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.

Multi Family for Sale in Holiday, FL

Search for Multi Family for Sale in Holiday, Florida. Browse all of Mashvisor’s Multi Family listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 3 Multi Family 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
5507 RIDDLE ROAD HOLIDAY, FL Just reduced! This spacious 2,400 sq ft duplex is situated on an oversized corner lot in H...	6 beds \| N/A baths \| 2,406 sq.ft.	$390,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 1.8% Airbnb Rental Income: $2176 Traditional Rental Income: $1587 Airbnb ROI: 1.91% Traditional ROI: 1.8%
1839 & 1841 HACIENDA WAY HOLIDAY, FL Four units in two duplex buildings on one lot. 1839 has an efficiency and a 2-1 unit with ...	4 beds \| N/A baths \| 1,972 sq.ft.	$460,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 3.69% Airbnb Rental Income: $2176 Traditional Rental Income: $2408 Airbnb ROI: 1.87% Traditional ROI: 3.69%
1818 And 1816 HACIENDA WAY HOLIDAY, FL FOR SALE. Nestled between Pinellas County (2.5 mi) and 5.2 mi to Downtown New Port Richeyâ...	6 beds \| N/A baths \| 1,527 sq.ft.	$380,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 4.39% Airbnb Rental Income: $2176 Traditional Rental Income: $2344 Airbnb ROI: 2.37% Traditional ROI: 4.39%
Other Investment Properties for Sale in Holiday
2228 SOCIETY DRIVE HOLIDAY , FL Discover peaceful living in this charming 2-bedroom, 1.5-bath home nestled along the banks...	2 beds \| 2 baths \| 1,039 sq.ft.	$254,900	Airbnb cash on cash: 4.3% Traditional cash on cash: 5.55% Airbnb Rental Income: $2176 Traditional Rental Income: $1927 Airbnb ROI: 4.3% Traditional ROI: 5.55%
2427 INDIAN KEY DRIVE HOLIDAY , FL One or more photo(s) has been virtually staged. MOTIVATED ESTATE - HUGE PRICE REDUCTION - ...	3 beds \| 2 baths \| 1,758 sq.ft.	$399,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 4.8% Airbnb Rental Income: $3151 Traditional Rental Income: $2960 Airbnb ROI: 3.41% Traditional ROI: 4.8%
2932 WINDRIDGE DRIVE HOLIDAY , FL Under contract-accepting backup offers. BRAND NEW ROOF INSTALLED (Oct 2025) !! Welcome to ...	3 beds \| 2 baths \| 1,662 sq.ft.	$399,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 5.34% Airbnb Rental Income: $3151 Traditional Rental Income: $2721 Airbnb ROI: 4.58% Traditional ROI: 5.34%
2329 BARRACUDA COURT HOLIDAY , FL Under contract-accepting backup offers. Very well MAINTAINED home priced right for you! Im...	3 beds \| 2 baths \| 1,740 sq.ft.	$339,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.3% Airbnb Rental Income: $3151 Traditional Rental Income: $2429 Airbnb ROI: 3.33% Traditional ROI: 3.3%
3516 NORLAND COURT HOLIDAY , FL Welcome to this stunning, fully renovated lakefront gem nestled in a peaceful Holiday neig...	3 beds \| 2 baths \| 1,334 sq.ft.	$260,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 7.82% Airbnb Rental Income: $3151 Traditional Rental Income: $2565 Airbnb ROI: 7.3% Traditional ROI: 7.82%
1913 BLUE RIVER ROAD HOLIDAY , FL Lakefront Pool Home in Gated Community â Not in a Flood Zone! Welcome to your private...	3 beds \| 3 baths \| 2,202 sq.ft.	$465,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 5.15% Airbnb Rental Income: $3151 Traditional Rental Income: $3351 Airbnb ROI: 3.05% Traditional ROI: 5.15%
2511 INDIAN KEY DRIVE HOLIDAY , FL One or more photo(s) has been virtually staged. One or more photos have been virtually sta...	4 beds \| 2 baths \| 2,027 sq.ft.	$399,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 4.68% Airbnb Rental Income: $4419 Traditional Rental Income: $2798 Airbnb ROI: 6.54% Traditional ROI: 4.68%
2807 BANNER STONE COURT HOLIDAY , FL Welcome to this stunning 4-bedroom, 3-bathroom home located in the desirable Key Vista com...	4 beds \| 3 baths \| 2,188 sq.ft.	$499,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 4.25% Airbnb Rental Income: $4419 Traditional Rental Income: $3079 Airbnb ROI: 5.14% Traditional ROI: 4.25%
3426 BLAYTON STREET HOLIDAY , FL $5,000 CREDIT BEING PROVIDED TO BUYER BY SELLER at closing for upgrades or closing costs. ...	2 beds \| 2 baths \| 1,164 sq.ft.	$215,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 8.25% Airbnb Rental Income: $2176 Traditional Rental Income: $2089 Airbnb ROI: 5.97% Traditional ROI: 8.25%
4345 TAHITIAN GARDENS CIRCLE #C HOLIDAY , FL JUST REDUCED! This two-bedroom, BATH & HALF condominium located at the back of a cul-de-sa...	2 beds \| 2 baths \| 825 sq.ft.	$143,500	Airbnb cash on cash: 8.05% Traditional cash on cash: 9.7% Airbnb Rental Income: $2176 Traditional Rental Income: $1851 Airbnb ROI: 8.05% Traditional ROI: 9.7%
4803 TRAFFORD ROAD HOLIDAY , FL This charming block home features a fenced backyard and a total of 1,402 square feet of li...	3 beds \| 2 baths \| 988 sq.ft.	$239,000	Airbnb cash on cash: 8.08% Traditional cash on cash: 5.58% Airbnb Rental Income: $3151 Traditional Rental Income: $1874 Airbnb ROI: 8.08% Traditional ROI: 5.58%
3301 ELKRIDGE DRIVE HOLIDAY , FL Wake up to tranquil living ON THE WATER in this spacious 3-bedroom, 2-bathroom home, perfe...	3 beds \| 2 baths \| 1,687 sq.ft.	$282,000	Airbnb cash on cash: 6.31% Traditional cash on cash: 7.51% Airbnb Rental Income: $3151 Traditional Rental Income: $2756 Airbnb ROI: 6.31% Traditional ROI: 7.51%
1225 GREENLEA DRIVE HOLIDAY , FL A POOL HOME and NO HOA, NO CDD and is in a NO FLOOD ZONE. It's in the charming Holiday La...	2 beds \| 2 baths \| 1,525 sq.ft.	$366,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 5.3% Airbnb Rental Income: $2176 Traditional Rental Income: $2474 Airbnb ROI: 2.83% Traditional ROI: 5.3%
4223 KIBLER LANE HOLIDAY , FL Under contract-accepting backup offers. Welcome to 4223 Kibler Lane â a charming 2-bedro...	2 beds \| 1 baths \| 816 sq.ft.	$170,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 7.88% Airbnb Rental Income: $2176 Traditional Rental Income: $1719 Airbnb ROI: 7.3% Traditional ROI: 7.88%
5828 MARIPOSA DRIVE HOLIDAY , FL Welcome to 5828 Mariposa Drive in Holiday, FL â a charming 2-bedroom, 2-bath home offeri...	2 beds \| 2 baths \| 973 sq.ft.	$216,500	Airbnb cash on cash: 5.87% Traditional cash on cash: 6.97% Airbnb Rental Income: $2176 Traditional Rental Income: $1851 Airbnb ROI: 5.87% Traditional ROI: 6.97%

