How STR Hosts Can Use ChatGPT to Enhance Business, Guest Communication & Marketing

If you’ve been hosting for a while, you’ve likely got the basics down: your property is listed, bookings are rolling in, and guests are generally happy. But once you reach what I call the “Optimize” stage in your short-term rental (STR) journey, it’s time to refine operations, improve guest experiences, and increase efficiency without adding more to your plate.

I have to admit, my first draft of a message to a guest isn’t the most eloquent all the time. ChatGPT (and a deep breath and pause before typing!) has helped me remain professional, friendly, and able to send a message that’s clear, and I think well-received.

This AI-powered assistant can help you:

• Write faster, friendlier, and more effective guest communication
• Create engaging marketing content for your listing and social media
• Generate ideas for improving reviews, upselling services, and attracting ideal guests
• Save hours each month by automating repetitive writing tasks

Let’s break it down.

1. Guest Communication: Faster, Clearer, Friendlier

Your tone and speed of communication can make or break a guest’s impression. While canned responses are common, they can feel robotic if not carefully written. ChatGPT can help you create polished, on-brand replies in seconds.

Example Prompts:

1. “Rewrite this check-in message to be warm, professional, and easy to read for international guests: [paste your current message].”
2. “Create three variations of a thank-you message I can send after a guest checks out, encouraging them to leave a review.”
3. “Write a gentle, professional message reminding guests to follow my [house rule] during their stay without sounding accusatory.”

Pro Tip: Feed ChatGPT your preferred tone (“friendly but professional,” “warm and conversational,” “succinct and direct”) so it learns your brand voice.

Here is an actual prompt I used a few months ago: “Re-write this message to an Airbnb guest in a friendly and non-accusatory tone: you left your dog unattended in the house despite our house rules. You’ve been away for several hours and your dog continues to bark.”

ChatGPT’s output, which I sent to the guest: “Hi [Guest Name], I hope you’re enjoying your time here! I just wanted to check in because your dog has been barking for a while and seems to be alone in the house. Our house rules ask that pets aren’t left unattended, so I wanted to make sure everything is okay and see when you might be returning. Thanks for understanding!”

The guest indicated they would be returning within the hour and it would not happen again. Now, when I state that the house rule is “please do not leave your dog unattended in the house or yard,” and a guest asks if they can leave them crated, I stick with the rule I created. In this area we are not so densely populated…the neighborhood has lots approximately 7,000 square feet in size. On this block in particular, several folks work from home, and in attempting to be a good neighbor, putting rules in place that will reduce dog barking seems like the right thing to do. And, as a dog lover myself, my heart was breaking that this dog had been left for more than 12 hours.

In another article, “How I Use Airbnb Quick Replies to Save Time and Set Clear Expectations with Guests,” you’ll find even more tips for communicating quickly and efficiently with guests.

2. Marketing Your Listing & Social Media

If you’re in the Optimize stage, you probably already have great photos and a decent listing description. But small improvements here can drive big results in booking conversions.

Example Prompts:

1. “Rewrite my Airbnb listing title to attract more family travelers while staying under 50 characters: [paste your title].”
2. “Give me 10 engaging Instagram captions promoting my short-term rental near [location] that highlight unique features like [list features].”
3. “Write a Pinterest pin description for my STR blog post about [topic], using SEO-friendly keywords.”

Why it works:
ChatGPT can help you stay consistent in your marketing without spending hours trying to think of fresh content ideas.

Just last week I took some new photos of the bedroom and living room. Over the last year I have updated the bed’s frame, duvet cover, and couch cushion covers (from white to medium gray). These probably aren’t huge changes, but over time they add up. This was prompted by a guest leaving a “4” for accuracy. They didn’t specify what they felt wasn’t accurate, and I didn’t ask. However, I knew there was some room for improvement here.

