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.

Woodlawn Investment Property for Sale in Holiday, FL

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

Showing 371 Woodlawn Investment Property 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
5309 Boardwalk St HOLIDAY, FL One or more photo(s) has been virtually staged. FINALLY!!!! This spacious 3 bedroom, 2.5 b...	3 beds \| 2 baths \| 1,848 sq.ft.	$449,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 5.05% Airbnb Rental Income: $3151 Traditional Rental Income: $3033 Airbnb ROI: 3.63% Traditional ROI: 5.05%
5828 Mariposa Dr 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.	$203,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 7.25% Airbnb Rental Income: $2176 Traditional Rental Income: $1851 Airbnb ROI: 6.11% Traditional ROI: 7.25%
2128 Shannon Dr 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.	$249,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 5.46% Airbnb Rental Income: $2176 Traditional Rental Income: $1773 Airbnb ROI: 4.85% Traditional ROI: 5.46%
1548 Landau St HOLIDAY, FL Discover the charm and potential of 1548 Landau, this clean and spacious 2-bedroom, 1-bath...	2 beds \| 1 baths \| 864 sq.ft.	$210,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 5.8% Airbnb Rental Income: $2176 Traditional Rental Income: $1715 Airbnb ROI: 5.36% Traditional ROI: 5.8%
1313 Chancellor Dr HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Di...	2 beds \| 1 baths \| 953 sq.ft.	$180,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 7.7% Airbnb Rental Income: $2176 Traditional Rental Income: $1829 Airbnb ROI: 6.56% Traditional ROI: 7.7%
5657 Oceanic Rd HOLIDAY, FL Welcome to 5657 Oceanic Rd in Holiday, Florida â a rare opportunity in a quiet, well-est...	4 beds \| 3 baths \| 3,553 sq.ft.	$629,900	Airbnb cash on cash: 4.66% Traditional cash on cash: 7.76% Airbnb Rental Income: $4419 Traditional Rental Income: $5346 Airbnb ROI: 4.66% Traditional ROI: 7.76%
1408 Jennings Dr HOLIDAY, FL Beautifully RENOVATED 3-bedroom, 2-bath home located in Flood Zone X (no flood insurance r...	3 beds \| 2 baths \| 1,102 sq.ft.	$319,900	Airbnb cash on cash: 5.33% Traditional cash on cash: 4.37% Airbnb Rental Income: $3151 Traditional Rental Income: $2131 Airbnb ROI: 5.33% Traditional ROI: 4.37%
5605 Oceanic Rd HOLIDAY, FL Welcome to this beautifully updated, move in ready dream home! Open floor plan, many updat...	3 beds \| 1 baths \| 1,511 sq.ft.	$279,000	Airbnb cash on cash: 6.63% Traditional cash on cash: 5.9% Airbnb Rental Income: $3151 Traditional Rental Income: $2243 Airbnb ROI: 6.63% Traditional ROI: 5.9%
4837 Vision Ave HOLIDAY, FL Ready to make the move! This 2 bedroom home turn key home with a bonus room could be the p...	2 beds \| 1 baths \| 1,076 sq.ft.	$245,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 5.73% Airbnb Rental Income: $2176 Traditional Rental Income: $1672 Airbnb ROI: 5.52% Traditional ROI: 5.73%
4626 Abdella Ln HOLIDAY, FL Charming 2-bedroom, 1-bath, 1-car garage home in Holiday, Florida! Roof 2015, New HVAC sys...	2 beds \| 1 baths \| 816 sq.ft.	$260,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 5.57% Airbnb Rental Income: $2176 Traditional Rental Income: $1831 Airbnb ROI: 4.72% Traditional ROI: 5.57%
5404 Front Dr HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Mu...	3 beds \| 2 baths \| 1,240 sq.ft.	$295,000	Airbnb cash on cash: 6.44% Traditional cash on cash: 5.41% Airbnb Rental Income: $3151 Traditional Rental Income: $2149 Airbnb ROI: 6.44% Traditional ROI: 5.41%
2152 Arcadia Rd HOLIDAY, FL Welcome to this beautifully updated 3-bedroom, 2-bathroom home located in Holiday, FL, jus...	3 beds \| 2 baths \| 1,088 sq.ft.	$319,900	Airbnb cash on cash: 6.07% Traditional cash on cash: 5.39% Airbnb Rental Income: $3151 Traditional Rental Income: $2223 Airbnb ROI: 6.07% Traditional ROI: 5.39%
1652 Marengo Dr HOLIDAY, FL Welcome to this charming, move-in-ready block home tucked away on a quiet street. This tho...	2 beds \| 1 baths \| 816 sq.ft.	$234,900	Airbnb cash on cash: 4.43% Traditional cash on cash: 3.47% Airbnb Rental Income: $2176 Traditional Rental Income: $1406 Airbnb ROI: 4.43% Traditional ROI: 3.47%
