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
808 Overlook Grove Drive Winter Haven, FL Sparkling 4 bedroom, 3 bath home located on a quiet cul-de-sac with no rear neighbors. Thi...	4 beds \| 3 baths \| 2,093 sq.ft.	$360,000	Airbnb cash on cash: 9.16% Traditional cash on cash: 5.23% Airbnb Rental Income: $5016 Traditional Rental Income: $2662 Airbnb ROI: 9.16% Traditional ROI: 5.23%
135 ELOISE OAKS DRIVE Winter Haven, FL ACCEPTING OFFERS NOW! PRICED TO SELL - NOW ONLY $369,900. ANNUAL HOA FEES PAID THROUGH DEC...	3 beds \| 2 baths \| 1,866 sq.ft.	$369,900	Airbnb cash on cash: 6.6% Traditional cash on cash: 4.26% Airbnb Rental Income: $4015 Traditional Rental Income: $2345 Airbnb ROI: 6.6% Traditional ROI: 4.26%
475 ARCHAIC DRIVE Winter Haven, FL Welcome to your perfect sanctuary in the heart of Central Florida! With a freshly repainte...	4 beds \| 3 baths \| 2,643 sq.ft.	$699,500	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.59% Airbnb Rental Income: $5016 Traditional Rental Income: $3637 Airbnb ROI: 4.13% Traditional ROI: 3.59%
3324 OAK HILL PLACE Winter Haven, FL Under contract-accepting backup offers. Upgraded Pool Home in Cypresswood Golf & Country C...	3 beds \| 2 baths \| 1,675 sq.ft.	$339,000	Airbnb cash on cash: 6.62% Traditional cash on cash: 4.35% Airbnb Rental Income: $4015 Traditional Rental Income: $2433 Airbnb ROI: 6.62% Traditional ROI: 4.35%
357 RUBY LAKE LOOP Winter Haven, FL Located in the gated community of Ruby Lake, this stunning 3-bedroom, 2-bath Cassidy Ox fl...	3 beds \| 2 baths \| 2,107 sq.ft.	$419,000	Airbnb cash on cash: 5.99% Traditional cash on cash: 4.54% Airbnb Rental Income: $4015 Traditional Rental Income: $2587 Airbnb ROI: 5.99% Traditional ROI: 4.54%
710 HERITAGE DRIVE NE Winter Haven, FL Dreamy Updated Pool Home in Sought-After Hamilton Pointe! Welcome to your own private ...	4 beds \| 2 baths \| 2,736 sq.ft.	$647,500	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%
3830 OSPREY POINTE CIRCLE Winter Haven, FL Beautiful community of Osprey Pointe on Lake Ned. This 2 bedroom/2 bath home is move in re...	2 beds \| 2 baths \| 1,438 sq.ft.	$265,000	Airbnb cash on cash: 5.86% Traditional cash on cash: 3.75% Airbnb Rental Income: $2962 Traditional Rental Income: $1751 Airbnb ROI: 5.86% Traditional ROI: 3.75%
413 RUBY LAKE PLACE Winter Haven, FL Welcome to this beautifully maintained saltwater pool home offering comfort, style, and a ...	4 beds \| 2 baths \| 2,172 sq.ft.	$465,000	Airbnb cash on cash: 6.41% Traditional cash on cash: 2.26% Airbnb Rental Income: $5016 Traditional Rental Income: $2185 Airbnb ROI: 6.41% Traditional ROI: 2.26%
934 LAKE ELBERT DRIVE SE Winter Haven, FL Welcome to a one-of-a-kind lakeside retreat in the heart of Winter Haven â a beautifully...	4 beds \| 2 baths \| 3,198 sq.ft.	$495,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 5.15% Airbnb Rental Income: $5016 Traditional Rental Income: $3322 Airbnb ROI: 6.59% Traditional ROI: 5.15%
457 ADRIEL AVENUE Winter Haven, FL Do not miss this nice size home with 4 bedrooms and 2 bathrooms. New Roof. Perfect layout,...	4 beds \| 2 baths \| 2,088 sq.ft.	$359,900	Airbnb cash on cash: 9.89% Traditional cash on cash: 5.15% Airbnb Rental Income: $5016 Traditional Rental Income: $2389 Airbnb ROI: 9.89% Traditional ROI: 5.15%
