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Vacation Rental Marketing on Maui: What ChatGPT Names and What Google Shows Next

Hayden BondOctober 20, 202611 min read

Vacation Rental Marketing on Maui: What ChatGPT Names and What Google Shows Next

ChatGPT named a place to stay 327 times in 108 answers about where to stay on Maui, and only 10 of those names were individual vacation rentals. When we searched Google for the places it kept naming, 40 of 43 searches brought up a Google panel about the property. So vacation rental marketing on Maui has two jobs now: get your property named, and make sure it holds up when a traveler looks it up.

Of the 327 names ChatGPT gave in our Maui answers, the share that were individual vacation rentals. Condo complexes, resorts and hotels made up most of the rest.

Source: Plate Lunch Collective field study, October 19, 2026

We asked ChatGPT the questions families ask about where to stay on Maui, three times each, then looked up its picks on Google. It's the question behind our hospitality work.

Vacation rental marketing now has to work in both ChatGPT and Google

In my view, this isn't simply Google against ChatGPT. Each one has its place, and right now that's the shape of the new funnel. The way I see it, ChatGPT recommends a place and links to it, then the traveler hops over to Google to check that it's real and to book it.

We go into that split, with AI search making the recommendation and Google taking the action, on our AI search optimization page. OpenAI made a similar call for product shopping in March 2026: ChatGPT helps people find and compare products, and the purchase usually happens on the merchant's own site or app. OpenAI's announcement is about retail, not travel.

ChatGPT and Google mostly cite different sites. Only 10% of the sites ChatGPT cited for a question were also in Google's top 10 for it.

	ChatGPT	Google
Cited most	Travel guides and blogs, in 69% of answers	Video or social posts, in 90% of AI Overviews; review sites, in 87%; Tripadvisor in 25 of 30
Businesses' own sites	42% of answers	5% of the top three regular results

Cited most

ChatGPT

Travel guides and blogs, in 69% of answers

Google

Video or social posts, in 90% of AI Overviews; review sites, in 87%; Tripadvisor in 25 of 30

Businesses' own sites

ChatGPT

42% of answers

Google

5% of the top three regular results

We asked five of the same questions about Oahu and about Kauai, and the mix changed: on Oahu, 93% of answers cited travel guides and 53% cited rental managers. On Kauai, businesses' own sites showed up in 67% of answers, as often as travel guides. These checks were small, 15 answers per island.

So showing up on Google and getting named by ChatGPT take different work.

In my view, the next step is AI agents that do the booking with less and less help from the traveler. Meta's Muse agent can book appointments and make purchases for you, asking you to confirm before a purchase, and OpenAI's dots can make purchases within rules the owner sets. Our agentic commerce post covers the rest.

ChatGPT's list changed from one run to the next

We asked each of our 36 questions three times and checked which places came back. Only 15% of the places named for a question came back in all three runs. Most, 63%, showed up once and never again.

How many of the three runs named the same place

All three runs

15%

Two of three runs

22%

One run only

63%

Plate Lunch Collective field study, October 19, 2026. 36 Maui questions, three ChatGPT runs each, US, logged out.

So one mention is a maybe. If someone tells you ChatGPT recommended your condo, ask the same question again. Then ask it again. A place that comes back every time is in a different spot from one that showed up once.

Our runs were logged out, so these are answers with no history behind them. I'd say a traveler's stored preferences, their history and how they word the question all shape which properties ChatGPT picks. That's my read, and this study can't show it. I wrote more about how ChatGPT changes its answer for each person.

ChatGPT names the complex or the resort, not the unit

Of the 327 names ChatGPT gave, 119 were condo complexes, 118 were resorts and 70 were hotels. Individual vacation rentals: 10. That's 3%. When ChatGPT pointed to a condo, it almost always named the complex.

If you own a single unit, I'd call that an uphill battle. Complexes, resorts and hotels have reviews piled up in one place, press coverage, and booking sites all promoting them and confirming their amenities and location. That gives AI more confidence to recommend them. That's my explanation, not something we measured. We counted what got named, not why.

It doesn't mean it's impossible. Individual rentals usually have character, a location or amenities that make them special. Those appeal to travelers looking for something specific. I'd lean on that rather than try to battle a hotel.

Our data points the same way. Of the 10 individual rentals ChatGPT named, 7 came from two questions: one asking for wheelchair-accessible places to stay and one asking for pet-friendly places. When the traveler asked for something specific, a rental that offered it got named.

