All Real Estate Services are offered through Chalet Realty (DBA of Mahalla Realty LLC).
Texas Real Estate Commission Consumer Protection NoticeTexas Real Estate Commission Information About Brokerage ServicesTREC DisclaimerChalet (“GetChalet Inc.”) provides general educational content and tools for real-estate investors. Chalet is not a law firm, CPA firm, or investment adviser, and does not provide tax, legal, or accounting advice. Nothing on this site creates a CPA-client, attorney-client, or fiduciary relationship. Tax laws change, and state rules may differ from federal rules (e.g., California decouples from federal bonus depreciation). Always consult your own qualified tax and legal professionals about your specific situation.
The term 'Airbnb' is used on our site in a colloquial sense, akin to saying 'I am going to Airbnb it.' This usage is intended to refer broadly to the concept of short-term rentals and not specifically to the Airbnb platform or services. Airbnb, Inc. is not affiliated with Chalet, nor does it endorse or sponsor our services. We use the term in this generalized manner to easily convey the idea of participating in short-term rental activities, recognizing 'Airbnb' as a term familiar to many in this context.
Affiliate & Referral Disclosure. Chalet may receive referral fees or other consideration when you engage with featured agents, lenders, cost-seg providers, or other partners referenced on this site. These relationships may influence which partners we present. We follow the FTC Endorsement Guides and aim to disclose material connections clearly and conspicuously.
Chalet (DBA of GetChalet Inc.) is not affiliated, associated, authorized, endorsed by, or in any way officially connected with Airbnb, Airbnb.com, or any of its subsidiaries or its affiliates. The official Airbnb website can be found at http://www.airbnb.com. The name "Airbnb" as well as related names, marks, emblems and images are registered trademarks of Airbnb, Inc.
3535 Malina Place, Wailea, HI, USA
Covers its debt with margin to spare at the current price.
Investment potential
Your scenario · adjust the levers below or open advanced settings to see how returns change
$110,308
$9,192/mo · at 79% occupancy & $751/night
$49,579
$4,132/mo after costs & mortgage
Cap rate
15.9%
Cash-on-cash
33.1%
DSCR
2.66
Confidence
Your assumptions
Revenue
$110,308/yr
Market avg: $110,308/yr · 79% occ · $751 ADR
Financing
$29,939/yr
Operating costs
$30,790/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 8 properties
$570–$943
Median $752
68%–83%
Median 79%
$74.1K–$196.0K
Median $103.9K
135–248
Median 195
This property · $110.3K
Comparable properties (8)
Cash flow potential High · Appreciation potential Medium
248 days available · 191 days booked ·
244 days available · 193 days booked ·
236 days available · 190 days booked ·
188 days available · 138 days booked ·
201 days available · 134 days booked ·
165 days available · 127 days booked ·
135 days available · 96 days booked ·
176 days available · 145 days booked ·
Revenue and occupancy reflect Chalet's modeled estimates from observed booking activity for comparable active listings. Individual results vary with management, seasonality, and pricing.
Who this property is for
The same property is a great buy for one investor and a trap for another. Here's the honest read.
1031 / high-equity buyer
~$123.5K
Year-1 tax shield
Buying with cash or low leverage removes the debt-coverage problem entirely, so the thesis rests on appreciation plus a large first-year write-off. At roughly 25% of purchase price, the shield is substantial enough to carry the deal on its own.
DSCR cash-flow buyer
2.66
DSCR at asking
At asking price the property clears the 1.20 DSCR most lenders require, so it should qualify for DSCR financing and cover its own debt service from day one. This is the buyer this deal is built for.
Price-disciplined buyer
—
Break-even purchase price
Even a deep discount doesn't get this deal to break even within a realistic range, so there's no price anchor to negotiate toward. A price-disciplined buyer should pass unless the revenue assumptions change.
For a buyer who materially participates and qualifies for the STR tax treatment.
$123.5K
Estimated first-year deduction · range $102.5K–$140.8K
Why this matters here
At a marginal bracket, this deduction can be worth $37.9K–$52.1K in estimated federal tax saved.
This only applies if you meet the IRS material-participation tests for short-term rentals and are not using a full-service property manager.
Estimate, subject to CPA review. Cost-segregation percentages shown here are illustrative and depend on an actual study of the property.
