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 261 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
404 TALAMONE DRIVE Winter Haven, FL BACK ON MARKET DUE TO BUYERS FAILED FINANCING!! MAGNIFICENT 4BR/3BA POOL HOME!! Located in...	4 beds \| 3 baths \| 2,221 sq.ft.	$485,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 4.02% Airbnb Rental Income: $5016 Traditional Rental Income: $3098 Airbnb ROI: 5.98% Traditional ROI: 4.02%
254 CLOVERDALE ROAD Winter Haven, FL Beautifully maintained 3-bedroom, 2-bath home located in the desirable Savanna Pointe comm...	3 beds \| 2 baths \| 1,463 sq.ft.	$259,900	Airbnb cash on cash: 9.85% Traditional cash on cash: 4.55% Airbnb Rental Income: $4015 Traditional Rental Income: $1858 Airbnb ROI: 9.85% Traditional ROI: 4.55%
357 RUBY LAKE LOOP Winter Haven, FL Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed ...	3 beds \| 2 baths \| 2,107 sq.ft.	$415,000	Airbnb cash on cash: 6.02% Traditional cash on cash: 4.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2438 Airbnb ROI: 6.02% Traditional ROI: 4.17%
710 HERITAGE DRIVE NE Winter Haven, FL Under contract-accepting backup offers. Seller Motivated! $5000 towards buyer concessions ...	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%
330 Sterling Drive Winter Haven, FL Beautiful and spacious home located in a great neighborhood with excellent schools and a g...	3 beds \| 2 baths \| 1,426 sq.ft.	$295,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 5.26% Airbnb Rental Income: $4015 Traditional Rental Income: $2215 Airbnb ROI: 8.65% Traditional ROI: 5.26%
225 FRANKLIN COURT Winter Haven, FL *PRICE REDUCTION* Refined luxury meets modern efficiency in this stunning 4-bedroom, 3...	4 beds \| 3 baths \| 2,362 sq.ft.	$429,900	Airbnb cash on cash: 7.26% Traditional cash on cash: 4.2% Airbnb Rental Income: $5016 Traditional Rental Income: $2761 Airbnb ROI: 7.26% Traditional ROI: 4.2%
2017 MISTY MORNING DRIVE Winter Haven, FL Under contract-accepting backup offers. RECENT $20K PRICE REDUCTION as of 3/10/2026!!...	3 beds \| 2 baths \| 1,728 sq.ft.	$360,000	Airbnb cash on cash: 6.83% Traditional cash on cash: 3.98% Airbnb Rental Income: $4015 Traditional Rental Income: $2193 Airbnb ROI: 6.83% Traditional ROI: 3.98%
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: 6.16% Airbnb Rental Income: $4015 Traditional Rental Income: $2573 Airbnb ROI: 8.02% Traditional ROI: 6.16%
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.	$362,500	Airbnb cash on cash: 7.33% Traditional cash on cash: 6.25% Airbnb Rental Income: $4015 Traditional Rental Income: $2792 Airbnb ROI: 7.33% Traditional ROI: 6.25%
123 ELOISE OAKS DRIVE Winter Haven, FL Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2018, offering th...	4 beds \| 3 baths \| 2,029 sq.ft.	$390,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 4.59% Airbnb Rental Income: $5016 Traditional Rental Income: $2625 Airbnb ROI: 8.33% Traditional ROI: 4.59%
406 RUBY LAKE PLACE Winter Haven, FL Under contract-accepting backup offers. Welcome home to Ruby Lake, an established gated ne...	4 beds \| 3 baths \| 2,835 sq.ft.	$629,000	Airbnb cash on cash: 4.35% Traditional cash on cash: 3.84% Airbnb Rental Income: $5016 Traditional Rental Income: $3695 Airbnb ROI: 4.35% Traditional ROI: 3.84%
2202 GARDEN LAKE DRIVE Winter Haven, FL Experience resort-style living in the prestigious gated community of Winterset, just minut...	3 beds \| 2 baths \| 1,442 sq.ft.	$249,000	Airbnb cash on cash: 9.62% Traditional cash on cash: 5.44% Airbnb Rental Income: $4015 Traditional Rental Income: $2174 Airbnb ROI: 9.62% Traditional ROI: 5.44%
2235 LAKERIDGE DRIVE Winter Haven, FL Welcome to 2235 Lakeridge Driveâan exceptional opportunity to own a beautifully designed...	3 beds \| 2 baths \| 1,893 sq.ft.	$315,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 5.36% Airbnb Rental Income: $4015 Traditional Rental Income: $2295 Airbnb ROI: 8.27% Traditional ROI: 5.36%
220 RUBY LAKE LANE Winter Haven, FL Welcome to this beautifully upgraded lakefront home nestled inside a private gated communi...	4 beds \| 3 baths \| 2,705 sq.ft.	$799,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.93% Airbnb Rental Income: $5016 Traditional Rental Income: $3807 Airbnb ROI: 3.17% Traditional ROI: 2.93%