5813 WINDRIDGE DRIVE Winter Haven, FL Updated 3-Bedroom Home with Modern Touches & Energy Efficiency in Winter Haven, FL This b...	4 beds \| 3 baths \| 2,320 sq.ft.	$345,000	Airbnb cash on cash: 9.9% Traditional cash on cash: 6.39% Airbnb Rental Income: $5016 Traditional Rental Income: $2854 Airbnb ROI: 9.9% Traditional ROI: 6.39%
113 CITRUS DRIVE Winter Haven, FL VERY MOTIVATED SELLER!! Welcome to this charming 3 Bedroom 2 Bath single-family home, wher...	3 beds \| 2 baths \| 2,016 sq.ft.	$289,900	Airbnb cash on cash: 9.11% Traditional cash on cash: 7.39% Airbnb Rental Income: $4015 Traditional Rental Income: $2685 Airbnb ROI: 9.11% Traditional ROI: 7.39%
2282 FIRESTONE PLACE Winter Haven, FL Welcome to Cypresswood Golf & Country Club Living! Discover this charming 2-bed, 2-bath, ...	2 beds \| 2 baths \| 1,164 sq.ft.	$205,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 4.97% Airbnb Rental Income: $2962 Traditional Rental Income: $1813 Airbnb ROI: 7.37% Traditional ROI: 4.97%
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.	$474,900	Airbnb cash on cash: 6.65% Traditional cash on cash: 4.19% Airbnb Rental Income: $5016 Traditional Rental Income: $2898 Airbnb ROI: 6.65% Traditional ROI: 4.19%
3372 LIVINGSTON WAY Winter Haven, FL Under contract-accepting backup offers. Welcome to this well-maintained 2-bedroom, 2-bath ...	2 beds \| 2 baths \| 1,275 sq.ft.	$250,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 4.37% Airbnb Rental Income: $2962 Traditional Rental Income: $1967 Airbnb ROI: 5.69% Traditional ROI: 4.37%
104 MORNING GLORY CIRCLE Winter Haven, FL NEW ROOF ~ MOTIVATED SELLER~PERFECT FOR BUYERS INSURANCE PREMIUM! Just listed in the desir...	3 beds \| 2 baths \| 1,806 sq.ft.	$328,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 5.27% Airbnb Rental Income: $4015 Traditional Rental Income: $2348 Airbnb ROI: 7.89% Traditional ROI: 5.27%
128 LAKE RING DRIVE Winter Haven, FL Back on the market no fault of the sellers! FHA appraisal complete and inspections too! ...	3 beds \| 2 baths \| 2,056 sq.ft.	$399,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 4.8% Airbnb Rental Income: $4015 Traditional Rental Income: $2496 Airbnb ROI: 6.56% Traditional ROI: 4.8%
2202 GARDEN LAKE DRIVE Winter Haven, FL Welcome to beautiful southeast Winter Haven, home to the Chain of Lakes and Legoland! This...	3 beds \| 2 baths \| 1,442 sq.ft.	$269,000	Airbnb cash on cash: 8.97% Traditional cash on cash: 4.88% Airbnb Rental Income: $4015 Traditional Rental Income: $2120 Airbnb ROI: 8.97% Traditional ROI: 4.88%
3998 BEDFORD AVENUE Winter Haven, FL If you are looking for a home in an active community with all the comfort, safety and amen...	4 beds \| 3 baths \| 2,277 sq.ft.	$469,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 2.87% Airbnb Rental Income: $5016 Traditional Rental Income: $2640 Airbnb ROI: 5.94% Traditional ROI: 2.87%
1383 BUCKEYE TRACE BOULEVARD Winter Haven, FL Under contract-accepting backup offers. Rare Find in a Gated Community! This beautiful 3-...	3 beds \| 2 baths \| 1,507 sq.ft.	$280,000	Airbnb cash on cash: 9.5% Traditional cash on cash: 5.82% Airbnb Rental Income: $4015 Traditional Rental Income: $2188 Airbnb ROI: 9.5% Traditional ROI: 5.82%
