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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3520 OVERLAND DRIVE HOLIDAY, FL Welcome to your waterfront oasis! This cozy home features 2 bedrooms and 2 bathrooms, alon...	2 beds \| 2 baths \| 1,068 sq.ft.	$285,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 6.46% Airbnb Rental Income: $2176 Traditional Rental Income: $2226 Airbnb ROI: 4.22% Traditional ROI: 6.46%
3749 DARLINGTON RD HOLIDAY, FL Back on Market! PRICE REDUCED! SELLER MOTIVATED! Whether you're a First Time Homebuyer, Sn...	3 beds \| 2 baths \| 1,056 sq.ft.	$260,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 5.11% Airbnb Rental Income: $3151 Traditional Rental Income: $1914 Airbnb ROI: 7.24% Traditional ROI: 5.11%
1753 FONT LANE HOLIDAY, FL Investment property - TENANT in place until MARCH 2025. Step into the realm of savvy inve...	2 beds \| 2 baths \| 1,485 sq.ft.	$289,900	Airbnb cash on cash: 3.47% Traditional cash on cash: 6.24% Airbnb Rental Income: $2176 Traditional Rental Income: $2381 Airbnb ROI: 3.47% Traditional ROI: 6.24%
3423 UMBER ROAD HOLIDAY, FL Welcome to your personal oasis in Holiday, Florida! This charming 3-bedroom, 2-bathroom po...	3 beds \| 2 baths \| 1,368 sq.ft.	$307,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 6.23% Airbnb Rental Income: $3151 Traditional Rental Income: $2340 Airbnb ROI: 6.56% Traditional ROI: 6.23%
4105 MOOG ROAD HOLIDAY, FL This stunning 2 bedroom, 2 bath home is immaculate and all the big items are done, so you ...	2 beds \| 2 baths \| 1,218 sq.ft.	$235,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 6.37% Airbnb Rental Income: $2176 Traditional Rental Income: $2013 Airbnb ROI: 4.63% Traditional ROI: 6.37%
3627 ORTONA DRIVE HOLIDAY, FL Location, Location, Location! Hard to find, rare and one of the nicest water front lots w...	2 beds \| 2 baths \| 1,542 sq.ft.	$269,000	Airbnb cash on cash: 3.77% Traditional cash on cash: 7.42% Airbnb Rental Income: $2176 Traditional Rental Income: $2551 Airbnb ROI: 3.77% Traditional ROI: 7.42%
3830 DARLINGTON ROAD HOLIDAY, FL Under contract-accepting backup offers. Assumable VA Loan with 3.186% Interest Rate for Up...	2 beds \| 2 baths \| 1,368 sq.ft.	$235,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 5.95% Airbnb Rental Income: $2176 Traditional Rental Income: $2032 Airbnb ROI: 4.12% Traditional ROI: 5.95%
3506 HOOVER DRIVE HOLIDAY, FL Under contract-accepting backup offers. PRICE REDUCED! READY FOR IMMEDIATE OCCUPANCY AND C...	2 beds \| 2 baths \| 1,368 sq.ft.	$241,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 5.67% Airbnb Rental Income: $2176 Traditional Rental Income: $1793 Airbnb ROI: 4.93% Traditional ROI: 5.67%
5331 SKYLAND DRIVE HOLIDAY, FL Price Improvement! Welcome to 5331 Skyland Dr. in the desirable Colonial Hills neighborhoo...	3 beds \| 2 baths \| 1,272 sq.ft.	$260,000	Airbnb cash on cash: 7.14% Traditional cash on cash: 5.6% Airbnb Rental Income: $3151 Traditional Rental Income: $2061 Airbnb ROI: 7.14% Traditional ROI: 5.6%
2646 HAWK ROOST COURT HOLIDAY, FL Introducing a Stunning Coastal Retreat in Key Vista. Welcome to this beautifully maintaine...	3 beds \| 2 baths \| 1,510 sq.ft.	$399,900	Airbnb cash on cash: 3.57% Traditional cash on cash: 3.01% Airbnb Rental Income: $3151 Traditional Rental Income: $2227 Airbnb ROI: 3.57% Traditional ROI: 3.01%