5507 Riddle Rd HOLIDAY, FL Just reduced! This spacious 2,400 sq ft duplex is situated on an oversized corner lot in H...	6 beds \| 2 baths \| 2,406 sq.ft.	$378,000	Airbnb cash on cash: 7.27% Traditional cash on cash: 1.89% Airbnb Rental Income: $4419 Traditional Rental Income: $1587 Airbnb ROI: 7.27% Traditional ROI: 1.89%
1414 Grand Blvd HOLIDAY, FL NEW ROOF JUST PUT ON AUGUST 2025,NEW FANS, AND THE INSIDE PAINTED! NEWER ELECTRIC, WINDOWS...	2 beds \| 2 baths \| 1,778 sq.ft.	$349,999	Airbnb cash on cash: 3.02% Traditional cash on cash: 7.81% Airbnb Rental Income: $2176 Traditional Rental Income: $3197 Airbnb ROI: 3.02% Traditional ROI: 7.81%
5131 Forum Blvd HOLIDAY, FL Major price reduction. Not a short sale. Welcome to this beautifully maintained 2-bedroo...	2 beds \| 2 baths \| 1,541 sq.ft.	$219,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 5.54% Airbnb Rental Income: $2176 Traditional Rental Income: $2268 Airbnb ROI: 2.86% Traditional ROI: 5.54%
4928 Lake Ridge Ln HOLIDAY, FL Short Sale. Welcome to this well maintained home, features 3-bedrooms, 1 bath and 1 attach...	3 beds \| 1 baths \| 1,036 sq.ft.	$249,900	Airbnb cash on cash: 6% Traditional cash on cash: 3.58% Airbnb Rental Income: $3151 Traditional Rental Income: $1865 Airbnb ROI: 6% Traditional ROI: 3.58%
5116 Plantation Dr HOLIDAY, FL Investor Opportunity! This beautifully maintained, income-producing 3-bedroom, 2-bathroom ...	3 beds \| 2 baths \| 1,446 sq.ft.	$322,500	Airbnb cash on cash: 5.38% Traditional cash on cash: 4.94% Airbnb Rental Income: $3151 Traditional Rental Income: $2304 Airbnb ROI: 5.38% Traditional ROI: 4.94%
4823 Aegean Ave HOLIDAY, FL 2025 Rebirth Property with Florida Classic Architecture: An upgraded modern gem home with ...	2 beds \| 1 baths \| 990 sq.ft.	$224,990	Airbnb cash on cash: 4.61% Traditional cash on cash: 4.75% Airbnb Rental Income: $2176 Traditional Rental Income: $1658 Airbnb ROI: 4.61% Traditional ROI: 4.75%
3124 Finch Dr HOLIDAY, FL Charming and affordable 2-bedroom, 1.5-bath home located in the Colonial Hills II subdivis...	2 beds \| 1 baths \| 1,128 sq.ft.	$220,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 8.5% Airbnb Rental Income: $2176 Traditional Rental Income: $2126 Airbnb ROI: 6.09% Traditional ROI: 8.5%
1200 Grand Blvd HOLIDAY, FL Move In Ready! Enjoy the ease of this move-in ready 3 bedroom, 2 bathroom, 1 car garage h...	3 beds \| 2 baths \| 1,320 sq.ft.	$284,000	Airbnb cash on cash: 7.06% Traditional cash on cash: 5.92% Airbnb Rental Income: $3151 Traditional Rental Income: $2115 Airbnb ROI: 7.06% Traditional ROI: 5.92%
2627 Charlan Ct HOLIDAY, FL Welcome to effortless living in Holidayâperfectly positioned between the historic charm ...	2 beds \| 2 baths \| 1,541 sq.ft.	$280,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 5.36% Airbnb Rental Income: $2176 Traditional Rental Income: $2392 Airbnb ROI: 2.45% Traditional ROI: 5.36%
3131 BIXLER COURT HOLIDAY, FL Presenting your new home in the desirable Tanglewood Mobile Village Condominium, a well-ma...	2 beds \| 2 baths \| 1,180 sq.ft.	$143,000	Airbnb cash on cash: 7.96% Traditional cash on cash: 10.06% Airbnb Rental Income: $2176 Traditional Rental Income: $1912 Airbnb ROI: 7.96% Traditional ROI: 10.06%
4936 Mile Stretch Dr HOLIDAY, FL One or more photo(s) has been virtually staged. Freshly painted interior and centrally loc...	3 beds \| 2 baths \| 1,244 sq.ft.	$265,000	Airbnb cash on cash: 7.68% Traditional cash on cash: 6.92% Airbnb Rental Income: $3151 Traditional Rental Income: $2247 Airbnb ROI: 7.68% Traditional ROI: 6.92%
2826 Raven Dr HOLIDAY, FL Enjoy Florida Living at itâs best, in this 2 bedroom 2 bath 1 car garage home in sunny H...	2 beds \| 2 baths \| 1,310 sq.ft.	$210,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 8.38% Airbnb Rental Income: $2176 Traditional Rental Income: $2106 Airbnb ROI: 6.07% Traditional ROI: 8.38%
5199 Forum Blvd HOLIDAY, FL Welcome to your bright, modern, and practically new corner unit townhome. Step inside to...	2 beds \| 2 baths \| 1,541 sq.ft.	$268,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 5.13% Airbnb Rental Income: $2176 Traditional Rental Income: $2314 Airbnb ROI: 2.47% Traditional ROI: 5.13%
5904 Springrun Ct HOLIDAY, FL Reduced Price. Owner Motivated. A Private, Park-Like Oasis with Unmatched Amenities Awaits...	3 beds \| 2 baths \| 2,284 sq.ft.	$465,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 5.21% Airbnb Rental Income: $3151 Traditional Rental Income: $3095 Airbnb ROI: 3.73% Traditional ROI: 5.21%
