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 187 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 Dr HOLIDAY, FL Welcome home to this charming 2-bedroom, 1.5-bath house offering comfort, convenience, and...	2 beds \| 1 baths \| 1,097 sq.ft.	$205,000	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 Dr HOLIDAY, FL Wake Up on the Water, Every Single Day, coffee in hand, mist rising off Lake Conley, and a...	2 beds \| 1 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 Dr 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%
2228 Parrot Fish Dr HOLIDAY, FL Auction Property. This Villa can be a "dream home" again. With a bit of thoughtful plannin...	3 beds \| 2 baths \| 1,876 sq.ft.	$269,900	Airbnb cash on cash: 2.35% Traditional cash on cash: 6.25% Airbnb Rental Income: $2121 Traditional Rental Income: $2570 Airbnb ROI: 2.35% Traditional ROI: 6.25%
1056 Tamarac Dr HOLIDAY, FL Virtually Staged. Spacious, move-in ready home with fully fenced front and back yards-perf...	2 beds \| 1 baths \| 1,272 sq.ft.	$234,916	Airbnb cash on cash: 2.42% Traditional cash on cash: 6.97% Airbnb Rental Income: $1410 Traditional Rental Income: $2017 Airbnb ROI: 2.42% Traditional ROI: 6.97%
3400 Bainbridge Dr HOLIDAY, FL Virtually Staged. Imagine 3400 Bainbridge Dr, recently refreshed with fresh exterior paint...	2 beds \| 2 baths \| 1,051 sq.ft.	$200,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 6.89% Airbnb Rental Income: $1410 Traditional Rental Income: $1798 Airbnb ROI: 2.85% Traditional ROI: 6.89%
1031 Conoley Ln 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: 6.3% Airbnb Rental Income: $2121 Traditional Rental Income: $1763 Airbnb ROI: 5.45% Traditional ROI: 6.3%
3225 Hearthstone Ct HOLIDAY, FL Beautifully Updated 3-Bedroom Home on an Oversized Cul-de-Sac Lot Welcome home! This beaut...	3 beds \| 2 baths \| 2,151 sq.ft.	$459,500	Airbnb cash on cash: 1.65% Traditional cash on cash: 4.75% Airbnb Rental Income: $2121 Traditional Rental Income: $2910 Airbnb ROI: 1.65% Traditional ROI: 4.75%
2128 Shannon Dr HOLIDAY, FL Under contract-accepting backup offers. Quintessential Florida Living in Holiday! Welcome ...	2 beds \| 1 baths \| 1,200 sq.ft.	$216,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 6.63% Airbnb Rental Income: $1410 Traditional Rental Income: $1756 Airbnb ROI: 2.86% Traditional ROI: 6.63%
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 Dr HOLIDAY, FL Beautiful 3-bedroom, 2-bath home situated on a fully fenced 1/4-acre corner lot with a pea...	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 Dr 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%
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%
3221 Roxbury Dr HOLIDAY, FL Summer may almost be over, but it's still not too late to own a pool home and enjoy the Fl...	2 beds \| 1 baths \| 1,136 sq.ft.	$252,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 6.14% Airbnb Rental Income: $1410 Traditional Rental Income: $1911 Airbnb ROI: 2.25% Traditional ROI: 6.14%
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 Dr HOLIDAY, FL SELLER IS MOTIVATED! Eligible buyers may be able to purchase this home with NO MONEY DOWN ...	3 beds \| 1 baths \| 1,104 sq.ft.	$213,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 6.77% Airbnb Rental Income: $2247 Traditional Rental Income: $1842 Airbnb ROI: 5.98% Traditional ROI: 6.77%
3555 Sheryl Hill Dr HOLIDAY, FL Buy this foreclosure deal the right way. Visit us at Auction.com, then login or create a f...	3 beds \| 2 baths \| 1,240 sq.ft.	$234,900	Airbnb cash on cash: 5.85% Traditional cash on cash: 6.99% Airbnb Rental Income: $2247 Traditional Rental Income: $1936 Airbnb ROI: 5.85% Traditional ROI: 6.99%
3228 Rock Valley Dr 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 Ln 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.	$295,000	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 Rd 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.	$265,000	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 St 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 Dr HOLIDAY, FL Welcome home to this move-in-ready 3-bedroom, 2-bathroom home in the established community...	3 beds \| 1 baths \| 1,076 sq.ft.	$239,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 7.72% Airbnb Rental Income: $2121 Traditional Rental Income: $2087 Airbnb ROI: 5.47% Traditional ROI: 7.72%
4841 Zodiac Ave HOLIDAY, FL Buy this foreclosure deal the right way. Visit us at Auction.com, then login or create a f...	3 beds \| 2 baths \| 1,191 sq.ft.	$270,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 5.98% Airbnb Rental Income: $2247 Traditional Rental Income: $1916 Airbnb ROI: 5.07% Traditional ROI: 5.98%
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 Ct HOLIDAY, FL "Luxury Living in an Exclusive Gated Community" Experience coastal elegance in this custom...	3 beds \| 3 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%
3313 Briar Cliff Dr HOLIDAY, FL Welcome to 3313 Briar Cliff Dr! This 3/2/1 BLOCK home sits high & dry in a non-flood zone....	3 beds \| 2 baths \| 1,417 sq.ft.	$239,900	Airbnb cash on cash: 4.16% Traditional cash on cash: 7.32% Airbnb Rental Income: $2121 Traditional Rental Income: $2294 Airbnb ROI: 4.16% Traditional ROI: 7.32%
3920 Beacon Square Dr 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 Dr 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: 4.08% Traditional cash on cash: 8.73% Airbnb Rental Income: $2247 Traditional Rental Income: $2779 Airbnb ROI: 4.08% Traditional ROI: 8.73%
3334 Coldwell Dr HOLIDAY, FL Move in ready 3 bedroom 1.5 bathroom home located in Holiday Fl. This home has and update ...	3 beds \| 1 baths \| 1,185 sq.ft.	$239,000	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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Holiday, FL

1023 Viking Dr

HOLIDAY, FL

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

$205,000

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 Dr

HOLIDAY, FL

2 beds | 1 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 Dr

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%

2228 Parrot Fish Dr

HOLIDAY, FL

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

$269,900

Airbnb cash on cash: 2.35%

Traditional cash on cash: 6.25%

Airbnb Rental Income: $2121

Traditional Rental Income: $2570

Airbnb ROI: 2.35%

Traditional ROI: 6.25%

1056 Tamarac Dr

HOLIDAY, FL

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

$234,916

Airbnb cash on cash: 2.42%

Traditional cash on cash: 6.97%

Airbnb Rental Income: $1410

Traditional Rental Income: $2017

Airbnb ROI: 2.42%

Traditional ROI: 6.97%

3400 Bainbridge Dr

HOLIDAY, FL

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

$200,000

Airbnb cash on cash: 2.85%

Traditional cash on cash: 6.89%

Airbnb Rental Income: $1410

Traditional Rental Income: $1798

Airbnb ROI: 2.85%

Traditional ROI: 6.89%

1031 Conoley Ln

HOLIDAY, FL

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

$230,000

Airbnb cash on cash: 5.45%

Traditional cash on cash: 6.3%

Airbnb Rental Income: $2121

Traditional Rental Income: $1763

Airbnb ROI: 5.45%

Traditional ROI: 6.3%

3225 Hearthstone Ct

HOLIDAY, FL

3 beds | 2 baths | 2,151 sq.ft.

$459,500

Airbnb cash on cash: 1.65%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $2121

Traditional Rental Income: $2910

Airbnb ROI: 1.65%