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 186 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
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%
2257 SAND BAY DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome to your entertainerâs dream homeâa stu...	3 beds \| 2 baths \| 1,630 sq.ft.	$459,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 4.63% Airbnb Rental Income: $3151 Traditional Rental Income: $2874 Airbnb ROI: 3.61% Traditional ROI: 4.63%
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%
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%
3426 PINON DR HOLIDAY, FL One or more photo(s) has been virtually staged. Move In Ready in Holiday Lake Estates. Fr...	3 beds \| 1 baths \| 884 sq.ft.	$225,000	Airbnb cash on cash: 8.56% Traditional cash on cash: 5.08% Airbnb Rental Income: $3151 Traditional Rental Income: $1696 Airbnb ROI: 8.56% Traditional ROI: 5.08%
3048 HOLIDAY LAKE DRIVE HOLIDAY, FL NO FLOOD ZONE. Lots of Updates. NEW LVP FLOORING throughout 2024. Remodeled Kitchen with N...	3 beds \| 2 baths \| 1,504 sq.ft.	$262,000	Airbnb cash on cash: 7.03% Traditional cash on cash: 5.04% Airbnb Rental Income: $3151 Traditional Rental Income: $1945 Airbnb ROI: 7.03% Traditional ROI: 5.04%
2640 ALBION STREET HOLIDAY, FL One or more photo(s) has been virtually staged. Paradise found at this waterfront home in ...	3 beds \| 2 baths \| 1,517 sq.ft.	$289,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 7.4% Airbnb Rental Income: $3151 Traditional Rental Income: $2738 Airbnb ROI: 6.3% Traditional ROI: 7.4%
3114 BLUFF BOULEVARD HOLIDAY, FL Luxury Waterfront Living in Baileyâs Bluff! THIS HOME HAS NEVER EXPERIENCED FLOODING FR...	3 beds \| 3 baths \| 3,234 sq.ft.	$1,450,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 0.54% Airbnb Rental Income: $3151 Traditional Rental Income: $3278 Airbnb ROI: -0.08% Traditional ROI: 0.54%
3140 BAHIA AVENUE HOLIDAY, FL Brand-new roof will be installed prior to closing! This updated La Villa Gardens home feat...	2 beds \| 1 baths \| 1,134 sq.ft.	$230,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 5.76% Airbnb Rental Income: $2176 Traditional Rental Income: $1673 Airbnb ROI: 5.54% Traditional ROI: 5.76%
5722 MARIPOSA DRIVE HOLIDAY, FL Welcome to your charming POOL home in Holiday, FL! This well maintained two-bedroom, two-b...	2 beds \| 2 baths \| 1,338 sq.ft.	$255,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 7.43% Airbnb Rental Income: $2176 Traditional Rental Income: $2312 Airbnb ROI: 4.58% Traditional ROI: 7.43%
2107 HARRISON DRIVE HOLIDAY, FL Priced to Sell! Here is your chance to stop renting and own a property at an affordable pr...	2 beds \| 2 baths \| 1,151 sq.ft.	$229,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 4.61% Airbnb Rental Income: $2176 Traditional Rental Income: $1657 Airbnb ROI: 4.46% Traditional ROI: 4.61%
1629 DARTMOUTH DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated 2-bedr...	2 beds \| 2 baths \| 1,461 sq.ft.	$275,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 8.19% Airbnb Rental Income: $2176 Traditional Rental Income: $2576 Airbnb ROI: 4.52% Traditional ROI: 8.19%
3518 MOOG Road HOLIDAY, FL Enjoy Florida living in this updated 3-bedroom, 2-bath home featuring a bright open layout...	3 beds \| 2 baths \| 1,514 sq.ft.	$289,900	Airbnb cash on cash: 6.86% Traditional cash on cash: 4.96% Airbnb Rental Income: $3151 Traditional Rental Income: $1917 Airbnb ROI: 6.86% Traditional ROI: 4.96%
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.	$289,900	Airbnb cash on cash: 6.96% Traditional cash on cash: 7.76% Airbnb Rental Income: $3151 Traditional Rental Income: $2657 Airbnb ROI: 6.96% Traditional ROI: 7.76%
5021 PHOENIX AVENUE HOLIDAY, FL Under contract-accepting backup offers. Location truly is everything with this well-mainta...	2 beds \| 2 baths \| 1,295 sq.ft.	$250,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 7.2% Airbnb Rental Income: $2176 Traditional Rental Income: $2179 Airbnb ROI: 4.85% Traditional ROI: 7.2%
2735 PLANTAIN DRIVE HOLIDAY, FL Welcome to Key Vista Villas, a premier gated 55+ community where low-maintenance living me...	2 beds \| 2 baths \| 1,555 sq.ft.	$329,900	Airbnb cash on cash: 2.42% Traditional cash on cash: 4.68% Airbnb Rental Income: $2176 Traditional Rental Income: $2327 Airbnb ROI: 2.42% Traditional ROI: 4.68%
4731 AEGEAN AVENUE HOLIDAY, FL One or more photo(s) has been virtually staged. Welcome to this charming Holiday home feat...	3 beds \| 1 baths \| 1,104 sq.ft.	$242,500	Airbnb cash on cash: 8.73% Traditional cash on cash: 5.9% Airbnb Rental Income: $3151 Traditional Rental Income: $1788 Airbnb ROI: 8.73% Traditional ROI: 5.9%
