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

[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!

[Bill Brandt]

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. 

Ps. If you don’t mind me asking,  What is break even? Maybe you’d get an offer from one of the “more well-off” members of BP. Cut out the real estate commissions and it could help you succeed. Or a great BP realtor might have a buyer if they knew what you were asking. Like I said, good luck, you’ve got a toughie for sure. 

[Jason Eisert]

Quote from @Bill Brandt:

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. 

[Jason Eisert]

Quote from @Bill Brandt:

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. 

Ps. If you don’t mind me asking,  What is break even? Maybe you’d get an offer from one of the “more well-off” members of BP. Cut out the real estate commissions and it could help you succeed. Or a great BP realtor might have a buyer if they knew what you were asking. Like I said, good luck, you’ve got a toughie for sure. 

@Bill BrandtHere's the breakdown: 

Bought it for $4.95M

Early loan payoff is ~$175k ($5M @5% 30 yr fixed investor note)

Conveyance Taxes ~$90k

Improvements $1.6M ($400k done on lower property)...  as a note - I own 2 - 5 acre properties. One has this mansion, and a second ~2000 sqft house. The lower property is covered in coffee and has a newly built ~800 sqft shop / deck. Has the ability to build 2 homes on it. The original owner in 2012 spent over $11M building the properties and over $1M on landscaping/coffee orchards.

Misc Other Expenses Incurred: $250,000

Total: Around $7.2M. I have the property below as well that I would sell with it for $800k. Total $8M breakeven. 

We have appraisals from Jan 2022 for the mansion property ONLY at $8.7M and a second at $9M.

[Jason Eisert]

Quote from @Henry T.:

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!

 Playboy did stay here before I knew it wasn't allowed... lol 

[Lauren Kormylo]

Quote from @Jason Eisert:

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.

 If the county is going to take notice of your bedroom count, it will initially be to this heading on your listing "16+ guests, 6 bedrooms, 11 beds, 7.5 baths".  Since it says 6 bedrooms there, it will be searchable for that number of bedrooms by Airbnb's search function.  That's really where you want to stick to specifying 5 bedrooms if you don't want to get on the county's radar.  Then in the description, you can say "The house has 5 bedrooms, with 2 other spacious flex rooms that add  sleeping areas. These flex rooms are depicted in our photos as Flex Room 1 and Flex Room 2 with a king bed and three full beds respectively, and have doors for privacy." That way people know they can function like a true bedroom with a door, and they're not an open den.  It's just a tweak on what you already have written.

[Jason Eisert]

Quote from @Lauren Kormylo:

Quote from @Jason Eisert:

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.

 If the county is going to take notice of your bedroom count, it will initially be to this heading on your listing "16+ guests, 6 bedrooms, 11 beds, 7.5 baths".  Since it says 6 bedrooms there, it will be searchable for that number of bedrooms by Airbnb's search function.  That's really where you want to stick to specifying 5 bedrooms if you don't want to get on the county's radar.  Then in the description, you can say "The house has 5 bedrooms, with 2 other spacious flex rooms that add  sleeping areas. These flex rooms are depicted in our photos as Flex Room 1 and Flex Room 2 with a king bed and three full beds respectively, and have doors for privacy." That way people know they can function like a true bedroom with a door, and they're not an open den.  It's just a tweak on what you already have written.

 This is great! Thank you so much for the advice :) 

[Carlos Ptriawan]

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!

well how do i say this, your location is in mountain, $2000 per night. My location is straight from your place but 3 meters from beach....

i don't know but location is too far away, i guess people going to kailua for the beach and not for the mountain, i could be wrong though...

[Monique P.]

Beautiful property Jason! The view is stunning! Looks like you're doing well compared to the other luxury homes nearby! You’ve got more of your calendar booked! 

If you haven’t checked out Richard Fertig yet, look into his YouTube channel starting with his most recent stuff in the last month. I’m sure you’d pick up on some novel  ideas you can incorporate.

Your open mindedness will get you far. All the best!

[Cole Schlack]

As an agent selling STVRs on the big island, I would say you are getting a good nightly rate at $18,000 per week(what is shows on your airbnb page) which I think is good for Kona.  You could sell and buy something in the Mauna Lani resort area which has more demand.  

