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Jason Eisert
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Need Advice: How to Increase Bookings for Unique Luxury Hawaiian Mansion

Jason Eisert
  • Rental Property Investor
  • Kailua-Kona, HI
Posted Apr 16 2024, 21:10

I am the owner of a 10,000 sqft luxury mansion in Hawaii that I have spent the past two years renovating and managing. We've found that the property is perfect for large families, yoga retreats, and corporate groups. Despite offering almost every amenity for an ideal vacation, my efforts to increase bookings through more than ten non-exclusive agreements with local property managers and continuous outreach to travel agents have not been fruitful. You can view the listing here: https://www.airbnb.com/rooms/739311990337556133.

I am seeking advice on more effective marketing strategies to enhance visibility and drive bookings for this unique place... It's got a large cost per night and our target demographic isn't "cookie cutter" like most listings. If anyone has insights, experiences, or can recommend specific platforms or techniques beneficial for marketing unique luxury vacation rentals, your guidance would be highly appreciated.

Thank you for sharing your expertise!

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Jonathan Greene#2 Starting Out Contributor
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Jonathan Greene#2 Starting Out Contributor
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Replied Apr 17 2024, 04:57

You are hamstrung by the community this is in. I reviewed your listing and you are targeting families which is a hard target for this big of a property. It certainly has appeal for family reunions and multiple families together, but you are almost telling them not to book. The listing description is very rigid (see below):

"This home is meant for families looking to create beautiful memories. With such a unique experience comes a responsibility to respect the land, home, and neighborhood. We love our community and the atmosphere we have cultivated for this newly renovated home. As such, there are strict requirements that Hawaii State Law Quiet Hours must be observed outside the home past 9:30 PM (feel free to go snuggle up with some popcorn in the 16-seater movie room!). We ask that groups who book are limited to one family. The pool, pickleball court, and lanai close at 10 PM each night for your safety and to observe quiet hours. This home can't be used for parties or events."

What one family is coming to use 11 beds and 7.5 baths? You either chose the wrong place to try to do this or you are overly restricting who can come. You basically sound like an overlord in your listing as if someone is going to get in trouble as a guest if they sneeze past 10 pm and that is not enticing at a high price tag like this to have to be careful.

The property looks great, but your description starts with telling them that you spent 1.2m in renovations. No one cares about that. Tell a story, but you can't tell it like this being so restrictive of who comes there.

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John Underwood
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John Underwood
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Replied Apr 17 2024, 05:35

You have a large property that multiple families or groups of friends will need to go in together on. They have to plan in advance for vacation days and to coordinate with everyone. 

This is an expensive place and it's not drivable so everyone needs to arrange and pay for airfare.

This is tough.

When you did your research prior to purchasing, did you find other similar properties that were already successful or is this more of a hope everything will work out?

You might want to hire a company that specializes in this type of marketing. 

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Jesse Turner
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Jesse Turner
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Replied Apr 17 2024, 06:49
Quote from @Jason Eisert:

I am the owner of a 10,000 sqft luxury mansion in Hawaii that I have spent the past two years renovating and managing. We've found that the property is perfect for large families, yoga retreats, and corporate groups. Despite offering almost every amenity for an ideal vacation, my efforts to increase bookings through more than ten non-exclusive agreements with local property managers and continuous outreach to travel agents have not been fruitful. You can view the listing here: https://www.airbnb.com/rooms/739311990337556133.

I am seeking advice on more effective marketing strategies to enhance visibility and drive bookings for this unique place... It's got a large cost per night and our target demographic isn't "cookie cutter" like most listings. If anyone has insights, experiences, or can recommend specific platforms or techniques beneficial for marketing unique luxury vacation rentals, your guidance would be highly appreciated.

Thank you for sharing your expertise!


 Jason, I sympathize with your situation. I think your current marketing target persona requires a very special type of marketing and connections. Those wealthy families are not usually booking trips the same way and on the same platforms as the mass vacationers.

Much like amenities and pricing, marketing should start with asking "what are my competitors doing?"

Are they getting published in lists from travel blogs? Are they using social media? Are they using a third party agent to drive bookings?

