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All Forum Posts by: Jason Eisert

Jason Eisert has started 5 posts and replied 30 times.

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Bill B.:

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. 


 Appriciate the advice. We essentially break even on the deal right now after all expenses. We have a 30 yr 5M 5% fixed investor note, so we are in a good position debt-wise. 

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Jay Hinrichs:
Quote from @Jason Eisert:
Quote from @Bill B.:

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?  

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
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.

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Bill B.:

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? 

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
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. 

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14

@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. 

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
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.

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14

@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. 

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Jay Hinrichs:
Quote from @Bill B.:

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!

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

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
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?