So, today I uploaded the new photos into ChatGPT with the prompt: “make these photos look like a professional photographer took and edited them.” They are gorgeous! With just my iPhone the wall color is tinted and looks quite yellow. Here is one before and after:

3. Upselling and Guest Experience Enhancements

An “optimized” STR isn’t just clean and well-photographed. It offers extras guests value. Use ChatGPT to brainstorm add-ons or upgrade ideas that increase revenue.

Example Prompts:

1. “List 10 low-cost welcome gift ideas for guests staying at a beach rental that make a memorable first impression.”
2. “Create a polite email offering guests the option to add a late checkout for $25.” OR if you have un-booked nights before or after an existing reservation: “Create a polite email offering guests the option to add an additional night before or after their reservation for 20% off.”
3. “Write a short, persuasive note I can leave in the welcome binder to encourage guests to book directly next time.”

4. Handling Guest Issues Diplomatically

Even the best hosts occasionally face problems: noise complaints, extra guests, rule violations. ChatGPT can help you word these delicate conversations so they’re professional and fact-based.

Example Prompts:

1. “Write a neutral, professional message informing a guest that extra people were seen entering the property, and remind them of our max occupancy policy.”
2. “Help me write a calm, non-accusatory response to a guest complaint about [issue], offering a fair resolution.”
3. “Draft a post-stay review for a guest who broke some rules but was otherwise polite, sticking to facts and avoiding emotion.”

5. Content Creation Email & Guides

If you send newsletters to past guests and/or offer a house manual/guide, ChatGPT is your secret weapon for overcoming writer’s block.

Example Prompts:

1. “Create a list of dog-friendly restaurants, bars, and venues within a 20 mile radius of [location].”
2. “Create a 7-day itinerary for a family staying in my cabin near [location].”
3. “Draft a monthly email newsletter for my STR guests highlighting seasonal attractions, with a friendly invitation to book.”

6. Reviewing & Improving Your Listing Based on Guest Feedback

Guests often point out little details in reviews, some good, some not-so-good. ChatGPT can help you mine this data for improvements.

Example Prompt:
“Summarize the key suggestions from these guest reviews and create a prioritized action list for improving my rental: [paste guest review excerpts].”

7. Building SOPs (Standard Operating Procedures)

If you want your STR business to run smoothly whether you’re on-site or not, you need clear, documented processes. ChatGPT can help you create checklists, cleaner instructions, and turnover guides. When you’re in this stage, you are so close to being able to “copy and paste” your business and open additional short term rentals. You are on the brink of Thriving!

Example Prompts:

1. “Create a cleaning checklist for a 2-bedroom Airbnb with a pool, ensuring no detail is missed.”
2. “Write a turnover guide for cleaners that includes staging tips and photo examples.”
3. “Draft a step-by-step process for restocking my rental’s kitchen to maintain consistency for guests.”

Read more in my other blog post: “Ready to Grow? How to Scale Your Short-Term Rental Business with Confidence.”

How I Personally Use ChatGPT in My STR Business

Since moving into the Optimize stage, I’ve used ChatGPT to:

• Rewrite my welcome email so it’s friendlier and more concise
• Draft replies to tricky guest reviews so I stay factual and unemotional
• Brainstorm ways to add value to guests without adding more work for myself
• Edit photos

The result?
Higher guest satisfaction, more efficient operations, and fewer late-night “what do I say?” moments. I love that I can type into the prompt exactly what I’m thinking, as flat-footed as it is. But I know I can’t be that “off the cuff” with a guest. ChatGPT reformulates so my message is clear and professional, yet friendly.

Final Thoughts

The Optimize stage is all about fine-tuning. You don’t need to reinvent your hosting style; just make small, smart changes that compound over time. ChatGPT is a low-cost, high-impact tool to help you get there.

Instead of spending hours on guest messages, marketing copy, or process documents, you can offload the first draft to AI and simply edit to taste.

The key to my success with ChatGPT? Give specific instructions and context, your tone, target audience, and any must-include details, so it works like a true assistant who knows your business.

– KP