Once you nail down how to play in the same market then you can get creative to find new marketing methods that are unique (or even guerrilla tactics).

Start by asking people in your network that you think would likely fit your target audience what they do when they're looking to book a multi-family vacation home.

Qualitative research then turns to quantitative, so gather ideas from your wealthy friends then do some try them out and be sure to ask any leads/guests "how did you hear about us?"

I look forward to hearing about your journey in solving your marketing need.

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Andrew Steffens
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Andrew Steffens
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Replied Apr 17 2024, 08:51

HI Jason

While the luxury market is growing (in most markets) it seems as though yours is in a bit of a class by itself.  Are there any true comps anywhere in Hawaii that are successful and maybe you could copy their strategy?

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Berry Starnes
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Berry Starnes
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Replied Apr 17 2024, 09:05

try and get the WSJ or Barron's to do a story on how your hawaii mansion isn't getting enough bookings.  By default the wealthy will read this and want to go and support you. Someone needs to do a spread on your property.  Just a thought.

also, extend the timeframe you can book out.  This will need many months of planning by multiple families or groups.  only allowing 1 or 2 months ahead will not work.

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Henry T.
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Replied Apr 17 2024, 09:10

That's quite a property. I can't imagine it being booked  regularly with a one family limit. I'd market for small corporate events and porn film location. That's a party house!

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Loren Clive
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Loren Clive
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Replied Apr 17 2024, 09:57

I can recommend some folks on Maui who specialize in these types of listings.

Do you yourself practice yoga? If you're looking to capture that market, it's not that big and might be worth networking with some yoga folks yourself to get the word out. And also staging the place with yoga props. 

Also research what types of events come to Kona, like Iron Man, paddling races, etc. and market to those folks.

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Replied Apr 17 2024, 10:23

You say “the property is perfect for large families, yoga retreats, and corporate groups.”. Then you say “We ask that groups who book are limited to one family.”. 

It can’t be both. A corporate retreat all from one family? A family who all want a yoga retreat?

I’d suggest:

Remove the one family line, heck remove as many restrictions as you can. 
Try midterm/longer bookings at a lower per day charge? (Someone spending months.)

If you want to remain in the STR/MTR business: See if it has any resale value. Can you sell and buy 2-3-4 properties better suited to travelers? It might be a great property for a very large extended well off family but your targeted traveling market is very small.

Good luck. Let us know how it turns out. 

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Michael Baum
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Michael Baum
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Replied Apr 17 2024, 13:59

Hey @Jason Eisert, it looks great and very cool but I agree with everyone else. It is a HUGE place for one family.

Essentially your listing basically states, don't come here unless you are a family with 18 kids. Otherwise, no thanks.

I understand you want to limit parties and I would as well but telling just about everyone other than a large family to stay away is not the way to handle it.

We have, what I consider, a large place on Lake Coeur d'Alene. it is 2700sqft and sleeps 10. We get all kinds of groups. Wedding people, bike rider groups, extended families in addition to one big family. No issues so far in 7 years.

Frankly, I would sell this place and do what @Bill Brandt said and get a couple of smaller places that would cash flow much better and be offered up to a wider audience.

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Lauren Kormylo
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Lauren Kormylo
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Replied Apr 17 2024, 15:38

Jason, your house is amazing, I love it. 

I have a few suggestions for your listing.  Your cover photo shows the house all in shadow, and it's not showing its best.  Either lighten the photo, or change it to one where sun is shining on the pool area.  I agree with Jonathan about not quoting the remodeling price.  In fact, I would not say anything about remodeling and how you turned the property into beautiful space.  That sounds like it wasn't great before, and guests don't need to know that.  Just tout how wonderful it is, without alluding to its history. 

When you say "According to county records, our home is permitted as a five-bedroom dwelling", that sounds strange.  I would say, "the home has 5 bedrooms, with other spacious sleeping areas".    But your listing says and you have photos for 6 bedrooms.  Specify whether those flex areas have a door for privacy so they can function as a true bedroom or not.  And having a floor plan with bed and bathroom locations would be helpful to large groups, since many people will not be in the formal bedrooms.  And guests will want to see which rooms have en suite bathrooms.  

