Vacation rentals market is currently evolving these days. managing vacation properties can be both rewarding and challenging. Whether you’re just starting out with a handful of properties or scaling up to manage dozens, the approach you take can dramatically affect your success, profitability, and sanity.
This post breaks down the key differences and provides actionable tips for managing a few properties (20 or less) versus multiple properties (30 or more)—with insights that will help you stay efficient, organized, and guest-focused at every stage.
Managing a Few Properties (20 or Less)
Managing fewer than 20 vacation rentals is typically more hands-on and personal. You often have more control over the guest experience, property maintenance, and pricing strategy.
✅ Tips for Success:
1. Personalize Guest Experiences
With fewer units, you have more time to go the extra mile. Add local touches, personalized welcome notes, or complimentary snacks. Guests love that warm, personal vibe.
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Check out Airbnb’s guide to creating a standout experience.
2. Use a Simple PMS (Property Management System)
You probably don’t need enterprise-level software yet. Tools like Hostaway or Lodgify can help automate booking calendars, guest messaging, and reviews without overwhelming you.
3. Automate Where Possible
Even with a small portfolio, automation saves time. Use tools like:
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PriceLabs for dynamic pricing
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Hospitable for automated guest messaging
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TurnoverBnB for cleaning schedules
4. Build a Reliable Local Team
If you’re managing remotely or juggling multiple markets, having a dependable housekeeper, handyman, and co-host is essential. Vet thoroughly, and pay fairly—it’s worth it.
5. Maintain Strong Owner Communication (If You Co-Host)
If you co-host properties for other owners, set clear expectations, provide regular updates, and be transparent about performance metrics.
Managing Multiple Properties (30 or More)
Vacation Rentals Scaling to 30+ properties changes the game entirely. It becomes less about individual touches and more about systems, standardization, and delegation.
✅ Tips for Success:
1. Upgrade to an Advanced PMS
At this scale, a robust PMS is essential. Consider platforms like:
These platforms offer enterprise features like multi-channel distribution, owner portals, trust accounting, and custom workflows.
2. Standardize Everything
For Vacation Rentals, Consistency is key for efficiency. Create SOPs (Standard Operating Procedures) for:
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Cleanings and inspections
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Guest communications
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Check-in/check-out processes
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Inventory and restocking
Keep documentation in tools like Notion or Google Drive.
3. Create Specialized Roles
Break your operations into specialized roles:
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Guest Experience Manager
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Maintenance Coordinator
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Revenue Manager
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Virtual Assistants for customer support or reviews
It would be best for Large number of Vacation Rentals, Outsourcing or hiring allows you to scale without burnout.
4. Build a Brand
At scale, brand trust is everything. Create a consistent name, logo, tone, and visual identity. Invest in a professional website with direct booking capabilities (try Boostly or Uplisting).
Having a brand also lets you centralize reviews and email marketing to grow guest loyalty.
5. Use Advanced Analytics
Revenue management at scale is all about data. Leverage tools like:
These help optimize pricing, monitor competition, and track performance across your entire portfolio.
Bridging the Gap: Scaling Without Losing Control
The transition from managing a few properties to dozens is one of the most critical phases for any short-term rental operator. Here are some things to keep in mind during the transition:
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Don’t rush scaling — quality over quantity. Nail down your systems before adding more units.
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Focus on delegation — hire before you’re overwhelmed.
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Leverage tech — every repetitive task can probably be automated or delegated.
As you grow, remember that guest satisfaction and operational efficiency must grow together. Keep tabs on reviews, response times, and maintenance metrics.
Final Thoughts
Whether you’re managing five cozy cottages or fifty high-performing homes, success comes down to structure, service, and smart systems. The fewer properties you manage, the more time you can spend curating experiences. But as you grow, it’s all about scaling sustainably—through technology, people, and processes.
Still deciding whether to stay lean or scale big? Start by mastering the first 5, then build out your systems like you already have 50. That mindset shift will prepare you for growth without chaos.
Looking to streamline your vacation rental operations?
Here are some helpful links to get started:
Want to learn how to position your property as a top vacation rental destination? CLICK HERE