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.	$355,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 4.06% Airbnb Rental Income: $5016 Traditional Rental Income: $2306 Airbnb ROI: 9.11% Traditional ROI: 4.06%
1 LAKE ELOISE LANE Winter Haven, FL Don't miss out on this amazing 4/3 single-family home with a pool near Lake Eloise in wint...	4 beds \| 3 baths \| 2,550 sq.ft.	$535,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.49% Airbnb Rental Income: $5016 Traditional Rental Income: $3270 Airbnb ROI: 5.93% Traditional ROI: 4.49%
3686 PLYMOUTH DRIVE Winter Haven, FL One or more photo(s) has been virtually staged. This spacious 4-bedroom, 3-bath home is lo...	4 beds \| 3 baths \| 2,404 sq.ft.	$369,900	Airbnb cash on cash: 7.77% Traditional cash on cash: 4.45% Airbnb Rental Income: $5016 Traditional Rental Income: $2841 Airbnb ROI: 7.77% Traditional ROI: 4.45%
1444 KINGFISH LN Winter Haven, FL Beautifully Maintained 2 bedroom, 2 bath home with a large 2 car garage, perfectly situate...	2 beds \| 2 baths \| 2,005 sq.ft.	$270,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 6.28% Airbnb Rental Income: $2962 Traditional Rental Income: $2249 Airbnb ROI: 6.4% Traditional ROI: 6.28%
2727 RUTLEDGE COURT Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to 2727 Rutledge Court, a beautifu...	3 beds \| 2 baths \| 1,536 sq.ft.	$235,000	Airbnb cash on cash: 9.94% Traditional cash on cash: 5.49% Airbnb Rental Income: $4015 Traditional Rental Income: $2168 Airbnb ROI: 9.94% Traditional ROI: 5.49%
207 24TH COURT SW Winter Haven, FL Welcome home to this charming 3-bedroom, 2-bath residence nestled on a spacious lot in the...	3 beds \| 2 baths \| 1,296 sq.ft.	$285,000	Airbnb cash on cash: 8.81% Traditional cash on cash: 6.34% Airbnb Rental Income: $4015 Traditional Rental Income: $2494 Airbnb ROI: 8.81% Traditional ROI: 6.34%
130 AUDUBON ROAD Winter Haven, FL BRAND NEW ROOF- 2026!!! LOOK AT THIS BEAUTIFUL 4 BEDROOM 2 BATH HOME BOASTING 2,503 SqFt....	4 beds \| 2 baths \| 2,503 sq.ft.	$346,000	Airbnb cash on cash: 9.67% Traditional cash on cash: 5.66% Airbnb Rental Income: $5016 Traditional Rental Income: $2689 Airbnb ROI: 9.67% Traditional ROI: 5.66%
221 WHITMAN ROAD Winter Haven, FL Under contract-accepting backup offers. Welcome to this well-maintained 3-bedroom, 2-bathr...	3 beds \| 2 baths \| 1,511 sq.ft.	$275,000	Airbnb cash on cash: 9.94% Traditional cash on cash: 5.8% Airbnb Rental Income: $4015 Traditional Rental Income: $2086 Airbnb ROI: 9.94% Traditional ROI: 5.8%
1051 LENA RUN COURT Winter Haven, FL Welcome home to this well-priced, beautifully maintained 4-bedroom, 2-bath residence locat...	4 beds \| 2 baths \| 2,428 sq.ft.	$477,555	Airbnb cash on cash: 6.67% Traditional cash on cash: 3.56% Airbnb Rental Income: $5016 Traditional Rental Income: $2604 Airbnb ROI: 6.67% Traditional ROI: 3.56%
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.	$440,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 3.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2393 Airbnb ROI: 5.02% Traditional ROI: 3.17%
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.	$289,900	Airbnb cash on cash: 9.13% Traditional cash on cash: 6.67% Airbnb Rental Income: $4015 Traditional Rental Income: $2485 Airbnb ROI: 9.13% Traditional ROI: 6.67%
250 VOLUSIA DRIVE Winter Haven, FL SELLER OFFERS $10,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYERâS CHOICE PRIOR TO C...	3 beds \| 2 baths \| 1,449 sq.ft.	$299,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 5.66% Airbnb Rental Income: $4015 Traditional Rental Income: $2186 Airbnb ROI: 9.11% Traditional ROI: 5.66%
3473 RALEIGH DRIVE Winter Haven, FL Welcome to easy, low-maintenance living in the highly sought-after 55+ gated community of ...	2 beds \| 2 baths \| 1,118 sq.ft.	$210,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 5.06% Airbnb Rental Income: $2962 Traditional Rental Income: $1988 Airbnb ROI: 6.53% Traditional ROI: 5.06%
