In this webinar, Hostaway’s team is joined by Kyle Loveland, CEO of Dream Space Luxury Rentals and Hostaway Special Projects Lead, to explore practical ways short-term rental operators can use AI today.
You’ll learn how to go beyond simple Q&A with ChatGPT and tap into its generative, insights-driven power. Kyle shares three actionable AI prompts that property managers can apply immediately to save time, boost efficiency, and increase revenue.
What you’ll discover in this session:
✅ How to analyze financial reports with AI to uncover booking trends, optimize ADR, and reduce turnover costs.
✅ How to create custom web pages (like FAQ sections) for your direct booking site—even if you’re not a developer.
✅ How to analyze guest conversations, identify FAQs, and generate message templates to streamline guest communication.
We also introduce the CRIT framework (Context, Role, Interview, Task) to help you write powerful AI prompts that deliver the best results.
Whether you’re new to AI or already experimenting, this session gives you concrete examples, tools, and strategies to get started today.
00:00 – Introduction & Welcome
00:36 – About Hostaway & our global community
01:03 – Hostaway Coachella & upcoming events
01:46 – Why real-life AI use cases matter
02:08 – Example: Using ChatGPT for customer support (dishwasher troubleshooting)
03:11 – Moving beyond Q&A: Generative AI & insights
03:56 – The CRIT Framework for better AI prompts (Context, Role, Interview, Task)
06:08 – Introducing Kyle Loveland & session overview
Prompt #1: Financial Report Analysis
07:58 – Setting up the financial analysis prompt
08:53 – Why analyzing beyond dashboards is key
09:43 – Identifying patterns to optimize ADR, occupancy & revenue
10:56 – Customizing prompts to fit your property goals
12:01 – GPT outputs: graphs, insights & KPIs
Prompt #2: Building Custom Web Pages
12:38 – Using ChatGPT to generate HTML for FAQ sections
13:26 – What “vibe coding” means & why it matters
14:36 – Tools beyond ChatGPT (Claude, Gemini, Grok)
15:24 – How to iterate & refine code with AI
16:10 – Adding AI-generated pages into Hostaway booking sites
16:53 – Customizing look, behavior & user experience
17:57 – Why FAQ pages are powerful for branding & SEO
18:44 – Example output of an AI-generated FAQ page
Prompt #3: Guest Conversation Analysis
20:28 – Extracting FAQs & templates from guest messages
21:08 – Why conversation analysis saves time & improves communication
22:27 – Using APIs & Google Scripts to pull data
23:27 – Automating conversation exports into Google Sheets
25:25 – Setting up API keys & integrations
26:12 – Running scripts to pull conversation history
26:33 – Uploading CSVs into ChatGPT for analysis
27:16 – Creating FAQs & even tone-of-voice guides for AI replies
Closing & Resources
28:39 – Bonus: Personalizing AI guest responses with brand tone
29:06 – Hostaway AI resources, support, and marketplace tools
29:26 – Hostaway CSM Office Hours webinars
29:43 – Wrap up & thank you
🔗 Find out how Hostaway's Vacation Rental Software boosts your business
🧡 About Hostaway 🧡
Hostaway is an All-in-One vacation rental software solution for growing property managers. From marketing and guest communication to operations and reporting, our platform helps you scale with ease. With over 100 integrated tools in our marketplace, Hostaway grows with you—whether you manage two listings or two thousand.
#AI #vacationrental #shorttermrentals #propertymanagement #vacationrentalsoftware