2016 DARTMOUTH DRIVE HOLIDAY, FL Auction Property. AUCTION PROPERTY! *Auction will run October 19th-29th* This 2 bedroo...	2 beds \| 2 baths \| 986 sq.ft.	$155,000	Airbnb cash on cash: 7.73% Traditional cash on cash: 8.87% Airbnb Rental Income: $2176 Traditional Rental Income: $1793 Airbnb ROI: 7.73% Traditional ROI: 8.87%
4345 TAHITIAN GARDENS CIRCLE #C HOLIDAY, FL Discover this turnkey two-bedroom, one-and-a-half bath condo featuring title and laminate ...	2 beds \| 2 baths \| 825 sq.ft.	$153,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 8.34% Airbnb Rental Income: $2176 Traditional Rental Income: $1851 Airbnb ROI: 6.79% Traditional ROI: 8.34%
1172 CHELSEA LANE HOLIDAY, FL Step into this 2 bed, 2 FULL bath, home and see it has a little bit of everything for a ne...	2 beds \| 2 baths \| 1,733 sq.ft.	$300,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 6.38% Airbnb Rental Income: $2176 Traditional Rental Income: $2332 Airbnb ROI: 3.88% Traditional ROI: 6.38%
5245 RIDDLE ROAD HOLIDAY, FL Situated in the serene Forest Hills neighborhood, this delightful 2-bedroom, 1.5-bath wate...	2 beds \| 2 baths \| 1,420 sq.ft.	$245,000	Airbnb cash on cash: 4.9% Traditional cash on cash: 8.61% Airbnb Rental Income: $2176 Traditional Rental Income: $2484 Airbnb ROI: 4.9% Traditional ROI: 8.61%
3151 BAHIA AVENUE HOLIDAY, FL Single Home 3 Bedrooms / 2 Bathrooms/ 2 Car Garages and POOL, Locate Holiday Florida, Subd...	3 beds \| 2 baths \| 1,528 sq.ft.	$360,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 5.32% Airbnb Rental Income: $3151 Traditional Rental Income: $2555 Airbnb ROI: 4.97% Traditional ROI: 5.32%
3353 COLUMBUS DR HOLIDAY, FL Two bedroom, plus bonus room home in Beacon Square subdivision is move-in ready! The kitc...	2 beds \| 2 baths \| 1,068 sq.ft.	$245,000	Airbnb cash on cash: 5.4% Traditional cash on cash: 6.17% Airbnb Rental Income: $2176 Traditional Rental Income: $1802 Airbnb ROI: 5.4% Traditional ROI: 6.17%
1827 GRAND BOULEVARD HOLIDAY, FL Now Available in SIESTA TERRACE! Come see this charming Home consisting of 2 bedrooms, 1 b...	2 beds \| 1 baths \| 827 sq.ft.	$195,900	Airbnb cash on cash: 6.44% Traditional cash on cash: 7.23% Airbnb Rental Income: $2176 Traditional Rental Income: $1773 Airbnb ROI: 6.44% Traditional ROI: 7.23%
3248 PRIMROSE DRIVE HOLIDAY, FL Under contract-accepting backup offers. This adorable 2 bedroom 1 bath home is not located...	2 beds \| 1 baths \| 792 sq.ft.	$165,000	Airbnb cash on cash: 7.5% Traditional cash on cash: 7.66% Airbnb Rental Income: $2176 Traditional Rental Income: $1649 Airbnb ROI: 7.5% Traditional ROI: 7.66%
3315 ROCK ROYAL DRIVE HOLIDAY, FL No Hurricane DamageâStorm Tested! No Flood Insurance Required! Motivated seller! Th...	3 beds \| 1 baths \| 956 sq.ft.	$229,800	Airbnb cash on cash: 8.87% Traditional cash on cash: 5.6% Airbnb Rental Income: $3151 Traditional Rental Income: $1727 Airbnb ROI: 8.87% Traditional ROI: 5.6%
5128 BILLINGS DRIVE HOLIDAY, FL *PRICE REDUCED* Welcome to your dream home in the heart of sunny Florida, where elegan...	3 beds \| 2 baths \| 1,442 sq.ft.	$279,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 6.02% Airbnb Rental Income: $3151 Traditional Rental Income: $2199 Airbnb ROI: 6.92% Traditional ROI: 6.02%
