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
2332 SALZBURG LOOP Winter Haven, FL PICTURE PERFECT! Imagine settling into this ideal low-maintenance home tailored for comfor...	2 beds \| 2 baths \| 1,595 sq.ft.	$244,900	Airbnb cash on cash: 7.58% Traditional cash on cash: 6.01% Airbnb Rental Income: $3280 Traditional Rental Income: $2180 Airbnb ROI: 7.58% Traditional ROI: 6.01%
10 W LAKE HAMILTON Circle Winter Haven, FL Welcome to 10 West Lake Hamilton Circle, a beautifully maintained four-bedroom, two-bathro...	4 beds \| 2 baths \| 2,400 sq.ft.	$485,000	Airbnb cash on cash: 6.8% Traditional cash on cash: 2.86% Airbnb Rental Income: $5128 Traditional Rental Income: $2297 Airbnb ROI: 6.8% Traditional ROI: 2.86%
132 DUVAL Road Winter Haven, FL This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearl...	2 beds \| 2 baths \| 1,260 sq.ft.	$280,000	Airbnb cash on cash: 7.06% Traditional cash on cash: 5.28% Airbnb Rental Income: $3280 Traditional Rental Income: $2076 Airbnb ROI: 7.06% Traditional ROI: 5.28%
1907 ELOISE COVE Drive Winter Haven, FL Imagine coming home to a place where elegance, comfort, and a wonderful lifestyle come tog...	4 beds \| 3 baths \| 2,888 sq.ft.	$449,900	Airbnb cash on cash: 8.5% Traditional cash on cash: 4.76% Airbnb Rental Income: $5578 Traditional Rental Income: $2885 Airbnb ROI: 8.5% Traditional ROI: 4.76%
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.	$392,900	Airbnb cash on cash: 7.37% Traditional cash on cash: 4.46% Airbnb Rental Income: $4440 Traditional Rental Income: $2438 Airbnb ROI: 7.37% Traditional ROI: 4.46%
408 LANIER Lane Winter Haven, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom block home perfectly position...	3 beds \| 2 baths \| 1,680 sq.ft.	$320,000	Airbnb cash on cash: 9.65% Traditional cash on cash: 5.54% Airbnb Rental Income: $4440 Traditional Rental Income: $2273 Airbnb ROI: 9.65% Traditional ROI: 5.54%
3541 RALEIGH Drive Winter Haven, FL Discover exceptional Florida living in this fabulous Eco Smart 3-bedroom, 3-bath home with...	3 beds \| 3 baths \| 2,006 sq.ft.	$345,000	Airbnb cash on cash: 6.71% Traditional cash on cash: 3.82% Airbnb Rental Income: $4440 Traditional Rental Income: $2572 Airbnb ROI: 6.71% Traditional ROI: 3.82%
4840 OLD LUCERNE PARK RD Winter Haven, FL Relax and Enjoy Lakefront Living on Beautiful Lake Lucerne! Situated on 0.84 acres, this u...	3 beds \| 2 baths \| 1,927 sq.ft.	$400,000	Airbnb cash on cash: 7% Traditional cash on cash: 5.69% Airbnb Rental Income: $4181 Traditional Rental Income: $2803 Airbnb ROI: 7% Traditional ROI: 5.69%
1500 AVENUE G NE Winter Haven, FL Welcome to this spacious and beautifully maintained 3-bedroom, 2-bath home offering over 2...	3 beds \| 2 baths \| 2,280 sq.ft.	$359,000	Airbnb cash on cash: 7.94% Traditional cash on cash: 6.17% Airbnb Rental Income: $4181 Traditional Rental Income: $2701 Airbnb ROI: 7.94% Traditional ROI: 6.17%
5288 GREEN Drive Winter Haven, FL Welcome to this spacious Biscayne floor plan in Lake Ashton, a gated 55+ GOLF community in...	3 beds \| 2 baths \| 1,847 sq.ft.	$314,000	Airbnb cash on cash: 7.73% Traditional cash on cash: 2.9% Airbnb Rental Income: $4440 Traditional Rental Income: $2085 Airbnb ROI: 7.73% Traditional ROI: 2.9%
325 MAJESTIC GARDENS Drive Winter Haven, FL Welcome to 325 Majestic Gardens Drive nestled in the desirable gated Gardens community of ...	3 beds \| 3 baths \| 2,034 sq.ft.	$345,000	Airbnb cash on cash: 8.34% Traditional cash on cash: 4.11% Airbnb Rental Income: $4440 Traditional Rental Income: $2140 Airbnb ROI: 8.34% Traditional ROI: 4.11%
464 TERRANOVA Street Winter Haven, FL Welcome home to this stunning 3-bedroom, 2-bathroom residence tucked into the sought-after...	3 beds \| 2 baths \| 1,893 sq.ft.	$359,900	Airbnb cash on cash: 7.73% Traditional cash on cash: 3.89% Airbnb Rental Income: $4440 Traditional Rental Income: $2213 Airbnb ROI: 7.73% Traditional ROI: 3.89%
4132 MARTINDALE Loop Winter Haven, FL Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the hig...	4 beds \| 3 baths \| 1,894 sq.ft.	$399,900	Airbnb cash on cash: 8.48% Traditional cash on cash: 3.02% Airbnb Rental Income: $5578 Traditional Rental Income: $2413 Airbnb ROI: 8.48% Traditional ROI: 3.02%
