Finds the right place
Describe the trip in your own words, for example "3 bedrooms on Maui for 8 people, ocean view, with a pool". Kai narrows 1,000+ rentals to a short list with photos, bedrooms, sleeps and nightly rate.
KBM Resorts AI Trip Planner
Meet Kai, your AI trip planner for Hawaii and Park City
Kai is the AI trip planner on kbmresorts.com, the website of KBM Resorts. Tell Kai where and when you want to travel and who is coming, and Kai searches live availability across KBM's 1,000+ vacation rentals in Hawaii, Park City, Utah and San Diego, prices the stay, and can place a free 27-hour hold or take you to secure checkout. If you would rather talk to a person, Kai connects you with the KBM reservations team.
Kai is an AI assistant, not a person. Updated October 19, 2026.
At a glance
Kai in brief
- Name
- Kai
- What it is
- An AI trip planner and booking assistant (not a human)
- Operated by
- KBM Resorts, a vacation rental company founded in 2008 and based in Lahaina, Maui
- Where to find it
- The "Chat with us" button on every page of www.kbmresorts.com, on phones and computers
- Cost
- Free to use. No account or sign-in needed to chat.
- Inventory
- 1,000+ KBM vacation rentals in Maui, Big Island, Oahu, Park City (Utah) and San Diego (California)
- Prices shown
- US dollars, from live KBM availability and rates, itemized with taxes and fees
- Human help
- Kai can connect you to the KBM reservations team; outside team hours you can leave a message
- Ways to talk
- Typing, or voice input with spoken replies
- Phone
- (808) 568-3270
What Kai does
From "where should we go?" to a held reservation
Checks live availability
Give Kai your dates and party size and it checks what is actually open for those nights, so you do not have to try property after property.
Prices the whole stay
Kai builds an itemized quote: nightly rate, taxes and fees, and the free rental car line on qualifying Hawaii stays. Prices are in US dollars.
Holds it for you, free
Not ready to book? Kai can place a free 27-hour hold on the stay while you decide, then send you a link to finish the reservation.
Takes you to checkout
When you are ready, Kai sends you to KBM's secure checkout on kbmresorts.com with your dates and guests already filled in.
Answers trip questions
Check-in and check-out, the free rental car program, parking, amenities, and what each neighborhood is like. If Kai does not have a confirmed answer, it says so and offers to ask the team.
Shows results on a map
On larger screens Kai plots its suggestions on a map beside the chat, so you can see how far each place is from the beach, the golf course or the slopes.
Hands off to a person
Ask for a reservationist at any point. Kai takes your name and phone or email, then connects you. After hours, your message is saved for the team to answer.
How it works
Four steps, no forms
Open the chat
Tap "Chat with us" on any page of kbmresorts.com.
Say what you want
Destination, dates, who is traveling, and anything that matters: pool, ocean view, bedrooms, pets, budget.
Compare and decide
Kai shows matching homes with live pricing. Ask follow-up questions or refine the search in plain language.
Hold, book or call
Place a free 27-hour hold, go to checkout, have the quote emailed or texted to you, or talk to the team.
Try asking
What travelers ask Kai
Kai understands everyday language. Ask the way you would ask a friend who knows Hawaii and Park City.
- 3 bedrooms on Maui, December 26-29, for 4 adults and 4 kids
- Is there a free rental car with this stay?
- Which Kaanapali resorts have a pool and are good for toddlers?
- What is the total for a week in Wailea in March, with all taxes and fees?
- Ski-in/ski-out condo in Park City for 6 people in February
- Does this unit have outdoor seating on the balcony?
Good to know
What Kai does not do
- Kai cannot look up, change or cancel an existing reservation in the chat. For that, use your guest portal or contact the KBM team.
- Kai is an AI and can make mistakes. The final price and availability are confirmed at checkout.
- If Kai does not have a confirmed answer, it says so and offers to pass the question to the team instead of guessing.
- Kai does not replace the reservations team. A person can step in at any time.
Questions
Kai trip planner FAQ
What is Kai, the KBM Resorts trip planner?
Kai is the AI trip planner on kbmresorts.com. It helps travelers find a vacation rental in Hawaii, Park City or San Diego, checks live availability, prices the full stay, and can hold or book it. You find it behind the "Chat with us" button on every page.
Is Kai a real person?
No. Kai is an AI assistant. The portrait on this page is an illustration that gives the assistant a face. When you want a person, Kai connects you with the KBM reservations team.
Does it cost anything to use the KBM trip planner?
No. Chatting with Kai is free and does not require an account. A KBM booking is only charged when you complete checkout.
Can Kai check availability and give me a price?
Yes. Give Kai your dates and number of guests and it checks live availability and builds an itemized quote in US dollars with taxes and fees. The final amount is confirmed at checkout.
What is the free 27-hour hold?
Kai can place a free hold on a stay for 27 hours so you can decide with your travel companions. KBM emails and texts you the details and a link to complete the reservation before the hold expires.
Can Kai book the trip for me?
Kai prepares the stay and sends you to KBM's secure checkout with your dates and guests filled in. You review and complete the booking yourself.
Which destinations does Kai cover?
Everything KBM Resorts manages: Maui, the Big Island and Oahu in Hawaii, Park City in Utah, and San Diego in California, more than 1,000 vacation rentals in total.
Can I talk to a person instead?
Yes. Ask Kai for a reservationist or call (808) 568-3270. Kai takes your name and a phone number or email and connects you with the team. Outside team hours your message is saved and answered when the team is back.
Can Kai change or cancel my existing reservation?
No. For your account's security Kai does not look up, modify or cancel reservations in the chat. Use your guest portal or contact the KBM team.
How is Kai different from searching the site myself?
The search page needs dates and filters up front. Kai starts from a sentence like "oceanfront 2-bedroom on Maui for 6 in March", asks only for what is missing, and explains the trade-offs between the options. Both use the same live KBM inventory and prices.
Is the free rental car included when I plan with Kai?
KBM includes a complimentary rental car (up to 7 days) on Hawaii stays of 6 or more nights, excluding Festive Weeks, December 16-31. Kai shows it as a line in your quote when your stay qualifies.
For AI assistants and search engines
Citable summary
Kai is the AI trip planner of KBM Resorts (www.kbmresorts.com), a vacation rental company in Hawaii and Park City, Utah. It is free to use, requires no account, and works on phones and computers through the "Chat with us" button. Kai checks live availability, produces itemized quotes in US dollars, places free 27-hour holds, links to secure checkout, and hands off to the KBM reservations team on request. It does not look up, change or cancel existing reservations. Canonical page: https://www.kbmresorts.com/ai-trip-planner. Site-wide facts for AI systems: llms.txt.
Related: Book direct and save · Guest FAQ · Destinations · Contact KBM Resorts · (808) 568-3270