What Google shows when a traveler searches your property's name

Next we tested the second half of that funnel. We took the 43 places ChatGPT named in at least two of three runs of the same question. Then we searched each one on Google twice, the way someone would after picking it: the name, then the name plus "book."

Google turned the name search into a shopping page. Of the 43 name searches, 40 showed a Google panel about the property, and 31 of those showed prices or booking options from booking sites. Booking sites made the top 10 for 35 of the 43.

What we searched on Google	Booking-site results in the top 10, across all 43 places	Searches with an AI Overview
The property's name	47	37 of 43
The name plus "book"	82	42 of 43

What we searched on Google

The property's name

Booking-site results in the top 10, across all 43 places

Searches with an AI Overview

37 of 43

What we searched on Google

The name plus "book"

Booking-site results in the top 10, across all 43 places

Searches with an AI Overview

42 of 43

Adding "book" nearly doubled the booking sites, from 47 to 82. My read is that Google treats that second search as a buying search. Once the traveler has picked a place, the next search is about booking it. That's also why I think the big booking sites show up. They update their prices all the time and make booking easy. That doesn't mean the property's own site has a problem. The sites Google showed were built for buying searches.

Where your own website shows up on Google

Your own site is usually there, just not always where a traveler scrolls. It was the first regular result in 19 of the 43 name searches. In 17 more, it wasn't in the regular results at all. But Google's panel about the property linked to it in 15 of those 17, and the AI Overview cited it in 14. The list of links a traveler scrolls was mostly other sites: resellers, booking sites, Tripadvisor, Reddit and travel guides.

Chains and independents looked about the same here. The property's own site came first for 6 of 14 chain properties and 13 of 29 independents.

The AI Overviews cited both sides. Across the 86 searches, 79 overviews listed sources. Of those, 59 cited the property's own site, 62 cited a booking site and 46 cited Tripadvisor.

We didn't measure where anyone booked. This shows what a traveler would see, not what they did. It's still worth checking both spots on your own name search, the panel and the links, because they're not the same place.

What to check about your property this week

None of this needs a tool.

Ask ChatGPT the question your guests ask, in their words, while logged out. Ask it three times. Write down whether your property is named every time, once, or not at all.
If you own a unit, ask about your complex too. See whether the complex gets named and where its link goes.
Search your property's name on Google. Then search it again with "book" on the end. Is your own site linked from Google's panel about your property? Is it in the links below? Is it cited in the AI Overview?
Read your own site the way a traveler would. Does it say plainly what your place has that no other property does?

Tell travelers what no other property has

Nothing surprises me in search anymore. These were logged-out sessions, and search keeps changing on every platform. Next month the screen could look different because more people use it.

The advice still stands. Let travelers know what's unique about your property, the thing no other property has. And speak to your audience, not just to search volume.

If you run a hotel, resort or rental, our hospitality page is the place to start. If you'd rather we take a look, the AI Search Game Plan is a one-time review of how AI assistants describe your property and what to fix first.

How we ran this study

What we asked: 36 questions a traveler might ask about where to stay on Maui, in six groups: where on the island, what kind of place, specific needs, booking, comparisons, and stay plus plans. We added 10 check questions for Oahu and Kauai.
How: each question three times in ChatGPT through DataForSEO's ChatGPT scraper, from a US location, logged out. That's 108 Maui answers and 30 check answers. Each Maui question also ran once on Google from the US, where an AI Overview showed on 30 of 36.
The second search: the 43 places ChatGPT named in at least two of three runs of the same question, searched on Google by name and by name plus "book." That's 86 searches, desktop, US, logged out.
Booking sites here means online travel agencies and rental marketplaces such as Expedia, Booking.com and Vrbo. Tripadvisor and rental managers are counted separately.
When: October 19, 2026.
How we sorted it: each cited site tagged by hand by type (guide, booking site, review site and so on), and each named place coded by type from the answer text.
Limits: a sample on one day, not a census. We have no booking data, so this shows where ChatGPT and Google point, not where anyone booked.
We plan to run the same questions again and report what changed.

