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REI Lense

Winter Haven, FL Mid-Term Rental Analysis

Analyze rental property cap rates, cash-on-cash returns, and cashflow for mid-term rental investments in Winter Haven, FL. Based on 30+ datapoints.

Winter Haven, FL Mid-Term Rental Investment Snapshot

Based on 30+ mid-term rental datapoints

Median Cap Rate

6.6%

Avg Cash on Cash

-0.7%

Median Cashflow

-$66/mo

Avg Rent Estimate

$3,112/mo

Avg Price

$311,249

Price Range

$150K – $550K

approximate

Rent to Price

1%

strong ratio

Positive Cashflow

41%

of analyzed properties

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

Winter Haven, FL presents a balanced mid-term rental profile across 30+ analyzed datapoints. A median 6.6% cap rate combined with -0.7% average cash-on-cash returns make this a solid market for investors blending furnished-rental yield with the operational simplicity of monthly stays at a mid-to-upper tier price point.

Across 30+ analyzed properties, Winter Haven, FL mid-term rental investments show a median monthly cashflow of -$66 with average furnished rent estimates of $3,112/month. These figures reflect real property data, not projections.

1816 5th St SE, Winter Haven, FL 33880

Price

$224,900

Rent

$2,688

CachFlow

$201

CoC

3.7

Full Analysis

218 HARTRIDGE HILLS DRIVE, Winter Haven, FL 33881

Price

$369,000

Rent

$3,459

CachFlow

-$409

CoC

-5.14

Full Analysis

2025 MARILYN AVENUE, Winter Haven, FL 33881

Price

$225,900

Rent

$3,582

CachFlow

$1,005

CoC

18.43

Full Analysis

427 W LAKE ELBERT DR NE, Winter Haven, FL 33881

Price

$384,200

Rent

$2,862

CachFlow

-$549

CoC

-6.68

Full Analysis

2019 KAPREE COURT, Winter Haven, FL 33884

Price

$336,700

Rent

$3,512

CachFlow

$222

CoC

3

Full Analysis
1–5 of 30+
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Winter Haven, FL Mid-Term Rental Market Insights

  • Median cashflow is -$66/month — careful deal selection is essential here
  • 6.6% median cap rate reflects a balanced risk-return profile
  • 41% positive cashflow rate means roughly two in five properties are cash-flow positive
  • Mid-to-upper tier market with properties priced about $150,000 to $550,000

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