Real Estate Investment Properties for Sale in Holiday, FL

Looking for investment property in Holiday, FL with high ROI ?

Explore a variety of short-term homes & houses in Holiday, FL. Invest wisely with VRBO & Holiday, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Holiday, FL

Search for Single Family Residential for Sale in Holiday, 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 158 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
1414 WHITEHALL LANE HOLIDAY, FL -- OWNERS MOTIVATED, LET'S MAKE A DEAL -- **Free 1% one-year interest rate buy down throug...	3 beds \| 2 baths \| 1,636 sq.ft.	$293,990	Airbnb cash on cash: 4.78% Traditional cash on cash: 6.65% Airbnb Rental Income: $2490 Traditional Rental Income: $2402 Airbnb ROI: 4.78% Traditional ROI: 6.65%
2228 SOCIETY DRIVE HOLIDAY, FL Price Improvement! Discover peaceful living in this charming 2-bedroom, 1.5-bath home nest...	2 beds \| 2 baths \| 1,039 sq.ft.	$239,900	Airbnb cash on cash: 1.53% Traditional cash on cash: 5.91% Airbnb Rental Income: $1336 Traditional Rental Income: $1917 Airbnb ROI: 1.53% Traditional ROI: 5.91%
2423 TRIGGERFISH COURT HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 2,462 sq.ft.	$500,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 3.81% Airbnb Rental Income: $1329 Traditional Rental Income: $3225 Airbnb ROI: -1.13% Traditional ROI: 3.81%
2228 PARROT FISH DRIVE HOLIDAY, FL âDue to seller/investor marketing restrictions, seller is only accepting offers from Own...	3 beds \| 2 baths \| 1,876 sq.ft.	$319,900	Airbnb cash on cash: 2.86% Traditional cash on cash: 5.13% Airbnb Rental Income: $2490 Traditional Rental Income: $2570 Airbnb ROI: 2.86% Traditional ROI: 5.13%
3433 TUCKAHOE PLACE HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	2 beds \| 2 baths \| 1,128 sq.ft.	$240,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 6.63% Airbnb Rental Income: $1336 Traditional Rental Income: $1965 Airbnb ROI: 2.05% Traditional ROI: 6.63%
3325 HONEYMOON LANE HOLIDAY, FL Welcome to waterfront living in Holiday! This beautifully maintained 2-bedroom, 2-bath hom...	2 beds \| 2 baths \| 1,334 sq.ft.	$250,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 8.62% Airbnb Rental Income: $1336 Traditional Rental Income: $2529 Airbnb ROI: 1.82% Traditional ROI: 8.62%
3426 COLDWELL DRIVE HOLIDAY, FL Discover your Florida retreat in the heart of Holiday Lake Estates! This beautifully refre...	4 beds \| 2 baths \| 1,116 sq.ft.	$275,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 6.54% Airbnb Rental Income: $1329 Traditional Rental Income: $2367 Airbnb ROI: 0.95% Traditional ROI: 6.54%
3401 SUPREME DRIVE HOLIDAY, FL WOW! Move in ready and full of potential! This charming home features bright open living...	2 beds \| 2 baths \| 1,442 sq.ft.	$264,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 6.67% Airbnb Rental Income: $1336 Traditional Rental Income: $2215 Airbnb ROI: 1.49% Traditional ROI: 6.67%
5828 MARIPOSA DRIVE HOLIDAY, FL Welcome to this beautifully maintained 2-bedroom, 2-bath home located in the heart of Holi...	2 beds \| 2 baths \| 973 sq.ft.	$199,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 8.13% Airbnb Rental Income: $1336 Traditional Rental Income: $1947 Airbnb ROI: 2.74% Traditional ROI: 8.13%
2128 SHANNON DRIVE HOLIDAY, FL Quintessential Florida Living in Holiday! Welcome to this charming 2-bedroom, 1-bath, 1-c...	2 beds \| 1 baths \| 1,200 sq.ft.	$214,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 6.66% Airbnb Rental Income: $1336 Traditional Rental Income: $1756 Airbnb ROI: 2.58% Traditional ROI: 6.66%
3103 BRIGHT DRIVE HOLIDAY, FL Dreaming of being on Holiday, EVERYDAY? Well your search is over and welcome to your new h...	2 beds \| 2 baths \| 1,457 sq.ft.	$328,950	Airbnb cash on cash: 0.51% Traditional cash on cash: 5.32% Airbnb Rental Income: $1336 Traditional Rental Income: $2410 Airbnb ROI: 0.51% Traditional ROI: 5.32%
3638 BIGELOW DRIVE HOLIDAY, FL Under contract-accepting backup offers. CORNER LOT-PRIVACY FENCE-Priced RIGHT!!--No HOA to...	2 beds \| 2 baths \| 1,096 sq.ft.	$214,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 6.97% Airbnb Rental Income: $1336 Traditional Rental Income: $1832 Airbnb ROI: 2.49% Traditional ROI: 6.97%
3114 BLUFF BOULEVARD HOLIDAY, FL Discover the charm of Floridaâs Gulf Coast in this beautifully crafted waterfront home, ...	3 beds \| 3 baths \| 3,234 sq.ft.	$1,265,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.92% Airbnb Rental Income: $2490 Traditional Rental Income: $4615 Airbnb ROI: -0.4% Traditional ROI: 1.92%