Your search for investment property begins and ends here

Multi Family for Sale in Holiday, FL

5507 RIDDLE ROAD

HOLIDAY, FL

6 beds | N/A baths | 2,406 sq.ft.

$390,000

Airbnb cash on cash: 1.91%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $2176

Traditional Rental Income: $1587

Airbnb ROI: 1.91%

Traditional ROI: 1.8%

1839 & 1841 HACIENDA WAY

HOLIDAY, FL

4 beds | N/A baths | 1,972 sq.ft.

$460,000

Airbnb cash on cash: 1.87%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $2176

Traditional Rental Income: $2408

Airbnb ROI: 1.87%

Traditional ROI: 3.69%

1818 And 1816 HACIENDA WAY

HOLIDAY, FL

6 beds | N/A baths | 1,527 sq.ft.

$380,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $2176

Traditional Rental Income: $2344

Airbnb ROI: 2.37%

Traditional ROI: 4.39%

Other Investment Properties for Sale in Holiday

HOLIDAY , FL

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

$254,900

Airbnb cash on cash: 4.3%

Traditional cash on cash: 5.55%

Airbnb Rental Income: $2176

Traditional Rental Income: $1927

Airbnb ROI: 4.3%

Traditional ROI: 5.55%

HOLIDAY , FL

3 beds | 2 baths | 1,758 sq.ft.

$399,000

Airbnb cash on cash: 3.41%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $3151

Traditional Rental Income: $2960

Airbnb ROI: 3.41%

Traditional ROI: 4.8%

HOLIDAY , FL

3 beds | 2 baths | 1,662 sq.ft.

$399,000

Airbnb cash on cash: 4.58%

Traditional cash on cash: 5.34%

Airbnb Rental Income: $3151

Traditional Rental Income: $2721

Airbnb ROI: 4.58%

Traditional ROI: 5.34%

HOLIDAY , FL

3 beds | 2 baths | 1,740 sq.ft.

$339,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $3151

Traditional Rental Income: $2429

Airbnb ROI: 3.33%

Traditional ROI: 3.3%

HOLIDAY , FL

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

$260,000

Airbnb cash on cash: 7.3%

Traditional cash on cash: 7.82%

Airbnb Rental Income: $3151

Traditional Rental Income: $2565

Airbnb ROI: 7.3%

Traditional ROI: 7.82%

HOLIDAY , FL

3 beds | 3 baths | 2,202 sq.ft.

$465,000