At the very end of the description, you say "This is a hosted rental."  Are you saying that you will be sleeping there too, or what does that mean?  Your heading says the guests are renting the entire villa. If you will be on the property, you should make that clear to guests. 

I priced some of your dates, and in Oct and Dec there are weeks that are $44,000 ! You are right that this will be harder to book, unless you can target the very wealthy. I have followed a guy named Bill Faeth for a few years now on his Facebook group and his YouTube channel. He focuses on luxury STR properties with loads of amenities as a way to stand above the crowd. He owns STRs and he co-hosts selective luxury properties for other owners too. You might look at his website, he also does coaching on targeting the luxury guest. I know he recommends having your own "landing page" for direct bookings, and using Facebook advertising among other things. I have used some of his tips, but I have not used his paid services so I can't personally recommend him, but his advice so far seems practical. https://www.billfaeth.com/



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Jay Hinrichs#1 All Forums Contributor
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Jay Hinrichs#1 All Forums Contributor
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Replied Apr 17 2024, 15:45
Quote from @Bill Brandt:

You say “the property is perfect for large families, yoga retreats, and corporate groups.”. Then you say “We ask that groups who book are limited to one family.”. 

It can’t be both. A corporate retreat all from one family? A family who all want a yoga retreat?

I’d suggest:

Remove the one family line, heck remove as many restrictions as you can. 
Try midterm/longer bookings at a lower per day charge? (Someone spending months.)

If you want to remain in the STR/MTR business: See if it has any resale value. Can you sell and buy 2-3-4 properties better suited to travelers? It might be a great property for a very large extended well off family but your targeted traveling market is very small.

Good luck. Let us know how it turns out. 


If I knew there was a pickle ball court anywhere near it I would not rent it.. they are loud and obnoxious.. although fun to play just not close to you..

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Jason Eisert
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Jason Eisert
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Replied Apr 17 2024, 18:26
Quote from @Jonathan Greene:

You are hamstrung by the community this is in. I reviewed your listing and you are targeting families which is a hard target for this big of a property. It certainly has appeal for family reunions and multiple families together, but you are almost telling them not to book. The listing description is very rigid (see below):

"This home is meant for families looking to create beautiful memories. With such a unique experience comes a responsibility to respect the land, home, and neighborhood. We love our community and the atmosphere we have cultivated for this newly renovated home. As such, there are strict requirements that Hawaii State Law Quiet Hours must be observed outside the home past 9:30 PM (feel free to go snuggle up with some popcorn in the 16-seater movie room!). We ask that groups who book are limited to one family. The pool, pickleball court, and lanai close at 10 PM each night for your safety and to observe quiet hours. This home can't be used for parties or events."

What one family is coming to use 11 beds and 7.5 baths? You either chose the wrong place to try to do this or you are overly restricting who can come. You basically sound like an overlord in your listing as if someone is going to get in trouble as a guest if they sneeze past 10 pm and that is not enticing at a high price tag like this to have to be careful.

The property looks great, but your description starts with telling them that you spent 1.2m in renovations. No one cares about that. Tell a story, but you can't tell it like this being so restrictive of who comes there.

@Jonathan Greene Thank you for your feedback. Your insights are indeed eye-opening, and I appreciate your straightforwardness. You're correct about the potential misalignment in my listing's target audience and its tone. The section stating, 'This home is meant for families...' was directly influenced by local regulations. Hawaii County operates as a "complaint-driven" county, so they don't enforce any rules unless someone complains. After a neighbor's complaint on my property, the county scrutinized my listing and told me that all Airbnb's on the island have to abide by a strict 'one family' rental rule. Something that nobody follows and transparently feels like they selectively enforced on me... About a year later, when I was in a meeting with the Planning Director, he mentioned this rule is unenforceable because any guest can say they are "family", and how do I verify that? This has placed me in a challenging position, as my competitors are not being held to the same standard due to lack of complaints against them. 

I don’t explicitly ask guests if they are family upon arrival. From my observations alone, it sometimes seems that not all groups who have stayed here fit the 'family' definition, but this has never caused any issues. Especially considering that we are in Hawaii where "everyone is Ohana". 