2216 OAK WIND DRIVE HOLIDAY, FL Welcome home to this charming 2 bedroom, 2 bathroom villa in the highly desirable Pinewood...	2 beds \| 2 baths \| 1,128 sq.ft.	$179,900	Airbnb cash on cash: 2.17% Traditional cash on cash: 8.79% Airbnb Rental Income: $1336 Traditional Rental Income: $2059 Airbnb ROI: 2.17% Traditional ROI: 8.79%
3706 CHESWICK DRIVE HOLIDAY, FL Welcome to this beautifully maintained property, boasting a fresh interior paint job in a ...	2 beds \| 2 baths \| 1,036 sq.ft.	$198,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 7.95% Airbnb Rental Income: $1336 Traditional Rental Income: $1864 Airbnb ROI: 2.95% Traditional ROI: 7.95%
3011 SHADOW OAKS DRIVE HOLIDAY, FL Spacious 3-bedroom, 2-bathroom home featuring laminate flooring throughout with tile in th...	3 beds \| 2 baths \| 1,480 sq.ft.	$329,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 6.19% Airbnb Rental Income: $2490 Traditional Rental Income: $2561 Airbnb ROI: 4.01% Traditional ROI: 6.19%
5026 MOOG ROAD HOLIDAY, FL Charming Updated Single-Family Home in Holiday with Spacious Fenced Yard. This home has be...	2 beds \| 1 baths \| 792 sq.ft.	$233,500	Airbnb cash on cash: 1.58% Traditional cash on cash: 5.13% Airbnb Rental Income: $1336 Traditional Rental Income: $1709 Airbnb ROI: 1.58% Traditional ROI: 5.13%
2406 SOCIETY DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome Home! This beautifully updated home is mov...	2 beds \| 2 baths \| 1,198 sq.ft.	$250,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 7.05% Airbnb Rental Income: $1336 Traditional Rental Income: $2327 Airbnb ROI: 1.11% Traditional ROI: 7.05%
3552 BLUEBELL LANE HOLIDAY, FL Under contract-accepting backup offers. Short Sale. MULTIPLE OFFERS RECEIVED. PLEASE SUBMI...	2 beds \| 2 baths \| 900 sq.ft.	$180,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 10.1% Airbnb Rental Income: $1336 Traditional Rental Income: $2133 Airbnb ROI: 3.05% Traditional ROI: 10.1%
2349 HAMA DRIVE HOLIDAY, FL WELCOME HOME to this meticulously maintained 3-bedroom, 2-bath waterfront home in Holiday'...	3 beds \| 2 baths \| 1,470 sq.ft.	$259,900	Airbnb cash on cash: 5.61% Traditional cash on cash: 9.04% Airbnb Rental Income: $2490 Traditional Rental Income: $2726 Airbnb ROI: 5.61% Traditional ROI: 9.04%
2146 SOCIETY DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. Tucked along the shores of Lake Conley, th...	2 beds \| 2 baths \| 1,371 sq.ft.	$265,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 7.91% Airbnb Rental Income: $1336 Traditional Rental Income: $2545 Airbnb ROI: 1.43% Traditional ROI: 7.91%
1313 CHANCELLOR DRIVE HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Di...	2 beds \| 2 baths \| 953 sq.ft.	$180,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 8.52% Airbnb Rental Income: $1336 Traditional Rental Income: $1889 Airbnb ROI: 2.88% Traditional ROI: 8.52%
2125 BARRACUDA COURT HOLIDAY, FL Under contract-accepting backup offers. Maintenance Free living, 3-Bedrooms 2.5-Bathrooms,...	3 beds \| 3 baths \| 1,740 sq.ft.	$342,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 3.67% Airbnb Rental Income: $2490 Traditional Rental Income: $2298 Airbnb ROI: 2.39% Traditional ROI: 3.67%
3625 Windham Drive HOLIDAY, FL Welcome to 3625 Windham Drive in the heart of Holiday, FL - a charming and move-in-ready 3...	3 beds \| 1 baths \| 1,200 sq.ft.	$225,000	Airbnb cash on cash: 6.39% Traditional cash on cash: 7.08% Airbnb Rental Income: $2490 Traditional Rental Income: $2034 Airbnb ROI: 6.39% Traditional ROI: 7.08%
3238 MELA COURT HOLIDAY, FL Amazing Price Reduction in Gated Neighborhood of Vista Lakes at Bailys Bluff - 5 Bedroom,...	5 beds \| 4 baths \| 3,198 sq.ft.	$499,900	Airbnb cash on cash: 0.8% Traditional cash on cash: 5.48% Airbnb Rental Income: $2273 Traditional Rental Income: $3892 Airbnb ROI: 0.8% Traditional ROI: 5.48%
4327 BEACON SQUARE DRIVE HOLIDAY, FL Welcome home! This charming Holiday gem is the perfect opportunity for first-time buyers. ...	3 beds \| 1 baths \| 1,104 sq.ft.	$214,000	Airbnb cash on cash: 6.95% Traditional cash on cash: 6.73% Airbnb Rental Income: $2490 Traditional Rental Income: $1842 Airbnb ROI: 6.95% Traditional ROI: 6.73%
