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 Single Family Residential For Sale in Winter Haven, FL

Search for Single Family Residential for Sale in Winter Haven, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 267 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
475 ARCHAIC DRIVE Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to your perfect sanctuary in the h...	4 beds \| 3 baths \| 2,643 sq.ft.	$674,500	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.76% Airbnb Rental Income: $5016 Traditional Rental Income: $3637 Airbnb ROI: 4.32% Traditional ROI: 3.76%
357 RUBY LAKE LOOP Winter Haven, FL Located in the gated community of Ruby Lake, this stunning 3-bedroom, 2-bath Cassidy Ox fl...	3 beds \| 2 baths \| 2,107 sq.ft.	$419,000	Airbnb cash on cash: 5.99% Traditional cash on cash: 4.54% Airbnb Rental Income: $4015 Traditional Rental Income: $2587 Airbnb ROI: 5.99% Traditional ROI: 4.54%
145 POLK DRIVE Winter Haven, FL Beautifully Remodeled, Move-In Ready Home in the Heart of Winter Haven! Welcome to this...	3 beds \| 2 baths \| 1,605 sq.ft.	$329,900	Airbnb cash on cash: 8.32% Traditional cash on cash: 5.43% Airbnb Rental Income: $4015 Traditional Rental Income: $2262 Airbnb ROI: 8.32% Traditional ROI: 5.43%
710 HERITAGE DRIVE NE Winter Haven, FL Seller Motivated! $5000 towards buyer concessions or buy down rate with approved offer. Dr...	4 beds \| 2 baths \| 2,736 sq.ft.	$647,499	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.21% Airbnb Rental Income: $5016 Traditional Rental Income: $3191 Airbnb ROI: 4.54% Traditional ROI: 3.21%
3830 OSPREY POINTE CIRCLE Winter Haven, FL Beautiful community of Osprey Pointe on Lake Ned. This 2 bedroom/2 bath home is move in re...	2 beds \| 2 baths \| 1,438 sq.ft.	$249,900	Airbnb cash on cash: 6.27% Traditional cash on cash: 4.03% Airbnb Rental Income: $2962 Traditional Rental Income: $1751 Airbnb ROI: 6.27% Traditional ROI: 4.03%
1424 WALLACE MANOR PASS Winter Haven, FL Welcome to this charming 3 bedroom, 2 bath home built in 2014, offering almost 1600 sq. ft...	3 beds \| 2 baths \| 1,578 sq.ft.	$270,000	Airbnb cash on cash: 9.56% Traditional cash on cash: 5.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2184 Airbnb ROI: 9.56% Traditional ROI: 5.74%
2343 SALZBURG LOOP Winter Haven, FL THIS WELL-MAINTAINED HOME IS LOCATED IN A GREAT 55+ COMMUNITY CENTRALLY LOCATED IN WINTER ...	3 beds \| 2 baths \| 1,948 sq.ft.	$327,500	Airbnb cash on cash: 7.71% Traditional cash on cash: 5.91% Airbnb Rental Income: $4015 Traditional Rental Income: $2603 Airbnb ROI: 7.71% Traditional ROI: 5.91%
457 ADRIEL AVENUE Winter Haven, FL Do not miss this nice size home with 4 bedrooms and 2 bathrooms. New Roof. Perfect layout,...	4 beds \| 2 baths \| 2,088 sq.ft.	$359,900	Airbnb cash on cash: 9.89% Traditional cash on cash: 5.15% Airbnb Rental Income: $5016 Traditional Rental Income: $2389 Airbnb ROI: 9.89% Traditional ROI: 5.15%
731 CANBERRA ROAD Winter Haven, FL Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought...	3 beds \| 2 baths \| 2,140 sq.ft.	$335,000	Airbnb cash on cash: 8.02% Traditional cash on cash: 6.11% Airbnb Rental Income: $4015 Traditional Rental Income: $2555 Airbnb ROI: 8.02% Traditional ROI: 6.11%
