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 263 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%
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: 4.12% Airbnb Rental Income: $4015 Traditional Rental Income: $2419 Airbnb ROI: 6.02% Traditional ROI: 4.12%
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.	$304,900	Airbnb cash on cash: 9.07% Traditional cash on cash: 5.95% Airbnb Rental Income: $4015 Traditional Rental Income: $2262 Airbnb ROI: 9.07% Traditional ROI: 5.95%
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: 5.58% Airbnb Rental Income: $4015 Traditional Rental Income: $2304 Airbnb ROI: 8.65% Traditional ROI: 5.58%
2343 SALZBURG LOOP Winter Haven, FL Under contract-accepting backup offers. THIS WELL-MAINTAINED HOME IS LOCATED IN A GREAT 55...	3 beds \| 2 baths \| 1,948 sq.ft.	$317,500	Airbnb cash on cash: 7.98% Traditional cash on cash: 5.14% Airbnb Rental Income: $4015 Traditional Rental Income: $2309 Airbnb ROI: 7.98% Traditional ROI: 5.14%
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: 4.01% Airbnb Rental Income: $5016 Traditional Rental Income: $2683 Airbnb ROI: 7.26% Traditional ROI: 4.01%
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: 5.67% Airbnb Rental Income: $4015 Traditional Rental Income: $2419 Airbnb ROI: 8.02% Traditional ROI: 5.67%
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: 5.76% Airbnb Rental Income: $4015 Traditional Rental Income: $2623 Airbnb ROI: 7.33% Traditional ROI: 5.76%
2282 FIRESTONE PLACE Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	2 beds \| 2 baths \| 1,164 sq.ft.	$165,000	Airbnb cash on cash: 9.34% Traditional cash on cash: 6.37% Airbnb Rental Income: $2962 Traditional Rental Income: $1813 Airbnb ROI: 9.34% Traditional ROI: 6.37%
1908 CROSSROADS BOULEVARD Winter Haven, FL UP TO $5000 BUYER CONCESSION TOWARDS CLOSING COSTS WITH APPROVED OFFER!!! SELLER MOTIVATED...	4 beds \| 3 baths \| 2,781 sq.ft.	$445,000	Airbnb cash on cash: 7.16% Traditional cash on cash: 4.23% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.16% Traditional ROI: 4.23%
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%
503 HAMILTON SHORES COURT NE Winter Haven, FL WELCOME TO THIS AMAZING POOL HOME SITUATED ON AN OVERSIZED (.43) ACRE LOT LOCATED IN HAMIL...	3 beds \| 3 baths \| 2,375 sq.ft.	$525,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 4.1% Airbnb Rental Income: $4015 Traditional Rental Income: $2868 Airbnb ROI: 4.69% Traditional ROI: 4.1%
2014 8TH TERRACE SE Winter Haven, FL Experience the best of Winter Haven living in this beautifully updated 4 bedroom, 3.5 bath...	4 beds \| 4 baths \| 2,722 sq.ft.	$465,000	Airbnb cash on cash: 7.09% Traditional cash on cash: 5.62% Airbnb Rental Income: $5016 Traditional Rental Income: $3352 Airbnb ROI: 7.09% Traditional ROI: 5.62%
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: 9.68% Traditional cash on cash: 5.47% Airbnb Rental Income: $4015 Traditional Rental Income: $2168 Airbnb ROI: 9.68% Traditional ROI: 5.47%
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.	$375,000	Airbnb cash on cash: 8.58% Traditional cash on cash: 3.64% Airbnb Rental Income: $5016 Traditional Rental Income: $2254 Airbnb ROI: 8.58% Traditional ROI: 3.64%
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: 4.52% Airbnb Rental Income: $5016 Traditional Rental Income: $3284 Airbnb ROI: 5.93% Traditional ROI: 4.52%
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: 3.8% Airbnb Rental Income: $5016 Traditional Rental Income: $2613 Airbnb ROI: 7.77% Traditional ROI: 3.8%
1028 S LAKE MARIAM DRIVE Winter Haven, FL Welcome to your slice of LAKEFRONT, POOL HOME paradise on the pristine shores of Lake Mari...	3 beds \| 3 baths \| 3,255 sq.ft.	$850,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 2.06% Airbnb Rental Income: $4015 Traditional Rental Income: $3074 Airbnb ROI: 2.17% Traditional ROI: 2.06%