2945 WOOD POINTE DRIVE HOLIDAY, FL Located within the 55+ area of the beautiful Key Vista gated community, this move-in-ready...	2 beds \| 2 baths \| 1,341 sq.ft.	$345,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 4% Airbnb Rental Income: $1336 Traditional Rental Income: $2265 Airbnb ROI: -0.14% Traditional ROI: 4%
4102 DARLINGTON ROAD HOLIDAY, FL Under contract-accepting backup offers. Great starter, retirement, or income rental home. ...	2 beds \| 2 baths \| 988 sq.ft.	$190,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 7.43% Airbnb Rental Income: $1336 Traditional Rental Income: $1867 Airbnb ROI: 2.21% Traditional ROI: 7.43%
5646 ANDREA DRIVE HOLIDAY, FL PRICE IMPROVEMENT!!! Welcome to your new home! Located in Holiday FL with no Hoa, CDD, and...	3 beds \| 2 baths \| 1,522 sq.ft.	$260,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 7.93% Airbnb Rental Income: $2490 Traditional Rental Income: $2546 Airbnb ROI: 5.24% Traditional ROI: 7.93%
3228 ROCK VALLEY DRIVE HOLIDAY, FL Welcome to this charming two bedroom, two bath home with a spacious Florida room that offe...	2 beds \| 2 baths \| 1,334 sq.ft.	$299,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 5.46% Airbnb Rental Income: $1336 Traditional Rental Income: $2073 Airbnb ROI: 1.38% Traditional ROI: 5.46%
2907 FEATHERSTONE DRIVE HOLIDAY, FL price adjustment and a very motived seller,,,Move-in ready and full of potential! This 2-b...	2 beds \| 2 baths \| 1,159 sq.ft.	$194,900	Airbnb cash on cash: -0.56% Traditional cash on cash: 5.43% Airbnb Rental Income: $1336 Traditional Rental Income: $2033 Airbnb ROI: -0.56% Traditional ROI: 5.43%
2817 PLANTAIN DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome home to 2817 Plantain Dr! This beautifully...	3 beds \| 2 baths \| 1,683 sq.ft.	$415,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 5.29% Airbnb Rental Income: $2490 Traditional Rental Income: $3290 Airbnb ROI: 1.68% Traditional ROI: 5.29%
3711 ELMWOOD DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome home! This charming and affordable starter...	2 beds \| 2 baths \| 1,096 sq.ft.	$205,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 6.95% Airbnb Rental Income: $1336 Traditional Rental Income: $1947 Airbnb ROI: 1.69% Traditional ROI: 6.95%
3320 COLUMBUS DRIVE HOLIDAY, FL Under contract-accepting backup offers. Looking for a home to entertain family and friends...	2 beds \| 2 baths \| 1,289 sq.ft.	$215,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 6.92% Airbnb Rental Income: $1336 Traditional Rental Income: $2065 Airbnb ROI: 1.32% Traditional ROI: 6.92%
2330 SOCIETY DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome to this waterfront pool home in the desira...	4 beds \| 3 baths \| 2,418 sq.ft.	$399,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 3.43% Airbnb Rental Income: $1329 Traditional Rental Income: $2363 Airbnb ROI: -0.43% Traditional ROI: 3.43%
3801 SABLEWOOD DRIVE HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	2 beds \| 2 baths \| 936 sq.ft.	$223,900	Airbnb cash on cash: 1.62% Traditional cash on cash: 6.08% Airbnb Rental Income: $1336 Traditional Rental Income: $1870 Airbnb ROI: 1.62% Traditional ROI: 6.08%
3105 PINON DRIVE HOLIDAY, FL Under contract-accepting backup offers. Auction Property. Short Sale. * * FANTASTIC OPPORT...	3 beds \| 2 baths \| 1,519 sq.ft.	$229,900	Airbnb cash on cash: 5.68% Traditional cash on cash: 9.29% Airbnb Rental Income: $2490 Traditional Rental Income: $2672 Airbnb ROI: 5.68% Traditional ROI: 9.29%
1817 DARTMOUTH DRIVE HOLIDAY, FL Don't miss out on this 3-bedroom 2-bath home just 2.5 miles from the BEACH and the Ancloe ...	3 beds \| 2 baths \| 1,457 sq.ft.	$249,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 8.73% Airbnb Rental Income: $2490 Traditional Rental Income: $2779 Airbnb ROI: 4.94% Traditional ROI: 8.73%
3334 COLDWELL DRIVE HOLIDAY, FL Move in ready 3 bedroom 1.5 bathroom home located in Holiday Fl. This home has and update ...	3 beds \| 2 baths \| 1,185 sq.ft.	$243,000	Airbnb cash on cash: 4.48% Traditional cash on cash: 5.3% Airbnb Rental Income: $2490 Traditional Rental Income: $2075 Airbnb ROI: 4.48% Traditional ROI: 5.3%
4843 CALAIS DRIVE HOLIDAY, FL Live the Florida Dream in this Beautiful 2 Bedroom 2 Bath Block Home with Oversized Garage...	2 beds \| 2 baths \| 1,088 sq.ft.	$235,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 5.17% Airbnb Rental Income: $1336 Traditional Rental Income: $1700 Airbnb ROI: 1.68% Traditional ROI: 5.17%

