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
1414 WHITEHALL LANE HOLIDAY, FL Under contract-accepting backup offers. -- OWNERS MOTIVATED, BRING ALL OFFERS -- **Free 1%...	3 beds \| 2 baths \| 1,636 sq.ft.	$288,900	Airbnb cash on cash: 4.11% Traditional cash on cash: 6.78% Airbnb Rental Income: $2239 Traditional Rental Income: $2402 Airbnb ROI: 4.11% Traditional ROI: 6.78%
2423 TRIGGERFISH COURT HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 2,462 sq.ft.	$500,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 3.81% Airbnb Rental Income: $1156 Traditional Rental Income: $3225 Airbnb ROI: -1.43% Traditional ROI: 3.81%
2228 Parrot Fish Dr HOLIDAY, FL âDue to seller/investor marketing restrictions, seller is only accepting offers from Own...	3 beds \| 2 baths \| 1,876 sq.ft.	$319,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 5.13% Airbnb Rental Income: $2239 Traditional Rental Income: $2570 Airbnb ROI: 2.16% Traditional ROI: 5.13%
3325 HONEYMOON LANE HOLIDAY, FL Welcome to waterfront living in Holiday! This beautifully maintained 2-bedroom, 2-bath hom...	2 beds \| 2 baths \| 1,334 sq.ft.	$250,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 8.62% Airbnb Rental Income: $1371 Traditional Rental Income: $2529 Airbnb ROI: 1.95% Traditional ROI: 8.62%
3401 Supreme Dr HOLIDAY, FL WOW! Move in ready and full of potential! This charming home features bright open living...	2 beds \| 2 baths \| 1,442 sq.ft.	$254,999	Airbnb cash on cash: 1.64% Traditional cash on cash: 6.78% Airbnb Rental Income: $1371 Traditional Rental Income: $2215 Airbnb ROI: 1.64% Traditional ROI: 6.78%
2128 SHANNON DRIVE 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.	$217,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 6.59% Airbnb Rental Income: $1371 Traditional Rental Income: $1756 Airbnb ROI: 2.69% Traditional ROI: 6.59%
3114 BLUFF BOULEVARD HOLIDAY, FL Discover the charm of Floridaâs Gulf Coast in this beautifully crafted waterfront home, ...	3 beds \| 3 baths \| 3,234 sq.ft.	$1,265,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.92% Airbnb Rental Income: $2239 Traditional Rental Income: $4615 Airbnb ROI: -0.58% Traditional ROI: 1.92%
2216 OAK WIND DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome home to this charming 2 bedroom, 2 bathroo...	2 beds \| 2 baths \| 1,128 sq.ft.	$169,900	Airbnb cash on cash: 2.53% Traditional cash on cash: 9.35% Airbnb Rental Income: $1371 Traditional Rental Income: $2059 Airbnb ROI: 2.53% Traditional ROI: 9.35%
3011 Shadow Oaks Dr HOLIDAY, FL Spacious 3-bedroom, 2-bath home situated on a fully fenced 1/4-acre corner lot with a peac...	3 beds \| 2 baths \| 1,480 sq.ft.	$319,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 6.41% Airbnb Rental Income: $2239 Traditional Rental Income: $2561 Airbnb ROI: 3.47% Traditional ROI: 6.41%
5026 Moog Rd HOLIDAY, FL COMPLETELY UPDATED including roof, Charming Single-Family Home in Holiday with Spacious Fe...	2 beds \| 1 baths \| 792 sq.ft.	$218,500	Airbnb cash on cash: 1.83% Traditional cash on cash: 5.4% Airbnb Rental Income: $1371 Traditional Rental Income: $1709 Airbnb ROI: 1.83% Traditional ROI: 5.4%
3552 BLUEBELL LANE HOLIDAY, FL Under contract-accepting backup offers. Short Sale. MULTIPLE OFFERS RECEIVED. PLEASE SUBMI...	2 beds \| 2 baths \| 900 sq.ft.	$180,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 10.1% Airbnb Rental Income: $1371 Traditional Rental Income: $2133 Airbnb ROI: 3.22% Traditional ROI: 10.1%
2146 SOCIETY DRIVE HOLIDAY, FL Under contract-accepting backup offers. Virtually Staged. Tucked along the shores of Lake ...	2 beds \| 2 baths \| 1,371 sq.ft.	$265,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 7.91% Airbnb Rental Income: $1371 Traditional Rental Income: $2545 Airbnb ROI: 1.54% Traditional ROI: 7.91%
1022 Bowsprit Ln #1022 HOLIDAY, FL Great location with beautiful pond view from most windows, friendly surroundings, nature a...	2 beds \| 2 baths \| 1,114 sq.ft.	$175,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 7.65% Airbnb Rental Income: $1371 Traditional Rental Income: $2196 Airbnb ROI: 0.19% Traditional ROI: 7.65%
