Airbnb Properties for Sale in Winter Haven, FL

Looking for a vacation rental investment in Winter Haven, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Haven, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winter Haven, FL

Q: What is the average Airbnb occupancy rate in Winter-haven, FL?

In July 2026, the average Airbnb occupancy rate in Winter-haven is 26%.

Q: How to get Winter-haven, FL Airbnb data?

Airbnb data on vacation rentals in Winter-haven, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter-haven, FL market insights, guest information and booking details, seasonality trends and historical Winter-haven, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1646 Tressel Ct Winter Haven, FL Nestled within a secure, gated community with impressively low HOA fees, this beautiful 4-...	4 beds \| 2 baths \| 1,846 sq.ft.	$280,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 5.08% Airbnb Rental Income: $2995 Traditional Rental Income: $2261 Airbnb ROI: 5.25% Traditional ROI: 5.08%
301 Terranova Blvd Winter Haven, FL Welcome to this beautifully maintained 4-bedroom, 2-bathroom home located in the desirable...	4 beds \| 2 baths \| 1,960 sq.ft.	$415,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.91% Airbnb Rental Income: $2995 Traditional Rental Income: $2079 Airbnb ROI: 3.49% Traditional ROI: 2.91%
3357 Timberline Rd W Winter Haven, FL Welcome to 3357 Timberline Rd W, located in the charming city of Winter Haven, FL. This ex...	4 beds \| 2 baths \| 1,675 sq.ft.	$265,000	Airbnb cash on cash: 6.44% Traditional cash on cash: 5.44% Airbnb Rental Income: $2995 Traditional Rental Income: $2044 Airbnb ROI: 6.44% Traditional ROI: 5.44%
507 Short Ln Winter Haven, FL ""SELLER MOTIVATED â PRICE IMPROVEMENT! BRING YOUR OFFER!"" Beautiful and well-maintain...	4 beds \| 2 baths \| 1,867 sq.ft.	$340,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 3.61% Airbnb Rental Income: $2995 Traditional Rental Income: $2102 Airbnb ROI: 4.25% Traditional ROI: 3.61%
292 Krenson Bay Loop Winter Haven, FL Welcome to 292 Krenson Bay Loop, a 2024-built block home located in a gated Winter Haven c...	4 beds \| 2 baths \| 1,820 sq.ft.	$329,900	Airbnb cash on cash: 4.73% Traditional cash on cash: 4.06% Airbnb Rental Income: $2995 Traditional Rental Income: $2098 Airbnb ROI: 4.73% Traditional ROI: 4.06%
724 W Central Ave Winter Haven, FL Great investment opportunity! Tenant-occupied property in a central location with strong r...	5 beds \| N/A baths \| 3,015 sq.ft.	$430,000	Airbnb cash on cash: 7.71% Traditional cash on cash: 4.61% Airbnb Rental Income: $5523 Traditional Rental Income: $3138 Airbnb ROI: 7.71% Traditional ROI: 4.61%
1015 CAREFREE COVE DRIVE Winter Haven, FL Short Sale. Bank approved price! Welcome to this beautifully updated 4-bedroom, 1.5-bath s...	4 beds \| 2 baths \| 1,104 sq.ft.	$220,000	Airbnb cash on cash: 8.2% Traditional cash on cash: 7.33% Airbnb Rental Income: $2995 Traditional Rental Income: $2126 Airbnb ROI: 8.2% Traditional ROI: 7.33%
2610 San Marco Way Winter Haven, FL Welcome to 2610 San Marco Way, a beautiful Highland Homes Raychel floor plan located in th...	4 beds \| 2 baths \| 1,819 sq.ft.	$329,900	Airbnb cash on cash: 4.91% Traditional cash on cash: 4.59% Airbnb Rental Income: $2995 Traditional Rental Income: $2209 Airbnb ROI: 4.91% Traditional ROI: 4.59%
1396 Axel Cir Winter Haven, FL Virtually Staged. Welcome to this beautifully updated, 5-bedroom, 3-bath home built in 202...	5 beds \| 3 baths \| 3,022 sq.ft.	$379,000	Airbnb cash on cash: 9.34% Traditional cash on cash: 5.33% Airbnb Rental Income: $5523 Traditional Rental Income: $2946 Airbnb ROI: 9.34% Traditional ROI: 5.33%
1904 3rd St NE Winter Haven, FL CONCESSIONS AVAILABLE! Welcome home to this beautifully updated 4 bed, 2 bath in the heart...	4 beds \| 2 baths \| 1,400 sq.ft.	$224,999	Airbnb cash on cash: 8.05% Traditional cash on cash: 7.26% Airbnb Rental Income: $2995 Traditional Rental Income: $2138 Airbnb ROI: 8.05% Traditional ROI: 7.26%
