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 233 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
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.	$309,500	Airbnb cash on cash: 5.39% Traditional cash on cash: 4.69% Airbnb Rental Income: $2962 Traditional Rental Income: $2076 Airbnb ROI: 5.39% Traditional ROI: 4.69%
254 CLOVERDALE ROAD Winter Haven, FL Under contract-accepting backup offers. Beautifully maintained 3-bedroom, 2-bath home loca...	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%
225 FRANKLIN COURT Winter Haven, FL Under contract-accepting backup offers. *PRICE REDUCTION* Refined luxury meets modern ...	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%
4840 OLD LUCERNE PARK RD Winter Haven, FL Lakefront Retreat on Beautiful Lake Lucerne! Situated on 0.84 acres, this updated 3-bedro...	3 beds \| 2 baths \| 1,927 sq.ft.	$425,000	Airbnb cash on cash: 6.19% Traditional cash on cash: 5.3% Airbnb Rental Income: $4015 Traditional Rental Income: $2803 Airbnb ROI: 6.19% Traditional ROI: 5.3%
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%
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.	$419,000	Airbnb cash on cash: 7.66% Traditional cash on cash: 4.55% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.66% Traditional ROI: 4.55%
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%
1716 TERRY CIR NE Winter Haven, FL Welcome to 1716 Terry Circle NE, Winter Haven, FL 33881, a beautifully maintained and full...	3 beds \| 2 baths \| 1,065 sq.ft.	$270,000	Airbnb cash on cash: 9.79% Traditional cash on cash: 4.76% Airbnb Rental Income: $4015 Traditional Rental Income: $1874 Airbnb ROI: 9.79% Traditional ROI: 4.76%
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 Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	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%
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%
4111 ISLAND LAKES DRIVE Winter Haven, FL Welcome to this beautifully maintained waterfront home on an oversized lot in the desirabl...	3 beds \| 2 baths \| 1,998 sq.ft.	$399,900	Airbnb cash on cash: 5.99% Traditional cash on cash: 4.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2688 Airbnb ROI: 5.99% Traditional ROI: 4.74%
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%
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%
250 VOLUSIA DRIVE Winter Haven, FL PRICE DROP! SELLER OFFERS $15,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYERâS CHOIC...	3 beds \| 2 baths \| 1,449 sq.ft.	$294,000	Airbnb cash on cash: 9.28% Traditional cash on cash: 5.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2186 Airbnb ROI: 9.28% Traditional ROI: 5.77%
5828 MARSH LANDING DRIVE Winter Haven, FL Under contract-accepting backup offers. Welcome to refined Florida living in the serene, g...	4 beds \| 2 baths \| 2,078 sq.ft.	$387,500	Airbnb cash on cash: 7.94% Traditional cash on cash: 5.58% Airbnb Rental Income: $5016 Traditional Rental Income: $3135 Airbnb ROI: 7.94% Traditional ROI: 5.58%
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.	$315,000	Airbnb cash on cash: 8.38% Traditional cash on cash: 5.84% Airbnb Rental Income: $4015 Traditional Rental Income: $2405 Airbnb ROI: 8.38% Traditional ROI: 5.84%
961 DREXEL AVENUE NE Winter Haven, FL *PRICE DECREASE* This unique 2-story home in Winter Haven is full of character and cha...	3 beds \| 2 baths \| 1,856 sq.ft.	$305,000	Airbnb cash on cash: 8.57% Traditional cash on cash: 6.1% Airbnb Rental Income: $4015 Traditional Rental Income: $2448 Airbnb ROI: 8.57% Traditional ROI: 6.1%
1394 OAKMONT DRIVE Winter Haven, FL Experience resort-style living in the highly sought-after gated 55+ golf community of Lake...	3 beds \| 2 baths \| 2,606 sq.ft.	$549,500	Airbnb cash on cash: 3.03% Traditional cash on cash: 1.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2511 Airbnb ROI: 3.03% Traditional ROI: 1.77%
340 Vail Dr Winter Haven, FL Beautifully updated home tucked away on a quiet cul-de-sac in the well-established Cedar C...	3 beds \| 3 baths \| 2,042 sq.ft.	$365,000	Airbnb cash on cash: 6.82% Traditional cash on cash: 5.03% Airbnb Rental Income: $4015 Traditional Rental Income: $2545 Airbnb ROI: 6.82% Traditional ROI: 5.03%
