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 145 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
1023 VIKING Drive HOLIDAY, FL Welcome home to this charming 2-bedroom, 1.5-bath house offering comfort, convenience, and...	2 beds \| 2 baths \| 1,097 sq.ft.	$215,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 7.15% Airbnb Rental Income: $1410 Traditional Rental Income: $1845 Airbnb ROI: 2.94% Traditional ROI: 7.15%
2228 SOCIETY Drive HOLIDAY, FL WATERFRONT LIVING on beautiful Lake Conley with access to Lake Nash, this 2-bedroom home o...	2 beds \| 2 baths \| 1,039 sq.ft.	$240,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 5.92% Airbnb Rental Income: $1410 Traditional Rental Income: $1917 Airbnb ROI: 1.82% Traditional ROI: 5.92%
3431 OVERLAND Drive HOLIDAY, FL MOVE-IN READY! Welcome home to this charming 3-bedroom, 2-bathroom home featuring a desira...	3 beds \| 2 baths \| 1,236 sq.ft.	$239,900	Airbnb cash on cash: 4.26% Traditional cash on cash: 6.48% Airbnb Rental Income: $2121 Traditional Rental Income: $2082 Airbnb ROI: 4.26% Traditional ROI: 6.48%
1056 TAMARAC Drive HOLIDAY, FL Virtually Staged. Spacious, move-in ready home with fully fenced front and back yards-perf...	2 beds \| 2 baths \| 1,272 sq.ft.	$239,916	Airbnb cash on cash: 2.42% Traditional cash on cash: 4.38% Airbnb Rental Income: $1410 Traditional Rental Income: $1430 Airbnb ROI: 2.42% Traditional ROI: 4.38%
3400 BAINBRIDGE Drive HOLIDAY, FL Virtually Staged. Imagine 3400 Bainbridge Dr, recently refreshed with fresh exterior paint...	2 beds \| 2 baths \| 1,051 sq.ft.	$212,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 5.06% Airbnb Rental Income: $1410 Traditional Rental Income: $1430 Airbnb ROI: 2.85% Traditional ROI: 5.06%
1031 CONOLEY Lane HOLIDAY, FL Welcome to 1031 Conoley Ln, a beautifully maintained and thoughtfully updated 3-bedroom, 1...	3 beds \| 1 baths \| 1,004 sq.ft.	$230,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 6.95% Airbnb Rental Income: $2121 Traditional Rental Income: $1906 Airbnb ROI: 5.45% Traditional ROI: 6.95%
3128 HARVARDSTON Loop HOLIDAY, FL Virtually Staged. Welcome to your beautifully updated Florida retreat in the heart of Holi...	3 beds \| 2 baths \| 1,048 sq.ft.	$279,900	Airbnb cash on cash: 4.24% Traditional cash on cash: 4.93% Airbnb Rental Income: $2121 Traditional Rental Income: $1763 Airbnb ROI: 4.24% Traditional ROI: 4.93%
3419 PALOMA Drive HOLIDAY, FL Welcome to this beautifully maintained home both inside and out with great landscaping bot...	2 beds \| 2 baths \| 1,070 sq.ft.	$253,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 5.94% Airbnb Rental Income: $1410 Traditional Rental Income: $1842 Airbnb ROI: 2.36% Traditional ROI: 5.94%
3011 SHADOW OAKS Drive HOLIDAY, FL Spacious 3-bedroom, 2-bath home situated on a fully fenced 1/4-acre corner lot with a peac...	3 beds \| 2 baths \| 1,480 sq.ft.	$319,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 6.41% Airbnb Rental Income: $2121 Traditional Rental Income: $2561 Airbnb ROI: 3.14% Traditional ROI: 6.41%
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.	$235,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 10.08% Airbnb Rental Income: $2121 Traditional Rental Income: $2726 Airbnb ROI: 4.91% Traditional ROI: 10.08%
1166 CHANCELLOR Drive HOLIDAY, FL Welcome to true waterfront living in this beautifully remodeled 4-bedroom, 3-bath home wit...	4 beds \| 3 baths \| 1,761 sq.ft.	$459,900	Airbnb cash on cash: -1% Traditional cash on cash: 5.07% Airbnb Rental Income: $956 Traditional Rental Income: $3221 Airbnb ROI: -1% Traditional ROI: 5.07%
2146 SOCIETY Drive HOLIDAY, FL Virtually Staged. OPPORTUNITY knocks!! Back on market due to buyers inability to perform. ...	2 beds \| 2 baths \| 1,371 sq.ft.	$259,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 8.11% Airbnb Rental Income: $1410 Traditional Rental Income: $2545 Airbnb ROI: 1.74% Traditional ROI: 8.11%
3238 MELA Court HOLIDAY, FL Under contract-accepting backup offers. Amazing Price Reduction in Gated Neighborhood of V...	5 beds \| 4 baths \| 3,198 sq.ft.	$499,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 5.48% Airbnb Rental Income: $2254 Traditional Rental Income: $3892 Airbnb ROI: 0.77% Traditional ROI: 5.48%
4327 BEACON SQUARE Drive HOLIDAY, FL This home can be purchased with NO MONEY DOWN Welcome home! This charming Holiday gem is t...	3 beds \| 1 baths \| 1,104 sq.ft.	$213,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 6.77% Airbnb Rental Income: $2121 Traditional Rental Income: $1842 Airbnb ROI: 5.46% Traditional ROI: 6.77%
2222 ARCADIA Road HOLIDAY, FL Virtually Staged. Welcome to this move-in ready 2-bedroom, 2-bath home with flexible livin...	2 beds \| 2 baths \| 1,088 sq.ft.	$247,500	Airbnb cash on cash: 2.17% Traditional cash on cash: 4.07% Airbnb Rental Income: $1410 Traditional Rental Income: $1430 Airbnb ROI: 2.17% Traditional ROI: 4.07%
5646 ANDREA Drive HOLIDAY, FL Your search ends here! This stunning three-bedroom, two-bathroom home boasts over 1500 squ...	3 beds \| 2 baths \| 1,522 sq.ft.	$250,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 8.28% Airbnb Rental Income: $2121 Traditional Rental Income: $2546 Airbnb ROI: 4.18% Traditional ROI: 8.28%