Your search for investment property begins and ends here

Single Family Homes for Sale in Holiday, FL

1414 WHITEHALL LANE

HOLIDAY, FL

3 beds | 2 baths | 1,636 sq.ft.

$293,990

Airbnb cash on cash: 4.78%

Traditional cash on cash: 6.65%

Airbnb Rental Income: $2490

Traditional Rental Income: $2402

Airbnb ROI: 4.78%

Traditional ROI: 6.65%

2228 SOCIETY DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,039 sq.ft.

$239,900

Airbnb cash on cash: 1.53%

Traditional cash on cash: 5.91%

Airbnb Rental Income: $1336

Traditional Rental Income: $1917

Airbnb ROI: 1.53%

Traditional ROI: 5.91%

2423 TRIGGERFISH COURT

HOLIDAY, FL

4 beds | 3 baths | 2,462 sq.ft.

$500,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $1329

Traditional Rental Income: $3225

Airbnb ROI: -1.13%

Traditional ROI: 3.81%

2228 PARROT FISH DRIVE

HOLIDAY, FL

3 beds | 2 baths | 1,876 sq.ft.

$319,900

Airbnb cash on cash: 2.86%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $2490

Traditional Rental Income: $2570

Airbnb ROI: 2.86%

Traditional ROI: 5.13%

3433 TUCKAHOE PLACE

HOLIDAY, FL

2 beds | 2 baths | 1,128 sq.ft.

$240,000

Airbnb cash on cash: 2.05%

Traditional cash on cash: 6.63%

Airbnb Rental Income: $1336

Traditional Rental Income: $1965

Airbnb ROI: 2.05%

Traditional ROI: 6.63%

3325 HONEYMOON LANE

HOLIDAY, FL

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

$250,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 8.62%

Airbnb Rental Income: $1336

Traditional Rental Income: $2529

Airbnb ROI: 1.82%

Traditional ROI: 8.62%

3426 COLDWELL DRIVE

HOLIDAY, FL

4 beds | 2 baths | 1,116 sq.ft.

$275,000

Airbnb cash on cash: 0.95%

Traditional cash on cash: 6.54%

Airbnb Rental Income: $1329

Traditional Rental Income: $2367

Airbnb ROI: 0.95%

Traditional ROI: 6.54%

3401 SUPREME DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,442 sq.ft.

$264,000

Airbnb cash on cash: 1.49%

Traditional cash on cash: 6.67%

Airbnb Rental Income: $1336

Traditional Rental Income: $2215

Airbnb ROI: 1.49%