2125 BARRACUDA COURT HOLIDAY, FL Under contract-accepting backup offers. Maintenance Free living, 3-Bedrooms 2.5-Bathrooms,...	3 beds \| 3 baths \| 1,740 sq.ft.	$342,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 3.67% Airbnb Rental Income: $2239 Traditional Rental Income: $2298 Airbnb ROI: 1.74% Traditional ROI: 3.67%
3238 MELA COURT HOLIDAY, FL Amazing Price Reduction in Gated Neighborhood of Vista Lakes at Bailys Bluff - 5 Bedroom,...	5 beds \| 4 baths \| 3,198 sq.ft.	$499,900	Airbnb cash on cash: 0.63% Traditional cash on cash: 5.48% Airbnb Rental Income: $2179 Traditional Rental Income: $3892 Airbnb ROI: 0.63% Traditional ROI: 5.48%
3535 GARFIELD DRIVE HOLIDAY, FL PRICED UNDER MARKET VALUE! 2-bedroom, 2 bath, almost 1100 square foot home with an attache...	2 beds \| 2 baths \| 1,096 sq.ft.	$175,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 8.9% Airbnb Rental Income: $1371 Traditional Rental Income: $1902 Airbnb ROI: 3.21% Traditional ROI: 8.9%
4327 Beacon Square Dr HOLIDAY, FL Welcome home! This charming Holiday gem is the perfect opportunity for first-time buyers. ...	3 beds \| 1 baths \| 1,104 sq.ft.	$214,000	Airbnb cash on cash: 5.92% Traditional cash on cash: 6.73% Airbnb Rental Income: $2239 Traditional Rental Income: $1842 Airbnb ROI: 5.92% Traditional ROI: 6.73%
2945 WOOD POINTE DRIVE HOLIDAY, FL Located within the 55+ area of the beautiful Key Vista gated community, this move-in-ready...	2 beds \| 2 baths \| 1,341 sq.ft.	$345,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4% Airbnb Rental Income: $1371 Traditional Rental Income: $2265 Airbnb ROI: -0.05% Traditional ROI: 4%
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.	$289,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 5.68% Airbnb Rental Income: $1371 Traditional Rental Income: $2073 Airbnb ROI: 1.57% Traditional ROI: 5.68%
1050 Deal Ln HOLIDAY, FL Turn-Key 3 bedroom home with Dual Primary Suites-Ideal for Multi-Generational Living or In...	3 beds \| 3 baths \| 1,667 sq.ft.	$315,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 4.63% Airbnb Rental Income: $2239 Traditional Rental Income: $2206 Airbnb ROI: 2.85% Traditional ROI: 4.63%
3801 Sailmaker Ln HOLIDAY, FL Welcome to this well-maintained 2 bedroom, 2 bath condominium in the coastal community of ...	2 beds \| 2 baths \| 1,318 sq.ft.	$160,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 7.78% Airbnb Rental Income: $1371 Traditional Rental Income: $2443 Airbnb ROI: -1.68% Traditional ROI: 7.78%
3240 Briar Cliff Dr HOLIDAY, FL Gulf Coast beaches and the iconic Tarpon Springs Sponge Docks just minutes away. This is t...	3 beds \| 2 baths \| 1,221 sq.ft.	$228,500	Airbnb cash on cash: 5.84% Traditional cash on cash: 7.82% Airbnb Rental Income: $2239 Traditional Rental Income: $2104 Airbnb ROI: 5.84% Traditional ROI: 7.82%
4749 Sunny Loop #4749 HOLIDAY, FL VILLA IS A NON-FLOOD ZONE X!! PERFECT SNOWBIRD VILLA! TURNKEY - FURNISHINGS OPTIONAL! C...	2 beds \| 2 baths \| 975 sq.ft.	$169,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.52% Airbnb Rental Income: $1371 Traditional Rental Income: $1870 Airbnb ROI: -0.14% Traditional ROI: 5.52%
3547 Wilson Dr HOLIDAY, FL PROPERTY HIGHLIGHTS â¢ Situated at approximately 14 feet elevation â home and street...	2 beds \| 1 baths \| 984 sq.ft.	$210,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 5.19% Airbnb Rental Income: $1371 Traditional Rental Income: $1660 Airbnb ROI: 1.88% Traditional ROI: 5.19%
2817 PLANTAIN DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome home to 2817 Plantain Dr! This beautifully...	3 beds \| 2 baths \| 1,683 sq.ft.	$415,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 5.29% Airbnb Rental Income: $2239 Traditional Rental Income: $3290 Airbnb ROI: 1.14% Traditional ROI: 5.29%
3711 ELMWOOD DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome home! This charming and affordable starter...	2 beds \| 2 baths \| 1,096 sq.ft.	$205,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 6.95% Airbnb Rental Income: $1371 Traditional Rental Income: $1947 Airbnb ROI: 1.84% Traditional ROI: 6.95%
