Airbnb market dataThrough 252 listingsHow we measure
A typical active Airbnb in Winter Haven, FL earned $21,400 in the 12 months to Sep 2026, with the median listing booked 50% of nights and an average nightly rate of $159 in Sep 2026.
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A typical active Winter Haven Airbnb earned $21,400 in the 12 months to Sep 2026. The top 25% of listings averaged $45,621, about 2.1× that. The bottom 25%, which includes rarely booked listings, averaged $2,367.
$2.4k
Bottom 25% average
$21.4k
Typical listing
$45.6k
Top 25% average
1-bedroom homes are the most common in Winter Haven (40% of listings).
| Bedrooms | Share of listings | Nightly rate | Occupancy | Est. revenue/yr |
|---|---|---|---|---|
| Studio | 2% | $110 | 58% | $23,099 |
| 1 bedroom | 40% | $92 | 52% | $17,590 |
| 2 bedrooms | 15% | $150 | 48% | $26,127 |
| 3 bedrooms |
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The best three months, Apr, Mar and Jul, brought in 31% of a typical Winter Haven listing's revenue over the 12 months to Sep 2026.
Apr brings in 1.8× as much as Oct
Typical monthly revenue per listing, Oct 2025–Sep 2026
33880 has the highest gross yield of the 3 Winter Haven zipcodes we rank, at 9.3%, with typical revenue of $23,522 a year.
Ranked by gross yield (typical yearly revenue ÷ median home value), last 12 months.
Yield isn't everything: zoning and HOA rules decide which streets allow short-term rentals.
The median Winter Haven home is worth $272,484 (Zillow, Aug 2026), down 2.7% in a year. At typical revenue that's a 7.9% gross yield, before the mortgage, taxes and running costs.
The 10 largest operators in Winter Haven each ran 4 or more listings as of May 2025.
and 3 more
Winter Haven ranks #55 of the 73 Florida markets we track by gross yield.
| # | Market | Gross yield | Revenue/yr | Home value |
|---|---|---|---|---|
| 1 | Hallandale, FL | 18.4% | $51,024 | |
| 2 | Deerfield Beach, FL | 18.3% | $49,836 | |
| 3 | Delray Beach, FL | 15.3% | $52,453 | |
| 4 | Panama City, FL |
None listed in Winter Haven right now, so here are others in Florida.
A typical active Airbnb in Winter Haven, FL earned $21,400 in the 12 months to Sep 2026. The median listing was booked 50% of nights, and the average nightly rate was $159 in Sep 2026. Against a median home value of $272,484, that's a 7.9% gross yield before the mortgage, taxes and running costs.
A typical active listing earned $21,400 in the 12 months to Sep 2026. The top 25% of listings averaged $45,621 and the bottom 25% $2,367. Estimated by size: 1-bedroom about $17,590; 2-bedroom about $26,127; 3-bedroom about $38,778 and 4-bedroom about $44,453 a year.
The typical listing was booked 50% of nights in the 12 months to Sep 2026, from 63% in March to 32% in September.
Based on 252 Winter Haven short-term rental listings tracked by Chalet, with data through Sep 2026. Home values come from the Zillow Home Value Index.
Airbnb data sites count different things. Some average every listing, including ones that are rarely booked; some use a whole metro area instead of the town; some use a calendar year. We show typical figures for active listings in Winter Haven over the last 12 months, and label each number with what it counts. Compare like with like before comparing sites.
| 26% |
| $215 |
| 49% |
| $38,778 |
| 4 bedrooms | 14% | $251 | 49% | $44,453 |
|---|
| 5 bedrooms | 3% | $423 | 62% | $95,926 |
|---|
Estimated revenue = nightly rate × occupancy × 365, last 12 months.
| Month | Revenue | Occupancy | Nightly rate | Revenue a year earlier |
|---|---|---|---|---|
| Oct 2025 | $1,347 | 50% | $125 | |
| Nov 2025 | $1,633 | 47% | $131 | |
| Dec 2025 | $1,867 | 53% | $150 | |
| Jan 2026 | $1,788 | 50% | $149 | |
| Feb 2026 | $1,738 | 53% | $154 | |
| Mar 2026 | $2,262 | 63% | $164 | |
| Apr 2026 | $2,377 | 61% | $159 | |
| May 2026 | $1,692 | 43% | $180 | |
| Jun 2026 | $1,847 | 56% | $194 | |
| Jul 2026 | $1,980 | 54% | $199 | |
| Aug 2026 | $1,347 | 35% | $173 | |
| Sep 2026 | $1,521 | 32% | $164 |
Of guests from the top 10 cities, 95% live within a day's drive.
and 3 more
| 14.7% |
| $41,932 |
| 5 | Boynton Beach, FL | 13.9% | $56,131 |
|---|
| 6 | Fort Walton Beach, FL | 13.9% | $44,747 |
|---|
| 7 | Gulf Breeze, FL | 13.4% | $64,110 |
|---|
| 8 | Pensacola, FL | 13.4% | $35,684 |
|---|
| 55 | Winter Haven, FL (this market) | 7.9% | $21,400 |
|---|
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April; March and July earned the most, bringing in 31% of a typical listing's revenue in the 12 months to Sep 2026.
$272,484 as of August 2026 (Zillow Home Value Index), down 2.7% in a year.
1-bedroom homes make up 40% of listings, earning an estimated $17,590 a year.
The top origin cities are Miami, FL (5.0% of guests); Winter Haven, FL (2.9% of guests) and Jacksonville, FL (2.4% of guests). Of guests from the top 10 cities, 95% live within a day's drive.
Chalet tracks 252 short-term rental listings in Winter Haven, FL, with data through Sep 2026.
For education only, not financial, legal or investment advice. Full methodology
