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
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%
2422 WOOD POINTE DRIVE HOLIDAY, FL Under contract-accepting backup offers. This Spectacular SOLAR-Powered, spacious 5-bedroom...	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%
2228 Society Dr HOLIDAY, FL Price Improvement! Discover peaceful living in this charming 2-bedroom, 1.5-bath home nest...	2 beds \| 1 baths \| 1,039 sq.ft.	$244,000	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%
2228 Parrot Fish Dr HOLIDAY, FL Worry Free living in this Gulfwinds Villa where Exterior Maintenance is included in your H...	3 beds \| 2 baths \| 1,876 sq.ft.	$329,900	Airbnb cash on cash: 4.59% Traditional cash on cash: 4.71% Airbnb Rental Income: $3151 Traditional Rental Income: $2475 Airbnb ROI: 4.59% Traditional ROI: 4.71%
2726 Featherstone Dr HOLIDAY, FL One or more photo(s) has been virtually staged. Welcome home to this beautifully maintaine...	2 beds \| 2 baths \| 1,232 sq.ft.	$189,900	Airbnb cash on cash: 3.24% Traditional cash on cash: 5.17% Airbnb Rental Income: $2176 Traditional Rental Income: $1981 Airbnb ROI: 3.24% Traditional ROI: 5.17%
2150 Parrot Fish Dr HOLIDAY, FL PRICE IMPROVEMENT â BELOW MARKET VALUE - NOW OFFERED AT $334,900 (REDUCED FROM $350,000!...	3 beds \| 2 baths \| 1,740 sq.ft.	$334,900	Airbnb cash on cash: 3.5% Traditional cash on cash: 3.03% Airbnb Rental Income: $3151 Traditional Rental Income: $2289 Airbnb ROI: 3.5% Traditional ROI: 3.03%
3627 Ortona Dr HOLIDAY, FL Experience the best of Florida living in a fully renovated, light-filled waterfront retrea...	3 beds \| 2 baths \| 1,542 sq.ft.	$318,500	Airbnb cash on cash: 5.66% Traditional cash on cash: 6.04% Airbnb Rental Income: $3151 Traditional Rental Income: $2551 Airbnb ROI: 5.66% Traditional ROI: 6.04%
1028 Orca Ct HOLIDAY, FL Welcome to 1028 Orca Court, a meticulously maintained 3-bedroom, 2-bathroom villa nestled ...	3 beds \| 2 baths \| 1,740 sq.ft.	$339,900	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.53% Airbnb Rental Income: $3151 Traditional Rental Income: $2430 Airbnb ROI: 3.55% Traditional ROI: 3.53%
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 Cir #C HOLIDAY, FL JUST REDUCED! This two-bedroom, BATH & HALF condominium located at the back of a cul-de-sa...	2 beds \| 1 baths \| 825 sq.ft.	$143,500	Airbnb cash on cash: 7.42% Traditional cash on cash: 9.07% Airbnb Rental Income: $2176 Traditional Rental Income: $1851 Airbnb ROI: 7.42% Traditional ROI: 9.07%
1225 Greenlea Dr 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.	$333,000	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 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.	$206,000	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.	$253,900	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%
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%
3048 Holiday Lake Dr 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%
3638 Bigelow Dr HOLIDAY, FL CORNER LOT-PRIVACY FENCE-Priced RIGHT!!--No HOA to worry about in this open floor plan hom...	2 beds \| 1 baths \| 1,096 sq.ft.	$219,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 7.1% Airbnb Rental Income: $2176 Traditional Rental Income: $1896 Airbnb ROI: 5.79% Traditional ROI: 7.1%
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 Dr HOLIDAY, FL LOW MONTHLY PAYMENT OPPORTUNITY â one of the only homes in Beacon Square located in Floo...	3 beds \| 2 baths \| 1,534 sq.ft.	$279,800	Airbnb cash on cash: 6.52% Traditional cash on cash: 5.79% Airbnb Rental Income: $3151 Traditional Rental Income: $2244 Airbnb ROI: 6.52% Traditional ROI: 5.79%
3706 CHESWICK DRIVE HOLIDAY, FL Welcome to this beautifully maintained property, boasting a fresh interior paint job in a ...	2 beds \| 2 baths \| 1,036 sq.ft.	$198,000	Airbnb cash on cash: 6.67% Traditional cash on cash: 7.95% Airbnb Rental Income: $2176 Traditional Rental Income: $1864 Airbnb ROI: 6.67% Traditional ROI: 7.95%
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%
3954 Sailmaker Ln HOLIDAY, FL Welcome to the wonderful Holiday Lake Villas, a desirable and conveniently located 55+ com...	2 beds \| 2 baths \| 1,318 sq.ft.	$125,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 7.75% Airbnb Rental Income: $2176 Traditional Rental Income: $2096 Airbnb ROI: 4.12% Traditional ROI: 7.75%
2107 Harrison Dr 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%
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.	$279,900	Airbnb cash on cash: 7.24% Traditional cash on cash: 8.07% Airbnb Rental Income: $3151 Traditional Rental Income: $2657 Airbnb ROI: 7.24% Traditional ROI: 8.07%
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%
2016 GULFVIEW DRIVE HOLIDAY, FL Under contract-accepting backup offers. Spectacular waterfront living in the highly sought...	3 beds \| 2 baths \| 2,723 sq.ft.	$1,299,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 1.18% Airbnb Rental Income: $3151 Traditional Rental Income: $3158 Airbnb ROI: 0.58% Traditional ROI: 1.18%
3625 Windham Dr HOLIDAY, FL Welcome to 3625 Windham Drive in the heart of Holiday, FL - a charming and move-in-ready 3...	3 beds \| 1 baths \| 1,200 sq.ft.	$219,999	Airbnb cash on cash: 8.97% Traditional cash on cash: 6.57% Airbnb Rental Income: $3151 Traditional Rental Income: $1925 Airbnb ROI: 8.97% Traditional ROI: 6.57%
3238 Mela Ct HOLIDAY, FL 5 Bedroom, 3.5 Bath, 2 Story home located in the Gated Community of Vista Lakes, perfectl...	5 beds \| 3 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%
3844 Redwood Dr HOLIDAY, FL Welcome to smart Florida living at 3844 Redwood Drive in Holiday, where affordability, dur...	2 beds \| 2 baths \| 948 sq.ft.	$219,000	Airbnb cash on cash: 5.37% Traditional cash on cash: 6.09% Airbnb Rental Income: $2176 Traditional Rental Income: $1776 Airbnb ROI: 5.37% Traditional ROI: 6.09%
4102 Darlington Rd HOLIDAY, FL Great starter home or retirement home. This comfortable home has 2 bedrooms, 2 bathrooms, ...	2 beds \| 1 baths \| 988 sq.ft.	$185,000	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%
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%
3138 Deergrass Ct 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.	$450,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 3.16% Airbnb Rental Income: $4419 Traditional Rental Income: $2564 Airbnb ROI: 5.36% Traditional ROI: 3.16%
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.	$299,000	Airbnb cash on cash: 3.87% Traditional cash on cash: 6.86% Airbnb Rental Income: $2176 Traditional Rental Income: $2467 Airbnb ROI: 3.87% Traditional ROI: 6.86%
2907 Featherstone Dr HOLIDAY, FL Move-in ready and full of potential! This 2-bedroom, 2-bath home features an open floorpla...	2 beds \| 2 baths \| 1,159 sq.ft.	$199,900	Airbnb cash on cash: 3.12% Traditional cash on cash: 4.7% Airbnb Rental Income: $2176 Traditional Rental Income: $1925 Airbnb ROI: 3.12% Traditional ROI: 4.7%
2909 Featherstone Dr 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.	$249,900	Airbnb cash on cash: 2.51% Traditional cash on cash: 4.16% Airbnb Rental Income: $2176 Traditional Rental Income: $2013 Airbnb ROI: 2.51% Traditional ROI: 4.16%
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.	$639,900	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%
1242 VIKING DRIVE HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. MO...	2 beds \| 2 baths \| 1,136 sq.ft.	$250,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 5.8% Airbnb Rental Income: $2176 Traditional Rental Income: $1935 Airbnb ROI: 4.49% Traditional ROI: 5.8%
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.	$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%
3711 Elmwood Dr HOLIDAY, FL Welcome home! This charming and affordable starter home is a perfect opportunity for buyer...	2 beds \| 2 baths \| 1,096 sq.ft.	$230,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 5.2% Airbnb Rental Income: $2176 Traditional Rental Income: $1865 Airbnb ROI: 4.18% Traditional ROI: 5.2%