264 MEREDITH BOULEVARD Winter Haven, FL Welcome to this stunning Dream Finders Bradley floorplan, located in the highly sought-aft...	4 beds \| 2 baths \| 1,598 sq.ft.	$279,990	Airbnb cash on cash: 7.18% Traditional cash on cash: 6.75% Airbnb Rental Income: $2995 Traditional Rental Income: $2195 Airbnb ROI: 7.18% Traditional ROI: 6.75%
248 MEREDITH BOULEVARD Winter Haven, FL Welcome to this stunning Bradley floorplan, located in the highly sought-after community o...	4 beds \| 2 baths \| 1,598 sq.ft.	$259,990	Airbnb cash on cash: 7.8% Traditional cash on cash: 7.34% Airbnb Rental Income: $2995 Traditional Rental Income: $2195 Airbnb ROI: 7.8% Traditional ROI: 7.34%
3307 FOX RIDGE DRIVE Winter Haven, FL Under contract-accepting backup offers. Short Sale. Welcome to your 3 bedroom 2 bathroom h...	4 beds \| 2 baths \| 1,253 sq.ft.	$250,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 6.59% Airbnb Rental Income: $2995 Traditional Rental Income: $2154 Airbnb ROI: 7.24% Traditional ROI: 6.59%
344 Alexzander Way Winter Haven, FL Welcome to this stunning 5-bedroom, 3-bath home located in the Jace Landing community of W...	5 beds \| 3 baths \| 2,696 sq.ft.	$389,000	Airbnb cash on cash: 9.36% Traditional cash on cash: 5.1% Airbnb Rental Income: $5523 Traditional Rental Income: $2860 Airbnb ROI: 9.36% Traditional ROI: 5.1%
780 Overlook Grove Dr Winter Haven, FL HOME WARRANTY INCLUDED! Need 4 bedrooms, but don't need to break the budget? This is what ...	4 beds \| 2 baths \| 1,583 sq.ft.	$272,500	Airbnb cash on cash: 5.9% Traditional cash on cash: 5.31% Airbnb Rental Income: $2995 Traditional Rental Income: $2156 Airbnb ROI: 5.9% Traditional ROI: 5.31%
302 DONALD LANE Winter Haven, FL Under contract-accepting backup offers. Check out this well-maintained 4-bedroom, 2-bath h...	4 beds \| 2 baths \| 1,512 sq.ft.	$215,000	Airbnb cash on cash: 8.44% Traditional cash on cash: 7.53% Airbnb Rental Income: $2995 Traditional Rental Income: $2120 Airbnb ROI: 8.44% Traditional ROI: 7.53%
4669 OSPREY WAY Winter Haven, FL This 4/2 home has a renovated interior showcasing modern upgrades throughout. The home fea...	4 beds \| 2 baths \| 1,992 sq.ft.	$309,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.02% Airbnb Rental Income: $2995 Traditional Rental Income: $2067 Airbnb ROI: 4.85% Traditional ROI: 4.02%
3905 WARBLER DRIVE Winter Haven, FL Under contract-accepting backup offers. Fully remodeled two story 4 bedrooms 3 bathrooms h...	4 beds \| 3 baths \| 2,101 sq.ft.	$282,900	Airbnb cash on cash: 5.96% Traditional cash on cash: 5.67% Airbnb Rental Income: $2995 Traditional Rental Income: $2231 Airbnb ROI: 5.96% Traditional ROI: 5.67%
1633 NANTUCKET WAY Winter Haven, FL Take advantage of an incredible builder promotion featuring low down payment options and b...	4 beds \| 2 baths \| 1,863 sq.ft.	$338,900	Airbnb cash on cash: 4.74% Traditional cash on cash: 3.98% Airbnb Rental Income: $2995 Traditional Rental Income: $2064 Airbnb ROI: 4.74% Traditional ROI: 3.98%
1491 Axel Cir Winter Haven, FL Winter Haven near the scenic Chain of Lakes, this 5 Bedroom 3 Bathroom home with two Flex ...	5 beds \| 3 baths \| 3,022 sq.ft.	$489,000	Airbnb cash on cash: 7.26% Traditional cash on cash: 6.36% Airbnb Rental Income: $5523 Traditional Rental Income: $4002 Airbnb ROI: 7.26% Traditional ROI: 6.36%
1328 Daisy Field Dr Winter Haven, FL HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake...	5 beds \| 3 baths \| 2,696 sq.ft.	$380,000	Airbnb cash on cash: 9.04% Traditional cash on cash: 4.58% Airbnb Rental Income: $5523 Traditional Rental Income: $2824 Airbnb ROI: 9.04% Traditional ROI: 4.58%
1392 Axel Cir Winter Haven, FL Discover this gem in the heart of Winter Haven! This spacious home with 5 bedrooms and 3 f...	5 beds \| 3 baths \| 2,523 sq.ft.	$370,000	Airbnb cash on cash: 9.99% Traditional cash on cash: 5.25% Airbnb Rental Income: $5523 Traditional Rental Income: $2770 Airbnb ROI: 9.99% Traditional ROI: 5.25%
2213 ROSE BOULEVARD Winter Haven, FL Welcome to 2213 Rose Blvd in Winter Havenâa beautifully maintained and like-new 4 bedroo...	4 beds \| 2 baths \| 1,851 sq.ft.	$289,900	Airbnb cash on cash: 5.99% Traditional cash on cash: 5.8% Airbnb Rental Income: $2995 Traditional Rental Income: $2254 Airbnb ROI: 5.99% Traditional ROI: 5.8%
