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: 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
3304 FOX RIDGE DRIVE Winter Haven, FL Great home available in Fox Ridge. This 2 bedroom, 2 bath, 2 car garage home is very well ...	2 beds \| 2 baths \| 1,153 sq.ft.	$239,900	Airbnb cash on cash: 7.85% Traditional cash on cash: 6% Airbnb Rental Income: $2962 Traditional Rental Income: $1860 Airbnb ROI: 7.85% Traditional ROI: 6%
475 Archaic Dr Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to an exceptional move in ready la...	4 beds \| 2 baths \| 2,643 sq.ft.	$649,500	Airbnb cash on cash: 4.49% Traditional cash on cash: 3.91% Airbnb Rental Income: $5016 Traditional Rental Income: $3637 Airbnb ROI: 4.49% Traditional ROI: 3.91%
404 TALAMONE DRIVE Winter Haven, FL MAGNIFICENT 4BR/3BA POOL HOME!! Located in the gated Winter Haven subdivision of Tuscanny,...	4 beds \| 3 baths \| 2,221 sq.ft.	$489,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.09% Airbnb Rental Income: $5016 Traditional Rental Income: $3150 Airbnb ROI: 5.93% Traditional ROI: 4.09%
145 Polk Dr 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.	$319,900	Airbnb cash on cash: 8.61% Traditional cash on cash: 5.63% Airbnb Rental Income: $4015 Traditional Rental Income: $2262 Airbnb ROI: 8.61% Traditional ROI: 5.63%
710 Heritage Dr 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%
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.	$322,500	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%
225 Franklin Ct Winter Haven, FL Refined luxury meets modern efficiency in this stunning 4-bedroom, 3-bath home located in ...	4 beds \| 3 baths \| 2,362 sq.ft.	$434,900	Airbnb cash on cash: 7.16% Traditional cash on cash: 3.95% Airbnb Rental Income: $5016 Traditional Rental Income: $2684 Airbnb ROI: 7.16% Traditional ROI: 3.95%
2017 Misty Morning Dr Winter Haven, FL Located on a quiet cul-de-sac within a small, quaint HOA, this beautifully remodeled 3-bed...	3 beds \| 2 baths \| 1,728 sq.ft.	$380,000	Airbnb cash on cash: 6.42% Traditional cash on cash: 3.68% Airbnb Rental Income: $4015 Traditional Rental Income: $2178 Airbnb ROI: 6.42% Traditional ROI: 3.68%
731 Canberra Rd 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%
379 WINTER RIDGE BOULEVARD #379 Winter Haven, FL LOW HOA WATERFRONT BRAND NEW ROOF 2025 Located in the wonderful Winter Ridge communi...	2 beds \| 2 baths \| 1,073 sq.ft.	$162,990	Airbnb cash on cash: 9.7% Traditional cash on cash: 5.26% Airbnb Rental Income: $2962 Traditional Rental Income: $1588 Airbnb ROI: 9.7% Traditional ROI: 5.26%
3334 Fox Ridge Dr 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.	$375,000	Airbnb cash on cash: 7.05% Traditional cash on cash: 5.6% Airbnb Rental Income: $4015 Traditional Rental Income: $2647 Airbnb ROI: 7.05% Traditional ROI: 5.6%
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 Blvd Winter Haven, FL UP TO $5000 BUYER CONCESSION TOWARDS CLOSING COSTS WITH APPROVED OFFER!!! SELLER MOTIVATED...	4 beds \| 3 baths \| 2,781 sq.ft.	$448,900	Airbnb cash on cash: 7.09% Traditional cash on cash: 4.49% Airbnb Rental Income: $5016 Traditional Rental Income: $2898 Airbnb ROI: 7.09% Traditional ROI: 4.49%
2202 Garden Lake Dr Winter Haven, FL Experience resort-style living in the prestigious gated community of Winterset, just minut...	3 beds \| 2 baths \| 1,442 sq.ft.	$264,900	Airbnb cash on cash: 9.05% Traditional cash on cash: 4.9% Airbnb Rental Income: $4015 Traditional Rental Income: $2120 Airbnb ROI: 9.05% Traditional ROI: 4.9%
220 Ruby Lake Ln 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: 3.14% Traditional cash on cash: 2.76% Airbnb Rental Income: $5016 Traditional Rental Income: $3702 Airbnb ROI: 3.14% Traditional ROI: 2.76%
4970 Mandolin Ct 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.	$379,000	Airbnb cash on cash: 8.48% Traditional cash on cash: 3.51% Airbnb Rental Income: $5016 Traditional Rental Income: $2223 Airbnb ROI: 8.48% Traditional ROI: 3.51%
3686 Plymouth Dr 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.	$369,900	Airbnb cash on cash: 7.77% Traditional cash on cash: 4.19% Airbnb Rental Income: $5016 Traditional Rental Income: $2748 Airbnb ROI: 7.77% Traditional ROI: 4.19%
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.	$295,000	Airbnb cash on cash: 5.78% Traditional cash on cash: 5.7% Airbnb Rental Income: $2962 Traditional Rental Income: $2256 Airbnb ROI: 5.78% Traditional ROI: 5.7%
2735 Rutledge Ct Winter Haven, FL Move-in-ready villa now available in the highly sought-after Verandahs at Lake Reeves comm...	2 beds \| 2 baths \| 1,419 sq.ft.	$225,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 6.05% Airbnb Rental Income: $2962 Traditional Rental Income: $2027 Airbnb ROI: 7.24% Traditional ROI: 6.05%
