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
3136 FAIRMOUNT DRIVE HOLIDAY, FL Welcome to this charming, immaculately maintained home in Holiday, near the Pasco/Pinellas...	2 beds \| 1 baths \| 1,026 sq.ft.	$245,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 5.63% Airbnb Rental Income: $2176 Traditional Rental Income: $1714 Airbnb ROI: 5.25% Traditional ROI: 5.63%
3749 DARLINGTON RD HOLIDAY, FL PRICED TO SELL! 10K REDUCTION! ASSUMABLE 5.875% VA LOAN to ANYONE who qualifies. Come see ...	3 beds \| 2 baths \| 1,056 sq.ft.	$250,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 5.3% Airbnb Rental Income: $3151 Traditional Rental Income: $1914 Airbnb ROI: 7.52% Traditional ROI: 5.3%
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.	$279,900	Airbnb cash on cash: 3.63% Traditional cash on cash: 6.49% Airbnb Rental Income: $2176 Traditional Rental Income: $2381 Airbnb ROI: 3.63% Traditional ROI: 6.49%
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 Under contract-accepting backup offers. This stunning 2 bedroom, 2 bath home is immaculate...	2 beds \| 2 baths \| 1,218 sq.ft.	$229,900	Airbnb cash on cash: 4.75% Traditional cash on cash: 6.53% Airbnb Rental Income: $2176 Traditional Rental Income: $2013 Airbnb ROI: 4.75% Traditional ROI: 6.53%
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%
3104 DOMINO DRIVE HOLIDAY, FL Charming 2-bedroom, 2-bath, 1-car garage home situated in a highly desirable community wit...	2 beds \| 2 baths \| 1,047 sq.ft.	$239,900	Airbnb cash on cash: 4.81% Traditional cash on cash: 6.15% Airbnb Rental Income: $2176 Traditional Rental Income: $1928 Airbnb ROI: 4.81% Traditional ROI: 6.15%
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.	$257,500	Airbnb cash on cash: 7.21% Traditional cash on cash: 5.67% Airbnb Rental Income: $3151 Traditional Rental Income: $2061 Airbnb ROI: 7.21% Traditional ROI: 5.67%
2646 HAWK ROOST COURT HOLIDAY, FL Under contract-accepting backup offers. Introducing a Stunning Coastal Retreat in Key Vist...	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%
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%
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 *****PRICE IMPROVEMENT***** Seller is MOTIVATED! Discover this turnkey two-bedroom, o...	2 beds \| 2 baths \| 825 sq.ft.	$150,000	Airbnb cash on cash: 6.94% Traditional cash on cash: 8.52% Airbnb Rental Income: $2176 Traditional Rental Income: $1851 Airbnb ROI: 6.94% Traditional ROI: 8.52%
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%
1626 ROUNDTREE ROAD HOLIDAY, FL Charming 3-Bedroom Home in Forest Hills with Modern Upgrades and Private Backyard Welco...	3 beds \| 2 baths \| 1,401 sq.ft.	$275,000	Airbnb cash on cash: 7.51% Traditional cash on cash: 6.95% Airbnb Rental Income: $3151 Traditional Rental Income: $2292 Airbnb ROI: 7.51% Traditional ROI: 6.95%
5245 RIDDLE ROAD HOLIDAY, FL Under contract-accepting backup offers. Situated in the serene Forest Hills neighborhood, ...	2 beds \| 2 baths \| 1,420 sq.ft.	$235,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 9.01% Airbnb Rental Income: $2176 Traditional Rental Income: $2484 Airbnb ROI: 5.14% Traditional ROI: 9.01%
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.	$350,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 5.5% Airbnb Rental Income: $3151 Traditional Rental Income: $2555 Airbnb ROI: 5.14% Traditional ROI: 5.5%
4233 DARLINGTON ROAD HOLIDAY, FL Auction Property. . Auction will run December 2nd to the 12th***This 3 bedrooms and 2 bath...	3 beds \| 2 baths \| 1,577 sq.ft.	$215,000	Airbnb cash on cash: 8.96% Traditional cash on cash: 9.68% Airbnb Rental Income: $3151 Traditional Rental Income: $2584 Airbnb ROI: 8.96% Traditional ROI: 9.68%
3800 CARIOCA ROAD HOLIDAY, FL Welcome to 3800 Carioca Rd, a charming 2-bedroom, 1-bathroom home with lots of great updat...	2 beds \| 1 baths \| 816 sq.ft.	$224,900	Airbnb cash on cash: 5.82% Traditional cash on cash: 6.06% Airbnb Rental Income: $2176 Traditional Rental Income: $1676 Airbnb ROI: 5.82% Traditional ROI: 6.06%
3523 KINGSBURY DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. This beautifully renovated and well mainta...	2 beds \| 2 baths \| 992 sq.ft.	$219,900	Airbnb cash on cash: 4.8% Traditional cash on cash: 4.7% Airbnb Rental Income: $2176 Traditional Rental Income: $1604 Airbnb ROI: 4.8% Traditional ROI: 4.7%
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.	$179,900	Airbnb cash on cash: 7.08% Traditional cash on cash: 7.95% Airbnb Rental Income: $2176 Traditional Rental Income: $1773 Airbnb ROI: 7.08% Traditional ROI: 7.95%
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.	$269,000	Airbnb cash on cash: 7.21% Traditional cash on cash: 6.27% Airbnb Rental Income: $3151 Traditional Rental Income: $2199 Airbnb ROI: 7.21% Traditional ROI: 6.27%
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%
4375 TAHITIAN GARDENS CIRCLE #B HOLIDAY, FL Welcome to this charming 2-bedroom, 1-bathroom condominium in the highly desirable Tahitia...	2 beds \| 1 baths \| 825 sq.ft.	$137,500	Airbnb cash on cash: 8.18% Traditional cash on cash: 7.12% Airbnb Rental Income: $2176 Traditional Rental Income: $1485 Airbnb ROI: 8.18% Traditional ROI: 7.12%
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%
4333 WESTWOOD DRIVE HOLIDAY, FL Assumable Mortgage at just a two percent interest rate! Experience maintenance-free living...	3 beds \| 2 baths \| 1,403 sq.ft.	$295,000	Airbnb cash on cash: 6.91% Traditional cash on cash: 6.43% Airbnb Rental Income: $3151 Traditional Rental Income: $2301 Airbnb ROI: 6.91% Traditional ROI: 6.43%
3737 BADEN DRIVE HOLIDAY, FL Under contract-accepting backup offers. Experience Luxurious Waterfront Living in Florida!...	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%
5722 MARIPOSA DRIVE HOLIDAY, FL Welcome to this charming 2-bedroom, 2-bath home in Holiday, FL, full of potential! The fro...	2 beds \| 2 baths \| 1,338 sq.ft.	$250,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 7.62% Airbnb Rental Income: $2176 Traditional Rental Income: $2312 Airbnb ROI: 4.71% Traditional ROI: 7.62%
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.	$174,999	Airbnb cash on cash: 6.78% Traditional cash on cash: 9.61% Airbnb Rental Income: $2176 Traditional Rental Income: $2096 Airbnb ROI: 6.78% Traditional ROI: 9.61%
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%
2336 PLEASANT HILL LANE HOLIDAY, FL Discover your Florida dream home in the sought-after Key Vista 55+ Gated Resort-Style Comm...	2 beds \| 2 baths \| 1,500 sq.ft.	$369,900	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.43% Airbnb Rental Income: $2176 Traditional Rental Income: $2592 Airbnb ROI: 1.64% Traditional ROI: 4.43%
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%
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 NOT IN A FLOOD ZONE! NO HURRICANE DAMAGE! NO HOA! Step into turn-key perfection! This 2 b...	2 beds \| 2 baths \| 1,689 sq.ft.	$355,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 5.44% Airbnb Rental Income: $2176 Traditional Rental Income: $2261 Airbnb ROI: 3.53% Traditional ROI: 5.44%
2647 ALBION STREET HOLIDAY, FL HUGE PRICE ADJUSTMENT! THIS HOME SURVIVED 2 HURRICANES WITH NO FLOOD DAMAGE. Welcome to th...	3 beds \| 2 baths \| 1,568 sq.ft.	$310,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 5.47% Airbnb Rental Income: $3151 Traditional Rental Income: $2272 Airbnb ROI: 6.04% Traditional ROI: 5.47%
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 Under contract-accepting backup offers. REDUCED TO SELL !! Impressive! This residence is p...	3 beds \| 2 baths \| 1,740 sq.ft.	$330,000	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.05% Airbnb Rental Income: $3151 Traditional Rental Income: $2334 Airbnb ROI: 4.39% Traditional ROI: 4.05%
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%