4007 CYPRESS LANDING S Winter Haven, FL Under contract-accepting backup offers. Welcome to your beautiful new home in the highly s...	2 beds \| 2 baths \| 1,578 sq.ft.	$234,900	Airbnb cash on cash: 7.29% Traditional cash on cash: 4.09% Airbnb Rental Income: $2962 Traditional Rental Income: $1569 Airbnb ROI: 7.29% Traditional ROI: 4.09%
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.	$544,900	Airbnb cash on cash: 5.84% Traditional cash on cash: 3.17% Airbnb Rental Income: $5016 Traditional Rental Income: $2631 Airbnb ROI: 5.84% Traditional ROI: 3.17%
3686 PLYMOUTH DRIVE Winter Haven, FL This beautifully updated 4-bedroom, 3-bath residence offers a spacious and thoughtfully de...	4 beds \| 3 baths \| 2,404 sq.ft.	$389,900	Airbnb cash on cash: 7.29% Traditional cash on cash: 3.89% Airbnb Rental Income: $5016 Traditional Rental Income: $2748 Airbnb ROI: 7.29% Traditional ROI: 3.89%
4569 MANDOLIN BOULEVARD Winter Haven, FL Welcome to 4569 Mandolin Blvd, a stylish and move-in ready four-bedroom, two-bathroom home...	4 beds \| 2 baths \| 1,665 sq.ft.	$360,000	Airbnb cash on cash: 9.63% Traditional cash on cash: 4.35% Airbnb Rental Income: $5016 Traditional Rental Income: $2208 Airbnb ROI: 9.63% Traditional ROI: 4.35%
2013 MARILYN AVENUE Winter Haven, FL Welcome to 2013 Marilyn Ave in Winter Haven! BRAND NEW ROOF! (08/01/2025)This 3-bedroom, 3...	3 beds \| 3 baths \| 1,943 sq.ft.	$320,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 4.62% Airbnb Rental Income: $4015 Traditional Rental Income: $2173 Airbnb ROI: 7.89% Traditional ROI: 4.62%
152 AUDUBON COURT Winter Haven, FL GREAT 3 BEDROOM, 2 BATHROOM HOME ON AN OVERSIZED (.42 AC) CORNER LOT WITH PEACEFUL VIEWS O...	3 beds \| 2 baths \| 2,490 sq.ft.	$337,500	Airbnb cash on cash: 7.96% Traditional cash on cash: 5.85% Airbnb Rental Income: $4015 Traditional Rental Income: $2488 Airbnb ROI: 7.96% Traditional ROI: 5.85%
5609 FOREST RIDGE DRIVE Winter Haven, FL AMAZING OPPORTUNITY IN WINTER HAVEN. This charming 3-bedroom, 2-bath block home is move-in...	3 beds \| 2 baths \| 1,534 sq.ft.	$295,000	Airbnb cash on cash: 9.12% Traditional cash on cash: 5.49% Airbnb Rental Income: $4015 Traditional Rental Income: $2149 Airbnb ROI: 9.12% Traditional ROI: 5.49%
465 LAS CRUCES Winter Haven, FL Under contract-accepting backup offers. Welcome to effortless Florida living in the charmi...	2 beds \| 2 baths \| 1,157 sq.ft.	$215,000	Airbnb cash on cash: 8.39% Traditional cash on cash: 6.01% Airbnb Rental Income: $2962 Traditional Rental Income: $1795 Airbnb ROI: 8.39% Traditional ROI: 6.01%
1012 ROBIN LANE Winter Haven, FL PRICED BELOW APPRAISED VALUE; SELLER OFFERING CLOSING COST ASSISTANCE -Priced in the $200'...	3 beds \| 2 baths \| 1,496 sq.ft.	$295,500	Airbnb cash on cash: 9% Traditional cash on cash: 5.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2091 Airbnb ROI: 9% Traditional ROI: 5.17%
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.	$534,400	Airbnb cash on cash: 3.97% Traditional cash on cash: 2.5% Airbnb Rental Income: $4015 Traditional Rental Income: $2424 Airbnb ROI: 3.97% Traditional ROI: 2.5%