3334 FOX RIDGE DRIVE Winter Haven, FL LAKEFRONT LIVING WITH NO HOA Welcome to 3334 Fox Ridge Drive â a beautifully maintained...	3 beds \| 3 baths \| 1,542 sq.ft.	$390,000	Airbnb cash on cash: 6.75% Traditional cash on cash: 5.35% Airbnb Rental Income: $4015 Traditional Rental Income: $2647 Airbnb ROI: 6.75% Traditional ROI: 5.35%
113 CITRUS DRIVE Winter Haven, FL Conventional loans only. VERY MOTIVATED SELLER!! Welcome to this charming 3 Bedroom 2 Bath...	3 beds \| 2 baths \| 2,016 sq.ft.	$285,000	Airbnb cash on cash: 9.29% Traditional cash on cash: 7.53% Airbnb Rental Income: $4015 Traditional Rental Income: $2685 Airbnb ROI: 9.29% Traditional ROI: 7.53%
2282 FIRESTONE PLACE Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to Cypresswood Golf & Country Club...	2 beds \| 2 baths \| 1,164 sq.ft.	$180,000	Airbnb cash on cash: 8.5% Traditional cash on cash: 5.78% Airbnb Rental Income: $2962 Traditional Rental Income: $1813 Airbnb ROI: 8.5% Traditional ROI: 5.78%
1908 CROSSROADS BOULEVARD Winter Haven, FL $5000 BUYER CONCESSION TOWARDS CLOSING COSTS WITH APPROVED OFFER!!! SELLER MOTIVATED! Imma...	4 beds \| 3 baths \| 2,781 sq.ft.	$455,000	Airbnb cash on cash: 6.98% Traditional cash on cash: 4.42% Airbnb Rental Income: $5016 Traditional Rental Income: $2898 Airbnb ROI: 6.98% Traditional ROI: 4.42%
114 BELMONT DRIVE Winter Haven, FL Welcome to this spacious and beautifully designed pool home, perfect for entertaining and ...	4 beds \| 2 baths \| 2,069 sq.ft.	$415,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 5.2% Airbnb Rental Income: $5016 Traditional Rental Income: $2856 Airbnb ROI: 8.12% Traditional ROI: 5.2%
2202 GARDEN LAKE DRIVE Winter Haven, FL Welcome to beautiful southeast Winter Haven, home to the Chain of Lakes and Legoland! This...	3 beds \| 2 baths \| 1,442 sq.ft.	$269,000	Airbnb cash on cash: 8.97% Traditional cash on cash: 4.88% Airbnb Rental Income: $4015 Traditional Rental Income: $2120 Airbnb ROI: 8.97% Traditional ROI: 4.88%
3998 BEDFORD AVENUE Winter Haven, FL If you are looking for the perfect home in an active community with all the comfort, safet...	4 beds \| 3 baths \| 2,277 sq.ft.	$464,900	Airbnb cash on cash: 6.03% Traditional cash on cash: 2.93% Airbnb Rental Income: $5016 Traditional Rental Income: $2640 Airbnb ROI: 6.03% Traditional ROI: 2.93%
220 RUBY LAKE LANE Winter Haven, FL Welcome to 220 Ruby Lake Lane, a stunning lakefront pool residence in the highly sought-af...	4 beds \| 3 baths \| 2,705 sq.ft.	$799,977	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.78% Airbnb Rental Income: $5016 Traditional Rental Income: $3702 Airbnb ROI: 3.17% Traditional ROI: 2.78%
4970 MANDOLIN COURT Winter Haven, FL Welcome to lakeside living in the Mandolin community! Inviting single story home with 4-be...	4 beds \| 2 baths \| 1,749 sq.ft.	$400,000	Airbnb cash on cash: 7.99% Traditional cash on cash: 3.28% Airbnb Rental Income: $5016 Traditional Rental Income: $2223 Airbnb ROI: 7.99% Traditional ROI: 3.28%
3686 PLYMOUTH DRIVE Winter Haven, FL This spacious 4-bedroom, 3-bath home is located in the desirable 55+ gated community of Tr...	4 beds \| 3 baths \| 2,404 sq.ft.	$388,900	Airbnb cash on cash: 7.29% Traditional cash on cash: 3.88% Airbnb Rental Income: $5016 Traditional Rental Income: $2748 Airbnb ROI: 7.29% Traditional ROI: 3.88%
3020 CANEEL STREET Winter Haven, FL GREAT OPPORTUNITY!!! Totally TURNKEY with all NEW FURNISHINGS!!! Welcome to carefree livin...	2 beds \| 2 baths \| 1,521 sq.ft.	$219,900	Airbnb cash on cash: 4.39% Traditional cash on cash: 2.03% Airbnb Rental Income: $2962 Traditional Rental Income: $1788 Airbnb ROI: 4.39% Traditional ROI: 2.03%