3136 COUNTRY CLUB CIRCLE Winter Haven, FL Welcome to a home that makes everyday living simple and enjoyable. Located in the establis...	3 beds \| 2 baths \| 1,690 sq.ft.	$290,000	Airbnb cash on cash: 8.79% Traditional cash on cash: 4.47% Airbnb Rental Income: $4015 Traditional Rental Income: $1978 Airbnb ROI: 8.79% Traditional ROI: 4.47%
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.	$349,900	Airbnb cash on cash: 7.41% Traditional cash on cash: 4.71% Airbnb Rental Income: $4015 Traditional Rental Income: $2269 Airbnb ROI: 7.41% Traditional ROI: 4.71%
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.	$524,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 2.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2691 Airbnb ROI: 3.72% Traditional ROI: 2.77%
144 BEVERLY DRIVE Winter Haven, FL NO HOA + POOL HOME + MINUTES TO THE CHAIN OF LAKES! This updated 4-bedroom, 3-bath Winter ...	4 beds \| 3 baths \| 2,492 sq.ft.	$389,900	Airbnb cash on cash: 8.7% Traditional cash on cash: 8.12% Airbnb Rental Income: $5016 Traditional Rental Income: $3781 Airbnb ROI: 8.7% Traditional ROI: 8.12%
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%
2218 ABBEY ROAD Winter Haven, FL Turnkey Villa in Stonebridge â Low Maintenance Living, Prime Location Step into easy ...	2 beds \| 2 baths \| 1,252 sq.ft.	$179,999	Airbnb cash on cash: 9.45% Traditional cash on cash: 7.71% Airbnb Rental Income: $2962 Traditional Rental Income: $1982 Airbnb ROI: 9.45% Traditional ROI: 7.71%
301 Terranova Boulevard Winter Haven, FL Welcome to this beautifully maintained 4-bedroom, 2-bathroom home located in the desirable...	4 beds \| 2 baths \| 1,960 sq.ft.	$415,000	Airbnb cash on cash: 7.95% Traditional cash on cash: 3.04% Airbnb Rental Income: $5016 Traditional Rental Income: $2079 Airbnb ROI: 7.95% Traditional ROI: 3.04%
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%
133 EL DORADO Winter Haven, FL Charming and well-maintained and can be your HOME in Winter Haven! This property features ...	2 beds \| 2 baths \| 1,639 sq.ft.	$255,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 5.9% Airbnb Rental Income: $2962 Traditional Rental Income: $2172 Airbnb ROI: 6.35% Traditional ROI: 5.9%
1590 VIENNA SQUARE DRIVE Winter Haven, FL Under contract-accepting backup offers. Welcome to Vienna Square â a vibrant, beautifull...	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.	$333,000	Airbnb cash on cash: 7.46% Traditional cash on cash: 5.76% Airbnb Rental Income: $4015 Traditional Rental Income: $2626 Airbnb ROI: 7.46% Traditional ROI: 5.76%
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%
140 KRENSON BAY LOOP Winter Haven, FL Welcome to this inviting 3BR/2BA home with a 2-car garage and 2,128 sq. ft. in a gated Win...	3 beds \| 2 baths \| 1,479 sq.ft.	$270,000	Airbnb cash on cash: 9.49% Traditional cash on cash: 5.39% Airbnb Rental Income: $4015 Traditional Rental Income: $2115 Airbnb ROI: 9.49% Traditional ROI: 5.39%
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: 7.7% Traditional cash on cash: 7.12% Airbnb Rental Income: $4015 Traditional Rental Income: $2977 Airbnb ROI: 7.7% Traditional ROI: 7.12%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Haven, FL

132 DUVAL ROAD

Winter Haven, FL

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

$309,500

Airbnb cash on cash: 5.39%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $2962

Traditional Rental Income: $2076

Airbnb ROI: 5.39%

Traditional ROI: 4.69%

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%

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%

4840 OLD LUCERNE PARK RD

Winter Haven, FL

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

$425,000

Airbnb cash on cash: 6.19%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $4015

Traditional Rental Income: $2803

Airbnb ROI: 6.19%

Traditional ROI: 5.3%

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%

1908 CROSSROADS BOULEVARD

Winter Haven, FL

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

$419,000

Airbnb cash on cash: 7.66%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $5016

Traditional Rental Income: $2772

Airbnb ROI: 7.66%

Traditional ROI: 4.55%

2202 GARDEN LAKE DRIVE

Winter Haven, FL

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%