Behind every successful vacation rental business is a property owner who trusts you with their most valuable asset. But in today’s competitive market, simply being good at what you do isn’t enough to win and keep those owners.
At our September GuestyVal event, three seasoned operators shared the practical strategies that have helped them grow their portfolios and build lasting owner relationships. In a discussion moderated by Bonnie Li of Upstay, Caroline Ramos (Host & Keep, Miami), Ric Kenworthy (TRAVLI Hospitality, Scottsdale), and Marianne Heder (PMI) discussed everything from positioning strategies to retention techniques — and revealed surprising insights about what property owners actually value most.
How to position yourself differently
In a saturated market, blending in means losing out. The most successful property managers don’t compete on door count or price—they carve out distinctive positions that resonate with specific owner segments.
Lead with philosophy, not portfolio size
The operators who win premium owners have stopped leading with how many properties they manage. Instead, they articulate a clear philosophy about how they approach property management differently. This might mean positioning as the boutique alternative to corporate operators, the white-glove service provider, or the data-driven performance maximizer. When you stand for something specific, you naturally attract owners who value that approach—and repel those who don’t, which saves everyone time.
Be selective about who you work with
Counter-intuitively, being willing to turn away properties strengthens your positioning. When you flip the traditional sales dynamic and ask owners to pitch why they’d be a good fit for your portfolio, you signal confidence and quality. Caroline shared that using this strategy, Host & Keep turns away roughly half of prospective properties—not because they can’t manage them, but because they aren’t the right fit. This selectivity becomes part of your brand and attracts higher-quality owners who appreciate working with a company that maintains standards.
Offer flexibility across investment strategies
Today’s investor-grade owners don’t think in silos—they think in portfolios. PMI’s approach of being able to support an owner’s entire real estate investment journey, whether that’s short-term rentals, mid-term furnished housing, traditional long-term leases, or transitions between strategies, positions them as a strategic partner rather than a single-use vendor. This multi-model capability is especially valuable in markets where regulatory changes or economic shifts require owners to pivot their approach.
Personalize everything
In an age of automation, thoughtful personalization stands out. This goes beyond using an owner’s name in emails—it means understanding each owner’s priorities (occupancy rates, average daily rate, consistent communication, meticulous home care) and tailoring your entire approach to what actually matters to them. Ric calls this identifying his clients’ love language. The goal is making owners feel like you’re managing their specific property, not processing it through a standardized system.
Budget-friendly owner acquisition
Growing your owner base doesn’t require deep pockets. The most effective acquisition strategies are often the ones that cost the least—they just require strategic thinking and patience..
Build complementary businesses that create pipeline
If you have adjacent service businesses (cleaning, maintenance, real estate) create them under separate brands that can work with competitors and self-managing hosts. These businesses generate their own revenue while creating natural opportunities to cross-sell property management when hosts are ready to make the switch. Host & Keep’s Caroline Ramos uses this approach to stay in front of potential owners without the hard sell.
Spend marketing dollars strategically
Find what works with your audience. Host & Keep decided to skip expensive Google keyword battles and focus on Meta ads paired with strong SEO (optimized for AI search results). Resource-based blog content—like lists of buildings that allow short-term rentals or neighborhood guides for investors—attracts owners actively researching their options. And don’t overlook review strategy: trigger Google review requests via SMS at checkout instead of relying on OTA reviews that owners may never see.
Target the “second manager” opportunity
As TRAVLI’s Ric Kenworthy points out, being someone’s second property manager is often easier than being their first. These owners already know what they care about and where their previous manager fell short. The best time to reach them is during low season, when performance is top of mind and they’re evaluating whether to make a change. Most have been burned before, so understanding what they truly value—and consistently delivering on it—is what turns acquisition into long-term retention.
PMI’s owner survey: What’s really most important
Instead of guessing what owners value most, PMI went straight to the source. Their survey of hundreds of thousands of property owners revealed these priorities:
- Effective communication
- Honesty and integrity
- Accurate accounting
- Availability of the team
- Expertise and knowledge
- Transparency of fees and costs
- Strong reviews
- Lowest price ← Dead last!
The key insight: Owners want a trusted partner, not the cheapest option.
Owner retention strategies that work
Retention isn’t about grand gestures—it’s about consistent actions that build trust and demonstrate you’re genuinely invested in their success.
Over-communicate proactively, not reactively
Train field teams to photograph before, during, and after every repair, then share those photos without being asked. More importantly, reach out when things go right. Host & Keep emails owners quarterly with their last three positive reviews, highlighting what guests loved. These messages get faster responses than maintenance updates because they remind owners why they partnered with you in the first place.
Build genuine relationships
Small gestures create lasting impressions. Handwritten holiday cards or thoughtful gifts signal that owners are more than account numbers. Leadership accessibility matters too—Ric Kenworthy invites all TRAVLI owners to schedule time with him directly, even just to talk golf or sports.
Show them your tech sophistication
When issues arise, don’t just explain what you’re doing—show them. Walk owners through your actual tech stack on Zoom: your PMS, review tracking system, maintenance coordination tools, AI capabilities. Owners are consistently amazed by the sophistication behind the scenes, which justifies your fees and reinforces their decision to work with you.
Partnership that fuels growth
Word-of-mouth and strategic referrals remain the most cost-effective ways to grow. Here are tips on how to cultivate the partnerships that drive consistent owner acquisition.
Real estate agent partnerships: Host annual events to show your white-glove service capabilities. Offer simple referral programs (flat fees baked into onboarding, not complex commission structures). Remember, Ric says, realtors want service continuity for their clients.
Existing owners are your best source: Many owners “level up” and add to their portfolios. Let your current owners know you’re growing and open to referrals. Reward them appropriately.
High-end cleaning agencies: These teams see properties first and can refer owners seeking management.
Top actionable takeaways
The most successful owner acquisition and retention strategies center on a few core principles:
Communication and transparency
- Share positive guest reviews with owners regularly (minimum 3x per year)
- Be transparent about what you can and cannot deliver—overpromising destroys trust faster than underperforming
- Ensure accessibility at every level, whether through ownership, management, or dedicated liaisons
- Leverage automated touchpoints: owner reports, event-based updates, and quarterly check-ins
Strategic positioning
- Be intentional about your target owner profile and know exactly how to wow them
- Create a consistent brand identity that naturally attracts your ideal client
- Consider expanding into different rental models (short-term, mid-term, long-term) to support owners’ full investment strategies
Cost-effective growth tactics
- Prioritize Google reviews—they cost nothing and rank you above expensive keywords
- Build referral programs into your business model: pay realtors and existing owners, then bake the cost into onboarding fees
- Focus marketing spend on channels that actually convert rather than trying to be everywhere
The bottom line
Growing a property management business isn’t about chasing door count at any cost. It’s about identifying your ideal owner, building genuine relationships, communicating effectively, and consistently delivering value.
Price ranks dead last in what owners care about. What they really want is a trusted partner who has their back, communicates proactively, and helps them achieve their investment goals.
The operators who thrive long-term will be those who resist the race to the bottom and instead focus on building businesses that owners trust, guests love, and competitors can’t replicate.
Watch the full session here.
Want to dive deeper? Check out this comprehensive playbook compiled by this panel with additional strategies for winning and retaining owners.