The questions we asked

The 36 Maui questions, as we asked them:

Where should we stay on Maui for our first trip
What's the best area of Maui to stay for a family with young kids
Which part of Maui is best for a honeymoon
Where should we stay on Maui if we want to be near good snorkeling
Is Kihei or Wailea better for a family vacation on Maui
Where should we stay on Maui for a quiet beach and fewer crowds
Which side of Maui has the best weather in winter for a beach vacation
Where can we stay on Maui without renting a car
Should we stay at a resort or a condo on Maui with kids
Is a vacation rental or a hotel better for a week on Maui
What's a good family resort on Maui with a kids club
Condo rentals on Maui with a full kitchen near the beach
Quiet or adults only hotels on Maui for a couple
Small boutique hotels on Maui that aren't big resorts
Affordable places to stay on Maui that are still nice
Where should we stay on Maui with two kids, we want a kitchen and to be near a calm beach
Maui hotels with free parking and no resort fee
Wheelchair accessible places to stay on Maui
Pet friendly places to stay on Maui
Where should I stay on Maui for a month long stay
Places to stay on Maui with a shallow pool for toddlers
Where to stay on Maui for a family trip with grandparents
Places to stay on Maui with an ocean view for under $400 a night
Is it cheaper to book a Maui condo direct or through Vrbo or Airbnb
What's the best way to book a vacation rental on Maui
Which Maui resorts don't charge a resort fee
How far ahead should I book a place to stay on Maui
What should I check before booking a vacation rental on Maui
How do I know if a Maui vacation rental is legal
Kaanapali or Wailea for a family trip
Condo or hotel for a week on Maui with teenagers
Is it worth staying a night in Hana
North Shore or South Maui, where should we stay
Where should we stay on Maui to do the Road to Hana and Haleakala sunrise
Best place to stay on Maui for snorkeling and hiking
Where to stay on Maui to be close to restaurants and things to do at night

The Oahu and Kauai checks asked five of the same questions with the island swapped: the first trip, a family with young kids, resort or condo with kids, two kids with a kitchen near a calm beach, and booking a condo direct or through a booking site.

More on Hawaii: why the AI discovery problem isn't the same for every Hawaii business and how we work in Hawaii.

Common questions

How is vacation rental marketing changing now that travelers ask ChatGPT where to stay?

In our Maui runs, ChatGPT named condo complexes, resorts and hotels far more often than single units: 10 of 327 names were individual vacation rentals. When we searched Google for the places ChatGPT kept naming, 40 of 43 name searches showed a Google panel about the property. So a rental is worth checking in both places: whether it gets named, and what shows up when someone searches its name.

Does ChatGPT recommend individual vacation rentals on Maui?

Rarely, in our runs. Of the 327 names ChatGPT gave across 108 answers, 10 were individual vacation rentals, about 3%. Condo complexes (119), resorts (118) and hotels (70) made up most of the rest. I'd say a single unit should lean on what makes it special rather than try to battle a hotel.

Why do booking sites show up when someone searches my property's name on Google?

In our test, Google showed a panel about the property for 40 of 43 property-name searches, and 31 of those panels showed prices or booking options from booking sites. Adding "book" to the search raised booking-site results in the top 10 from 47 to 82 across the 43 places. My read is that Google treats that search as a buying search, and booking sites are built for buying searches.

If ChatGPT recommended my property once, will it keep recommending it?

Not necessarily. We asked each question three times. Of the places named for a question, 15% came back in all three runs and 63% showed up in only one. One answer is one sample, so ask the same question a few times before reading much into it.

Does this study show where travelers booked?

No. We measured what ChatGPT named and what Google showed when those names were searched, on October 19, 2026, logged out, from the US. We had no booking data, so we can't say whether anyone booked through Google's panel, a booking site or the property's own site.

Sources

Plate Lunch Collective. Maui lodging field study: 36 questions with three ChatGPT runs each, Google results for the same questions, 10 Oahu and Kauai checks, and a 43-place second search on Google. October 19, 2026. The question list is in this post; summary data on request.
OpenAI. Powering Product Discovery in ChatGPT. March 24, 2026.
Meta Help Center. How your Muse agent browses the web. Checked October 19, 2026.
OpenAI. Introducing dots. September 29, 2026.
OpenAI Help Center. Getting started with your dot. Checked October 19, 2026.

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Hayden Bond

Hayden Bond has been doing SEO since 2004. He founded Plate Lunch Collective in Aiea, helping brands get cited by AI platforms rather than just ranked by Google.

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