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: What is the average Airbnb occupancy rate in Winter-haven, FL?

In May 2026, the average Airbnb occupancy rate in Winter-haven is 84%.

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
2500 21ST STREET NW #23 Winter Haven, FL Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to ...	2 beds \| 3 baths \| 1,334 sq.ft.	$178,000	Airbnb cash on cash: 8.84% Traditional cash on cash: 6.49% Airbnb Rental Income: $2962 Traditional Rental Income: $1881 Airbnb ROI: 8.84% Traditional ROI: 6.49%
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%
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.	$427,500	Airbnb cash on cash: 7.3% Traditional cash on cash: 4.23% Airbnb Rental Income: $5016 Traditional Rental Income: $2761 Airbnb ROI: 7.3% Traditional ROI: 4.23%
731 CANBERRA ROAD Winter Haven, FL Under contract-accepting backup offers. Just REDUCED!! Welcome to this beautifully maintai...	3 beds \| 2 baths \| 2,140 sq.ft.	$325,000	Airbnb cash on cash: 8.29% Traditional cash on cash: 6.38% Airbnb Rental Income: $4015 Traditional Rental Income: $2573 Airbnb ROI: 8.29% Traditional ROI: 6.38%
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%
1908 CROSSROADS BOULEVARD Winter Haven, FL Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region...	4 beds \| 3 baths \| 2,781 sq.ft.	$419,900	Airbnb cash on cash: 7.64% Traditional cash on cash: 4.54% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.64% Traditional ROI: 4.54%
321 ORANGE BLOSSOM DRIVE Winter Haven, FL Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is ...	2 beds \| 3 baths \| 1,407 sq.ft.	$215,500	Airbnb cash on cash: 6.22% Traditional cash on cash: 4.93% Airbnb Rental Income: $2962 Traditional Rental Income: $2015 Airbnb ROI: 6.22% Traditional ROI: 4.93%
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 Estates, your opportunity to enjoy the Florida lifestyle in one ...	3 beds \| 2 baths \| 1,893 sq.ft.	$305,000	Airbnb cash on cash: 8.57% Traditional cash on cash: 5.57% Airbnb Rental Income: $4015 Traditional Rental Income: $2295 Airbnb ROI: 8.57% Traditional ROI: 5.57%
220 RUBY LAKE LANE Winter Haven, FL Under contract-accepting backup offers. Welcome to this beautifully upgraded lakefront hom...	4 beds \| 3 baths \| 2,705 sq.ft.	$789,900	Airbnb cash on cash: 3.22% Traditional cash on cash: 2.97% Airbnb Rental Income: $5016 Traditional Rental Income: $3807 Airbnb ROI: 3.22% Traditional ROI: 2.97%
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%
2735 RUTLEDGE COURT Winter Haven, FL Under contract-accepting backup offers. Move-in-ready, one-story townhome is now available...	2 beds \| 2 baths \| 1,419 sq.ft.	$220,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 6.03% Airbnb Rental Income: $2962 Traditional Rental Income: $1990 Airbnb ROI: 7.42% Traditional ROI: 6.03%
811 22ND STREET NW Winter Haven, FL "Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven...	3 beds \| 3 baths \| 1,408 sq.ft.	$269,990	Airbnb cash on cash: 9.56% Traditional cash on cash: 6.68% Airbnb Rental Income: $4015 Traditional Rental Income: $2422 Airbnb ROI: 9.56% Traditional ROI: 6.68%
1051 LENA RUN COURT Winter Haven, FL Under contract-accepting backup offers. Welcome home to this well-priced, beautifully main...	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 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%
202 SAINT LUCIE ROAD Winter Haven, FL **Location, Location, Location! Seller offering $10,000 toward buyer closing costs, prepai...	3 beds \| 2 baths \| 1,764 sq.ft.	$328,999	Airbnb cash on cash: 7.98% Traditional cash on cash: 6.23% Airbnb Rental Income: $4015 Traditional Rental Income: $2616 Airbnb ROI: 7.98% Traditional ROI: 6.23%
1075 8TH STREET NW Winter Haven, FL Income-Generating Property with Two In-Law Suites, sitting on a huge lot with a pool!! Max...	4 beds \| N/A baths \| 1,985 sq.ft.	$480,000	Airbnb cash on cash: 7.04% Traditional cash on cash: 4.33% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.04% Traditional ROI: 4.33%
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 Under contract-accepting backup offers. Welcome to easy, low-maintenance living in the hig...	2 beds \| 2 baths \| 1,118 sq.ft.	$207,500	Airbnb cash on cash: 6.62% Traditional cash on cash: 5.13% Airbnb Rental Income: $2962 Traditional Rental Income: $1988 Airbnb ROI: 6.62% Traditional ROI: 5.13%
524 HAINES TRAIL Winter Haven, FL Beautifully maintained, highly upgraded home in a quiet, conveniently located community. F...	3 beds \| 2 baths \| 1,980 sq.ft.	$329,000	Airbnb cash on cash: 7.98% Traditional cash on cash: 5.55% Airbnb Rental Income: $4015 Traditional Rental Income: $2405 Airbnb ROI: 7.98% Traditional ROI: 5.55%