3048 HOLIDAY LAKE DRIVE HOLIDAY, FL Step into this inviting 3 Bedroom, 1 Bathroom Home, One-Car Garage, and experience this pe...	3 beds \| 1 baths \| 1,359 sq.ft.	$299,500	Airbnb cash on cash: 6.05% Traditional cash on cash: 4.3% Airbnb Rental Income: $3151 Traditional Rental Income: $1945 Airbnb ROI: 6.05% Traditional ROI: 4.3%
5507 FOREST HILLS DRIVE HOLIDAY, FL Great opportunity for a handy person. House has been vacant for several years; used for st...	2 beds \| 2 baths \| 1,865 sq.ft.	$199,900	Airbnb cash on cash: 5.53% Traditional cash on cash: 8.21% Airbnb Rental Income: $2176 Traditional Rental Income: $2132 Airbnb ROI: 5.53% Traditional ROI: 8.21%
3737 BADEN DRIVE HOLIDAY, FL Experience Luxurious Waterfront Living in Florida! This beautiful 4-bedroom, 3-bathroom, 2...	4 beds \| 3 baths \| 2,001 sq.ft.	$389,900	Airbnb cash on cash: 7.58% Traditional cash on cash: 6.98% Airbnb Rental Income: $4419 Traditional Rental Income: $3273 Airbnb ROI: 7.58% Traditional ROI: 6.98%
3248 EISENHOWER DRIVE HOLIDAY, FL Charming Move-In Ready Home in Aloha Gardens! NO FLOOD INSURANCE REQUIRED!!!! Prepare t...	3 beds \| 2 baths \| 1,368 sq.ft.	$299,000	Airbnb cash on cash: 6.38% Traditional cash on cash: 5.28% Airbnb Rental Income: $3151 Traditional Rental Income: $2128 Airbnb ROI: 6.38% Traditional ROI: 5.28%
3312 HONEYMOON LANE HOLIDAY, FL One or more photo(s) has been virtually staged.Welcome to this charming 2-bedroom, 1.5-bat...	2 beds \| 2 baths \| 1,320 sq.ft.	$230,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 6.32% Airbnb Rental Income: $2176 Traditional Rental Income: $1992 Airbnb ROI: 4.63% Traditional ROI: 6.32%
3103 BIGELOW DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome to this beautifully remodeled home in Aloh...	2 beds \| 1 baths \| 936 sq.ft.	$220,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 6.48% Airbnb Rental Income: $2176 Traditional Rental Income: $1785 Airbnb ROI: 5.7% Traditional ROI: 6.48%
3309 JACKSON DRIVE HOLIDAY, FL Captivating single family home in Holiday, FL. Welcome to 3309 Jackson Dr., a 2 bedroom, 1...	2 beds \| 1 baths \| 984 sq.ft.	$285,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 4.39% Airbnb Rental Income: $2176 Traditional Rental Income: $1800 Airbnb ROI: 3.74% Traditional ROI: 4.39%
1332 MAYBURY DRIVE HOLIDAY, FL Charming and nicely updated 3BR/2BA single family home located on a corner lot. This home...	3 beds \| 2 baths \| 1,393 sq.ft.	$314,900	Airbnb cash on cash: 5.43% Traditional cash on cash: 4.45% Airbnb Rental Income: $3151 Traditional Rental Income: $2146 Airbnb ROI: 5.43% Traditional ROI: 4.45%
6321 STAUNTON DRIVE HOLIDAY, FL ***Back on the market Buyers unable to perform due to the Hurricanes and - NOT IN A FLOOD...	2 beds \| 2 baths \| 1,689 sq.ft.	$359,200	Airbnb cash on cash: 3.47% Traditional cash on cash: 5.36% Airbnb Rental Income: $2176 Traditional Rental Income: $2261 Airbnb ROI: 3.47% Traditional ROI: 5.36%
2647 ALBION STREET HOLIDAY, FL Welcome to this beautiful 3 bedroom, 2 bath home located in the heart of Aloha Gardens com...	3 beds \| 2 baths \| 1,568 sq.ft.	$325,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 5.18% Airbnb Rental Income: $3151 Traditional Rental Income: $2272 Airbnb ROI: 5.72% Traditional ROI: 5.18%