2013 MARILYN AVENUE Winter Haven, FL Welcome to 2013 Marilyn Ave in Winter Haven! BRAND NEW ROOF! (08/01/2025)This 3-bedroom, 3...	3 beds \| 3 baths \| 1,943 sq.ft.	$320,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 4.62% Airbnb Rental Income: $4015 Traditional Rental Income: $2173 Airbnb ROI: 7.89% Traditional ROI: 4.62%
5357 HOGAN LANE Winter Haven, FL One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with...	3 beds \| 2 baths \| 2,363 sq.ft.	$489,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 2.82% Airbnb Rental Income: $4015 Traditional Rental Income: $2424 Airbnb ROI: 4.43% Traditional ROI: 2.82%
3912 BALDWIN LANE Winter Haven, FL Under contract-accepting backup offers. What? Furniture and a golf cart? Just bring your t...	2 beds \| 2 baths \| 1,719 sq.ft.	$295,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1.84% Airbnb Rental Income: $2962 Traditional Rental Income: $1837 Airbnb ROI: 3.43% Traditional ROI: 1.84%
273 MARIPOSA Winter Haven, FL LOVELY FULL-SIZE HOME ON A CORNER LOT. Step inside and you'll find a generous family room ...	3 beds \| 2 baths \| 1,966 sq.ft.	$294,000	Airbnb cash on cash: 9% Traditional cash on cash: 6.21% Airbnb Rental Income: $4015 Traditional Rental Income: $2385 Airbnb ROI: 9% Traditional ROI: 6.21%
1246 31ST STREET NW Winter Haven, FL Welcome to this charming 2-bedroom, 1-bathroom home in the West Cannon Heights neighborhoo...	2 beds \| 1 baths \| 840 sq.ft.	$198,900	Airbnb cash on cash: 10% Traditional cash on cash: 6.38% Airbnb Rental Income: $2962 Traditional Rental Income: $1595 Airbnb ROI: 10% Traditional ROI: 6.38%
264 RUBY LAKE LANE Winter Haven, FL Lakefront Gem in Southeast Winter Haven! This Clean and ready to Move In 4 Bedroom, 2 bat...	4 beds \| 2 baths \| 2,217 sq.ft.	$750,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 2.56% Airbnb Rental Income: $5016 Traditional Rental Income: $3171 Airbnb ROI: 3.73% Traditional ROI: 2.56%
5392 CHANDLER DRIVE Winter Haven, FL PRICE IMPROVEMENT!!! Peaceful Waterfront Living! Many Beautiful Features & Oversized Livi...	4 beds \| 3 baths \| 3,034 sq.ft.	$349,900	Airbnb cash on cash: 8.99% Traditional cash on cash: 4.79% Airbnb Rental Income: $5016 Traditional Rental Income: $2611 Airbnb ROI: 8.99% Traditional ROI: 4.79%
108 LAKE SEARS DRIVE Winter Haven, FL One or more photo(s) has been virtually staged. Lakefront Haven in Winter Haven! Welcom...	4 beds \| 2 baths \| 1,688 sq.ft.	$395,000	Airbnb cash on cash: 8.85% Traditional cash on cash: 4.72% Airbnb Rental Income: $5016 Traditional Rental Income: $2465 Airbnb ROI: 8.85% Traditional ROI: 4.72%
3201 OAK TREE LANE Winter Haven, FL Schedule your showing now for this bright and airy 3-bedroom, 2-bath split-plan gem in the...	3 beds \| 2 baths \| 1,376 sq.ft.	$265,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 4.99% Airbnb Rental Income: $4015 Traditional Rental Income: $2125 Airbnb ROI: 9.11% Traditional ROI: 4.99%
1062 MEDINAH DRIVE Winter Haven, FL Location, Lifestyle & Leisure â All in One! Discover the perfect blend of comfort, conv...	2 beds \| 2 baths \| 1,398 sq.ft.	$229,990	Airbnb cash on cash: 6.39% Traditional cash on cash: 5.34% Airbnb Rental Income: $2962 Traditional Rental Income: $2051 Airbnb ROI: 6.39% Traditional ROI: 5.34%