1313 CHANCELLOR DRIVE HOLIDAY, FL Bring all your outdoor toys to 1313 Chancellor Drive! Plenty of RV and boat/other parking ...	2 beds \| 2 baths \| 953 sq.ft.	$209,900	Airbnb cash on cash: 5.86% Traditional cash on cash: 6.89% Airbnb Rental Income: $2176 Traditional Rental Income: $1829 Airbnb ROI: 5.86% Traditional ROI: 6.89%
1023 ORCA COURT HOLIDAY, FL Under contract-accepting backup offers. GORGEOUS! GORGEOUS! GORGEOUS! Welcome to the Highl...	3 beds \| 2 baths \| 1,740 sq.ft.	$379,300	Airbnb cash on cash: 3.15% Traditional cash on cash: 2.93% Airbnb Rental Income: $3151 Traditional Rental Income: $2360 Airbnb ROI: 3.15% Traditional ROI: 2.93%
2016 GULFVIEW DRIVE HOLIDAY, FL Spectacular waterfront living in the highly sought-after Baileyâs Bluff community! REMOD...	3 beds \| 2 baths \| 2,723 sq.ft.	$1,459,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 0.94% Airbnb Rental Income: $3151 Traditional Rental Income: $3158 Airbnb ROI: 0.41% Traditional ROI: 0.94%
3238 MELA COURT HOLIDAY, FL 5 Bedroom, 3.5 Bath, 2 Story home located in the Gated Community of Vista Lakes, perfectl...	5 beds \| 4 baths \| 3,198 sq.ft.	$575,000	Airbnb cash on cash: 6.77% Traditional cash on cash: 5.32% Airbnb Rental Income: $6270 Traditional Rental Income: $4260 Airbnb ROI: 6.77% Traditional ROI: 5.32%
4102 DARLINGTON ROAD HOLIDAY, FL Great starter home or retirement home. This comfortable home has 2 bedrooms, 2 bathrooms, ...	2 beds \| 2 baths \| 988 sq.ft.	$215,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 6.48% Airbnb Rental Income: $2176 Traditional Rental Income: $1870 Airbnb ROI: 5.28% Traditional ROI: 6.48%
3138 DEERGRASS COURT HOLIDAY, FL Short Sale. Welcome to 3138 Deergrass Ct, nestled in the charming Glenwood of Gulf Trace n...	4 beds \| 3 baths \| 2,525 sq.ft.	$480,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 2.9% Airbnb Rental Income: $4419 Traditional Rental Income: $2564 Airbnb ROI: 4.97% Traditional ROI: 2.9%
3217 ROCK VALLEY DRIVE HOLIDAY, FL FULLY FURNISHED! Perfect for snowbirds or rental investment opportunity, rent as soon as y...	4 beds \| 2 baths \| 1,600 sq.ft.	$325,000	Airbnb cash on cash: 8.93% Traditional cash on cash: 6.1% Airbnb Rental Income: $4419 Traditional Rental Income: $2630 Airbnb ROI: 8.93% Traditional ROI: 6.1%
4706 DARLINGTON ROAD HOLIDAY, FL Well-kept home in Holiday with fast access to US19. Shopping and beaches close by. No floo...	2 beds \| 2 baths \| 816 sq.ft.	$199,900	Airbnb cash on cash: 6.07% Traditional cash on cash: 7.45% Airbnb Rental Income: $2176 Traditional Rental Income: $1886 Airbnb ROI: 6.07% Traditional ROI: 7.45%
2909 FEATHERSTONE DRIVE HOLIDAY, FL Turnkey 2-Bed, 2-Bath Home with Premium Amenities â Minutes from Top Destinations Own...	2 beds \| 2 baths \| 1,232 sq.ft.	$254,900	Airbnb cash on cash: 2.45% Traditional cash on cash: 4.06% Airbnb Rental Income: $2176 Traditional Rental Income: $2013 Airbnb ROI: 2.45% Traditional ROI: 4.06%
5657 OCEANIC ROAD HOLIDAY, FL Welcome to your dream home! This 4-bedroom, 3.5-bath home offers the perfect blend of comf...	4 beds \| 4 baths \| 3,553 sq.ft.	$649,900	Airbnb cash on cash: 4.58% Traditional cash on cash: 7.63% Airbnb Rental Income: $4419 Traditional Rental Income: $5346 Airbnb ROI: 4.58% Traditional ROI: 7.63%
2630 COLDSTONE LANE HOLIDAY, FL Welcome to this stunning 3 bedroom, 3 bathroom home with a versatile bonus room, 3-car gar...	3 beds \| 3 baths \| 1,998 sq.ft.	$479,999	Airbnb cash on cash: 3.03% Traditional cash on cash: 4.34% Airbnb Rental Income: $3151 Traditional Rental Income: $3027 Airbnb ROI: 3.03% Traditional ROI: 4.34%
3145 DOMINO DRIVE HOLIDAY, FL Short Sale. Well-maintained 2-bedroom, 2-bath home with a versatile bonus room, spacious 2...	2 beds \| 2 baths \| 1,440 sq.ft.	$335,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 4.48% Airbnb Rental Income: $2176 Traditional Rental Income: $2294 Airbnb ROI: 2.35% Traditional ROI: 4.48%

Your search for investment property begins and ends here

Single Family Homes for Sale in Holiday, FL

2228 SOCIETY DRIVE

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%

2257 SAND BAY DRIVE

HOLIDAY, FL

3 beds | 2 baths | 1,630 sq.ft.

$459,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $3151

Traditional Rental Income: $2874

Airbnb ROI: 3.61%

Traditional ROI: 4.63%

2427 INDIAN KEY DRIVE

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%

2932 WINDRIDGE DRIVE

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%

2329 BARRACUDA COURT

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%

3516 NORLAND COURT

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%

1913 BLUE RIVER ROAD

HOLIDAY, FL

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

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%