1015 ROBIN Lane Winter Haven, FL HUGE PRICE DROP! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home tucked ...	3 beds \| 2 baths \| 1,632 sq.ft.	$349,000	Airbnb cash on cash: 8.25% Traditional cash on cash: 4.41% Airbnb Rental Income: $4440 Traditional Rental Income: $2252 Airbnb ROI: 8.25% Traditional ROI: 4.41%
7380 BENT GRASS Drive Winter Haven, FL Welcome to PARADISE! Enjoy a HEATED, SALTWATER POOL, located on almost half an acre (0.42)...	4 beds \| 3 baths \| 2,775 sq.ft.	$559,900	Airbnb cash on cash: 6.25% Traditional cash on cash: 3.81% Airbnb Rental Income: $5578 Traditional Rental Income: $3182 Airbnb ROI: 6.25% Traditional ROI: 3.81%
280 SANTA ROSA Drive Winter Haven, FL This property went under contract fast and it's back on the market, no fault of the owner....	3 beds \| 2 baths \| 2,251 sq.ft.	$399,500	Airbnb cash on cash: 6.76% Traditional cash on cash: 4.06% Airbnb Rental Income: $4440 Traditional Rental Income: $2500 Airbnb ROI: 6.76% Traditional ROI: 4.06%
1075 8TH Street NW Winter Haven, FL RENOVATED, SPACIOUS, AND JUST MINUTES FROM LAKE HOWARD! Discover this beautifully renovate...	4 beds \| 3 baths \| 1,985 sq.ft.	$480,000	Airbnb cash on cash: 7.23% Traditional cash on cash: 4.31% Airbnb Rental Income: $5128 Traditional Rental Income: $2772 Airbnb ROI: 7.23% Traditional ROI: 4.31%
645 AVENUE M SE Winter Haven, FL LOOK AT THIS WELL-KEPT 3 BEDROOM, 2 BATH HOME WITH LOTS OF STORAGE, PRIVACY AND NO HOA!!! ...	3 beds \| 2 baths \| 1,959 sq.ft.	$330,000	Airbnb cash on cash: 9.14% Traditional cash on cash: 5.98% Airbnb Rental Income: $4440 Traditional Rental Income: $2529 Airbnb ROI: 9.14% Traditional ROI: 5.98%
235 6TH Street NW #507 Winter Haven, FL A piece of Winter Haven history with a view to match! Originally built in 1924 as one of F...	1 beds \| 1 baths \| 714 sq.ft.	$140,000	Airbnb cash on cash: 7.9% Traditional cash on cash: 5.7% Airbnb Rental Income: $2315 Traditional Rental Income: $1444 Airbnb ROI: 7.9% Traditional ROI: 5.7%
4043 BEDFORD Avenue Winter Haven, FL UPGRADED HOME IN THE GATED RESORT-STYLE COMMUNITY OF TRADITIONS: Meticulously maintained a...	2 beds \| 2 baths \| 1,871 sq.ft.	$359,900	Airbnb cash on cash: 3.78% Traditional cash on cash: 1.72% Airbnb Rental Income: $3280 Traditional Rental Income: $1848 Airbnb ROI: 3.78% Traditional ROI: 1.72%
2500 21ST Street NW #22 Winter Haven, FL PRICE DROP! Welcome to easy Florida living at this beautifully updated 2-bedroom, 2.5-bath...	2 beds \| 3 baths \| 1,334 sq.ft.	$178,490	Airbnb cash on cash: 8.55% Traditional cash on cash: 6.07% Airbnb Rental Income: $3012 Traditional Rental Income: $1900 Airbnb ROI: 8.55% Traditional ROI: 6.07%
1475 GRAND CAYMAN Circle Winter Haven, FL Virtually Staged. WATERFRONT LIVING ON BEAUTIFUL LAKE DEXTER-PRIVATE DOCK - OVERSIZED CORN...	3 beds \| 2 baths \| 2,066 sq.ft.	$359,000	Airbnb cash on cash: 7.76% Traditional cash on cash: 5.87% Airbnb Rental Income: $4440 Traditional Rental Income: $2874 Airbnb ROI: 7.76% Traditional ROI: 5.87%
409 21ST Street SW Winter Haven, FL Stunning 2 story 3 bath Spanish home with attention to details. This home has been renovat...	4 beds \| 1 baths \| 2,322 sq.ft.	$550,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 5.68% Airbnb Rental Income: $5578 Traditional Rental Income: $4002 Airbnb ROI: 6.57% Traditional ROI: 5.68%
725 HERITAGE Drive NE Winter Haven, FL BEAUTIFUL HAMILTON POINTE POOL HOME! Welcome to this 4-bedroom, 2.5-bath pool home sits on...	4 beds \| 3 baths \| 3,114 sq.ft.	$560,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 4.61% Airbnb Rental Income: $5128 Traditional Rental Income: $3730 Airbnb ROI: 5.29% Traditional ROI: 4.61%
4 CASARENA Court Winter Haven, FL This dynamically unique home in Winter Haven offers waterfront living, with direct access ...	3 beds \| 3 baths \| 3,911 sq.ft.	$524,000	Airbnb cash on cash: 4% Traditional cash on cash: 2.77% Airbnb Rental Income: $4181 Traditional Rental Income: $2691 Airbnb ROI: 4% Traditional ROI: 2.77%