2727 Rutledge Ct 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: 9.72% Traditional cash on cash: 5.12% Airbnb Rental Income: $4015 Traditional Rental Income: $2115 Airbnb ROI: 9.72% Traditional ROI: 5.12%
3020 Caneel St 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%
207 24th Ct 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.	$290,000	Airbnb cash on cash: 8.64% Traditional cash on cash: 3.33% Airbnb Rental Income: $4015 Traditional Rental Income: $1705 Airbnb ROI: 8.64% Traditional ROI: 3.33%
130 Audubon Rd 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.	$347,900	Airbnb cash on cash: 9.61% Traditional cash on cash: 5.93% Airbnb Rental Income: $5016 Traditional Rental Income: $2787 Airbnb ROI: 9.61% Traditional ROI: 5.93%
714 Magnolia Pl #714 Winter Haven, FL Where Every Day Feels Like VacationâLakefront Condo! Desirable Upstairs condominium with...	2 beds \| 2 baths \| 1,078 sq.ft.	$235,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 2.65% Airbnb Rental Income: $2962 Traditional Rental Income: $1686 Airbnb ROI: 5.32% Traditional ROI: 2.65%
5357 Hogan Ln 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.	$459,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.07% Airbnb Rental Income: $4015 Traditional Rental Income: $2424 Airbnb ROI: 4.78% Traditional ROI: 3.07%
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%
1075 8th St NW Winter Haven, FL Income-Generating Property with Two In-Law Suites, sitting on a huge lot with a pool!! Max...	4 beds \| 3 baths \| 1,985 sq.ft.	$480,000	Airbnb cash on cash: 7.04% Traditional cash on cash: 5.22% Airbnb Rental Income: $5016 Traditional Rental Income: $3171 Airbnb ROI: 7.04% Traditional ROI: 5.22%
264 Ruby Lake Ln Winter Haven, FL Discover a lakefront retreat in Southeast Winter Haven! This pristine, move-in-ready 4 Be...	4 beds \| 2 baths \| 2,217 sq.ft.	$740,000	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 Dr 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%
3201 OAK TREE LANE Winter Haven, FL Welcome home to this beautiful three bedroom, two bathroom single family residence located...	3 beds \| 2 baths \| 1,376 sq.ft.	$260,000	Airbnb cash on cash: 9.3% Traditional cash on cash: 5.1% Airbnb Rental Income: $4015 Traditional Rental Income: $2125 Airbnb ROI: 9.3% Traditional ROI: 5.1%
905 HILLSIDE COURT S Winter Haven, FL Under contract-accepting backup offers. Welcome to this lovely 3 bedroom and 2 bath home, ...	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 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: 4.76% Airbnb Rental Income: $2962 Traditional Rental Income: $2220 Airbnb ROI: 5.06% Traditional ROI: 4.76%
2512 Sherwood St Winter Haven, FL A beautiful family home is now available in the desirable gated community of Crossroads at...	4 beds \| 3 baths \| 2,697 sq.ft.	$469,990	Airbnb cash on cash: 6.05% Traditional cash on cash: 3.53% Airbnb Rental Income: $5016 Traditional Rental Income: $2883 Airbnb ROI: 6.05% Traditional ROI: 3.53%
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 Ln Winter Haven, FL Welcome to this beautifully updated and immaculately maintained home that truly stands out...	3 beds \| 2 baths \| 1,728 sq.ft.	$360,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 4.31% Airbnb Rental Income: $4015 Traditional Rental Income: $2200 Airbnb ROI: 7.07% Traditional ROI: 4.31%
10 Jimmy Lee Rd 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.	$434,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 3.54% Airbnb Rental Income: $4015 Traditional Rental Income: $2286 Airbnb ROI: 5.69% Traditional ROI: 3.54%
1156 Brenton Manor Dr Winter Haven, FL Seller will contribute up to $5,000 BUYER CLOSING COSTS WITH AN ACCEPTABLE OFFER. This mov...	3 beds \| 2 baths \| 1,770 sq.ft.	$299,900	Airbnb cash on cash: 7.74% Traditional cash on cash: 4.66% Airbnb Rental Income: $4015 Traditional Rental Income: $2253 Airbnb ROI: 7.74% Traditional ROI: 4.66%
751 Avenue B SW Winter Haven, FL Charming property with plenty of desirable features! This 3 bedrooms 2 baths remodeled hom...	3 beds \| 2 baths \| 1,361 sq.ft.	$295,000	Airbnb cash on cash: 9.01% Traditional cash on cash: 5.97% Airbnb Rental Income: $4015 Traditional Rental Income: $2310 Airbnb ROI: 9.01% Traditional ROI: 5.97%
1211 Lake Loop Winter Haven, FL Welcome to this beautifully maintained 3-bed, 2-bath home on a spacious fenced corner lot....	3 beds \| 2 baths \| 1,547 sq.ft.	$329,500	Airbnb cash on cash: 8.1% Traditional cash on cash: 4.7% Airbnb Rental Income: $4015 Traditional Rental Income: $2103 Airbnb ROI: 8.1% Traditional ROI: 4.7%
751 Avenue D SW Winter Haven, FL This duplex is the ultimate opportunity for a rental investment or âhouse hackâ - with...	3 beds \| N/A baths \| 1,406 sq.ft.	$339,500	Airbnb cash on cash: 7.4% Traditional cash on cash: 3.61% Airbnb Rental Income: $4015 Traditional Rental Income: $1946 Airbnb ROI: 7.4% Traditional ROI: 3.61%