Originally, the property was designed as a retreat center, but it didn't receive the necessary planning approvals for broader use beyond a single family residence. 

I’m going to rework the description to better reflect this and to make it more inviting and less restrictive. Any further suggestions on how to navigate these regulatory challenges while appealing to a broader audience would be greatly appreciated. How have others in similar situations managed to balance such constraints? As a note... there are properties on the island that are "luxury" but per building department officials my house is the largest residential house on the big island with the biggest residential pool. 

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Jason Eisert
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Jason Eisert
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Replied Apr 17 2024, 18:54
Quote fro:

You have a large property that multiple families or groups of friends will need to go in together on. They have to plan in advance for vacation days and to coordinate with everyone. 

This is an expensive place and it's not drivable so everyone needs to arrange and pay for airfare.

This is tough.

When you did your research prior to purchasing, did you find other similar properties that were already successful or is this more of a hope everything will work out?

You might want to hire a company that specializes in this type of marketing. 

@John Underwood do you happen to know of any companies that specialize in this kind of marketing?

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Jason Eisert
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Jason Eisert
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Replied Apr 17 2024, 18:55
Quote from @Jay Hinrichs:
Quote from @Bill Brandt:

You say “the property is perfect for large families, yoga retreats, and corporate groups.”. Then you say “We ask that groups who book are limited to one family.”. 

It can’t be both. A corporate retreat all from one family? A family who all want a yoga retreat?

I’d suggest:

Remove the one family line, heck remove as many restrictions as you can. 
Try midterm/longer bookings at a lower per day charge? (Someone spending months.)

If you want to remain in the STR/MTR business: See if it has any resale value. Can you sell and buy 2-3-4 properties better suited to travelers? It might be a great property for a very large extended well off family but your targeted traveling market is very small.

Good luck. Let us know how it turns out. 


If I knew there was a pickle ball court anywhere near it I would not rent it.. they are loud and obnoxious.. although fun to play just not close to you..

 @Jay Hinrichs it's a private pickleball court on our property for their exclusive use. I'll need to clarify that!

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Jason Eisert
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Jason Eisert
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Replied Apr 17 2024, 19:01

@Berry Starnes is it easy to have WSJ or Barron's do a story? I looked online and it looks like you can email them with stories but from experience I've found it's better to talk to someone who knows them already. 

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Jay Hinrichs#1 All Forums Contributor
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Jay Hinrichs#1 All Forums Contributor
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Replied Apr 17 2024, 19:07
Quote from @Jason Eisert:
Quote from @Jay Hinrichs:
Quote from @Bill Brandt:

You say “the property is perfect for large families, yoga retreats, and corporate groups.”. Then you say “We ask that groups who book are limited to one family.”. 

It can’t be both. A corporate retreat all from one family? A family who all want a yoga retreat?

I’d suggest:

Remove the one family line, heck remove as many restrictions as you can. 
Try midterm/longer bookings at a lower per day charge? (Someone spending months.)

If you want to remain in the STR/MTR business: See if it has any resale value. Can you sell and buy 2-3-4 properties better suited to travelers? It might be a great property for a very large extended well off family but your targeted traveling market is very small.

Good luck. Let us know how it turns out. 


If I knew there was a pickle ball court anywhere near it I would not rent it.. they are loud and obnoxious.. although fun to play just not close to you..

 @Jay Hinrichs it's a private pickleball court on our property for their exclusive use. I'll need to clarify that!


got it..  those courts are going up everywhere and cities are having issues with the noise they make.  but when your playing it who cares right.. I will be in Honolulu this Friday for 10 days myself. 

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Jason Eisert
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Jason Eisert
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Replied Apr 17 2024, 19:09
Quote from @Jesse Turner:
Quote from @Jason Eisert:

I am the owner of a 10,000 sqft luxury mansion in Hawaii that I have spent the past two years renovating and managing. We've found that the property is perfect for large families, yoga retreats, and corporate groups. Despite offering almost every amenity for an ideal vacation, my efforts to increase bookings through more than ten non-exclusive agreements with local property managers and continuous outreach to travel agents have not been fruitful. You can view the listing here: https://www.airbnb.com/rooms/739311990337556133.

