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
1415 RUSSEL LANE HOLIDAY, FL Under contract-accepting backup offers. PRICED TO SELL! Welcome to this charm in the desir...	2 beds \| 1 baths \| 1,356 sq.ft.	$195,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 6.28% Airbnb Rental Income: $2176 Traditional Rental Income: $1660 Airbnb ROI: 6.09% Traditional ROI: 6.28%
5321 MOSAIC DRIVE HOLIDAY, FL Under contract-accepting backup offers. SHINING STAR PROPERTY! SELLER IS OFFERING A $5000....	2 beds \| 2 baths \| 1,141 sq.ft.	$250,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 6.55% Airbnb Rental Income: $2176 Traditional Rental Income: $2033 Airbnb ROI: 4.82% Traditional ROI: 6.55%
2329 BARRACUDA COURT HOLIDAY, FL Under contract-accepting backup offers. Imagine the opportunity to wake and enjoy your mor...	3 beds \| 2 baths \| 1,740 sq.ft.	$344,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 3.24% Airbnb Rental Income: $3151 Traditional Rental Income: $2429 Airbnb ROI: 3.27% Traditional ROI: 3.24%
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.	$270,000	Airbnb cash on cash: 7% Traditional cash on cash: 7.5% Airbnb Rental Income: $3151 Traditional Rental Income: $2565 Airbnb ROI: 7% Traditional ROI: 7.5%
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.	$469,900	Airbnb cash on cash: 3.01% Traditional cash on cash: 5.09% Airbnb Rental Income: $3151 Traditional Rental Income: $3351 Airbnb ROI: 3.01% Traditional ROI: 5.09%
1028 Orca Court HOLIDAY, FL Investment opportunity with great tenants in place. Welcome to this beautifully updated 3-...	3 beds \| 2 baths \| 1,740 sq.ft.	$350,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 3.59% Airbnb Rental Income: $3151 Traditional Rental Income: $2430 Airbnb ROI: 3.61% Traditional ROI: 3.59%
2511 INDIAN KEY DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. PRICE IMPROVEMENT \| NEW ROOF INSTALLED \| M...	4 beds \| 2 baths \| 2,027 sq.ft.	$410,000	Airbnb cash on cash: 6.34% Traditional cash on cash: 4.53% Airbnb Rental Income: $4419 Traditional Rental Income: $2798 Airbnb ROI: 6.34% Traditional ROI: 4.53%
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%
3640 CHESWICK DRIVE HOLIDAY, FL Under contract-accepting backup offers. Come and see this well maintained 2/2 in the ideal...	2 beds \| 2 baths \| 1,024 sq.ft.	$210,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 7.73% Airbnb Rental Income: $2176 Traditional Rental Income: $1918 Airbnb ROI: 6.26% Traditional ROI: 7.73%
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.	$143,900	Airbnb cash on cash: 8.02% Traditional cash on cash: 9.67% Airbnb Rental Income: $2176 Traditional Rental Income: $1851 Airbnb ROI: 8.02% Traditional ROI: 9.67%
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%
2115 ERIN DR HOLIDAY, FL One or more photo(s) has been virtually staged. ** MOTIVATED SELLER! * BRING ALL OFFERS **...	3 beds \| 2 baths \| 1,116 sq.ft.	$259,900	Airbnb cash on cash: 7.5% Traditional cash on cash: 5.81% Airbnb Rental Income: $3151 Traditional Rental Income: $2024 Airbnb ROI: 7.5% Traditional ROI: 5.81%
1172 CHELSEA LANE HOLIDAY, FL Under contract-accepting backup offers. Step into this 2 bed, 2 FULL bath, home and see it...	2 beds \| 2 baths \| 1,733 sq.ft.	$255,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 7.66% Airbnb Rental Income: $2176 Traditional Rental Income: $2332 Airbnb ROI: 4.72% Traditional ROI: 7.66%
3426 COLDWELL DRIVE HOLIDAY, FL Discover your Florida retreat in the heart of Holiday Lake Estates! This beautifully refre...	4 beds \| 2 baths \| 1,116 sq.ft.	$300,000	Airbnb cash on cash: 9.91% Traditional cash on cash: 4.99% Airbnb Rental Income: $4419 Traditional Rental Income: $2102 Airbnb ROI: 9.91% Traditional ROI: 4.99%
1225 GREENLEA DRIVE HOLIDAY, FL This lovely POOL HOME has NO HOA, NO CDD and is in a NO FLOOD ZONE. It's in the charming ...	2 beds \| 2 baths \| 1,525 sq.ft.	$377,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 5.12% Airbnb Rental Income: $2176 Traditional Rental Income: $2474 Airbnb ROI: 2.72% Traditional ROI: 5.12%
3447 PALOMA DR HOLIDAY, FL Welcome to this meticulously maintained home offering 3 spacious bedrooms, 2 full bathroom...	3 beds \| 2 baths \| 1,628 sq.ft.	$310,000	Airbnb cash on cash: 6.67% Traditional cash on cash: 6.2% Airbnb Rental Income: $3151 Traditional Rental Income: $2302 Airbnb ROI: 6.67% Traditional ROI: 6.2%
3621 BEACON SQUARE DRIVE HOLIDAY, FL 2.87% ASSUMABLE MORTGAGE OPPORTUNITY!!! This charming one-story block home in Holiday, FL ...	2 beds \| 2 baths \| 1,016 sq.ft.	$180,000	Airbnb cash on cash: 7.39% Traditional cash on cash: 9.12% Airbnb Rental Income: $2176 Traditional Rental Income: $1921 Airbnb ROI: 7.39% Traditional ROI: 9.12%
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%
2153 Parrot Fish Drive HOLIDAY, FL Live the Florida lifestyle in this spacious, maintenance-free villa located just minutes f...	3 beds \| 2 baths \| 1,876 sq.ft.	$325,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 5.65% Airbnb Rental Income: $3151 Traditional Rental Income: $2388 Airbnb ROI: 5.81% Traditional ROI: 5.65%