[Matthew Paul]

Nice place , great view . But maybe I am not rich enough to be able to spend that type of money for a fancy place to sleep . When I go on vacation with family and friends we spend our time doing things , spending money on fun , seeing the sights , going out to eat , drinking too much . 

The clients you are targeting is a very small part of the population , they can afford to stay anywhere they want .  I see a beautiful big house with a great view of the ocean , with a pool and hot tub  for a whole lot of money . But not much more than that .  

[Andrew Steffens]

Quote from @Jason Eisert:

@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. 

 I personally dont but maybe @Bryan Vukelich can help.  He is in Waikiki but maybe he can help.  Best of luck!

[Jay Hinrichs]

Quote from @Jason Eisert:

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?  

No magic answer from me. My Dad bought a condo in Maui in about 67 so we have been going to the islands ever since. Not everything in Hawaii is gold.. and you have a ton of competition .  I did have a good friend from Portland ( X philly eagle) who bought a small boutique resort in Kona about 8 to 10 rooms and that seems to have gone well for him over the years but price points were lower than the big hotels on the water or in Golf course settings.

Others that I know that tried to do high end luxury in the islands did not fare well at all either . Perfect example of this is the lots fronting the ocean in Honolulu Kahala area the stretch from Diamond head to the Kahala resort .. These properties take years to sell and they have big numbers on them 10 mil and up and almost 100% are sold to Japanese or lately Chinese.. . My friends we are going to see Tomorrow live a block off the water and we have been looking for lots to do an infill there with no luck the last 3 years.

So again I am no expert on that market just what I have observed over the last 57 years of going there 1 to 3 times a year.. I did have another bizz partner that had an ocean front condo in Kona and he liked that knowing him it was probably a well over a 1 to 2 mil prop.

the build it and they will come does not always work.. your just going to have run the math try what your doing now which is get advise on who to market that prop ( which I have no clue how to do) and see how it goes.

[Luke Masaschi]

In all seriousness you look pretty packed... much more than properties in the area. Im not sure what you are looking for but have you used airdna to look at the areas average occupancies month to month compared to yours? I would assume you are most likely beating the market. The only way I see you getting more bookings would be marketing off airbnb on a direct booking website. Shoot me a message I can try and help as I beat my market in the slow months by staying 80% full but I use unique pricing strategy.

[Jason Eisert]

Quote from @Luke Masaschi:

In all seriousness you look pretty packed... much more than properties in the area. Im not sure what you are looking for but have you used airdna to look at the areas average occupancies month to month compared to yours? I would assume you are most likely beating the market. The only way I see you getting more bookings would be marketing off airbnb on a direct booking website. Shoot me a message I can try and help as I beat my market in the slow months by staying 80% full but I use unique pricing strategy.

We do have a direct booking site really hard to compare our house to the market standard because we do not fit within the cookie cutter Airbnb that most of Airdna represents. 

it feels like we are in a completely different sector than any any Airbnb because of the uniqueness of the property. What I mean by that is it almost feels like Airbnb isn’t the platform we should be using to rent this place out. Some of that stems from the fact that there are no comparables but a lot of it stems from the fact that everyone from Airbnb that stays in our home says the home is insane and they are blown away and the pictures don’t do it justice. When I say that, all I hear is, I didn’t do a very good job at marketing the property and could have provided more value in the marketing and thus a higher price per night. 

[Steve K.]

It looks like an awesome property! I second the advice above about taking out the language about only one family staying there. It seems like a great family reunion/ company retreat/ yoga retreat etc. type of place and is obviously too large to make sense for one family, unless that family is Genghis Khan and his kids ;). 

You might take out this part at the end also: "Lastly, it is important to note that if noise ordinance rules are not adhered to, you will forfeit the remaining nights of your stay with no reimbursement." Maybe leave that in the fine print somewhere, but not in the listing itself. I'd be scared that if one of my kids cried too loud or something we'd get kicked out, become homeless in Kailua Kona and lose a lot of money. It just seems a bit heavy-handed to me and if anyone is that much of a problem, they're probably not going to be the type to bother reading that far into the listing, or to be scared off by it. 

