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.

Investment Property for Sale in Holiday, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2422 WOOD POINTE DRIVE HOLIDAY, FL This Spectacular SOLAR-Powered, spacious 5-bedroom plus office home offers stunning waterf...	5 beds \| 3 baths \| 3,002 sq.ft.	$499,900	Airbnb cash on cash: 8.15% Traditional cash on cash: 4.67% Airbnb Rental Income: $6270 Traditional Rental Income: $3410 Airbnb ROI: 8.15% Traditional ROI: 4.67%
3520 OVERLAND DRIVE HOLIDAY, FL Waterfront Living with Optional Civic Association Amenities! Welcome to this tastefully up...	2 beds \| 2 baths \| 1,068 sq.ft.	$279,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 6.6% Airbnb Rental Income: $2176 Traditional Rental Income: $2226 Airbnb ROI: 4.31% Traditional ROI: 6.6%
2228 SOCIETY DRIVE HOLIDAY, FL Price Improvement! Discover peaceful living in this charming 2-bedroom, 1.5-bath home nest...	2 beds \| 2 baths \| 1,039 sq.ft.	$249,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 5.71% Airbnb Rental Income: $2176 Traditional Rental Income: $1927 Airbnb ROI: 4.42% Traditional ROI: 5.71%
2150 PARROT FISH DRIVE HOLIDAY, FL Welcome to your Florida retreat in the beautiful Gulfwinds Community! Experience relaxed, ...	3 beds \| 2 baths \| 1,740 sq.ft.	$360,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 2.67% Airbnb Rental Income: $3151 Traditional Rental Income: $2289 Airbnb ROI: 3.11% Traditional ROI: 2.67%
2427 INDIAN KEY DRIVE HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. MO...	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%
1913 BLUE RIVER ROAD HOLIDAY, FL Under contract-accepting backup offers. Lakefront Pool Home in Gated Community â Not in ...	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.	$370,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 5.11% Airbnb Rental Income: $4419 Traditional Rental Income: $2798 Airbnb ROI: 7.12% Traditional ROI: 5.11%
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%
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%
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.	$354,500	Airbnb cash on cash: 2.95% Traditional cash on cash: 5.5% Airbnb Rental Income: $2176 Traditional Rental Income: $2474 Airbnb ROI: 2.95% Traditional ROI: 5.5%
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.	$210,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 7.22% Airbnb Rental Income: $2176 Traditional Rental Income: $1851 Airbnb ROI: 6.08% Traditional ROI: 7.22%
4940 PICTURE AVENUE HOLIDAY, FL Beautifully maintained 3-bedroom home offering comfort, updates, and coastal convenience! ...	3 beds \| 2 baths \| 1,276 sq.ft.	$259,999	Airbnb cash on cash: 7.71% Traditional cash on cash: 6.89% Airbnb Rental Income: $3151 Traditional Rental Income: $2235 Airbnb ROI: 7.71% Traditional ROI: 6.89%
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.	$219,900	Airbnb cash on cash: 8.77% Traditional cash on cash: 5.21% Airbnb Rental Income: $3151 Traditional Rental Income: $1696 Airbnb ROI: 8.77% Traditional ROI: 5.21%
5352 MOSAIC DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. Light, bright, and move-in ready in Forest...	2 beds \| 2 baths \| 1,113 sq.ft.	$199,000	Airbnb cash on cash: 6.58% Traditional cash on cash: 8.39% Airbnb Rental Income: $2176 Traditional Rental Income: $1966 Airbnb ROI: 6.58% Traditional ROI: 8.39%
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.	$249,900	Airbnb cash on cash: 7.41% Traditional cash on cash: 5.33% Airbnb Rental Income: $3151 Traditional Rental Income: $1945 Airbnb ROI: 7.41% Traditional ROI: 5.33%
2640 ALBION STREET HOLIDAY, FL One or more photo(s) has been virtually staged. Interest Rate Buydown Opportunity! Paradis...	3 beds \| 2 baths \| 1,517 sq.ft.	$287,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 7.46% Airbnb Rental Income: $3151 Traditional Rental Income: $2738 Airbnb ROI: 6.35% Traditional ROI: 7.46%
3707 PINEHURST DRIVE HOLIDAY, FL One of the only homes in Beacon Square located in Flood Zone X with no flood insurance req...	3 beds \| 2 baths \| 1,534 sq.ft.	$285,000	Airbnb cash on cash: 6.39% Traditional cash on cash: 5.67% Airbnb Rental Income: $3151 Traditional Rental Income: $2244 Airbnb ROI: 6.39% Traditional ROI: 5.67%
3954 SAILMAKER LANE HOLIDAY, FL Welcome to the wonderful Holiday Lake Villas, a desirable and conveniently located 55+ com...	2 beds \| 2 baths \| 1,318 sq.ft.	$149,900	Airbnb cash on cash: 8.04% Traditional cash on cash: 11.32% Airbnb Rental Income: $2176 Traditional Rental Income: $2096 Airbnb ROI: 8.04% Traditional ROI: 11.32%
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.	$219,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 4.86% Airbnb Rental Income: $2176 Traditional Rental Income: $1657 Airbnb ROI: 4.7% Traditional ROI: 4.86%
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%
2118 PARROT FISH DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. Welcome to the carefree lifestyle in Gulfw...	3 beds \| 2 baths \| 1,740 sq.ft.	$369,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.9% Airbnb Rental Income: $3151 Traditional Rental Income: $2423 Airbnb ROI: 3.95% Traditional ROI: 3.9%
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%
1037 NORMANDY BOULEVARD HOLIDAY, FL Get ready to fall in love this fully renovated home is one of Holiday's most desirable com...	2 beds \| 1 baths \| 840 sq.ft.	$219,900	Airbnb cash on cash: 5.41% Traditional cash on cash: 5.63% Airbnb Rental Income: $2176 Traditional Rental Income: $1669 Airbnb ROI: 5.41% Traditional ROI: 5.63%
2735 PLANTAIN DRIVE HOLIDAY, FL NEW PRICE! Welcome to Key Vista Villas, a premier gated 55+ community where low-maintenanc...	2 beds \| 2 baths \| 1,555 sq.ft.	$319,900	Airbnb cash on cash: 2.52% Traditional cash on cash: 4.86% Airbnb Rental Income: $2176 Traditional Rental Income: $2327 Airbnb ROI: 2.52% Traditional ROI: 4.86%
4731 AEGEAN AVENUE 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.	$242,000	Airbnb cash on cash: 8.75% Traditional cash on cash: 5.91% Airbnb Rental Income: $3151 Traditional Rental Income: $1788 Airbnb ROI: 8.75% Traditional ROI: 5.91%
1313 CHANCELLOR DRIVE HOLIDAY, FL NO HOA! Perfect home for retirement, downsize, first home. Bring all your outdoor toys to...	2 beds \| 2 baths \| 953 sq.ft.	$199,900	Airbnb cash on cash: 6.2% Traditional cash on cash: 7.28% Airbnb Rental Income: $2176 Traditional Rental Income: $1829 Airbnb ROI: 6.2% Traditional ROI: 7.28%
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.	$200,000	Airbnb cash on cash: 5.74% Traditional cash on cash: 7.03% Airbnb Rental Income: $2176 Traditional Rental Income: $1870 Airbnb ROI: 5.74% Traditional ROI: 7.03%
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%
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 Assumable 2.375 VA Loan available to qualified buyers. Welcome to your dream home! This 4-...	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 Under contract-accepting backup offers. Welcome to this stunning 3 bedroom, 3 bathroom hom...	3 beds \| 3 baths \| 1,998 sq.ft.	$474,999	Airbnb cash on cash: 3.07% Traditional cash on cash: 4.4% Airbnb Rental Income: $3151 Traditional Rental Income: $3027 Airbnb ROI: 3.07% Traditional ROI: 4.4%
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%
1408 JENNINGS DRIVE 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.	$339,900	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%
3242 BEACON SQUARE DRIVE HOLIDAY, FL Welcome to this upscale, beautifully remodeled two-bedroom home in the Beacon Square area ...	2 beds \| 1 baths \| 848 sq.ft.	$225,000	Airbnb cash on cash: 5.85% Traditional cash on cash: 6.14% Airbnb Rental Income: $2176 Traditional Rental Income: $1686 Airbnb ROI: 5.85% Traditional ROI: 6.14%
3410 BROOKFIELD DRIVE HOLIDAY, FL PRICE IMPROVEMENT!!! Welcome to your very own slice of FLORIDA PARADISE!! This beauti...	2 beds \| 2 baths \| 1,283 sq.ft.	$234,999	Airbnb cash on cash: 4.83% Traditional cash on cash: 7.63% Airbnb Rental Income: $2176 Traditional Rental Income: $2247 Airbnb ROI: 4.83% Traditional ROI: 7.63%
5038 COLONNADE AVENUE HOLIDAY, FL Under contract-accepting backup offers. Nestled on a quiet cul-de-sac, this charming 2-bed...	2 beds \| 2 baths \| 960 sq.ft.	$240,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 6.18% Airbnb Rental Income: $2176 Traditional Rental Income: $1905 Airbnb ROI: 4.94% Traditional ROI: 6.18%