5128 BILLINGS DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome to your beautifully maintained and move-in...	2 beds \| 2 baths \| 1,442 sq.ft.	$249,900	Airbnb cash on cash: 4.36% Traditional cash on cash: 6.8% Airbnb Rental Income: $2176 Traditional Rental Income: $2199 Airbnb ROI: 4.36% Traditional ROI: 6.8%
1338 PERSIMMON DRIVE HOLIDAY, FL Under contract-accepting backup offers. Charming Corner Lot Home with Room to Grow! Welco...	2 beds \| 1 baths \| 872 sq.ft.	$235,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 5.07% Airbnb Rental Income: $2176 Traditional Rental Income: $1648 Airbnb ROI: 4.97% Traditional ROI: 5.07%
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.	$299,000	Airbnb cash on cash: 6.06% Traditional cash on cash: 7.13% Airbnb Rental Income: $3151 Traditional Rental Income: $2738 Airbnb ROI: 6.06% Traditional ROI: 7.13%
4375 TAHITIAN GARDENS CIRCLE #B HOLIDAY, FL Under contract-accepting backup offers. Welcome to this charming 2-bedroom, 1-bathroom con...	2 beds \| 1 baths \| 825 sq.ft.	$119,900	Airbnb cash on cash: 9.47% Traditional cash on cash: 8.26% Airbnb Rental Income: $2176 Traditional Rental Income: $1485 Airbnb ROI: 9.47% Traditional ROI: 8.26%
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.	$1,550,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 0.44% Airbnb Rental Income: $3151 Traditional Rental Income: $3278 Airbnb ROI: -0.14% Traditional ROI: 0.44%
3205 MOOG ROAD HOLIDAY, FL Welcome to this spacious single family home located in the sought after Beacon Square neig...	2 beds \| 2 baths \| 1,698 sq.ft.	$235,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 7.4% Airbnb Rental Income: $2176 Traditional Rental Income: $2290 Airbnb ROI: 4.4% Traditional ROI: 7.4%
3427 CANTRELL STREET HOLIDAY, FL SELLER HAPPY TO CONTRIBUTE TO BUYERâS CLOSING COSTS! This charming 3-bedroom, 1-bath blo...	3 beds \| 1 baths \| 1,176 sq.ft.	$224,500	Airbnb cash on cash: 9.54% Traditional cash on cash: 7.19% Airbnb Rental Income: $3151 Traditional Rental Income: $1937 Airbnb ROI: 9.54% Traditional ROI: 7.19%
3140 BAHIA AVENUE HOLIDAY, FL Waterfront canal home in Flood Zone X â no flood insurance required! A brand-new roof wi...	2 beds \| 1 baths \| 1,134 sq.ft.	$240,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 5.49% Airbnb Rental Income: $2176 Traditional Rental Income: $1673 Airbnb ROI: 5.28% Traditional ROI: 5.49%
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.	$265,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 7.12% Airbnb Rental Income: $2176 Traditional Rental Income: $2312 Airbnb ROI: 4.37% Traditional ROI: 7.12%
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.	$159,900	Airbnb cash on cash: 7.49% Traditional cash on cash: 10.58% Airbnb Rental Income: $2176 Traditional Rental Income: $2096 Airbnb ROI: 7.49% Traditional ROI: 10.58%
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%
3526 OVERLAND DRIVE HOLIDAY, FL Stunning home overlooking a lake! Gorgeous 3 bedroom, 2 bathroom, 1 car garage. Totally re...	3 beds \| 2 baths \| 1,766 sq.ft.	$269,900	Airbnb cash on cash: 6.96% Traditional cash on cash: 9.97% Airbnb Rental Income: $3151 Traditional Rental Income: $3205 Airbnb ROI: 6.96% Traditional ROI: 9.97%
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.	$285,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 7.87% Airbnb Rental Income: $2176 Traditional Rental Income: $2576 Airbnb ROI: 4.33% Traditional ROI: 7.87%
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.	$299,000	Airbnb cash on cash: 6.72% Traditional cash on cash: 7.5% Airbnb Rental Income: $3151 Traditional Rental Income: $2657 Airbnb ROI: 6.72% Traditional ROI: 7.5%
2801 Banner Stone Court HOLIDAY, FL Come see this spacious 3 bed 2 bath plus extra room home tucked away in the beautiful comm...	3 beds \| 2 baths \| 1,953 sq.ft.	$406,125	Airbnb cash on cash: 3.85% Traditional cash on cash: 4.42% Airbnb Rental Income: $3151 Traditional Rental Income: $2652 Airbnb ROI: 3.85% Traditional ROI: 4.42%
1023 ORCA COURT HOLIDAY, FL GORGEOUS! GORGEOUS! GORGEOUS! Welcome to the Highly Sought-After Community of Gulfwinds! ...	3 beds \| 2 baths \| 1,740 sq.ft.	$379,500	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%
2452 BIG PINE DRIVE HOLIDAY, FL Under contract-accepting backup offers. Stunning, move-in-ready, single-family home locate...	3 beds \| 2 baths \| 1,750 sq.ft.	$394,900	Airbnb cash on cash: 3.68% Traditional cash on cash: 3.51% Airbnb Rental Income: $3151 Traditional Rental Income: $2375 Airbnb ROI: 3.68% Traditional ROI: 3.51%
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%
1615 COCKLESHELL DRIVE HOLIDAY, FL Welcome to this beautifully maintained 2-bedroom, 1-bathroom home nestled in the heart of ...	2 beds \| 1 baths \| 880 sq.ft.	$240,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 4.8% Airbnb Rental Income: $2176 Traditional Rental Income: $1685 Airbnb ROI: 4.53% Traditional ROI: 4.8%