Real Estate investment in Holiday, FL

There are 351 properties for sale in the city of Holiday . The median list price in Holiday is $239,900 and the average price per square foot is $182. In March 2026, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $2,004.

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

There are 351 investment properties available for sale in Holiday.

In 2026, 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

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%

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%

2228 Society Dr

HOLIDAY, FL

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

$244,000

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%

2228 Parrot Fish Dr

HOLIDAY, FL

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

$329,900

Airbnb cash on cash: 4.59%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $3151

Traditional Rental Income: $2475

Airbnb ROI: 4.59%

Traditional ROI: 4.71%

2726 Featherstone Dr

HOLIDAY, FL

2 beds | 2 baths | 1,232 sq.ft.

$189,900

Airbnb cash on cash: 3.24%

Traditional cash on cash: 5.17%

Airbnb Rental Income: $2176

Traditional Rental Income: $1981

Airbnb ROI: 3.24%

Traditional ROI: 5.17%

2150 Parrot Fish Dr

HOLIDAY, FL

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

$334,900

Airbnb cash on cash: 3.5%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $3151

Traditional Rental Income: $2289

Airbnb ROI: 3.5%

Traditional ROI: 3.03%

3627 Ortona Dr

HOLIDAY, FL

3 beds | 2 baths | 1,542 sq.ft.

$318,500

Airbnb cash on cash: 5.66%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $3151

Traditional Rental Income: $2551

Airbnb ROI: 5.66%

Traditional ROI: 6.04%

1028 Orca Ct

HOLIDAY, FL

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

$339,900

Airbnb cash on cash: 3.55%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $3151

Traditional Rental Income: $2430

Airbnb ROI: 3.55%