Real Estate investment in Holiday, FL

There are 213 properties for sale in the city of Holiday . The median list price in Holiday is $239,950 and the average price per square foot is $180. In December 2025, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $2,017.

Holiday, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 213 investment properties available for sale in Holiday.

In 2025, the best neighborhood to buy investment property is HOLIDAY.

The ROI for Short-Term is higher than the Long-Term in Holiday with average rental income of $2,176.

Your search for investment property begins and ends here

Investment Property for Sale in Holiday, FL

2422 WOOD POINTE DRIVE

HOLIDAY, FL

5 beds | 3 baths | 3,002 sq.ft.

$499,900

Airbnb cash on cash: 8.15%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $6270

Traditional Rental Income: $3410

Airbnb ROI: 8.15%

Traditional ROI: 4.67%

3520 OVERLAND DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,068 sq.ft.

$279,000

Airbnb cash on cash: 4.31%

Traditional cash on cash: 6.6%

Airbnb Rental Income: $2176

Traditional Rental Income: $2226

Airbnb ROI: 4.31%

Traditional ROI: 6.6%

2228 SOCIETY DRIVE

HOLIDAY, FL

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

$249,000

Airbnb cash on cash: 4.42%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $2176

Traditional Rental Income: $1927

Airbnb ROI: 4.42%

Traditional ROI: 5.71%

2150 PARROT FISH DRIVE

HOLIDAY, FL

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

$360,000

Airbnb cash on cash: 3.11%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $3151

Traditional Rental Income: $2289

Airbnb ROI: 3.11%

Traditional ROI: 2.67%

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%

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.

$370,000

Airbnb cash on cash: 7.12%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $4419

Traditional Rental Income: $2798

Airbnb ROI: 7.12%

Traditional ROI: 5.11%

2807 BANNER STONE COURT

HOLIDAY, FL

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%