Real Estate investment in Holiday, FL

There are 209 properties for sale in the city of Holiday . The median list price in Holiday is $249,990 and the average price per square foot is $182. In September 2025, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $1,989.

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

There are 209 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

1415 RUSSEL LANE

HOLIDAY, FL

2 beds | 1 baths | 1,356 sq.ft.

$195,000

Airbnb cash on cash: 6.09%

Traditional cash on cash: 6.28%

Airbnb Rental Income: $2176

Traditional Rental Income: $1660

Airbnb ROI: 6.09%

Traditional ROI: 6.28%

5321 MOSAIC DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,141 sq.ft.

$250,000

Airbnb cash on cash: 4.82%

Traditional cash on cash: 6.55%

Airbnb Rental Income: $2176

Traditional Rental Income: $2033

Airbnb ROI: 4.82%

Traditional ROI: 6.55%

2329 BARRACUDA COURT

HOLIDAY, FL

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

$344,000

Airbnb cash on cash: 3.27%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $3151

Traditional Rental Income: $2429

Airbnb ROI: 3.27%

Traditional ROI: 3.24%

3516 NORLAND COURT

HOLIDAY, FL

3 beds | 2 baths | 1,334 sq.ft.

$270,000

Airbnb cash on cash: 7%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $3151

Traditional Rental Income: $2565

Airbnb ROI: 7%

Traditional ROI: 7.5%

1913 BLUE RIVER ROAD

HOLIDAY, FL

3 beds | 3 baths | 2,202 sq.ft.

$469,900

Airbnb cash on cash: 3.01%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $3151

Traditional Rental Income: $3351

Airbnb ROI: 3.01%

Traditional ROI: 5.09%

1028 Orca Court

HOLIDAY, FL

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

$350,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $3151

Traditional Rental Income: $2430

Airbnb ROI: 3.61%

Traditional ROI: 3.59%

2511 INDIAN KEY DRIVE

HOLIDAY, FL

4 beds | 2 baths | 2,027 sq.ft.

$410,000

Airbnb cash on cash: 6.34%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $4419

Traditional Rental Income: $2798

Airbnb ROI: 6.34%

Traditional ROI: 4.53%

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%