5245 Bluejay Dr HOLIDAY, FL This beautifully updated corner-lot home offers exceptional value and versatility, with am...	2 beds \| 2 baths \| 1,310 sq.ft.	$299,900	Airbnb cash on cash: 3.8% Traditional cash on cash: 5.43% Airbnb Rental Income: $2176 Traditional Rental Income: $2102 Airbnb ROI: 3.8% Traditional ROI: 5.43%
1705 Cosmos Dr HOLIDAY, FL Well-maintained 2-bedroom, 2-bathroom home located on a desirable corner lot in Holiday. O...	2 beds \| 2 baths \| 1,259 sq.ft.	$249,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 6.76% Airbnb Rental Income: $2176 Traditional Rental Income: $2113 Airbnb ROI: 4.84% Traditional ROI: 6.76%
1037 Tamarac Dr HOLIDAY, FL Stunning Updated Home in Holiday â Move-In Ready! Welcome to 1037 Tamarac Drive, a be...	2 beds \| 2 baths \| 1,557 sq.ft.	$249,900	Airbnb cash on cash: 4.18% Traditional cash on cash: 6.72% Airbnb Rental Income: $2176 Traditional Rental Income: $2224 Airbnb ROI: 4.18% Traditional ROI: 6.72%
3420 Chickadee Dr HOLIDAY, FL 3 BEDROOM, 2 BATHROOM (SECOND BATH IS IN THE GARAGE), 1 CAR GARAGE POOL HOME. COMPLETELY R...	3 beds \| 1 baths \| 1,344 sq.ft.	$309,900	Airbnb cash on cash: 5.75% Traditional cash on cash: 5.53% Airbnb Rental Income: $3151 Traditional Rental Income: $2370 Airbnb ROI: 5.75% Traditional ROI: 5.53%
1321 Honor Dr HOLIDAY, FL Welcome to 1321 Honor Dr in Holiday, FLâa 2-bedroom, 1-bath single-family home offering ...	2 beds \| 1 baths \| 816 sq.ft.	$179,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 6.79% Airbnb Rental Income: $2176 Traditional Rental Income: $1644 Airbnb ROI: 6.68% Traditional ROI: 6.79%
4706 Burney Dr HOLIDAY, FL This cozy, WATERFRONT home is nestled in Holiday, surrounded by Tarpon Springs, New Port R...	2 beds \| 2 baths \| 1,167 sq.ft.	$185,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 9.01% Airbnb Rental Income: $2176 Traditional Rental Income: $2128 Airbnb ROI: 6.3% Traditional ROI: 9.01%
5412 Golden Nugget Dr HOLIDAY, FL Beautiful 2-bedroom, 1.5-bathroom home in the heart of Holiday, featuring new windows, a l...	2 beds \| 1 baths \| 1,108 sq.ft.	$225,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 6.82% Airbnb Rental Income: $2176 Traditional Rental Income: $1966 Airbnb ROI: 5.28% Traditional ROI: 6.82%
1833 Rising Sun Dr HOLIDAY, FL Welcome to the 55+ community of Sunrise Square Villas! This beautiful and move-in ready vi...	2 beds \| 2 baths \| 975 sq.ft.	$154,900	Airbnb cash on cash: 7.98% Traditional cash on cash: 8.74% Airbnb Rental Income: $2176 Traditional Rental Income: $1739 Airbnb ROI: 7.98% Traditional ROI: 8.74%
1053 Grand Blvd HOLIDAY, FL Discover your waterfront haven at 1053 Grand Blvd in Holiday, FL! This beautifully updated...	3 beds \| 2 baths \| 1,778 sq.ft.	$450,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 4.99% Airbnb Rental Income: $3151 Traditional Rental Income: $2887 Airbnb ROI: 3.92% Traditional ROI: 4.99%
4731 Aegean Ave HOLIDAY, FL One or more photo(s) has been virtually staged. PRICE DROPWelcome to this charming Hol...	3 beds \| 1 baths \| 1,104 sq.ft.	$241,499	Airbnb cash on cash: 8.77% Traditional cash on cash: 5.92% Airbnb Rental Income: $3151 Traditional Rental Income: $1788 Airbnb ROI: 8.77% Traditional ROI: 5.92%
4817 CALAIS DRIVE HOLIDAY, FL Under contract-accepting backup offers. https://listings.textured.media/sites/pggownl/unbr...	2 beds \| 2 baths \| 1,088 sq.ft.	$208,000	Airbnb cash on cash: 6.5% Traditional cash on cash: 8.01% Airbnb Rental Income: $2176 Traditional Rental Income: $1922 Airbnb ROI: 6.5% Traditional ROI: 8.01%
1925 Patriot Ln HOLIDAY, FL Brand new mobile home!!! It's large, well lit with brand new windows for lots of natural ...	2 beds \| 2 baths \| 747 sq.ft.	$149,000	Airbnb cash on cash: 9.3% Traditional cash on cash: 9.51% Airbnb Rental Income: $2176 Traditional Rental Income: $1655 Airbnb ROI: 9.3% Traditional ROI: 9.51%
3125 Birkdale Dr HOLIDAY, FL Stunning lakefront views at an attractive price! Welcome to 3125 Birkdale Drive, a perfect...	2 beds \| 2 baths \| 1,048 sq.ft.	$135,000	Airbnb cash on cash: 8.73% Traditional cash on cash: 9.66% Airbnb Rental Income: $2176 Traditional Rental Income: $1754 Airbnb ROI: 8.73% Traditional ROI: 9.66%