I am seeking advice on more effective marketing strategies to enhance visibility and drive bookings for this unique place... It's got a large cost per night and our target demographic isn't "cookie cutter" like most listings. If anyone has insights, experiences, or can recommend specific platforms or techniques beneficial for marketing unique luxury vacation rentals, your guidance would be highly appreciated.

Thank you for sharing your expertise!


 Jason, I sympathize with your situation. I think your current marketing target persona requires a very special type of marketing and connections. Those wealthy families are not usually booking trips the same way and on the same platforms as the mass vacationers.

Much like amenities and pricing, marketing should start with asking "what are my competitors doing?"

Are they getting published in lists from travel blogs? Are they using social media? Are they using a third party agent to drive bookings?

Once you nail down how to play in the same market then you can get creative to find new marketing methods that are unique (or even guerrilla tactics).

Start by asking people in your network that you think would likely fit your target audience what they do when they're looking to book a multi-family vacation home.

Qualitative research then turns to quantitative, so gather ideas from your wealthy friends then do some try them out and be sure to ask any leads/guests "how did you hear about us?"

I look forward to hearing about your journey in solving your marketing need.

@Jesse Turner thank you for your advice on tailoring our marketing approach. It's true that we face unique challenges with our property. In Kona, there are no direct competitors to our property's scale and offerings. While there are homes that accommodate up to 16 guests, they often squeeze three bunk beds into one room, which is far from comparable to our expansive and amenity-rich estate. The closest properties that match the luxury aspect are about an hour north, featuring modern high-end luxury, whereas our property offers a 'commercial' luxury due to its size, amenities, and prime location.


Interestingly, during our property appraisal, the uniqueness of our home led the bank to require two separate appraisals. Both appraisers confirmed that there are no comparable properties ('no comps'), highlighting our unique market position.

Regarding the market, as I mentioned to Jonathan Greene, many of our competitors can host large groups without the restrictions we face. I've adhered strictly to compliance, which has limited our ability to host similar groups. This compliance issue is something I'm grappling with as I explore marketing strategies.

I'm particularly interested in finding marketing companies that specialize in unique luxury properties. If you know of any that could assist with promoting our distinctive offering effectively, your recommendation would be invaluable.

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Jason Eisert
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Jason Eisert
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Replied Apr 17 2024, 19:10

@Andrew Steffens there aren't any comps here in Kona (or I would say even on the big island). Anyone who "could" be a comp is able to do things that we can't given our zoning. If you know of any properties that may fall into this category around you I'd love to peek at their listing / reach out to them. 

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Jason Eisert
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Jason Eisert
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Replied Apr 17 2024, 19:12
Quote from @Loren Clive:

I can recommend some folks on Maui who specialize in these types of listings.

Do you yourself practice yoga? If you're looking to capture that market, it's not that big and might be worth networking with some yoga folks yourself to get the word out. And also staging the place with yoga props. 

Also research what types of events come to Kona, like Iron Man, paddling races, etc. and market to those folks.

@Loren Clive I'd love any recommendations you can provide! 

I personally don't do yoga regularly but I have in the past! We do have yoga 'gear' here at the house. Do you do marketing on Google / Facebook too? I'm curious what "marketing" I could do outside of having it listed on the various booking sites. 

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Jay Hinrichs#1 All Forums Contributor
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Jay Hinrichs#1 All Forums Contributor
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Replied Apr 17 2024, 19:16
I see your way up the mountain away from the ocean.. how close is golf and restaurants ?

beach..  how far is that ?  given location it may not be as high end as your thinking it is compared to water front in Maui or Kahala in Honolulu area .. I suspect your not going to attract many Asian visitors to this location either.

I wonder if its sort of a white elephant as it were.

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Jason Eisert
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Jason Eisert
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Replied Apr 17 2024, 19:17
Quote from @Bill Brandt:

You say “the property is perfect for large families, yoga retreats, and corporate groups.”. Then you say “We ask that groups who book are limited to one family.”. 