3843 ELOISE ESTATES Court Winter Haven, FL HUGE PRICE REDUCTION! POND-VIEW MOVE-IN READY HOME! Enjoy a serene setting and modern upda...	3 beds \| 2 baths \| 1,600 sq.ft.	$280,000	Airbnb cash on cash: 9.62% Traditional cash on cash: 5.75% Airbnb Rental Income: $4181 Traditional Rental Income: $2273 Airbnb ROI: 9.62% Traditional ROI: 5.75%
12 SAINT KITTS Circle Winter Haven, FL Welcome to the beautifully maintained 3-bedroom, 2-bath home with a bonus room in the desi...	3 beds \| 2 baths \| 1,639 sq.ft.	$294,000	Airbnb cash on cash: 9.88% Traditional cash on cash: 5.48% Airbnb Rental Income: $4440 Traditional Rental Income: $2293 Airbnb ROI: 9.88% Traditional ROI: 5.48%
4123 ISLAND LAKES Drive Winter Haven, FL CHAIN OF LAKES LAKEFRONT LIVING on Lake Rochelle! Welcome to Island Lakes, where everyday ...	4 beds \| 2 baths \| 1,990 sq.ft.	$470,000	Airbnb cash on cash: 6.91% Traditional cash on cash: 3.34% Airbnb Rental Income: $5128 Traditional Rental Income: $2514 Airbnb ROI: 6.91% Traditional ROI: 3.34%
851 VIENNA Drive Winter Haven, FL Better Than New 2022 Home - Move-In Ready! VA Assumable Mortgage!!! Welcome to this beauti...	3 beds \| 2 baths \| 1,569 sq.ft.	$279,900	Airbnb cash on cash: 9.69% Traditional cash on cash: 4.54% Airbnb Rental Income: $4440 Traditional Rental Income: $2151 Airbnb ROI: 9.69% Traditional ROI: 4.54%
809 MAGNOLIA Place Winter Haven, FL Waterfront Living - Renovated Interior - Private Garage. Imagine ending your day with a be...	2 beds \| 2 baths \| 1,308 sq.ft.	$235,000	Airbnb cash on cash: 6.5% Traditional cash on cash: 3.81% Airbnb Rental Income: $3280 Traditional Rental Income: $1946 Airbnb ROI: 6.5% Traditional ROI: 3.81%
230 SHORE Drive Winter Haven, FL Your own slice of Lake Daisy. This updated lakefront ranch style home sits on 100 feet of ...	3 beds \| 2 baths \| 1,502 sq.ft.	$415,000	Airbnb cash on cash: 6.69% Traditional cash on cash: 4.1% Airbnb Rental Income: $4440 Traditional Rental Income: $2504 Airbnb ROI: 6.69% Traditional ROI: 4.1%
301 Terranova Boulevard Winter Haven, FL Discover this spacious 4-bedroom, 2-bath, 1,960 SqFt home in the gated Terranova community...	4 beds \| 2 baths \| 1,960 sq.ft.	$379,900	Airbnb cash on cash: 9.94% Traditional cash on cash: 3.26% Airbnb Rental Income: $5578 Traditional Rental Income: $2079 Airbnb ROI: 9.94% Traditional ROI: 3.26%
3946 BEDFORD Avenue Winter Haven, FL Welcome to 3946 Bedford Avenue, located in Traditions at Lake Ruby, one of Winter Haven's ...	3 beds \| 2 baths \| 1,996 sq.ft.	$367,500	Airbnb cash on cash: 5.98% Traditional cash on cash: 2.62% Airbnb Rental Income: $4440 Traditional Rental Income: $2351 Airbnb ROI: 5.98% Traditional ROI: 2.62%
1010 EDGEWATER Drive Winter Haven, FL FULLY REMODELED WATERFRONT HOME,PRIVATE POOL and BOAT DOCK WITH LIFT and NO HOA! Enjoy the...	4 beds \| 3 baths \| 2,346 sq.ft.	$795,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 1.95% Airbnb Rental Income: $5578 Traditional Rental Income: $2735 Airbnb ROI: 4.27% Traditional ROI: 1.95%
919 AVENUE S SE Winter Haven, FL Welcome to 991 S SE in Winter Haven. This beautifully upgraded, turnkey home is being offe...	3 beds \| 2 baths \| 1,751 sq.ft.	$330,000	Airbnb cash on cash: 8.85% Traditional cash on cash: 7.12% Airbnb Rental Income: $4440 Traditional Rental Income: $2977 Airbnb ROI: 8.85% Traditional ROI: 7.12%
150 EL DORADO #305 Winter Haven, FL Discover the perfect blend of comfort, convenience, and relaxed Florida living in this inv...	2 beds \| 2 baths \| 1,372 sq.ft.	$129,900	Airbnb cash on cash: 8.98% Traditional cash on cash: 0% Airbnb Rental Income: $3280 Traditional Rental Income: $1423 Airbnb ROI: 8.98% Traditional ROI: 0%
4599 REYNOSA Drive SW Winter Haven, FL Some homes are built. Others are crafted. Tucked away in a quiet Winter Haven neighborhood...	3 beds \| 2 baths \| 2,309 sq.ft.	$309,999	Airbnb cash on cash: 9.57% Traditional cash on cash: 6.32% Airbnb Rental Income: $4440 Traditional Rental Income: $2561 Airbnb ROI: 9.57% Traditional ROI: 6.32%