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.	$289,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 5.68% Airbnb Rental Income: $1410 Traditional Rental Income: $2073 Airbnb ROI: 1.69% Traditional ROI: 5.68%
1050 DEAL Lane HOLIDAY, FL Turn-Key 3 bedroom home with Dual Primary Suites-Ideal for Multi-Generational Living or In...	3 beds \| 3 baths \| 1,667 sq.ft.	$305,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 4.81% Airbnb Rental Income: $2121 Traditional Rental Income: $2206 Airbnb ROI: 2.63% Traditional ROI: 4.81%
3029 HUNTINGTON Road HOLIDAY, FL Virtually Staged. Welcome to 3029 Huntington Road, a well-maintained 3-bedroom, 2-bath hom...	3 beds \| 2 baths \| 1,486 sq.ft.	$272,500	Airbnb cash on cash: 3.4% Traditional cash on cash: 6.3% Airbnb Rental Income: $2121 Traditional Rental Income: $2324 Airbnb ROI: 3.4% Traditional ROI: 6.3%
3124 LECANTO Street HOLIDAY, FL Welcome home to this beautifully updated residence featuring modern finishes and a bright,...	2 beds \| 1 baths \| 1,104 sq.ft.	$205,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 6.06% Airbnb Rental Income: $1410 Traditional Rental Income: $1770 Airbnb ROI: 2.03% Traditional ROI: 6.06%
3849 LUMA Drive HOLIDAY, FL Welcome home to this move-in-ready 3-bedroom, 2-bathroom home in the established community...	3 beds \| 2 baths \| 1,076 sq.ft.	$239,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 6.92% Airbnb Rental Income: $2121 Traditional Rental Income: $1906 Airbnb ROI: 5.47% Traditional ROI: 6.92%
2030 GULFVIEW Drive HOLIDAY, FL "Gulf Access Waterfront Home in Historic Baileys Bluff Estates" A rare opportunity to own ...	2 beds \| 2 baths \| 2,280 sq.ft.	$799,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 1.44% Airbnb Rental Income: $1410 Traditional Rental Income: $2850 Airbnb ROI: -1.07% Traditional ROI: 1.44%
3020 SHEPPARDS CROOK Court HOLIDAY, FL "Luxury Living in an Exclusive Gated Community" Experience coastal elegance in this custom...	3 beds \| 4 baths \| 2,367 sq.ft.	$579,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.28% Airbnb Rental Income: $2121 Traditional Rental Income: $2269 Airbnb ROI: 0.01% Traditional ROI: 1.28%
3547 WILSON Drive HOLIDAY, FL -PROPERTY HIGHLIGHTS: Large corner lot with NO HOA. Fully fenced backyard with double-gate...	2 beds \| 1 baths \| 984 sq.ft.	$199,900	Airbnb cash on cash: 2.4% Traditional cash on cash: 5.95% Airbnb Rental Income: $1410 Traditional Rental Income: $1660 Airbnb ROI: 2.4% Traditional ROI: 5.95%
2332 CHANCERY Drive HOLIDAY, FL Beautifully updated throughout, this 3-bedroom, 2-bathroom home with a 1-car garage offers...	3 beds \| 2 baths \| 1,151 sq.ft.	$274,900	Airbnb cash on cash: 3.36% Traditional cash on cash: 4.01% Airbnb Rental Income: $2121 Traditional Rental Income: $1748 Airbnb ROI: 3.36% Traditional ROI: 4.01%
3920 BEACON SQUARE Drive HOLIDAY, FL NEW PRICE + A RARE 3.625% ASSUMABLE FHA MORTGAGE OPPORTUNITY! Qualified buyers could have ...	2 beds \| 2 baths \| 992 sq.ft.	$239,900	Airbnb cash on cash: 1.92% Traditional cash on cash: 6.39% Airbnb Rental Income: $1410 Traditional Rental Income: $1998 Airbnb ROI: 1.92% Traditional ROI: 6.39%
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: 3.63% Traditional cash on cash: 8.73% Airbnb Rental Income: $2121 Traditional Rental Income: $2779 Airbnb ROI: 3.63% 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: 3.14% Traditional cash on cash: 5.3% Airbnb Rental Income: $2121 Traditional Rental Income: $2075 Airbnb ROI: 3.14% Traditional ROI: 5.3%
3127 DOLE Street HOLIDAY, FL Welcome to this beautifully updated 2-bedroom, 2-bath, 2-car garage home offering 1,184 sq...	2 beds \| 2 baths \| 1,184 sq.ft.	$297,400	Airbnb cash on cash: 0.98% Traditional cash on cash: 4.66% Airbnb Rental Income: $1410 Traditional Rental Income: $2018 Airbnb ROI: 0.98% Traditional ROI: 4.66%
4130 CRESTFIELD Avenue HOLIDAY, FL Welcome to this 2-bedroom,1-bath home located in the heart of Holiday! This well-maintaine...	2 beds \| 1 baths \| 1,004 sq.ft.	$222,900	Airbnb cash on cash: 1.98% Traditional cash on cash: 5.54% Airbnb Rental Income: $1410 Traditional Rental Income: $1737 Airbnb ROI: 1.98% Traditional ROI: 5.54%
3818 MOOG Road HOLIDAY, FL Short Sale. Opportunity awaits with this well-located property full of potential! Convenie...	2 beds \| 1 baths \| 848 sq.ft.	$215,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 5.52% Airbnb Rental Income: $1410 Traditional Rental Income: $1662 Airbnb ROI: 2.21% Traditional ROI: 5.52%
2152 ARCADIA Road 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.	$273,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 5.94% Airbnb Rental Income: $2121 Traditional Rental Income: $1998 Airbnb ROI: 4.31% Traditional ROI: 5.94%
3852 SUNRAY Drive HOLIDAY, FL Virtually Staged. INVESTMENT OPPORTUNITY OR FIRST-TIME HOMEOWNER OPPORTUNITY IN A OPORTUNE...	2 beds \| 2 baths \| 1,088 sq.ft.	$239,900	Airbnb cash on cash: 1.73% Traditional cash on cash: 3.69% Airbnb Rental Income: $1410 Traditional Rental Income: $1430 Airbnb ROI: 1.73% Traditional ROI: 3.69%