3912 BALDWIN LANE Winter Haven, FL What? Furniture and a golf cart? Just bring your toothbrush! Your maintenance-free lifesty...	2 beds \| 2 baths \| 1,719 sq.ft.	$295,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1.84% Airbnb Rental Income: $2962 Traditional Rental Income: $1837 Airbnb ROI: 3.43% Traditional ROI: 1.84%
202 SAINT LUCIE ROAD Winter Haven, FL Corner Lot Charmer in SE Winter Haven â Price Improvement! NO HOA, Major Upgrades & Clos...	3 beds \| 2 baths \| 1,764 sq.ft.	$349,999	Airbnb cash on cash: 7.5% Traditional cash on cash: 5.86% Airbnb Rental Income: $4015 Traditional Rental Income: $2616 Airbnb ROI: 7.5% Traditional ROI: 5.86%
1924 ELOISE COVE DRIVE Winter Haven, FL Welcome to 1924 Eloise Cove Drive, a spacious 4 bedroom home with 3 full baths in the desi...	4 beds \| 3 baths \| 2,513 sq.ft.	$440,000	Airbnb cash on cash: 8.09% Traditional cash on cash: 5.07% Airbnb Rental Income: $5016 Traditional Rental Income: $2746 Airbnb ROI: 8.09% Traditional ROI: 5.07%
1075 8TH STREET NW Winter Haven, FL Income-Generating Property with Two In-Law Suites!! Maximize your rental income potential ...	4 beds \| N/A baths \| 1,985 sq.ft.	$498,999	Airbnb cash on cash: 6.74% Traditional cash on cash: 4.98% Airbnb Rental Income: $5016 Traditional Rental Income: $3171 Airbnb ROI: 6.74% Traditional ROI: 4.98%
2 BRIDGEWATER DRIVE Winter Haven, FL Under contract-accepting backup offers. * SIGNIFICANT SAVINGS-HUGE PRICE REDUCTION* ...	4 beds \| 3 baths \| 3,472 sq.ft.	$484,900	Airbnb cash on cash: 7.35% Traditional cash on cash: 6.34% Airbnb Rental Income: $5016 Traditional Rental Income: $3534 Airbnb ROI: 7.35% Traditional ROI: 6.34%
5392 CHANDLER DRIVE Winter Haven, FL Peaceful Waterfront Views! Many Beautiful Features & Oversized Living Areas Great for Ente...	4 beds \| 3 baths \| 3,034 sq.ft.	$424,900	Airbnb cash on cash: 7.25% Traditional cash on cash: 3.78% Airbnb Rental Income: $5016 Traditional Rental Income: $2611 Airbnb ROI: 7.25% Traditional ROI: 3.78%
1503 EAGLE POND DRIVE #1503 Winter Haven, FL Introducing a must-see condo in the esteemed gated community of Cypress Wood, this charmin...	2 beds \| 2 baths \| 1,017 sq.ft.	$169,500	Airbnb cash on cash: 9.67% Traditional cash on cash: 6.83% Airbnb Rental Income: $2962 Traditional Rental Income: $1821 Airbnb ROI: 9.67% Traditional ROI: 6.83%
2037 SAN MARCOS DRIVE SE #443 Winter Haven, FL Under contract-accepting backup offers. Here we have a charming 2 bedroom, 2 bath turnkey ...	2 beds \| 2 baths \| 967 sq.ft.	$160,000	Airbnb cash on cash: 9% Traditional cash on cash: 6.24% Airbnb Rental Income: $2962 Traditional Rental Income: $1858 Airbnb ROI: 9% Traditional ROI: 6.24%
1935 AUSTIN TERRACE Winter Haven, FL Under contract-accepting backup offers. NEW ROOF PRIOR TO CLOSING! Nestled in the hear...	3 beds \| 3 baths \| 2,494 sq.ft.	$425,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 4.69% Airbnb Rental Income: $4015 Traditional Rental Income: $2841 Airbnb ROI: 5.48% Traditional ROI: 4.69%
4105 OAK DRIVE Winter Haven, FL New Lower price!!! Looking for a charming home, with land? Come check out this cute home o...	2 beds \| 1 baths \| 1,253 sq.ft.	$258,000	Airbnb cash on cash: 7.06% Traditional cash on cash: 5.13% Airbnb Rental Income: $2962 Traditional Rental Income: $1809 Airbnb ROI: 7.06% Traditional ROI: 5.13%

