We Asked ChatGPT to Manage Our Rental—And Its Advice Was Alarmingly Good

Oh, ChatGPT. You’re our future robot overlord, aren’t you? From writing haikus on the fly to helping people create meal plans and fine-tune their resumes, you’ve offered no shortage of ways to help people streamline their lives (and, perhaps, make them fear for their jobs).

With a down-ish economy, back-to-office mandates up and way more houses available on Airbnb, we’ve had a much harder time solidly booking Maywood, our medium-term rental. As we started brainstorming ways to drum up business, we thought about the buzzy new bot everyone’s talking about, and decided to challenge ChatGPT: What’s the best way to rent out our Airbnb right now?

(Note: We’ve trimmed some of the answers to eliminate redundancies.)

The initial advice was pretty basic, but good for any newbies:

• Optimize your listing: Make sure your listing has high-quality photos and a detailed description of your property, including information about the amenities and local attractions.
• Set a competitive price: Research other listings in your area to make sure you’re pricing your property competitively.
• Respond quickly to inquiries: Responding promptly to potential guests can increase the chances that they’ll book your property.
• Keep your calendar up to date: Make sure your calendar is always up to date so that potential guests can see when your property is available.
• Get good reviews: Encourage guests to leave reviews and respond to any negative feedback promptly.
• Be available for your guests: Answer any questions they might have and be responsive to any issues that arise during their stay.

So we dug deeper: What, specifically, could we do to rent out our Airbnb in Clearwater, Florida?

• Target the right audience: Clearwater is a popular vacation destination, so consider targeting families, couples, and groups of friends looking for a beach getaway.
• Leverage local attractions: Clearwater is home to many popular attractions such as the Clearwater Marine Aquarium…Make sure to mention these local attractions in your listing to attract potential guests.
• Utilize local events and festivals: Clearwater hosts many events and festivals throughout the year, such as the Clearwater Beach Taste Fest and the Clearwater Jazz Holiday. Consider offering discounts or special deals to guests attending these events.
• Optimize your listing for the season: Clearwater’s peak tourist season is during the winter months, so make sure your listing is optimized for those months.
• Partner with local businesses: Consider partnering with local businesses such as restaurants, rental companies, and tour operators to offer your guests discounts and special deals.
• Use social media platforms: Utilize social media platforms like Instagram, Facebook and Twitter to promote your listing and reach a larger audience.
• Make sure you are following all local laws, regulations and taxes.
• Be flexible with your rental policies: Consider being more flexible with your rental policies, such as allowing pets or offering longer stays at a discounted rate.
• Create a loyalty program: Create a loyalty program to encourage repeat business by offering discounts or other incentives to guests who have stayed with you before.
• Offer additional services: Consider offering additional services such as airport transportation, rental car or bike rental, or a meal delivery service to make the guest experience more enjoyable and convenient.
• Use targeted advertising: Use targeted advertising to reach potential guests who are most likely to book your property.
• Update your property: Keep your property updated and well-maintained to ensure that it remains attractive to potential guests.
• Get involved in your community: Get involved in your local community by supporting local events, festivals, and charities. This can help to raise awareness of your property and attract potential guests.
• Continuously evaluate your pricing strategy: Keep an eye on your pricing strategy, look at the industry trends, check your competitors and adjust accordingly to attract more bookings
• Utilize corporate housing platforms: List your property on corporate housing platforms such as Hometogo and Furnished Finder, which cater to long-term renters.
• Offer flexible lease terms: Consider offering flexible lease terms, such as month-to-month leases, to attract guests who are looking for a more flexible rental option.
• Partner with relocation services: Partner with relocation services to help fill your property with guests who are moving to the area for work or other reasons.
• Network with local employers: Network with local employers to learn about their housing needs for employees who may be relocating to the area.

So, What Are We Doing With All This Info?

This was the point where we got inspired, and decided to start testing an exclusive discount for our Instagram followers (which generated a few inquiries) and diversifying our listings (we’ve joined VRBO and Furnished Finder, and we’re looking into Google Vacation Rentals). Our next step is to try partnering with relocation services in the area, and if all else fails, discounting stays just to cover (most) of our costs.

If you’re an Airbnb or vacation rental host, what strategies are you trying? Is there anything we’re overlooking, in your opinion? I’d love to hear from you at candace[at]lifebetweenweeknds.com.