Some states do not conform to federal bonus depreciation, so your state may not allow the same first-year treatment shown above.
Chalet can introduce a cost-segregation partner — this is not tax, legal, or financial advice.
How cash-on-cash return moves with purchase price. The marked line is break-even (1.0 DSCR).
At this price: cash-on-cash +33.1%, DSCR 2.66, cash flow $49,579/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $375,000 | 48.6% | 3.54 | Positive |
| -22% | $390,000 | 46.3% | 3.41 | Positive |
| -15% | $425,000 | 41.4% | 3.12 | Positive |
| -8% | $460,000 | 37.2% | 2.89 | Positive |
| Asking | $500,000 | 33.1% | 2.66 | Positive |
| +8% | $540,000 | 29.4% | 2.46 | Positive |
| +15% | $575,000 | 26.6% | 2.31 | Positive |
Break-even price
Out of range
This deal does not reach break-even within ±25% of asking.
Discount needed
—
The gap between asking and the price a cash-flow buyer can underwrite.
If refi to 5.5% in 24 mo
+$4,388/yr
Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.
Annual avg $9,192 · peaks at $15,032 in Dec
Annual avg 75% · peaks at 87% in Jan
$4,132/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$145,000
Return on cash:51.4%
You qualify for STR financing
Your DSCR is 2.66 · lenders typically require 1.0+.
Get matched with 2–3 vetted STR lenders, free.
What the deal returns over the hold — including the tax shield, which is the whole point for an appreciation buyer.
Levered IRR
53.0%
over 5-yr hold, with tax shield
Equity multiple
3.8×
total proceeds vs. $145,000 invested
Projected value at exit
$638,141
year 5 · 5.0% annual appreciation
Tax shield contribution
+11.1 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $128,809 | $25,000 | $95,274 | $249,083 |
| Year 2 | $132,894 | $51,250 | $146,508 | $330,652 |
| Year 3 | $137,274 | $78,813 | $199,421 | $415,507 |
| Year 4 | $141,970 | $107,753 | $254,038 | $503,762 |
| Year 5 | $147,007 | $138,141 | $310,386 | $595,534 |
Projection, not a promise.
Assumes 5.0% annual appreciation, 1.5% rent growth (operating costs held flat), and that the property qualifies for short-term-rental tax treatment. The year-1 depreciation shield depends on a real cost-segregation study and your tax situation — consult a CPA.
Appreciation is the dominant driver of this return. When cash flow is negative, the deal depends on the property gaining value — it is not paying for itself from income.
Appreciation, rent growth, and financing rates are editable under Edit financials.
STR deals turn on local rules and demand that a generalist agent misses. Chalet matches you with a vetted Wailea agent who knows which properties actually cash flow — and which to avoid.
© 2026 Chalet. All rights reserved.
This analysis is generated by Chalet's Airbnb Calculator
Visit getchalet.com for more tools
Real Estate Investment Analysis & Market Insights
Disclaimer. This page and the data presented are for informational purposes only. The information provided should not be construed as financial, legal, or investment advice. Market conditions can change rapidly, and past performance does not guarantee future results. Always consult with qualified professionals before making investment decisions.
3300 Wailea Alanui Dr unit 13f, Kihei, HI 96753, USA
1 bed 2 bath 2 guests
Revenue
$54,271/yr
Daily Rate
$315
Occupancy
0.8%
2777 S Kihei Rd unit c208, Kihei, HI 96753, USA
2 bed 2 bath 6 guests
Revenue
$75,921/yr
2747 S Kihei Rd apt j009, Kihei, HI 96753, USA
2 bed 2 bath 6 guests
Revenue
$75,881/yr
35 Walaka St apt l204, Kihei, HI 96753, USA
1 bed 1 bath 2 guests
Revenue
$46,754/yr
22 Waimahaihai St, Kihei, HI 96753, USA
3 bed 3 bath 8 guests
Revenue
$135,529/yr
22 Waimahaihai St, Kihei, HI 96753, USA
3 bed 3 bath 8 guests
Revenue
$135,529/yr
Daily Rate
$412
Occupancy
0.7%
Daily Rate
$398
Occupancy
0.7%
Daily Rate
$242
Occupancy
0.7%
Daily Rate
$729
Occupancy
0.7%
Daily Rate
$729
Occupancy
0.7%