With it being such a unique property, I bet you'll start getting repeat customers and as you build up positive reviews and the same people start booking it again year after year, your schedule will fill up more. Maybe reach out to some groups that are good candidates for coming every year and see if you can get them to book the next year in advance. This could be folks who have stayed there before, or just groups that you come across who would be a good fit to stay there. Perhaps offer a discount for booking well in advance.  

 The photos that you have look good to me, but there's always room for improvement I suppose and if "the photos don't do this place justice", is the feedback that you're getting, then perhaps you can find a way for the photos to better represent the attributes of the property. Do you have a Matterport 3D virtual tour? 

[Meghan Hubner]

I would alter the listing to showcase the experience you are offering larger family groups and retreats. Then I would start with picking up the phone and calling all retreats, yoga studios, wedding planners etc in your local area. Being that your property has a very specific audience you shouldn't soley rely on the platform marketing your location. I would probably run an open house or something for all the wedding planners in the area, maybe include bridal shops and florists too. 

[Bryan Vukelich]

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!

 Hi Jason, Congrats on owning such a beautiful property on the Big Island.   I completely agree with @Lauren Kormylo about cover pic.  And for a property of that caliber, I highly recommend you spend the money on a professional photographer for high quality and artistic photos.  You have some great pics already but a bunch of the photos would "pop" much more if they were properly lite as well as proper vertical lines.  And perhaps also do a video tour like this?  I've have had property managers tell me the video tours are of value to them. 

I also agree with others on creating own marketing/booking site for the property and to do target marketing.  Also, I used to work with Hawaii Life - they are very successful with the higher end market in Hawaii both with sales and property management.  Maybe you can find a way to partner with them to market your property?

Perhaps also reach out to production companies who might want to use the home for music videos, commercials, television shows or movies.  

[Matthew Mellon]

The property is beautiful! I had many suggestions as I started reading through the comments but they all kind of went out the window when I read your concerns with the code enforcements, previous complaint, etc. It seems like you may know be paranoid to make any errors or attract any bookings that may cause issues. 

So what can be done, if anything, to get past the issues you are having with the neighbors?

[Carlos Ptriawan]

Quote from @Cole Schlack:

As an agent selling STVRs on the big island, I would say you are getting a good nightly rate at $18,000 per week(what is shows on your airbnb page) which I think is good for Kona.  You could sell and buy something in the Mauna Lani resort area which has more demand.  

totally, either in mauna lani or kukio bay.

these kind of price is more intended to celebrity or C-level executive vacationeer. So I'm bit curious about the decision of the location.

[Carlos Ptriawan]

Quote from @Jason Eisert:

Quote from @Luke Masaschi:

In all seriousness you look pretty packed... much more than properties in the area. Im not sure what you are looking for but have you used airdna to look at the areas average occupancies month to month compared to yours? I would assume you are most likely beating the market. The only way I see you getting more bookings would be marketing off airbnb on a direct booking website. Shoot me a message I can try and help as I beat my market in the slow months by staying 80% full but I use unique pricing strategy.

We do have a direct booking site really hard to compare our house to the market standard because we do not fit within the cookie cutter Airbnb that most of Airdna represents. 

it feels like we are in a completely different sector than any any Airbnb because of the uniqueness of the property. What I mean by that is it almost feels like Airbnb isn’t the platform we should be using to rent this place out. Some of that stems from the fact that there are no comparables but a lot of it stems from the fact that everyone from Airbnb that stays in our home says the home is insane and they are blown away and the pictures don’t do it justice. When I say that, all I hear is, I didn’t do a very good job at marketing the property and could have provided more value in the marketing and thus a higher price per night. 

 Britney Spears, Matt Damon, some prominent political figure, they choose the area where Cole is mentioning.

[Carlos Ptriawan]

Quote from @Luke Masaschi:

In all seriousness you look pretty packed... much more than properties in the area. Im not sure what you are looking for but have you used airdna to look at the areas average occupancies month to month compared to yours? I would assume you are most likely beating the market. The only way I see you getting more bookings would be marketing off airbnb on a direct booking website. Shoot me a message I can try and help as I beat my market in the slow months by staying 80% full but I use unique pricing strategy.

currently in 2024 , there's slight reduction of booking all over island due to lesser number of tourism arrival. It seems the inflation and maui fire impacted tourism more this year.