Your search for investment property begins and ends here

Woodlawn Investment Property for Sale in Holiday, FL

5309 Boardwalk St

HOLIDAY, FL

3 beds | 2 baths | 1,848 sq.ft.

$449,000

Airbnb cash on cash: 3.63%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $3151

Traditional Rental Income: $3033

Airbnb ROI: 3.63%

Traditional ROI: 5.05%

5828 Mariposa Dr

HOLIDAY, FL

2 beds | 2 baths | 973 sq.ft.

$203,000

Airbnb cash on cash: 6.11%

Traditional cash on cash: 7.25%

Airbnb Rental Income: $2176

Traditional Rental Income: $1851

Airbnb ROI: 6.11%

Traditional ROI: 7.25%

2128 Shannon Dr

HOLIDAY, FL

2 beds | 1 baths | 1,200 sq.ft.

$249,900

Airbnb cash on cash: 4.85%

Traditional cash on cash: 5.46%

Airbnb Rental Income: $2176

Traditional Rental Income: $1773

Airbnb ROI: 4.85%

Traditional ROI: 5.46%

1548 Landau St

HOLIDAY, FL

2 beds | 1 baths | 864 sq.ft.

$210,000

Airbnb cash on cash: 5.36%

Traditional cash on cash: 5.8%

Airbnb Rental Income: $2176

Traditional Rental Income: $1715

Airbnb ROI: 5.36%

Traditional ROI: 5.8%

1313 Chancellor Dr

HOLIDAY, FL

2 beds | 1 baths | 953 sq.ft.

$180,000

Airbnb cash on cash: 6.56%

Traditional cash on cash: 7.7%

Airbnb Rental Income: $2176

Traditional Rental Income: $1829

Airbnb ROI: 6.56%

Traditional ROI: 7.7%

5657 Oceanic Rd

HOLIDAY, FL

4 beds | 3 baths | 3,553 sq.ft.

$629,900

Airbnb cash on cash: 4.66%

Traditional cash on cash: 7.76%

Airbnb Rental Income: $4419

Traditional Rental Income: $5346

Airbnb ROI: 4.66%

Traditional ROI: 7.76%

1408 Jennings Dr

HOLIDAY, FL

3 beds | 2 baths | 1,102 sq.ft.

$319,900

Airbnb cash on cash: 5.33%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $3151

Traditional Rental Income: $2131

Airbnb ROI: 5.33%

Traditional ROI: 4.37%

5605 Oceanic Rd

HOLIDAY, FL

3 beds | 1 baths | 1,511 sq.ft.

$279,000

Airbnb cash on cash: 6.63%

Traditional cash on cash: 5.9%

Airbnb Rental Income: $3151

Traditional Rental Income: $2243

Airbnb ROI: 6.63%