4856 Summerfield Cir Winter Haven, FL One or more photo(s) has been virtually staged. Discover the perfect blend of modern updat...	4 beds \| 2 baths \| N/A	$299,900	Airbnb cash on cash: 5.35% Traditional cash on cash: 4.91% Airbnb Rental Income: $2995 Traditional Rental Income: $2184 Airbnb ROI: 5.35% Traditional ROI: 4.91%
1373 Lucerne Loop Rd NE Winter Haven, FL Situated in the heart of Central Florida's growing Polk County corridor, 1373 Lucerne Loop...	4 beds \| 2 baths \| 1,746 sq.ft.	$269,000	Airbnb cash on cash: 5.75% Traditional cash on cash: 5.66% Airbnb Rental Income: $2995 Traditional Rental Income: $2285 Airbnb ROI: 5.75% Traditional ROI: 5.66%
288 Meredith Blvd Winter Haven, FL Virtually Staged. Under Construction. Ready by August 2026 The Bradley looks and feels bi...	4 beds \| 2 baths \| 1,598 sq.ft.	$294,990	Airbnb cash on cash: 6.77% Traditional cash on cash: 5.69% Airbnb Rental Income: $2995 Traditional Rental Income: $2007 Airbnb ROI: 6.77% Traditional ROI: 5.69%
445 Mckenna Dr Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to this thoughtfully designed sing...	4 beds \| 2 baths \| 1,694 sq.ft.	$299,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 4.83% Airbnb Rental Income: $2995 Traditional Rental Income: $1985 Airbnb ROI: 5.98% Traditional ROI: 4.83%
1018 Brimstone Cir Winter Haven, FL Like-New Casa Fresca Home with a VA Assumable Rate @ 4.99%! This Jazmin Floorplan in Harmo...	5 beds \| 3 baths \| 2,457 sq.ft.	$475,000	Airbnb cash on cash: 7.97% Traditional cash on cash: 4.27% Airbnb Rental Income: $5523 Traditional Rental Income: $2770 Airbnb ROI: 7.97% Traditional ROI: 4.27%
1055 30TH STREET NW Winter Haven, FL Price Improvement Move-in ready and fully remodeled from top to bottom, this 4-bedroom...	4 beds \| 1 baths \| 1,020 sq.ft.	$199,900	Airbnb cash on cash: 9.82% Traditional cash on cash: 6.89% Airbnb Rental Income: $2995 Traditional Rental Income: $1751 Airbnb ROI: 9.82% Traditional ROI: 6.89%
1473 Lucerne Loop Rd NE Winter Haven, FL Built in 2019 and thoughtfully designed for modern living, this well-maintained 4-bedroom,...	4 beds \| 2 baths \| 1,599 sq.ft.	$260,000	Airbnb cash on cash: 5.95% Traditional cash on cash: 5.65% Airbnb Rental Income: $2995 Traditional Rental Income: $2229 Airbnb ROI: 5.95% Traditional ROI: 5.65%
1517 AXEL CIRCLE Winter Haven, FL Under contract-accepting backup offers. Winter Haven home near Chain of Lakes featuring 5 ...	5 beds \| 3 baths \| 3,022 sq.ft.	$489,000	Airbnb cash on cash: 7.26% Traditional cash on cash: 4.84% Airbnb Rental Income: $5523 Traditional Rental Income: $3306 Airbnb ROI: 7.26% Traditional ROI: 4.84%
2122 River Hawk Loop Winter Haven, FL Under Construction. Under Construction. Welcome to the Residences at Winter Haven, a new s...	4 beds \| 2 baths \| 1,741 sq.ft.	$344,900	Airbnb cash on cash: 5.43% Traditional cash on cash: 5.1% Airbnb Rental Income: $2995 Traditional Rental Income: $2202 Airbnb ROI: 5.43% Traditional ROI: 5.1%
1061 SANDPIPER LOOP Winter Haven, FL Fall in love with this stunning 5-bedroom, 3-bath home with a 3-car garage, perfectly situ...	5 beds \| 3 baths \| 2,472 sq.ft.	$465,000	Airbnb cash on cash: 7.64% Traditional cash on cash: 3.86% Airbnb Rental Income: $5523 Traditional Rental Income: $2771 Airbnb ROI: 7.64% Traditional ROI: 3.86%
563 Honey Bell Rd Winter Haven, FL Welcome to 563 Honey Bell Rd, a home that beautifully blends modern comfort, style, and th...	4 beds \| 2 baths \| 1,851 sq.ft.	$305,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 4.61% Airbnb Rental Income: $2995 Traditional Rental Income: $2262 Airbnb ROI: 4.77% Traditional ROI: 4.61%
300 Meredith Blvd Winter Haven, FL Virtually Staged. Under Construction. Hillcrest floorplan, located in the highly sought-af...	4 beds \| 2 baths \| 1,758 sq.ft.	$314,990	Airbnb cash on cash: 6.28% Traditional cash on cash: 5.99% Airbnb Rental Income: $2995 Traditional Rental Income: $2220 Airbnb ROI: 6.28% Traditional ROI: 5.99%