1511 PLUM TREE ROAD HOLIDAY, FL If you need room, THIS is your house! Very unexpectedly large home in a super nice part o...	3 beds \| 2 baths \| 1,663 sq.ft.	$269,900	Airbnb cash on cash: 7.91% Traditional cash on cash: 7.38% Airbnb Rental Income: $3151 Traditional Rental Income: $2301 Airbnb ROI: 7.91% Traditional ROI: 7.38%
2231 BARRACUDA COURT HOLIDAY, FL REDUCED TO SELL !! Impressive! This residence is primed for immediate occupancy and boasts...	3 beds \| 2 baths \| 1,740 sq.ft.	$350,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 3.77% Airbnb Rental Income: $3151 Traditional Rental Income: $2334 Airbnb ROI: 4.08% Traditional ROI: 3.77%
4036 SUNRAY DRIVE HOLIDAY, FL Check out this LAKE-FRONT living, MINUTES FROM PINELLAS COUNTY AND THE GULF OF MEXICO...un...	3 beds \| 2 baths \| 1,842 sq.ft.	$350,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 5.82% Airbnb Rental Income: $3151 Traditional Rental Income: $2805 Airbnb ROI: 4.7% Traditional ROI: 5.82%
3615 HOLIDAY LAKE DRIVE HOLIDAY, FL Under contract-accepting backup offers. Immediate Occupancy! Move In Ready! AFFORDABLE! NO...	2 beds \| 1 baths \| 894 sq.ft.	$209,900	Airbnb cash on cash: 5.56% Traditional cash on cash: 6.6% Airbnb Rental Income: $2176 Traditional Rental Income: $1832 Airbnb ROI: 5.56% Traditional ROI: 6.6%
2711 COLDSTONE LANE HOLIDAY, FL Welcome to your dream home in the gated resort-style community of Key Vista, located in be...	4 beds \| 3 baths \| 2,195 sq.ft.	$474,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 3.18% Airbnb Rental Income: $4419 Traditional Rental Income: $2745 Airbnb ROI: 4.87% Traditional ROI: 3.18%
3238 MELA COURT HOLIDAY, FL 2017 Newer built home in the private gated community of VISTA LAKES - 5 bedroom, 3.5 bath,...	5 beds \| 4 baths \| 3,198 sq.ft.	$647,500	Airbnb cash on cash: 5.91% Traditional cash on cash: 4.63% Airbnb Rental Income: $6270 Traditional Rental Income: $4260 Airbnb ROI: 5.91% Traditional ROI: 4.63%
4903 MIRAGE AVENUE HOLIDAY, FL Potentially four bedrooms (2 rooms are currently used as bonus rooms), two bathrooms (seco...	2 beds \| 2 baths \| 1,250 sq.ft.	$219,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 7.13% Airbnb Rental Income: $2176 Traditional Rental Income: $2013 Airbnb ROI: 5.25% Traditional ROI: 7.13%
4041 STAR ISLAND DR HOLIDAY, FL Donât let this incredible waterfront oasis slip away! No flooding and never lost power t...	2 beds \| 2 baths \| 1,746 sq.ft.	$325,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 7.06% Airbnb Rental Income: $2176 Traditional Rental Income: $2973 Airbnb ROI: 2.65% Traditional ROI: 7.06%
3814 STAYSAIL LANE #3814 HOLIDAY, FL Welcome to your coastal retreat in the heart of Holiday, Florida! This beautifully maintai...	2 beds \| 2 baths \| 1,296 sq.ft.	$175,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 7.87% Airbnb Rental Income: $2176 Traditional Rental Income: $2351 Airbnb ROI: 3.51% Traditional ROI: 7.87%
5441 CELCUS DRIVE HOLIDAY, FL Now Available in Forest Hills! Come see this charming Home consisting of 3 bedrooms, 2 bat...	3 beds \| 2 baths \| 1,338 sq.ft.	$235,900	Airbnb cash on cash: 8.41% Traditional cash on cash: 6.98% Airbnb Rental Income: $3151 Traditional Rental Income: $2119 Airbnb ROI: 8.41% Traditional ROI: 6.98%