4009 BEDFORD AVENUE Winter Haven, FL This fabulous Eco-Smart home is nestled in the highly desirable, maintenance-free, gated c...	3 beds \| 2 baths \| 1,871 sq.ft.	$322,900	Airbnb cash on cash: 6.86% Traditional cash on cash: 3.93% Airbnb Rental Income: $4015 Traditional Rental Income: $2266 Airbnb ROI: 6.86% Traditional ROI: 3.93%
4105 OAK DRIVE Winter Haven, FL New Lower price!!! Looking for a charming home, with land? Come check out this cute home o...	2 beds \| 1 baths \| 1,253 sq.ft.	$258,000	Airbnb cash on cash: 7.06% Traditional cash on cash: 5.13% Airbnb Rental Income: $2962 Traditional Rental Income: $1809 Airbnb ROI: 7.06% Traditional ROI: 5.13%
905 HILLSIDE COURT S Winter Haven, FL Welcome to this lovely 3 bedroom and 2 bath home, where modern comfort meets spacious Flor...	3 beds \| 2 baths \| 2,077 sq.ft.	$384,999	Airbnb cash on cash: 6.51% Traditional cash on cash: 4.87% Airbnb Rental Income: $4015 Traditional Rental Income: $2564 Airbnb ROI: 6.51% Traditional ROI: 4.87%
2853 ATTWATER LOOP Winter Haven, FL Welcome to 2853 Attwater Loop â a warm and inviting home in Traditions at Lake Ruby, one...	2 beds \| 2 baths \| 1,385 sq.ft.	$215,000	Airbnb cash on cash: 4.92% Traditional cash on cash: 4.63% Airbnb Rental Income: $2962 Traditional Rental Income: $2220 Airbnb ROI: 4.92% Traditional ROI: 4.63%
403 SAINT ANNS DRIVE Winter Haven, FL Under contract-accepting backup offers. NEW ROOF to be installed 10-27-25. Welcome HOME!!...	3 beds \| 2 baths \| 1,596 sq.ft.	$275,000	Airbnb cash on cash: 9.53% Traditional cash on cash: 6.55% Airbnb Rental Income: $4015 Traditional Rental Income: $2384 Airbnb ROI: 9.53% Traditional ROI: 6.55%
1152 BOWLINE STREET Winter Haven, FL PRICE IMPROVEMENT!!! Welcome Home! This 3BR/2BA home located on a corner lot in the gated...	3 beds \| 2 baths \| 1,585 sq.ft.	$314,900	Airbnb cash on cash: 7.87% Traditional cash on cash: 4.67% Airbnb Rental Income: $4015 Traditional Rental Income: $2207 Airbnb ROI: 7.87% Traditional ROI: 4.67%
305 HERNANDO ROAD Winter Haven, FL Welcome to your Dream home!! Step into this stunning residence through a spacious, light-f...	4 beds \| 3 baths \| 2,569 sq.ft.	$485,000	Airbnb cash on cash: 6.74% Traditional cash on cash: 5.79% Airbnb Rental Income: $5016 Traditional Rental Income: $3557 Airbnb ROI: 6.74% Traditional ROI: 5.79%
4034 DORAL Winter Haven, FL Welcome to this very well kept home located in the desirable SE Winter Haven community of ...	4 beds \| 3 baths \| 2,674 sq.ft.	$399,900	Airbnb cash on cash: 9.22% Traditional cash on cash: 7.61% Airbnb Rental Income: $5016 Traditional Rental Income: $3389 Airbnb ROI: 9.22% Traditional ROI: 7.61%
6011 COUNTRY WALK LANE Winter Haven, FL Pride of ownership shines in this well-built and meticulously maintained 3-bedroom, 2-bath...	3 beds \| 2 baths \| 1,728 sq.ft.	$375,000	Airbnb cash on cash: 7.2% Traditional cash on cash: 4.48% Airbnb Rental Income: $4015 Traditional Rental Income: $2200 Airbnb ROI: 7.2% Traditional ROI: 4.48%
10 JIMMY LEE ROAD Winter Haven, FL Experience the best of both worlds â peaceful country living just minutes from town! Tuc...	3 beds \| 2 baths \| 1,680 sq.ft.	$498,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 2.97% Airbnb Rental Income: $4015 Traditional Rental Income: $2286 Airbnb ROI: 4.84% Traditional ROI: 2.97%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Haven, FL

