Sign up for our newsletter
Monthly insights, tips, and exclusive offers for STR investors.
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.
33 Henderson DR, Naples, FL 34114
Priced too high to cash-flow with a loan — an equity or tax play, not income.
Investment potential
Your scenario · adjust the levers below or open advanced settings to see how returns change
$48,674
$4,056/mo · at 59% occupancy & $297/night
-$4,042
-$337/mo after costs & mortgage
Cap rate
5.2%
Cash-on-cash
-2.7%
DSCR
0.86
Confidence
Your assumptions
Revenue
$48,674/yr
Market avg: $48,674/yr · 59% occ · $297 ADR
Financing
$29,939/yr
Operating costs
$22,778/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 6 properties
$209–$456
Median $292
40%–70%
Median 59%
$33.7K–$67.3K
Median $46.0K
230–365
Median 329
This property · $48.7K
Comparable properties (6)
Cash flow potential Medium · Appreciation potential Medium
365 days available · 198 days booked ·
365 days available · 191 days booked ·
271 days available · 153 days booked ·
298 days available · 168 days booked ·
360 days available · 144 days booked ·
230 days available · 152 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.
Price-disciplined buyer
$432.5K
Break-even purchase price
The deal pencils only if you buy right. At ~14% below the Zestimate the numbers reach break-even — treat that as a negotiation anchor, not a fantasy. Pay asking and the math stops working.
DSCR cash-flow buyer
0.86
DSCR at asking
At asking price the property doesn't cover its own debt service, so it won't qualify for DSCR financing as modeled. If you need cash flow from day one, look at a mid-term-rental fallback or a different Naples submarket.
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 -2.7%, DSCR 0.86, cash flow -$4,042/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $375,000 | 2.9% | 1.15 | Positive |
| -22% | $390,000 | 2.1% | 1.11 | Positive |
| -15% | $425,000 | 0.3% | 1.02 | At break-even |
| -8% | $460,000 | -1.2% | 0.94 | Below break-even |
| Asking | $500,000 | -2.7% | 0.86 | Below break-even |
| +8% | $540,000 | -4.0% | 0.80 | Below break-even |
| +15% | $575,000 | -5.0% | 0.75 | Below break-even |
Break-even price
$432,491
~14% under Zestimate. Where this property reaches 1.0 DSCR and neutral cash flow.
Discount needed
−$67,509
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 $4,056 · peaks at $7,413 in Feb
Annual avg 55% · peaks at 76% in Feb
−$337/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$145,000
Return on cash:14.5%
DSCR below 1.0 — but you can still qualify
Your DSCR is 0.86 · 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
16.5%
over 5-yr hold, with tax shield
Equity multiple
1.9×
total proceeds vs. $145,000 invested
Projected value at exit
$638,141
year 5 · 5.0% annual appreciation
Tax shield contribution
+6.8 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $128,809 | $25,000 | $41,653 | $195,462 |
| Year 2 | $132,894 | $51,250 | $38,341 | $222,485 |
| Year 3 | $137,274 | $78,813 | $35,770 | $251,857 |
| Year 4 | $141,970 | $107,753 | $33,952 | $283,675 |
| Year 5 | $147,007 | $138,141 | $32,896 | $318,044 |
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 Naples 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.
1322 Henderson Creek Drive, Naples, FL, USA
3 bed 2 bath 8 guests
Revenue
$36,895/yr
Daily Rate
$318
Occupancy
0.6%
9185 Celeste Dr, Naples, FL, USA
2 bed 2 bath 6 guests
Revenue
$84,316/yr
9067 Capistrano Street North, Naples, FL, USA
3 bed 2 bath 8 guests
Revenue
$39,374/yr
9022 Michael Circle, Naples, FL, USA
3 bed 2 bath 8 guests
Revenue
$59,354/yr
9009 Michael Circle, Naples, FL, USA
2 bed 2 bath 6 guests
Revenue
$84,316/yr
9037 Alturas Street, Naples, FL, USA
3 bed 2 bath 8 guests
Revenue
$39,374/yr
Daily Rate
$275
Occupancy
0.6%
Daily Rate
$317
Occupancy
0.6%
Daily Rate
$349
Occupancy
0.5%
Daily Rate
$275
Occupancy
0.6%
Daily Rate
$317
Occupancy
0.6%