264 RUBY LAKE LANE Winter Haven, FL Under contract-accepting backup offers. Central Florida Lakefront home for sale now with a...	4 beds \| 2 baths \| 2,217 sq.ft.	$699,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 2.59% Airbnb Rental Income: $5016 Traditional Rental Income: $3025 Airbnb ROI: 4.07% Traditional ROI: 2.59%
5329 HOGAN LANE Winter Haven, FL Under contract-accepting backup offers. Welcome to 5329 Hogan Lane in the beautiful gated ...	3 beds \| 2 baths \| 1,847 sq.ft.	$349,000	Airbnb cash on cash: 6.71% Traditional cash on cash: 3.72% Airbnb Rental Income: $4015 Traditional Rental Income: $2178 Airbnb ROI: 6.71% Traditional ROI: 3.72%
5392 CHANDLER DRIVE Winter Haven, FL PEACEFUL WATERFRONT Living! Many Beautiful Features & Oversized Living Areas Great for Ent...	4 beds \| 3 baths \| 3,034 sq.ft.	$349,900	Airbnb cash on cash: 8.99% Traditional cash on cash: 5.87% Airbnb Rental Income: $5016 Traditional Rental Income: $2967 Airbnb ROI: 8.99% Traditional ROI: 5.87%
5828 MARSH LANDING DRIVE Winter Haven, FL Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakes...	4 beds \| 2 baths \| 2,078 sq.ft.	$387,500	Airbnb cash on cash: 7.94% Traditional cash on cash: 5.58% Airbnb Rental Income: $5016 Traditional Rental Income: $3135 Airbnb ROI: 7.94% Traditional ROI: 5.58%
2708 ATTWATER LOOP Winter Haven, FL Under contract-accepting backup offers. Impeccably maintained home in the sought-after Tra...	3 beds \| 2 baths \| 1,561 sq.ft.	$269,999	Airbnb cash on cash: 8.62% Traditional cash on cash: 5.21% Airbnb Rental Income: $4015 Traditional Rental Income: $2288 Airbnb ROI: 8.62% Traditional ROI: 5.21%
2853 ATTWATER LOOP Winter Haven, FL Looking for a low-maintenance home in a 55+ community in Winter Haven, Florida? This 2019-...	2 beds \| 2 baths \| 1,385 sq.ft.	$210,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.71% Airbnb Rental Income: $2962 Traditional Rental Income: $2210 Airbnb ROI: 5.06% Traditional ROI: 4.71%
961 DREXEL AVENUE NE Winter Haven, FL *HUGE PRICE DECREASE*This unique 2-story home in Winter Haven is full of character and...	3 beds \| 2 baths \| 1,856 sq.ft.	$320,000	Airbnb cash on cash: 8.13% Traditional cash on cash: 5.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2448 Airbnb ROI: 8.13% Traditional ROI: 5.77%
210 NASSAU ROAD Winter Haven, FL Under contract-accepting backup offers. This beautifully updated split floor plan home in ...	3 beds \| 2 baths \| 1,987 sq.ft.	$518,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.43% Airbnb Rental Income: $4015 Traditional Rental Income: $2876 Airbnb ROI: 5.01% Traditional ROI: 4.43%
2512 SHERWOOD STREET Winter Haven, FL Under contract-accepting backup offers. A beautiful family home is now available in the de...	4 beds \| 3 baths \| 2,697 sq.ft.	$469,990	Airbnb cash on cash: 6.05% Traditional cash on cash: 3.43% Airbnb Rental Income: $5016 Traditional Rental Income: $2841 Airbnb ROI: 6.05% Traditional ROI: 3.43%
802 MARCIA LOOP Winter Haven, FL Welcome to 802 Marcia Loop, a LAKEFRONT property located in southeast Winter Haven! The pr...	3 beds \| 2 baths \| 1,539 sq.ft.	$359,900	Airbnb cash on cash: 7.18% Traditional cash on cash: 4.55% Airbnb Rental Income: $4015 Traditional Rental Income: $2269 Airbnb ROI: 7.18% Traditional ROI: 4.55%
305 HERNANDO ROAD Winter Haven, FL Listing price reduced!!! Enjoy the quaint living in this deed restricted community! Step i...	4 beds \| 3 baths \| 2,569 sq.ft.	$479,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 6.35% Airbnb Rental Income: $5016 Traditional Rental Income: $3792 Airbnb ROI: 6.79% Traditional ROI: 6.35%
6011 COUNTRY WALK LANE Winter Haven, FL Under contract-accepting backup offers. Welcome to this beautifully updated and immaculate...	3 beds \| 2 baths \| 1,728 sq.ft.	$330,000	Airbnb cash on cash: 8.03% Traditional cash on cash: 4.98% Airbnb Rental Income: $4015 Traditional Rental Income: $2210 Airbnb ROI: 8.03% Traditional ROI: 4.98%
1156 BRENTON MANOR DRIVE Winter Haven, FL Beautifully updated and impeccably cared for, this 3-bedroom, 2-bath residence blends mode...	3 beds \| 2 baths \| 1,770 sq.ft.	$299,999	Airbnb cash on cash: 8.15% Traditional cash on cash: 5.2% Airbnb Rental Income: $4015 Traditional Rental Income: $2324 Airbnb ROI: 8.15% Traditional ROI: 5.2%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Haven, FL

