STRROI is a short-term rental (STR) investment analysis platform. It pulls live MLS listings, scores every property for STR return on investment (ROI) using real Airbnb comps, and generates AI-written deal memos, so investors can underwrite deals faster and with more confidence.

How does the buy rating work?

Every property is scored 1-10 based on cash-on-cash return (35%), cap rate (30%), monthly cash flow (20%), and property quality signals (15%). Scores of 8-10 are Strong Buy, 6-7 are Buy, 4-5 are Hold, and below 4 are Pass.

What data does STRROI use?

STRROI combines live MLS listing data with real short-term rental comp data: the same active listings your competition will be booking. Cap rates, ADR, occupancy, and cash flow are all calculated from real market data, not estimates.

What is an AI Deal Memo?

An AI Deal Memo is a full investment analysis document generated by AI in under 30 seconds. It includes an investment thesis, comparable rental analysis, risk factors, financing scenarios, sensitivity tables, and a buy/pass recommendation, formatted to share with partners or lenders.

Is there a free plan?

Yes. The free plan gives you full access to the STRROI interface using demo market data, so you can explore every feature before committing. Paid plans start at $24/month and unlock live MLS searches, real STR comps, and AI-powered analysis.

How is STRROI different from AirDNA or Mashvisor?

AirDNA and Mashvisor show you STR performance data for properties you already own or are researching manually. STRROI starts from live for-sale MLS listings and automatically underwriting each one for STR viability, so you're finding deals, not just analyzing them. The AI Deal Memo feature is also unique: no other STR tool generates a full underwriting memo from live comps.

Southeast1.3% avg cap rateLive · 41 active listings

Key West, FL

Southernmost point - premium year-round island STR

Key West is America's southernmost city and one of the most supply-constrained STR markets in the US. The island's physical size limits new construction, the Conch Republic culture drives intense brand loyalty, and the tropical climate supports year-round demand. STR regulations are among the most complex in Florida - licensing, registration, and inspection requirements apply.

1.3%

Avg Cap Rate

Net operating income / price

62%

Avg Occupancy

Annual average

$195

Avg Nightly Rate

All property types

$2.3M

Avg List Price

STR-viable properties

41 active listings in Key West are analyzed and ranked right now

Scored 1-10 against real Airbnb comps. See which properties rank highest and why.

See the ranked listings

Estimated Annual Performance

Gross rental revenue

62% occ × $195/night

$44,129

Est. operating expenses

Mgmt, cleaning, supplies, insurance (~40%)

- $17,652

Est. net operating income

Before mortgage & depreciation

$26,477

At $2.3M avg price

Implied cap rate

1.1%

* Estimates based on market averages. Individual property performance varies. Always run a full underwriting analysis.

Why Investors Choose Key West

Supply-constrained island market - limited new inventory possible

Year-round tropical climate eliminates seasonal off-peak

Premium pricing relative to property size - walkable, dense market

Review FL STR licensing requirements - active regulation applies

Peak season: Year-round (peaks: Fantasy Fest Oct, spring break)

Top property types: Conch House, Cottage, Condo, Duplex

Primary zip: 33040, 33042

Market averages, not guarantees. Cap rates, occupancy, and nightly rates are market-wide averages based on active STR listings and historical data. Individual property performance depends on location, amenities, management, and listing quality. Always run a full underwriting analysis before purchasing.Stats sourced from 41 active listings · last updated Jul 1, 2026

Run a live analysis in Key West

Search active MLS listings in Key West and instantly see cap rates, cash flow projections, and STR comp-backed nightly rates - all in one underwriting report.

Search Key West Listings

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