Vacation Rentals in Winter Haven

There are 304 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 $295,000 and the average price per square foot is $169. The cash on cash return on vacation rentals in Winter Haven is 9.00%. 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 304 Airbnb properties available for sale in Winter Haven.

In 2025, the best neighborhood to buy short term rental property is Winter Haven.

In September 2025, 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

808 Overlook Grove Drive

Winter Haven, FL

4 beds | 3 baths | 2,093 sq.ft.

$360,000

Airbnb cash on cash: 9.16%

Traditional cash on cash: 5.23%

Airbnb Rental Income: $5016

Traditional Rental Income: $2662

Airbnb ROI: 9.16%

Traditional ROI: 5.23%

135 ELOISE OAKS DRIVE

Winter Haven, FL

3 beds | 2 baths | 1,866 sq.ft.

$369,900

Airbnb cash on cash: 6.6%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $4015

Traditional Rental Income: $2345

Airbnb ROI: 6.6%

Traditional ROI: 4.26%

475 ARCHAIC DRIVE

Winter Haven, FL

4 beds | 3 baths | 2,643 sq.ft.

$699,500

Airbnb cash on cash: 4.13%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $5016

Traditional Rental Income: $3637

Airbnb ROI: 4.13%

Traditional ROI: 3.59%

3324 OAK HILL PLACE

Winter Haven, FL

3 beds | 2 baths | 1,675 sq.ft.

$339,000

Airbnb cash on cash: 6.62%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $4015

Traditional Rental Income: $2433

Airbnb ROI: 6.62%

Traditional ROI: 4.35%

357 RUBY LAKE LOOP

Winter Haven, FL

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

$419,000

Airbnb cash on cash: 5.99%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $4015

Traditional Rental Income: $2587

Airbnb ROI: 5.99%

Traditional ROI: 4.54%

710 HERITAGE DRIVE NE

Winter Haven, FL

4 beds | 2 baths | 2,736 sq.ft.

$647,500

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%

3830 OSPREY POINTE CIRCLE

Winter Haven, FL

2 beds | 2 baths | 1,438 sq.ft.

$265,000

Airbnb cash on cash: 5.86%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2962

Traditional Rental Income: $1751

Airbnb ROI: 5.86%

Traditional ROI: 3.75%

413 RUBY LAKE PLACE

Winter Haven, FL

4 beds | 2 baths | 2,172 sq.ft.

$465,000

Airbnb cash on cash: 6.41%

Traditional cash on cash: 2.26%

Airbnb Rental Income: $5016

Traditional Rental Income: $2185

Airbnb ROI: 6.41%