Vacation Rentals in Winter Haven

There are 502 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 $285,000 and the average price per square foot is $167. The cash on cash return on vacation rentals in Winter Haven is 10.00%. The average monthly short term rental income in Winter Haven is $4,015.

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

There are 502 Airbnb properties available for sale in Winter Haven.

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

In February 2026, the average Airbnb occupancy rate in Winter Haven is 84%.

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

3304 FOX RIDGE DRIVE

Winter Haven, FL

2 beds | 2 baths | 1,153 sq.ft.

$239,900

Airbnb cash on cash: 7.85%

Traditional cash on cash: 6%

Airbnb Rental Income: $2962

Traditional Rental Income: $1860

Airbnb ROI: 7.85%

Traditional ROI: 6%

475 Archaic Dr

Winter Haven, FL

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

$649,500

Airbnb cash on cash: 4.49%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $5016

Traditional Rental Income: $3637

Airbnb ROI: 4.49%

Traditional ROI: 3.91%

404 TALAMONE DRIVE

Winter Haven, FL

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

$489,000

Airbnb cash on cash: 5.93%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $5016

Traditional Rental Income: $3150

Airbnb ROI: 5.93%

Traditional ROI: 4.09%

145 Polk Dr

Winter Haven, FL

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

$319,900

Airbnb cash on cash: 8.61%

Traditional cash on cash: 5.63%

Airbnb Rental Income: $4015

Traditional Rental Income: $2262

Airbnb ROI: 8.61%

Traditional ROI: 5.63%

710 Heritage Dr 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%

2343 Salzburg Loop

Winter Haven, FL

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

$322,500

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%

225 Franklin Ct

Winter Haven, FL

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

$434,900

Airbnb cash on cash: 7.16%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $5016

Traditional Rental Income: $2684

Airbnb ROI: 7.16%

Traditional ROI: 3.95%

2017 Misty Morning Dr

Winter Haven, FL

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

$380,000

Airbnb cash on cash: 6.42%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $4015

Traditional Rental Income: $2178

Airbnb ROI: 6.42%