961 DREXEL AVENUE NE Winter Haven, FL ***PRICE DECREASE +++ SELLER IS OFFERING $5000 in seller concessions!!! This unique 2-stor...	3 beds \| 2 baths \| 1,856 sq.ft.	$315,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 5.88% Airbnb Rental Income: $4015 Traditional Rental Income: $2448 Airbnb ROI: 8.27% Traditional ROI: 5.88%
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%
725 HERITAGE DRIVE NE Winter Haven, FL One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe c...	4 beds \| 3 baths \| 3,114 sq.ft.	$559,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 4.62% Airbnb Rental Income: $5016 Traditional Rental Income: $3730 Airbnb ROI: 5.12% Traditional ROI: 4.62%
3208 TIMBERLINE ROAD Winter Haven, FL MOVE-IN READY & COMPLETELY REMODELED! This stunning home features a bright, open layout w...	2 beds \| 2 baths \| 1,043 sq.ft.	$240,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 5.56% Airbnb Rental Income: $2962 Traditional Rental Income: $1845 Airbnb ROI: 7.47% Traditional ROI: 5.56%
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.	$529,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 2.73% Airbnb Rental Income: $4015 Traditional Rental Income: $2691 Airbnb ROI: 3.68% Traditional ROI: 2.73%
144 BEVERLY DRIVE Winter Haven, FL FLORIDA LIVING AT ITS BEST! Pool home + oversized lot + NO HOA + Chain of Lakes access jus...	4 beds \| 3 baths \| 2,492 sq.ft.	$405,900	Airbnb cash on cash: 8.32% Traditional cash on cash: 7.77% Airbnb Rental Income: $5016 Traditional Rental Income: $3781 Airbnb ROI: 8.32% Traditional ROI: 7.77%
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: 9.09% Traditional cash on cash: 5.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2273 Airbnb ROI: 9.09% Traditional ROI: 5.74%
851 VIENNA DRIVE Winter Haven, FL Better Than New 2022 Home â Move-In Ready! VA Assumable Mortgage!!! Welcome to this b...	3 beds \| 2 baths \| 1,569 sq.ft.	$279,900	Airbnb cash on cash: 8.35% Traditional cash on cash: 4.54% Airbnb Rental Income: $4015 Traditional Rental Income: $2151 Airbnb ROI: 8.35% Traditional ROI: 4.54%
525 DRAYTON ROAD Winter Haven, FL Under contract-accepting backup offers. BEAT NEW CONSTRUCTION COSTS! Seller offering up to...	3 beds \| 2 baths \| 1,876 sq.ft.	$289,900	Airbnb cash on cash: 8.53% Traditional cash on cash: 5.3% Airbnb Rental Income: $4015 Traditional Rental Income: $2273 Airbnb ROI: 8.53% Traditional ROI: 5.3%
1590 VIENNA SQUARE DRIVE Winter Haven, FL Welcome to Vienna Square, a beautifully maintained 55+ gated community offering resort-sty...	2 beds \| 2 baths \| 1,231 sq.ft.	$210,000	Airbnb cash on cash: 7.97% Traditional cash on cash: 6.6% Airbnb Rental Income: $2962 Traditional Rental Income: $2006 Airbnb ROI: 7.97% Traditional ROI: 6.6%
1806 17TH STREET NW Winter Haven, FL Mediterranean Revival residence combining historic charm, remarkable updates, and an ideal...	3 beds \| 2 baths \| 1,750 sq.ft.	$360,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 6.04% Airbnb Rental Income: $4015 Traditional Rental Income: $2730 Airbnb ROI: 7.3% Traditional ROI: 6.04%
339 LAKE SMART CIRCLE Winter Haven, FL Motivated Seller. Introducing a beautifully maintained home offering an excellent and func...	3 beds \| 3 baths \| 2,173 sq.ft.	$339,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 5.65% Airbnb Rental Income: $4015 Traditional Rental Income: $2626 Airbnb ROI: 7.31% Traditional ROI: 5.65%
2349 SALZBURG LOOP Winter Haven, FL HERONS, CRANES, EGRETS, AND DUCKS! You'll have a birds eye view of Florida's most beautifu...	3 beds \| 3 baths \| 1,724 sq.ft.	$309,900	Airbnb cash on cash: 7.11% Traditional cash on cash: 3.62% Airbnb Rental Income: $4015 Traditional Rental Income: $2139 Airbnb ROI: 7.11% Traditional ROI: 3.62%
257 MEADOWBROOK BOULEVARD Winter Haven, FL PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucern...	3 beds \| 2 baths \| 1,725 sq.ft.	$287,950	Airbnb cash on cash: 8.06% Traditional cash on cash: 5.14% Airbnb Rental Income: $4015 Traditional Rental Income: $2364 Airbnb ROI: 8.06% Traditional ROI: 5.14%
702 COUNTRY LANE NE #702 Winter Haven, FL LAKEFRONT LIVING AT IT'S BEST! REFRESHED FIRST FLOOR 2BR-2BA CONDO WITH COVERED PARKING A...	2 beds \| 2 baths \| 1,252 sq.ft.	$169,500	Airbnb cash on cash: 8.83% Traditional cash on cash: 2.78% Airbnb Rental Income: $2962 Traditional Rental Income: $1302 Airbnb ROI: 8.83% Traditional ROI: 2.78%

