By Tara Hubbard, Wonderfield Farm

Whether you’re launching your first listing or ready to scale a boutique short-term rental brand, this guide distills real-world wisdom into practical steps to get started, avoid burnout, and create a guest experience that earns five stars while staying true to who you are.

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Table of Contents

1. Getting Started
2. Guest Communication & Automation
3. Branding, Positioning & Setting Expectations
4. The Psychology of Hospitality
5. Listing Optimization & Setup
6. Operations: Check-In, Directions, & Daily Details
7. Dealing with Issues & Refund Requests
8. Risk, Insurance & Legal Considerations
9. Events, Experiences & Regenerative Touches
10. Bonus Tips: What I Wish I Knew

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1. Getting Started

• Hosting on Airbnb is more than listing a property, it’s a hospitality business.
• Start small, learn fast, and think long-term: automation, branding, and boundaries are essential from the beginning.

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2. Guest Communication & Automation

• Use platforms like Hospitable to automate:
  • Booking confirmations
  • Check-in instructions
  • FAQs (e.g., WiFi info, window quirks)
  • Check-out procedures
• Automation reduces guest messaging by 80%—saving your sanity.
• AI is promising, but be careful not to lose your human, nature-based tone if that’s central to your brand.

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3. Branding, Positioning & Setting Expectations

• Be brutally honest in your listing: highlight what isn’t included (e.g., no TV, no WiFi) and celebrate what is e.g. biodiversity (there may be bugs), slow living (no wifi).
• Undersell, then overdeliver. Avoid guest disappointment by:
  • Clearly communicating quirks and limitations.
  • Reframing them as intentional design choices: “We celebrate biodiversity, so you may encounter spiders or wasps.”
• Include details like:
  • “No air conditioning” → “Our rooms are naturally cooled by thick stone walls.”
  • “No TV” → “Instead, reconnect with nature under ancient oaks.”

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4. The Psychology of Hospitality

• Guests often just need reassurance, not perfection.
• When something goes wrong, show them you’re on it—even if you can’t fix it right away.
  • Send someone to check on the issue = instant peace of mind.
• The “Flight Attendant Theory”: Guests pick up on your energy. Stay calm, confident, and responsive.

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5. Listing Optimization & Setup

• Photos should be accurate! Don’t oversell.
• Use all available sections in the listing to paint a full picture:
  • “The Space”
  • “Guest Access”
  • “Other Things to Note”
  • “Neighborhood”
• Include a Welcome Booklet:
  • House quirks
  • How-to guides (water heater, windows)
  • Local tips
  • Your story and property history

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6. Operations: Check-In, Directions & Daily Details

• Self Check-In is king – guests love autonomy.
• Use a lockbox or keypad and send instructions 3–5 days prior.
• Ensure your map pin and directions are 100% accurate.
• Keep laminated cheat sheets inside for:
  • WiFi
  • Instructions for home + property

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7. Dealing with Issues & Refund Requests

• Airbnb often sides with the guest, especially if you don’t have clear documentation.
• Be ready for “problem guests” who want to leave and make a case for a refund.
• Always respond professionally:
  • “We’re sorry you’re not comfortable. Our listing accurately reflects the experience and we’ve delivered the stay promised.”
• Document quirks, warnings, and rules in both the listing and welcome book.

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8. Risk, Insurance & Legal Considerations

• In the U.S., layers of protection matter:
  • LLC for liability protection
  • General liability insurance
  • Airbnb’s Host Guarantee (often up to $1M in coverage)
  • Agritourism legal protections (for farm-based properties)
• Know your local requirements (permits, business licenses, insurance).

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9. Events, Experiences & Regenerative Touches

• Hosting yoga, cooking classes, or nature walks? Frame it as an included experience for guests.
• Build regenerative value:
  • Use high-quality, sustainable materials (e.g., 100% cotton linens, reusable soap dispensers)
  • Support local vendors (e.g., soaps, coffee roasters)
  • Invest in your community and highlight that impact in your listing

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10. Bonus Tips: What I Wish I Knew

• Don’t host events + guests simultaneously until you have strong systems.
• Keep communication on-platform unless you deeply trust the guest.
• Choose a strict cancellation policy to avoid last-minute losses.
• Build your listing for your ideal guest, not everyone.
• Be ready for the unexpected. From broken lightbulbs to scared cows, stay graceful under pressure.