Your search for investment property begins and ends here

Single Family Homes for Sale in Holiday, FL

1023 VIKING Drive

HOLIDAY, FL

2 beds | 2 baths | 1,097 sq.ft.

$215,000

Airbnb cash on cash: 2.94%

Traditional cash on cash: 7.15%

Airbnb Rental Income: $1410

Traditional Rental Income: $1845

Airbnb ROI: 2.94%

Traditional ROI: 7.15%

2228 SOCIETY Drive

HOLIDAY, FL

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

$240,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 5.92%

Airbnb Rental Income: $1410

Traditional Rental Income: $1917

Airbnb ROI: 1.82%

Traditional ROI: 5.92%

3431 OVERLAND Drive

HOLIDAY, FL

3 beds | 2 baths | 1,236 sq.ft.

$239,900

Airbnb cash on cash: 4.26%

Traditional cash on cash: 6.48%

Airbnb Rental Income: $2121

Traditional Rental Income: $2082

Airbnb ROI: 4.26%

Traditional ROI: 6.48%

1056 TAMARAC Drive

HOLIDAY, FL

2 beds | 2 baths | 1,272 sq.ft.

$239,916

Airbnb cash on cash: 2.42%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $1410

Traditional Rental Income: $1430

Airbnb ROI: 2.42%

Traditional ROI: 4.38%

3400 BAINBRIDGE Drive

HOLIDAY, FL

2 beds | 2 baths | 1,051 sq.ft.

$212,000

Airbnb cash on cash: 2.85%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $1410

Traditional Rental Income: $1430

Airbnb ROI: 2.85%

Traditional ROI: 5.06%

1031 CONOLEY Lane

HOLIDAY, FL

3 beds | 1 baths | 1,004 sq.ft.

$230,000

Airbnb cash on cash: 5.45%

Traditional cash on cash: 6.95%

Airbnb Rental Income: $2121

Traditional Rental Income: $1906

Airbnb ROI: 5.45%

Traditional ROI: 6.95%

3128 HARVARDSTON Loop

HOLIDAY, FL

3 beds | 2 baths | 1,048 sq.ft.

$279,900

Airbnb cash on cash: 4.24%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $2121

Traditional Rental Income: $1763

Airbnb ROI: 4.24%

Traditional ROI: 4.93%

3419 PALOMA Drive

HOLIDAY, FL

2 beds | 2 baths | 1,070 sq.ft.

$253,000

Airbnb cash on cash: 2.36%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $1410

Traditional Rental Income: $1842

Airbnb ROI: 2.36%