Vacation Rentals in Winter Haven

There are 264 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 $284,900 and the average price per square foot is $166. 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 264 Airbnb properties available for sale in Winter Haven.

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

In May 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

2500 21ST STREET NW #23

Winter Haven, FL

2 beds | 3 baths | 1,334 sq.ft.

$178,000

Airbnb cash on cash: 8.84%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $2962

Traditional Rental Income: $1881

Airbnb ROI: 8.84%

Traditional ROI: 6.49%

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%

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.

$427,500

Airbnb cash on cash: 7.3%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $5016

Traditional Rental Income: $2761

Airbnb ROI: 7.3%

Traditional ROI: 4.23%

731 CANBERRA ROAD

Winter Haven, FL

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

$325,000

Airbnb cash on cash: 8.29%

Traditional cash on cash: 6.38%

Airbnb Rental Income: $4015

Traditional Rental Income: $2573

Airbnb ROI: 8.29%

Traditional ROI: 6.38%

3334 FOX RIDGE DRIVE

Winter Haven, FL

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%

1908 CROSSROADS BOULEVARD

Winter Haven, FL

4 beds | 3 baths | 2,781 sq.ft.

$419,900

Airbnb cash on cash: 7.64%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $5016

Traditional Rental Income: $2772

Airbnb ROI: 7.64%