10 Questions You Should Ask Before Signing with a Vacation Rental Property Manager
I want to write this post from a slightly different angle than my usual ones.
Instead of talking about what we do, I want to give you the framework I would use if I were a homeowner evaluating property management companies — including ours. Because I think the best service we can offer anyone considering this decision is clarity, not a sales pitch.
These are the ten questions that matter most. The answers you get will tell you nearly everything you need to know about whether a management company is actually prepared to steward your investment.
1. How does your portfolio perform versus the local market, and what’s your proof?
Ask for real numbers — not marketing language. A strong manager should be able to show you portfolio-level occupancy, ADR, and RevPAR trends against a defensible market comparison, plus specific year-over-year movement in recent quarters.
For context: our portfolio consistently runs occupancy materially above the Bolivar Peninsula market average, with RevPAR outperformance that compounds in peak season. In January 2026 — one of the softest low-season months the Texas coast had seen in years — our portfolio’s bookings were up 45% year-over-year, with 78% of those reservations at the same rate or higher than the prior year. Numbers like that are what a real revenue management operation produces, and any manager you evaluate should be able to talk about theirs with the same specificity.
2. What percentage of your bookings come through direct channels?
This is the question that reveals whether a company has built a real business or is entirely dependent on Airbnb and Vrbo. OTA dependency is a revenue risk — platforms change their algorithms, their fee structures, and their policies without warning. A manager with strong direct booking capability has built a buffer against that risk.
The industry average for direct bookings is under 15%. Ask where they are — and ask how they’re driving direct traffic. SEO? Email marketing? Paid ads? If the answer is vague, it probably reflects the reality. (Our Texas Coast portfolio runs above 30% direct-booking share.)
3. What is your review and rating average — and how do you manage it?
Ask for their current Airbnb rating and whether they hold Superhost status. More importantly, ask what their active review strategy looks like. Reviews aren’t just a trailing indicator — they’re a performance lever that affects search ranking, booking conversion, and the rates you can charge.
Only 8% of professional managers achieve Superhost status. Ask why theirs do or don’t. And ask specifically about Guest Favorites status on Airbnb, review-transfer strategy across platforms (Airbnb, Vrbo, Vacasa), and how the team handles three-star reviews.
4. What specific protection does my home have against guest damage — and who pays for it?
Dig into this one. “We have a damage deposit” and “$1M in coverage” are very different answers. Ask exactly what’s covered, what the claims process looks like, whether they handle it or you do, and what protections exist for liability, not just property damage.
Then ask the question most managers won’t volunteer: “Who pays for the protection program?” Some large national managers charge owners directly for the coverage. Our program carries up to $1M in real property coverage, $1M in liability, $25K in contents, and $15K in bed-bug protection — at no cost to the homeowner. The program is funded outside of your net payout. If you want the full mechanics of how we structured that, I’d rather walk you through it on a call.
Also ask about guest screening. ID verification? Risk pattern screening? Minimum age enforcement? The best damage claim is the one that never has to be filed.
5. Who specifically handles pricing, and how often do they review my property?
Dynamic pricing software is table stakes — most managers have it. What matters is who’s looking at your property’s performance and how often. Ask if there’s a dedicated in-house revenue team (not a software license and a part-time operator). Ask how they handle gap nights, holiday pricing, and local events. Ask what “human oversight” of your pricing actually looks like week to week.
If the answer is “the software handles it,” that tells you something important.
6. Do you have an in-house cleaning and inspection team, or do you outsource?
In-house teams mean consistent standards, direct accountability, and faster response to issues. Outsourced cleaning networks mean variable quality and a longer chain of communication when something goes wrong.
Ask how inspections are conducted after every stay, whether they’re documented, and what platform they use for property operations tracking. Ask what a failed inspection triggers in their process. Ask whether experienced cleaners have a promotion path into Inspector roles — it’s one of the best indicators of whether the manager takes review quality seriously.
7. What does your marketing infrastructure actually look like?
This is where a lot of companies get vague. Push for specifics: do they have a dedicated in-house marketing team, or is marketing a secondary task handled by operations staff? Do they run paid advertising? SEO? Email marketing to a proprietary guest database? How many campaigns per month? What does their list size look like?
Ask who builds and maintains their direct booking website. Ask whether they have a developer on staff. The difference between a real marketing program and a few social media posts is significant — and it shows up in your direct-booking rate.
8. What is your communication policy with homeowners?
Ask specifically: how quickly can you expect a response to email or phone? Who are your day-to-day contacts? What visibility do you have into your property’s calendar, financials, and maintenance status?
The things that frustrate homeowners most are rarely bad news — they’re silence and uncertainty. Ask whether you’ll have a real app with real-time access. Ask whether the manager operates with a centralized Homeowner Support function (one number, one team, same-day response) or a distributed model where you chase a single rep across voicemails. (We tried the distributed model; it didn’t meet our standard; we moved back to centralized Homeowner Support in late 2025. Ask us about it.)
9. What are your fees — all of them?
Management fee percentages vary widely, but the percentage alone doesn’t tell you what you need to know. Ask every one of the following in plain language:
• Coordination fees on third-party contractors. (Ours: 20% up to $150, 10% above $150, with a $300 approval threshold on any invoice.)
• Ancillary fee splits on pet fees, early check-in, late check-out. (Ours: 50/50 in the homeowner’s favor. Most managers keep 100%.)
• OTA integration fees, photography costs, onboarding fees, setup costs.
• Whether you can pay a contractor directly and skip the coordination fee (you can, with us).
Understand the full fee picture before you compare numbers. A company charging a higher percentage with no hidden fees may cost you less than one with a low headline rate and a long list of add-ons.
10. What are the contract terms — and what happens if it’s not working?
Ask how long the initial term is and what the exit process looks like if either party isn’t satisfied. A manager who’s confident in their results typically doesn’t need to lock homeowners in with long, punitive contract terms. Flexible terms signal confidence. Rigid terms with heavy exit penalties are worth examining carefully.
Also ask: “What happens when the transition itself is rough?” Any honest manager has had a transition that didn’t go smoothly. The right answer isn’t “that never happens.” It’s a specific story about what they learned and what they changed. Our own is public — we retired a distributed Property Manager model in late 2025 and returned to a centralized Homeowner Support structure after hearing the feedback from owners. Our structure changed. Our commitment didn’t.
I hope this framework is useful whether you’re evaluating us or evaluating others. The right property management partner should be able to answer all ten of these questions clearly and specifically. If they can’t, that’s important information.
And if you’d like to ask us all ten directly, I’m happy to sit down with you and walk through each one. Bring your last 12 months of owner statements and I’ll run the comparison in about 20 minutes.
Felipe Caldeira, CEO & Managing Partner, www.bolivarvacations.com | www.casagosanantonio.com
