The ChatGPT AI Roadmap to Short Term Rental Success

by The Darwinian Doctor

In this post, I outline the artificial intelligence driven plan that ChatGPT created to improve my short term rental business.

This post may contain affiliate links.

The Airbnb Bust

Has the Airbnb Bust affected your short term rental business?  This phenomenon basically refers to a slump in booking, daily rates, and revenue for short term rental owners.  While it obviously varies from market to market, the general themes are consistent:  oversupply of short term rentals, combined with decreased demand, is leading to less profit for short term rental owners.  

As the linked article above states, though, this isn’t the case everywhere.  In fact, 2022 was Airbnb’s first profitable year.  Also, AirDNA estimated that overall short term rental demand increased in 2022 about 20% year over year.  

So clearly, there’s short term rental demand out there.  But due to increased competition in some markets, the demand may be preferentially funneling to the owners who are fully optimizing their short term rental business.  

My Experience in Broken Bow

As I’ve written about before, I have a luxury short term rental in Broken Bow, OK. We bought this cabin about 1 year ago at what I can now see was the height of the real estate market. Since then, the income has been overall good, but variable from month to month.

I’ve noticed a decrease in average daily rates and bookings, so I’m looking for suggestions on how to funnel more of that short term rental traffic to my cabin.

You can check out the cabin on our private booking site:

But what should we do to actually change to increase bookings?

ChatGPT to the rescue

I decided to use the expertise of ChatGPT to help me improve my short term rental business. Specifically, I asked it this: “How do I increase the bookings and profitability of my short term rental, which is a 4 bedroom cabin in broken bow, Oklahoma.”

 Below, I’ve transcribed the suggestions that ChatGPT gave me, as well as where I am on instituting the plan.  

What is ChatGPT?  

For those of you who’ve been living under a rock, I’ll give you a succinct explanation about the nature of this exciting form of artificial intelligence.

ChatGPT is the one of the first artificial intelligence tools that is widely being used by the public.  It’s a “large language model,” which means that it’s been trained on terabytes of text data and can now generate responses to text prompts that are very similar to human generated text. ChatGPT is a form of “generative AI” that can generate new, unique content.

What makes Chat GPT unique is its incredibly natural and convincing responses.  After it responds, you can ask it for more details, redirect conversations, and hone in your desired response.  It’s really something you have to experience to understand. 

You can do this by going to this website and creating a free account:

I pay a monthly subscription to get access to the latest and greatest iteration of the tool:  ChatGPT-4, which excels at reasoning skills.

ChatGPT’s response

The artificial intelligence tool first gave me a general game plan.

“To increase bookings and profitability for your 4-bedroom cabin in Broken Bow, Oklahoma, you’ll need to optimize your property’s online presence, improve guest experiences, and promote it effectively on social media.”


It then gave me more details.

 “Here’s a comprehensive plan to help you achieve these goals:”

Optimize your online listing

  • High-quality photos: Invest in professional photography to showcase your property in the best light. Include pictures of all rooms, exterior, and any amenities.
  • Detailed description: Write a compelling and detailed description, highlighting the unique features, amenities, and nearby attractions. Don’t forget to mention the cabin’s capacity, rules, and any extra services you offer.
  • Competitive pricing: Research similar properties in the area and set competitive prices. Use dynamic pricing tools to adjust your rates based on demand, seasonality, and local events. 
  • Reviews: Encourage your guests to leave reviews and promptly respond to them. Positive reviews can significantly impact your listing’s visibility and booking conversion rates.

Last week, I got busy instituting these suggestions.

Luckily, I already have high quality photos for my property.  While they’re not as good as the photos for my short term rental in Palm Springs, I think the photos of the cabin adequately highlight its rustic beauty.  I did decide that my previous first photo was too dark, so I switched it to an inviting shot of the patio.  

Prior opening photo
New opening photo

I took another look at the description of the property, and I made sure that my settings in the OwnerRez management software matched what popped up on the Airbnb listing

Next, I decided to make the property pet friendly, so I updated that in the description and added appropriate fees for this as well. 