Real Estate investment in Holiday, FL

There are 271 properties for sale in the city of Holiday . The median list price in Holiday is $249,900 and the average price per square foot is $196. In December 2024, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $2,030.

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

There are 271 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

3136 FAIRMOUNT DRIVE

HOLIDAY, FL

2 beds | 1 baths | 1,026 sq.ft.

$245,000

Airbnb cash on cash: 5.25%

Traditional cash on cash: 5.63%

Airbnb Rental Income: $2176

Traditional Rental Income: $1714

Airbnb ROI: 5.25%

Traditional ROI: 5.63%

3749 DARLINGTON RD

HOLIDAY, FL

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

$250,000

Airbnb cash on cash: 7.52%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $3151

Traditional Rental Income: $1914

Airbnb ROI: 7.52%

Traditional ROI: 5.3%

1753 FONT LANE

HOLIDAY, FL

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

$279,900

Airbnb cash on cash: 3.63%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $2176

Traditional Rental Income: $2381

Airbnb ROI: 3.63%

Traditional ROI: 6.49%

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.

$229,900

Airbnb cash on cash: 4.75%

Traditional cash on cash: 6.53%

Airbnb Rental Income: $2176

Traditional Rental Income: $2013

Airbnb ROI: 4.75%

Traditional ROI: 6.53%

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%

3104 DOMINO DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,047 sq.ft.

$239,900

Airbnb cash on cash: 4.81%

Traditional cash on cash: 6.15%

Airbnb Rental Income: $2176

Traditional Rental Income: $1928

Airbnb ROI: 4.81%

Traditional ROI: 6.15%

5331 SKYLAND DRIVE

HOLIDAY, FL

3 beds | 2 baths | 1,272 sq.ft.

$257,500

Airbnb cash on cash: 7.21%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $3151

Traditional Rental Income: $2061

Airbnb ROI: 7.21%