Vacation Rentals in Winter Haven

There are 265 vacation rental properties available for sale in the city of Winter Haven . The median list price of Airbnb properties available for sale in Winter Haven is $294,814 and the average price per square foot is $173. The cash on cash return on vacation rentals in Winter Haven is 3.00%. The average monthly short term rental income in Winter Haven is $1,757.

Winter Haven, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 265 Airbnb properties available for sale in Winter Haven.

In 2026, the best neighborhood to buy short term rental property is Winter Haven.

In July 2026, the average Airbnb occupancy rate in Winter Haven is 26%.

Airbnb data on vacation rentals in Winter Haven, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter Haven, FL market insights, guest information and booking details, seasonality trends and historical Winter Haven, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winter Haven, FL

1646 Tressel Ct

Winter Haven, FL

4 beds | 2 baths | 1,846 sq.ft.

$280,000

Airbnb cash on cash: 5.25%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $2995

Traditional Rental Income: $2261

Airbnb ROI: 5.25%

Traditional ROI: 5.08%

301 Terranova Blvd

Winter Haven, FL

4 beds | 2 baths | 1,960 sq.ft.

$415,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $2995

Traditional Rental Income: $2079

Airbnb ROI: 3.49%

Traditional ROI: 2.91%

3357 Timberline Rd W

Winter Haven, FL

4 beds | 2 baths | 1,675 sq.ft.

$265,000

Airbnb cash on cash: 6.44%

Traditional cash on cash: 5.44%

Airbnb Rental Income: $2995

Traditional Rental Income: $2044

Airbnb ROI: 6.44%

Traditional ROI: 5.44%

507 Short Ln

Winter Haven, FL

4 beds | 2 baths | 1,867 sq.ft.

$340,000

Airbnb cash on cash: 4.25%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $2995

Traditional Rental Income: $2102

Airbnb ROI: 4.25%

Traditional ROI: 3.61%

292 Krenson Bay Loop

Winter Haven, FL

4 beds | 2 baths | 1,820 sq.ft.

$329,900

Airbnb cash on cash: 4.73%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $2995

Traditional Rental Income: $2098

Airbnb ROI: 4.73%

Traditional ROI: 4.06%

724 W Central Ave

Winter Haven, FL

5 beds | N/A baths | 3,015 sq.ft.

$430,000

Airbnb cash on cash: 7.71%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $5523

Traditional Rental Income: $3138

Airbnb ROI: 7.71%

Traditional ROI: 4.61%

1015 CAREFREE COVE DRIVE

Winter Haven, FL

4 beds | 2 baths | 1,104 sq.ft.

$220,000

Airbnb cash on cash: 8.2%

Traditional cash on cash: 7.33%

Airbnb Rental Income: $2995

Traditional Rental Income: $2126

Airbnb ROI: 8.2%

Traditional ROI: 7.33%

2610 San Marco Way

Winter Haven, FL

4 beds | 2 baths | 1,819 sq.ft.

$329,900

Airbnb cash on cash: 4.91%

Traditional cash on cash: 4.59%

Airbnb Rental Income: $2995

Traditional Rental Income: $2209

Airbnb ROI: 4.91%