It can’t be both. A corporate retreat all from one family? A family who all want a yoga retreat?

I’d suggest:

Remove the one family line, heck remove as many restrictions as you can. 
Try midterm/longer bookings at a lower per day charge? (Someone spending months.)

If you want to remain in the STR/MTR business: See if it has any resale value. Can you sell and buy 2-3-4 properties better suited to travelers? It might be a great property for a very large extended well off family but your targeted traveling market is very small.

Good luck. Let us know how it turns out. 

Thank you for your insights—they certainly challenge me to think differently about our approach. Regarding the apparent contradictions in our marketing, you're right; it does sound conflicting. The 'one family' restriction was imposed by local regulations, not by choice. We intended the property to cater to a variety of groups including corporate and yoga retreats. We've since been working through the bureaucratic challenges with the county which initially influenced our restrictive advertising.

In 2022, we did attempt to list the property for sale after renovating it from a near-dilapidated state. Unfortunately, we didn't receive any offers during that period, which coincided with our struggles with county regulations. Now, even though the red tape has lessened and selling might be feasible, the current high interest rates could make it difficult to find buyers willing to invest at a price that reflects the property’s true value. I'm curious what you would do if you were me... I explained my situation in a response to @Jonathan Greene above. As the property won't sell above breakeven, how would you go about holding it? 

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Jay Hinrichs#1 All Forums Contributor
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Jay Hinrichs#1 All Forums Contributor
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Replied Apr 17 2024, 19:19
Quote from @Jason Eisert:
Quote from @Bill Brandt:

You say “the property is perfect for large families, yoga retreats, and corporate groups.”. Then you say “We ask that groups who book are limited to one family.”. 

It can’t be both. A corporate retreat all from one family? A family who all want a yoga retreat?

I’d suggest:

Remove the one family line, heck remove as many restrictions as you can. 
Try midterm/longer bookings at a lower per day charge? (Someone spending months.)

If you want to remain in the STR/MTR business: See if it has any resale value. Can you sell and buy 2-3-4 properties better suited to travelers? It might be a great property for a very large extended well off family but your targeted traveling market is very small.

Good luck. Let us know how it turns out. 

Thank you for your insights—they certainly challenge me to think differently about our approach. Regarding the apparent contradictions in our marketing, you're right; it does sound conflicting. The 'one family' restriction was imposed by local regulations, not by choice. We intended the property to cater to a variety of groups including corporate and yoga retreats. We've since been working through the bureaucratic challenges with the county which initially influenced our restrictive advertising.

In 2022, we did attempt to list the property for sale after renovating it from a near-dilapidated state. Unfortunately, we didn't receive any offers during that period, which coincided with our struggles with county regulations. Now, even though the red tape has lessened and selling might be feasible, the current high interest rates could make it difficult to find buyers willing to invest at a price that reflects the property’s true value. I'm curious what you would do if you were me... I explained my situation in a response to @Jonathan Greene above. As the property won't sell above breakeven, how would you go about holding it? 


interest rates dont affect properties at this price point. I think what you have is a location issue and might very well have over improved it for the area.
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User Stats

30
Posts
13
Votes
Jason Eisert
  • Rental Property Investor
  • Kailua-Kona, HI
13
Votes |
30
Posts
Jason Eisert
  • Rental Property Investor
  • Kailua-Kona, HI
Replied Apr 17 2024, 19:23
Quote from @Lauren Kormylo:

Jason, your house is amazing, I love it. 

I have a few suggestions for your listing.  Your cover photo shows the house all in shadow, and it's not showing its best.  Either lighten the photo, or change it to one where sun is shining on the pool area.  I agree with Jonathan about not quoting the remodeling price.  In fact, I would not say anything about remodeling and how you turned the property into beautiful space.  That sounds like it wasn't great before, and guests don't need to know that.  Just tout how wonderful it is, without alluding to its history. 

When you say "According to county records, our home is permitted as a five-bedroom dwelling", that sounds strange.  I would say, "the home has 5 bedrooms, with other spacious sleeping areas".    But your listing says and you have photos for 6 bedrooms.  Specify whether those flex areas have a door for privacy so they can function as a true bedroom or not.  And having a floor plan with bed and bathroom locations would be helpful to large groups, since many people will not be in the formal bedrooms.  And guests will want to see which rooms have en suite bathrooms.  

