Seeking advice on short term rental feasibility

Member since 2025 · 2 posts · 9 votes

Hey everyone!
Thinking of shifting into the luxury short term rental space in Hawaii. The only feasible way for my numbers to work out is if I “self manage” the marketing aspect. We’d have boots-on-the-ground but was curious if anyone has any advice/insights on going with this strategy?
I simply can’t invest for only equity right now, so breakeven cash flow is important.

Thanks in advance!

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Andrew SteffensBusiness Member

Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes

11mo

@Bryan Vukelich is my go to for all things Hawaii

I will say hiring the right PM can add value. For example I offer a limited service product in FL at 10% and I can show I am beating the market 10-12% here through marketing on 15+ channels (Abnb, VRBO, Google Vacation Rentals, BDC, Cap 1 Travel, Marriott Homes & Villas, etc).

[email protected]813-563-0877

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Jason WrayPro Member
Banker · Nationwide · Member since 2020 · 2k+ posts · 1k+ votes
11mo
Taylor,
Have you ever given any thought to buying outside Hawaii in other states like Florida for example... I ask because I have family that owns in Hawaii and switched gears and started buying in Florida due to the better puchase prices and Short term rental markets picking up.
[email protected]727-637-4289
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- John UnderwoodPro Member
  Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
  11mo
  Quote from @Jason Wray:
  
  Taylor,
  Have you ever given any thought to buying outside Hawaii in other states like Florida for example... I ask because I have family that owns in Hawaii and switched gears and started buying in Florida due to the better puchase prices and Short term rental markets picking up.
  
  Not to mention that Florida is more STR friendly and people can drive there.
  1 Reply
Loren Clive
Residential Real Estate Broker · Paia, HI · Member since 2016 · 479 posts · 311 votes
11mo
I've lived in Maui 20 years and currently self-manage one property. You can do it! Dm me with any questions
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Andrew SteffensBusiness Member
Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
11mo
@Bryan Vukelich is my go to for all things Hawaii
I will say hiring the right PM can add value. For example I offer a limited service product in FL at 10% and I can show I am beating the market 10-12% here through marketing on 15+ channels (Abnb, VRBO, Google Vacation Rentals, BDC, Cap 1 Travel, Marriott Homes & Villas, etc).
[email protected]813-563-0877
Vacation Rentals of Florida53 Reviews
Website View Page
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Collin HaysBusiness Member
Property Manager · Gatlinburg, TN · Member since 2020 · 3k+ posts · 4k+ votes
11mo
What Andrew said. A good PM should easily outperform a self-manager.
[email protected]806-672-7102
SMOKY MOUNTAIN FALLS INC.51 Review
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Melissa HaworthBusiness Member
Real Estate Agent · The Panhandle | The Emerald Coast | Panama City Beach | Destin · Member since 2017 · 266 posts · 103 votes
11mo
Hey! Love that you’re looking into luxury STRs. Hawaii’s definitely a dreamy market, and self-managing the marketing side can be a solid way to make the numbers work. If you’ve got good boots-on-the-ground support, taking charge of branding, guest messaging, and social can absolutely move the needle on cash flow.

That said, I’ll echo what a few others have mentioned, if breakeven (or better) is the goal right now, you might want to take a look at the Florida Panhandle. I invest and work here (think Destin, 30A, Panama City Beach), and while it’s still competitive, the barrier to entry is a lot more manageable than Hawaii. Plus, you’ve got strong year-round demand, especially from drive-to markets, and some serious cash-flowing potential if you buy right.

Happy to chat more if you ever want insight on how investors are pulling this off here. Either way, excited to see where you land!
[email protected]469-658-2869
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Duc Ong
Real Estate Agent · Honolulu, HI · Member since 2015 · 450 posts · 196 votes
10mo
@Account Closed
You can definitely make luxury STRs work here, but the numbers get tight fast in Hawaii so you’re smart to look at self-managing the marketing. With good boots-on-the-ground, taking control of branding, guest messaging, and filling your own calendar can help your margins.

One thing I’ll add that hasn’t been mentioned is looking at mid term rentals. A lot of investors here use a hybrid model. You still get higher rates than long term, but with way less turnover, fewer cleanings, and more predictable occupancy. On Oahu, you get plenty of travel nurses, corporate stays, military orders, insurance displacement, and remote workers coming for 1 to 3 months.

It’s not as sexy as nightly, but cash flow is often steadier and the regulations are clearer in many areas.

If you're set on luxury STR, just make sure the zoning and HOA truly allow it and underwrite using real seasonality. If you ever want some examples of what's performing well here, happy to share.
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Shakur Granger
Real Estate Agent · Triad North Carolina · Member since 2025 · 50 posts · 13 votes
10mo
Really interesting market to explore. I've been looking at different STR models lately (not Hawaii specifically), and one thing that keeps coming up is how big of a difference the marketing side makes compared to traditional PM.

A couple things I’ve noticed from other investors’ experiences:

• Direct booking + strong branding can make a huge impact in high-end STR markets

• Relying fully on OTAs (Airbnb/VRBO) in luxury areas usually leaves money on the table

• Having solid boots-on-the-ground is huge — not just for cleaning/turnovers, but for fast response times, quality control, and protecting the guest experience

• Areas with high traveler expectations tend to reward hosts who manage the “guest journey” themselves

Break-even cash flow being important makes sense, especially with Hawaii’s pricing and regulations. A lot of people I’ve talked to who self-manage the marketing side do it mainly because it gives them more control over ADR and occupancy.

Curious — have you compared numbers between self-managing the guest/marketing side vs. outsourcing it? I’ve seen both models work depending on the market.
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Reyjie Sobebe
Member since 2025 · 29 posts · 7 votes
10mo
If you’re looking at luxury STRs in Hawaii, self-managing the marketing can absolutely make the difference between bleeding cash and breaking even especially with the management premiums out there. The big thing is treating it less like “self-management” and more like running a micro-hospitality brand. Consistent visuals, fast response times, and a strong direct-booking strategy matter a lot more in the luxury tier than on standard Airbnb listings. Boots-on-the-ground is great, but make sure they’re dialed in on guest expectations luxury guests notice everything.

One thing that helped me when we scaled was keeping every hour of work organized, especially the marketing and operational tasks. I use automated tools to track the time I put into the business so I can prove participation and keep everything clean for tax season. It’s not a magic fix, but it does make the “self-manage” side a lot more structured.

If your numbers are close, tightening up the branding, pricing strategy, and guest experience usually does more for cash flow than people expect.
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