In terms of pricing, I revisited the price settings on Pricelabs, which is the dynamic pricing software that I use for my short term rentals.  This indicated that average daily rates had slipped quite a bit since the last time I checked.  I adjusted my prices down to the 60th percentile for my type of property (from $525 to $457 a night). 

Next ChatGPT recommendations:  Improve the Guest Experience

The next suggestions that I got from ChatGPT had to do with the guest experience in my short term rental.

The Guest Experience

  • Welcome guide: Create a comprehensive welcome guide with clear instructions for check-in/out, house rules, and recommendations for local attractions, restaurants, and activities.
  • Amenities: Ensure your cabin is well-stocked with essential amenities, such as Wi-Fi, toiletries, linens, and kitchen supplies. Consider adding unique features or extras like a hot tub, game room, or outdoor activities to make your property stand out.
  • Communication: Be responsive and proactive in your communication with guests. Provide them with a direct contact number for any inquiries or assistance during their stay.

I already have a comprehensive digital welcome guide to the cabin.  We email this to all our guests a week prior to their stay.  The guide has all of the information listed above.  

I’d also consider our cabin already well stocked with high speed internet, a hot tub, high quality Brooklinen linens, and comprehensive kitchen supplies.  

Well stocked kitchen

In terms of communication, we recently created an OpenPhone account, which is a virtual phone number that is provided to our guests.  Between me and my virtual business manager, we will have 24/7 coverage for concerns.  

ChatGPT recommendations:  Social Media Promotion

The next set of suggestions from ChatGPT focused on the social media presence for my short term rental.

Social media promotion:

  • Platforms: Create dedicated profiles for your cabin on popular social media platforms like Instagram, Facebook, and Pinterest.
  • Content: Post regular content showcasing your cabin, local attractions, events, and guest experiences. Use high-quality images, engaging captions, and relevant hashtags to increase visibility.

This was certainly an area that was lacking.  Although I have a strong blog and social media presence via the Darwinian Doctor, I can’t say the same for the short term rental business.

So last week, I created an Instagram account and linked this to the Facebook page for the business.  I also created a plan with my digital business manager to post regular videos and photos of the property on these social media outlets.  

ChatGPT Recommendations: Miscellaneous

Next, the AI tool recommended a hodgepodge of other suggestions that I have yet to implement:

  • Collaborations: Partner with local businesses, travel influencers, and bloggers to promote your property and reach a broader audience.
  • Ads: Run targeted social media advertising campaigns to reach potential guests who may be interested in visiting Broken Bow.
  • Utilize multiple booking platforms:
    • Listing sites: List your cabin on multiple short-term rental platforms like Airbnb, Vrbo, and to increase visibility and reach a wider audience.
    • Local tourism sites: Partner with local tourism websites or travel agencies to promote your cabin.
  • Offer promotions and incentives:
    • Discounts: Provide special discounts for off-peak seasons, longer stays, or repeat guests to encourage bookings.
    • Package deals: Create package deals that include local attractions or activities to make your property more appealing to potential guests.


In conclusion, there are a lot of things to do if you feel your short term rental isn’t pulling its weight. If you can do all of this, perhaps you can avoid the Airbnb Bust and bring in more revenue!

So the purpose of this post is really two-fold. First, I want to give you some insight into ways to improve your short term rental business. Secondly, I want to encourage you to take advantage of artificial intelligence. We’re now firmly in the age of AI, and those who don’t learn how to use this technology will be left behind.

As for a parting comment, I’ll leave it up to ChatGPT:

In conclusion, harnessing the power of artificial intelligence, particularly through ChatGPT’s valuable insights, has significantly elevated my short-term rental experience, and I wholeheartedly recommend others to embrace this cutting-edge technology to optimize their property’s potential.


–The Darwinian Doctor

Are you excited to improve your short term rental? Or did you just get distracted by the power and promise of artificial intelligence? I’ll be happy with either outcome. Let me know in the comments below, and please subscribe to the blog!

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Since everyone is different, it may not be appropriate to generalize my doctorly advice to your own situation. Please run all medical, life, and financial advice by your own physician or financial professionals before applying it to your own life! Consider all information for your entertainment only!

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