404 TALAMONE DRIVE

Winter Haven, FL

4 beds | 3 baths | 2,221 sq.ft.

$485,000

Airbnb cash on cash: 5.98%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $5016

Traditional Rental Income: $3098

Airbnb ROI: 5.98%

Traditional ROI: 4.02%

254 CLOVERDALE ROAD

Winter Haven, FL

3 beds | 2 baths | 1,463 sq.ft.

$259,900

Airbnb cash on cash: 9.85%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $4015

Traditional Rental Income: $1858

Airbnb ROI: 9.85%

Traditional ROI: 4.55%

357 RUBY LAKE LOOP

Winter Haven, FL

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

$415,000

Airbnb cash on cash: 6.02%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $4015

Traditional Rental Income: $2438

Airbnb ROI: 6.02%

Traditional ROI: 4.17%

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%

330 Sterling Drive

Winter Haven, FL

3 beds | 2 baths | 1,426 sq.ft.

$295,000

Airbnb cash on cash: 8.65%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $4015

Traditional Rental Income: $2215

Airbnb ROI: 8.65%

Traditional ROI: 5.26%

225 FRANKLIN COURT

Winter Haven, FL

4 beds | 3 baths | 2,362 sq.ft.

$429,900

Airbnb cash on cash: 7.26%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $5016

Traditional Rental Income: $2761

Airbnb ROI: 7.26%

Traditional ROI: 4.2%

2017 MISTY MORNING DRIVE

Winter Haven, FL

3 beds | 2 baths | 1,728 sq.ft.

$360,000

Airbnb cash on cash: 6.83%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $4015

Traditional Rental Income: $2193

Airbnb ROI: 6.83%

Traditional ROI: 3.98%

731 CANBERRA ROAD

Winter Haven, FL

3 beds | 2 baths | 2,140 sq.ft.

$335,000

Airbnb cash on cash: 8.02%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $4015

Traditional Rental Income: $2573

Airbnb ROI: 8.02%