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.	$285,000	Airbnb cash on cash: 6.01% Traditional cash on cash: 5.9% Airbnb Rental Income: $2962 Traditional Rental Income: $2249 Airbnb ROI: 6.01% Traditional ROI: 5.9%
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: 5.28% Airbnb Rental Income: $4015 Traditional Rental Income: $2123 Airbnb ROI: 9.94% Traditional ROI: 5.28%
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: 5.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2334 Airbnb ROI: 8.81% Traditional ROI: 5.74%
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: 5.39% Airbnb Rental Income: $5016 Traditional Rental Income: $2602 Airbnb ROI: 9.67% Traditional ROI: 5.39%
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: 3.02% Airbnb Rental Income: $5016 Traditional Rental Income: $2360 Airbnb ROI: 6.67% Traditional ROI: 3.02%
5357 HOGAN LANE Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. WA...	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: 6.23% Airbnb Rental Income: $4015 Traditional Rental Income: $2365 Airbnb ROI: 9.13% Traditional ROI: 6.23%
250 VOLUSIA DRIVE Winter Haven, FL SELLER IS OFFERING $10K IN CONCESSIONS! Welcome to this charming 3-bedroom, 2-bathroom hom...	3 beds \| 2 baths \| 1,449 sq.ft.	$299,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 5.18% Airbnb Rental Income: $4015 Traditional Rental Income: $2050 Airbnb ROI: 9.11% Traditional ROI: 5.18%
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.	$215,000	Airbnb cash on cash: 6.36% Traditional cash on cash: 4.24% Airbnb Rental Income: $2962 Traditional Rental Income: $1849 Airbnb ROI: 6.36% Traditional ROI: 4.24%
264 RUBY LAKE LANE Winter Haven, FL Central Florida Lakefront home for sale now with a HUGE PRICE IMPROVEMENT! Move in ready 4...	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: 3.42% Airbnb Rental Income: $5016 Traditional Rental Income: $2350 Airbnb ROI: 7.94% Traditional ROI: 3.42%
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: 4.87% Airbnb Rental Income: $2962 Traditional Rental Income: $2241 Airbnb ROI: 5.06% Traditional ROI: 4.87%
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: 4.86% Airbnb Rental Income: $4015 Traditional Rental Income: $2175 Airbnb ROI: 8.13% Traditional ROI: 4.86%
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: 4.36% Airbnb Rental Income: $4015 Traditional Rental Income: $2204 Airbnb ROI: 7.18% Traditional ROI: 4.36%
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: 5.84% Airbnb Rental Income: $5016 Traditional Rental Income: $3563 Airbnb ROI: 6.79% Traditional ROI: 5.84%
6011 COUNTRY WALK LANE Winter Haven, FL Welcome to this beautifully updated and immaculately maintained home that truly stands out...	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%

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%

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: 4.12%

Airbnb Rental Income: $4015

Traditional Rental Income: $2419

Airbnb ROI: 6.02%

Traditional ROI: 4.12%

145 POLK DRIVE

Winter Haven, FL

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

$304,900

Airbnb cash on cash: 9.07%

Traditional cash on cash: 5.95%

Airbnb Rental Income: $4015

Traditional Rental Income: $2262

Airbnb ROI: 9.07%

Traditional ROI: 5.95%

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: 5.58%

Airbnb Rental Income: $4015

Traditional Rental Income: $2304

Airbnb ROI: 8.65%

Traditional ROI: 5.58%

2343 SALZBURG LOOP

Winter Haven, FL

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

$317,500

Airbnb cash on cash: 7.98%

Traditional cash on cash: 5.14%

Airbnb Rental Income: $4015

Traditional Rental Income: $2309

Airbnb ROI: 7.98%

Traditional ROI: 5.14%

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: 4.01%

Airbnb Rental Income: $5016

Traditional Rental Income: $2683

Airbnb ROI: 7.26%

Traditional ROI: 4.01%

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%