REI Lense

REI Lense

Winter Haven, FL Short-Term Rental / Airbnb Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for short-term rental / airbnb investments in Winter Haven, FL. Based on 15+ datapoints.

Winter Haven, FL Short-Term Rental / Airbnb Investment Snapshot

Based on 15+ short-term rental / airbnb datapoints

Median Cap Rate

4.9%

Avg Cash on Cash

-4.4%

Median Cashflow

-$177/mo

Avg Rent Estimate

$3,037/mo

Avg Price

$307,250

Price Range

$215,000 - $484,200

Rent to Price

0.99%

okay ratio

Positive Cashflow

43%

of analyzed properties

Recent real estate investor listings analysed as short-term rental / airbnb deals in Winter Haven, FL

Winter Haven, FL is an emerging short-term rental market with growing investor interest. With 15+ datapoints analyzed so far, early metrics suggest opportunity for Airbnb investors willing to enter before the market matures. Current average cash-on-cash returns sit at -4.4%.

Across 15+ analyzed properties, Winter Haven, FL STR investments show a median monthly cashflow of -$177 with an average estimated nightly-rate-adjusted revenue of $3,037/month. These figures reflect real property data, not projections.

136 Lake Ring Dr, Winter Haven, FL 33880

Price

$301,800

Rent

$3,330

CachFlow

-$58

CoC

-0.86

Full Analysis

3407 Fox Ridge St, Winter Haven, FL 33884

Price

$266,900

Rent

$3,644

CachFlow

$216

CoC

3.5

Full Analysis

3971 Cypress Lndg W, Winter Haven, FL 33884

Price

$284,300

Rent

$3,578

CachFlow

$153

CoC

2.36

Full Analysis

220 Ruby Lake Ln, Winter Haven, FL 33884

Price

$782,800

Rent

$5,174

CachFlow

-$2,117

CoC

-13.48

Full Analysis

131 Ruby Lake Dr, Winter Haven, FL 33884

Price

$375,000

Rent

$3,593

CachFlow

-$536

CoC

-6.65

Full Analysis
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Winter Haven, FL Airbnb Market Insights

  • Median cashflow is -$177/month — careful deal selection is essential here
  • 4.9% median cap rate is typical of appreciation-focused markets
  • 43% positive cashflow rate means roughly two in five properties are cash-flow positive
  • Mid-to-upper tier market with properties from $215,000 to $484,200
  • Early-stage market data — revisit as more properties are analyzed for stronger signals

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