Vacation Rentals in Winter Haven

There are 170 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 $286,863 and the average price per square foot is $169. The cash on cash return on vacation rentals in Winter Haven is 12.00%. The average monthly short term rental income in Winter Haven is $4,181.

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

There are 170 Airbnb properties available for sale in Winter Haven.

In November 2026, the average Airbnb occupancy rate in Winter Haven is N/A%.

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

2332 SALZBURG LOOP

Winter Haven, FL

2 beds | 2 baths | 1,595 sq.ft.

$244,900

Airbnb cash on cash: 7.58%

Traditional cash on cash: 6.01%

Airbnb Rental Income: $3280

Traditional Rental Income: $2180

Airbnb ROI: 7.58%

Traditional ROI: 6.01%

10 W LAKE HAMILTON Circle

Winter Haven, FL

4 beds | 2 baths | 2,400 sq.ft.

$485,000

Airbnb cash on cash: 6.8%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $5128

Traditional Rental Income: $2297

Airbnb ROI: 6.8%

Traditional ROI: 2.86%

132 DUVAL Road

Winter Haven, FL

2 beds | 2 baths | 1,260 sq.ft.

$280,000

Airbnb cash on cash: 7.06%

Traditional cash on cash: 5.28%

Airbnb Rental Income: $3280

Traditional Rental Income: $2076

Airbnb ROI: 7.06%

Traditional ROI: 5.28%

1907 ELOISE COVE Drive

Winter Haven, FL

4 beds | 3 baths | 2,888 sq.ft.

$449,900

Airbnb cash on cash: 8.5%

Traditional cash on cash: 4.76%

Airbnb Rental Income: $5578

Traditional Rental Income: $2885

Airbnb ROI: 8.5%

Traditional ROI: 4.76%

357 RUBY LAKE Loop

Winter Haven, FL

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

$392,900

Airbnb cash on cash: 7.37%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $4440

Traditional Rental Income: $2438

Airbnb ROI: 7.37%

Traditional ROI: 4.46%

408 LANIER Lane

Winter Haven, FL

3 beds | 2 baths | 1,680 sq.ft.

$320,000

Airbnb cash on cash: 9.65%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $4440

Traditional Rental Income: $2273

Airbnb ROI: 9.65%

Traditional ROI: 5.54%

3541 RALEIGH Drive

Winter Haven, FL

3 beds | 3 baths | 2,006 sq.ft.

$345,000

Airbnb cash on cash: 6.71%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $4440

Traditional Rental Income: $2572

Airbnb ROI: 6.71%

Traditional ROI: 3.82%

4840 OLD LUCERNE PARK RD

Winter Haven, FL

3 beds | 2 baths | 1,927 sq.ft.

$400,000

Airbnb cash on cash: 7%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $4181

Traditional Rental Income: $2803

Airbnb ROI: 7%