Real Estate investment in Holiday, FL

There are 242 properties for sale in the city of Holiday . The median list price in Holiday is $250,000 and the average price per square foot is $192. In November 2024, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $2,062.

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

There are 242 investment properties available for sale in Holiday.

In 2024, 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

3520 OVERLAND DRIVE

HOLIDAY, FL

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

$285,000

Airbnb cash on cash: 4.22%

Traditional cash on cash: 6.46%

Airbnb Rental Income: $2176

Traditional Rental Income: $2226

Airbnb ROI: 4.22%

Traditional ROI: 6.46%

3749 DARLINGTON RD

HOLIDAY, FL

3 beds | 2 baths | 1,056 sq.ft.

$260,000

Airbnb cash on cash: 7.24%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $3151

Traditional Rental Income: $1914

Airbnb ROI: 7.24%

Traditional ROI: 5.11%

1753 FONT LANE

HOLIDAY, FL

2 beds | 2 baths | 1,485 sq.ft.

$289,900

Airbnb cash on cash: 3.47%

Traditional cash on cash: 6.24%

Airbnb Rental Income: $2176

Traditional Rental Income: $2381

Airbnb ROI: 3.47%

Traditional ROI: 6.24%

3423 UMBER ROAD

HOLIDAY, FL

3 beds | 2 baths | 1,368 sq.ft.

$307,000

Airbnb cash on cash: 6.56%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $3151

Traditional Rental Income: $2340

Airbnb ROI: 6.56%

Traditional ROI: 6.23%

4105 MOOG ROAD

HOLIDAY, FL

2 beds | 2 baths | 1,218 sq.ft.

$235,000

Airbnb cash on cash: 4.63%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $2176

Traditional Rental Income: $2013

Airbnb ROI: 4.63%

Traditional ROI: 6.37%

3627 ORTONA DRIVE

HOLIDAY, FL

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

$269,000

Airbnb cash on cash: 3.77%

Traditional cash on cash: 7.42%

Airbnb Rental Income: $2176

Traditional Rental Income: $2551

Airbnb ROI: 3.77%

Traditional ROI: 7.42%

3830 DARLINGTON ROAD

HOLIDAY, FL

2 beds | 2 baths | 1,368 sq.ft.

$235,000

Airbnb cash on cash: 4.12%

Traditional cash on cash: 5.95%

Airbnb Rental Income: $2176

Traditional Rental Income: $2032

Airbnb ROI: 4.12%

Traditional ROI: 5.95%

3506 HOOVER DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,368 sq.ft.

$241,000

Airbnb cash on cash: 4.93%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $2176

Traditional Rental Income: $1793

Airbnb ROI: 4.93%