At the very end of the description, you say "This is a hosted rental."  Are you saying that you will be sleeping there too, or what does that mean?  Your heading says the guests are renting the entire villa. If you will be on the property, you should make that clear to guests. 

I priced some of your dates, and in Oct and Dec there are weeks that are $44,000 ! You are right that this will be harder to book, unless you can target the very wealthy. I have followed a guy named Bill Faeth for a few years now on his Facebook group and his YouTube channel. He focuses on luxury STR properties with loads of amenities as a way to stand above the crowd. He owns STRs and he co-hosts selective luxury properties for other owners too. You might look at his website, he also does coaching on targeting the luxury guest. I know he recommends having your own "landing page" for direct bookings, and using Facebook advertising among other things. I have used some of his tips, but I have not used his paid services so I can't personally recommend him, but his advice so far seems practical. https://www.billfaeth.com/



Lauren, thank you so much for your kind words and the valuable suggestions for our listing. I'll need to work on the cover photo. In fact, almost all the guests tell me "the photos dont do it justice" when they come stay in the home. It's very difficult to capture such a massive property. If you know any photographers that you recommend I'm open to suggestions!


 Also, I'll be removing mentions of the renovation costs and the property’s past condition. I like the suggestion. The logic makes sense. 

Regarding the bedroom count, I say "five bedrooms" because if I advertise 6 I am nervous that the county will come after me and shut me down for advertising more than what it's permitted as. The home was built with 7 bedrooms but they called them "Living Room" and "Lunch Room" despite obviously being bedrooms. However, I am not sure how I could creatively say that without crossing the line with the county. I'd be open to any suggestions you may have.

Thank you for your feedback!!! Look forward to your thoughts.

User Stats

30
Posts
13
Votes
Jason Eisert
  • Rental Property Investor
  • Kailua-Kona, HI
13
Votes |
30
Posts
Jason Eisert
  • Rental Property Investor
  • Kailua-Kona, HI
Replied Apr 17 2024, 19:24
Quote from @Jay Hinrichs:
Quote from @Jason Eisert:
Quote from @Bill Brandt:

You say “the property is perfect for large families, yoga retreats, and corporate groups.”. Then you say “We ask that groups who book are limited to one family.”. 

It can’t be both. A corporate retreat all from one family? A family who all want a yoga retreat?

I’d suggest:

Remove the one family line, heck remove as many restrictions as you can. 
Try midterm/longer bookings at a lower per day charge? (Someone spending months.)

If you want to remain in the STR/MTR business: See if it has any resale value. Can you sell and buy 2-3-4 properties better suited to travelers? It might be a great property for a very large extended well off family but your targeted traveling market is very small.

Good luck. Let us know how it turns out. 

Thank you for your insights—they certainly challenge me to think differently about our approach. Regarding the apparent contradictions in our marketing, you're right; it does sound conflicting. The 'one family' restriction was imposed by local regulations, not by choice. We intended the property to cater to a variety of groups including corporate and yoga retreats. We've since been working through the bureaucratic challenges with the county which initially influenced our restrictive advertising.

In 2022, we did attempt to list the property for sale after renovating it from a near-dilapidated state. Unfortunately, we didn't receive any offers during that period, which coincided with our struggles with county regulations. Now, even though the red tape has lessened and selling might be feasible, the current high interest rates could make it difficult to find buyers willing to invest at a price that reflects the property’s true value. I'm curious what you would do if you were me... I explained my situation in a response to @Jonathan Greene above. As the property won't sell above breakeven, how would you go about holding it? 


interest rates dont affect properties at this price point. I think what you have is a location issue and might very well have over improved it for the area.

What would you do if you were in my shoes @Jay Hinrichs?  

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Replied Apr 17 2024, 19:25

Seller financing? Long term rental? Can you split it in to a duplex? Take a “break even” sale before interest, utilities, taxes, insurance eat you up? Talk to some “high end” realtors and see if they have opinions? Good luck.