ Green Flag Answer:
“Our fee is calculated transparently, and we’ll show you exactly what it’s based on. You’ll see this clearly on every owner statement.”
2. What Is Actually Included in Your ‘Full-Service’ Management?
Why this matters:
“Full-service” often excludes essentials like inspections, compliance, or pricing oversight.
🚩 Red Flag Answer:
“We handle everything.”
(No written breakdown, lots of assumptions.)
✅ Green Flag Answer:
“We clearly define what’s included: guest communication, pricing, inspections, cleaning coordination, maintenance oversight, and compliance with no surprises.”
3. Are There Any Fees Beyond the Management Percentage?
Why this matters:
Hidden fees are one of the biggest profit killers for Orlando STR owners.
🚩 Red Flag Answer:
“Nothing major, just standard stuff.”
(Vague language = future surprises.)
✅ Green Flag Answer:
“We disclose all costs upfront and provide itemized owner statements, so you always know where your money goes.”
4. Is Your Fee Based on Gross or Net Revenue?
Why this matters:
This single detail can cost owners thousands per year.
🚩 Red Flag Answer:
“I’m not sure. It’s just what the system calculates.”
✅ Green Flag Answer:
“We explain how fees are calculated and why that structure is fair to owners.”
5. How Do You Price Properties in Orlando’s Highly Seasonal Market?
Why this matters:
Orlando pricing changes weekly. Static pricing leaves money on the table.
🚩 Red Flag Answer:
“We use automated pricing and let it run.”
✅ Green Flag Answer:
“We use dynamic pricing combined with local market insight, Disney calendars, events, holidays, and booking trends to actively optimize rates.”
6. How Often Are Rates Actively Reviewed and Adjusted?
Why this matters:
Dynamic pricing tools still require human oversight.
🚩 Red Flag Answer:
“The software handles it.”
✅ Green Flag Answer:
“Rates are reviewed frequently and adjusted when market conditions shift.”
7. Who Handles Cleaning, and How Is Quality Controlled?
Why this matters:
Cleanliness is the #1 driver of reviews and repeat bookings.
🚩 Red Flag Answer:
“We use cleaners.”
(No inspection process mentioned.)
✅ Green Flag Answer:
“Every turnover is inspected using checklists and photo documentation to ensure consistent standards.”
8. How Are Maintenance Issues Handled and Approved?
Why this matters:
Poor maintenance communication leads to inflated bills and unhappy owners.
🚩 Red Flag Answer:
“We just fix what needs fixing.”
✅ Green Flag Answer:
“We have clear approval thresholds, transparent vendor billing, and keep owners informed.”
9. Do You Mark Up Maintenance or Vendor Costs?
Why this matters:
Hidden markups quietly reduce ROI.
🚩 Red Flag Answer:
“That’s just part of management.”
✅ Green Flag Answer:
“Vendor costs are billed transparently, and you can review invoices anytime.”
10. How Do You Handle Orlando STR Licensing, Taxes, and Compliance?
Why this matters:
Orlando enforcement is increasing, and fines add up fast.
🚩 Red Flag Answer:
“That’s usually the owner’s responsibility.”
✅ Green Flag Answer:
“We handle licensing and tax collection, filings, and stay current with local regulations.”
11. What Happens If a Guest Has an Issue at 2 a.m.?
Why this matters:
Late-night issues are common in Orlando.
🚩 Red Flag Answer:
“They can message us through the platform.”
✅ Green Flag Answer:
“We provide 24/7 guest support with local response capabilities.”
12. Who Owns the Listing, Reviews, and Guest Data?
Why this matters:
Some managers lock owners into their ecosystem.
🚩 Red Flag Answer:
“Our company owns the listings.”
✅ Green Flag Answer:
“The property and performance history belong to you.”
13. What Does Your Contract Look Like?
Why this matters:
Long lock-ins protect managers, not owners.
🚩 Red Flag Answer:
“One-year minimum with penalties.”
✅ Green Flag Answer:
“Our agreement is flexible because we retain owners through performance.”
14. How Do I Track Performance and Finances?
Why this matters:
Transparency builds trust.
🚩 Red Flag Answer:
“We send summaries.”
✅ Green Flag Answer:
“You’ll have access to detailed, itemized reports and real-time performance data.”
15. What Makes You Different From Other Orlando STR Managers?
Why this matters:
This reveals confidence or lack of it.
🚩 Red Flag Answer:
“We’re cheaper” or “We’re bigger.”
✅ Green Flag Answer:
“We combine local expertise, transparent pricing, active revenue management, and owner-first accountability.”
Why These Questions Protect Your Investment
Orlando STR owners don’t fail because demand disappears. They fail because costs quietly outpace performance.Asking these questions forces clarity. The right property manager will welcome them. The wrong one will dodge, generalize, or rush you to sign.
Why Orlando Owners Choose FunStay Florida
At FunStay Florida, we built our property management service around these exact questions, because we’re vacation rental owners ourselves. We believe Orlando owners deserve:
- Transparent, net-focused pricing
- No hidden fees or vendor markups
- Local expertise, not remote call centers
- Flexible contracts with zero lock-ins
If you’re comparing managers or already working with one, we’re happy to walk through your current setup and show you, clearly and honestly, where you stand.
No pressure. No sales tactics. Just real numbers.