475 ARCHAIC DRIVE

Winter Haven, FL

4 beds | 3 baths | 2,643 sq.ft.

$674,500

Airbnb cash on cash: 4.32%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $5016

Traditional Rental Income: $3637

Airbnb ROI: 4.32%

Traditional ROI: 3.76%

357 RUBY LAKE LOOP

Winter Haven, FL

3 beds | 2 baths | 2,107 sq.ft.

$419,000

Airbnb cash on cash: 5.99%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $4015

Traditional Rental Income: $2587

Airbnb ROI: 5.99%

Traditional ROI: 4.54%

145 POLK DRIVE

Winter Haven, FL

3 beds | 2 baths | 1,605 sq.ft.

$329,900

Airbnb cash on cash: 8.32%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $4015

Traditional Rental Income: $2262

Airbnb ROI: 8.32%

Traditional ROI: 5.43%

710 HERITAGE DRIVE NE

Winter Haven, FL

4 beds | 2 baths | 2,736 sq.ft.

$647,499

Airbnb cash on cash: 4.54%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $5016

Traditional Rental Income: $3191

Airbnb ROI: 4.54%

Traditional ROI: 3.21%

3830 OSPREY POINTE CIRCLE

Winter Haven, FL

2 beds | 2 baths | 1,438 sq.ft.

$249,900

Airbnb cash on cash: 6.27%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $2962

Traditional Rental Income: $1751

Airbnb ROI: 6.27%

Traditional ROI: 4.03%

1424 WALLACE MANOR PASS

Winter Haven, FL

3 beds | 2 baths | 1,578 sq.ft.

$270,000

Airbnb cash on cash: 9.56%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $4015

Traditional Rental Income: $2184

Airbnb ROI: 9.56%

Traditional ROI: 5.74%

2343 SALZBURG LOOP

Winter Haven, FL

3 beds | 2 baths | 1,948 sq.ft.

$327,500

Airbnb cash on cash: 7.71%

Traditional cash on cash: 5.91%

Airbnb Rental Income: $4015

Traditional Rental Income: $2603

Airbnb ROI: 7.71%

Traditional ROI: 5.91%

457 ADRIEL AVENUE

Winter Haven, FL

4 beds | 2 baths | 2,088 sq.ft.

$359,900

Airbnb cash on cash: 9.89%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $5016

Traditional Rental Income: $2389

Airbnb ROI: 9.89%