2330 SOCIETY DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome to this waterfront pool home in the desira...	4 beds \| 3 baths \| 2,418 sq.ft.	$399,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 3.43% Airbnb Rental Income: $1156 Traditional Rental Income: $2363 Airbnb ROI: -0.81% Traditional ROI: 3.43%
3105 PINON DRIVE HOLIDAY, FL Under contract-accepting backup offers. Auction Property. Short Sale. * * FANTASTIC OPPORT...	3 beds \| 2 baths \| 1,519 sq.ft.	$229,900	Airbnb cash on cash: 4.72% Traditional cash on cash: 9.29% Airbnb Rental Income: $2239 Traditional Rental Income: $2672 Airbnb ROI: 4.72% Traditional ROI: 9.29%
4704 Koala Dr HOLIDAY, FL Come check out this gorgeous updated waterfront pool home featuring an open, inviting floo...	2 beds \| 2 baths \| 1,303 sq.ft.	$325,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 4.57% Airbnb Rental Income: $1371 Traditional Rental Income: $2040 Airbnb ROI: 1.01% Traditional ROI: 4.57%
3334 Coldwell Dr HOLIDAY, FL Move in ready 3 bedroom 1.5 bathroom home located in Holiday Fl. This home has and update ...	3 beds \| 1 baths \| 1,185 sq.ft.	$243,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 5.3% Airbnb Rental Income: $2239 Traditional Rental Income: $2075 Airbnb ROI: 3.57% Traditional ROI: 5.3%
4843 Calais Dr HOLIDAY, FL Live the Florida Dream in this Beautiful 2 Bedroom 2 Bath Block Home with Oversized Garage...	2 beds \| 1 baths \| 1,088 sq.ft.	$230,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 5.3% Airbnb Rental Income: $1371 Traditional Rental Income: $1700 Airbnb ROI: 1.87% Traditional ROI: 5.3%
2906 Windridge Dr HOLIDAY, FL Welcome to 2906 Windridge Drive a large lake front lot where peace of mind meets luxury li...	3 beds \| 2 baths \| 1,647 sq.ft.	$359,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 5.71% Airbnb Rental Income: $2239 Traditional Rental Income: $2922 Airbnb ROI: 2.01% Traditional ROI: 5.71%
3127 Dole St HOLIDAY, FL Welcome to this beautifully updated 2-bedroom, 2-bath, 2-car garage home offering 1,184 sq...	2 beds \| 2 baths \| 1,184 sq.ft.	$299,900	Airbnb cash on cash: 0.84% Traditional cash on cash: 4.61% Airbnb Rental Income: $1371 Traditional Rental Income: $2018 Airbnb ROI: 0.84% Traditional ROI: 4.61%
1240 Chelsea Ln HOLIDAY, FL Discover the charm of 1240 Chelsea Ln, located in the heart of Holiday, FL. This inviting ...	2 beds \| 1 baths \| 996 sq.ft.	$205,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 5.4% Airbnb Rental Income: $1371 Traditional Rental Income: $1598 Airbnb ROI: 2.08% Traditional ROI: 5.4%
3510 Allandale Dr HOLIDAY, FL BRAND NEW AC - June 2026! Newer roof 2022! Welcome to this beautifully maintained 2-bedroo...	2 beds \| 2 baths \| 1,368 sq.ft.	$235,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 6.66% Airbnb Rental Income: $1371 Traditional Rental Income: $2081 Airbnb ROI: 1.58% Traditional ROI: 6.66%
3409 Springfield Dr HOLIDAY, FL Stunning Pool Home with Breathtaking Lake Views in Beacon Square! This beautifully remodel...	2 beds \| 2 baths \| 1,519 sq.ft.	$324,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.89% Airbnb Rental Income: $1371 Traditional Rental Income: $1979 Airbnb ROI: 0.52% Traditional ROI: 3.89%
2344 Tahitian Dr HOLIDAY, FL Short Sale. Spacious 4-bedroom, 2-bath block home in Holiday offering a functional split f...	4 beds \| 2 baths \| 1,377 sq.ft.	$220,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 5.49% Airbnb Rental Income: $1156 Traditional Rental Income: $1803 Airbnb ROI: 0.77% Traditional ROI: 5.49%
4329 Tahitian Gardens Cir #B HOLIDAY, FL Welcome to this move-in ready two-bedroom, one and a half-bath condo in the desirable 55+ ...	2 beds \| 1 baths \| 768 sq.ft.	$124,900	Airbnb cash on cash: 2.24% Traditional cash on cash: 8.29% Airbnb Rental Income: $1371 Traditional Rental Income: $1681 Airbnb ROI: 2.24% Traditional ROI: 8.29%
4009 STAR ISLAND DRIVE HOLIDAY, FL WATERFRONT POOL HOME WITH STUNNING CANAL VIEWS, PRIVATE DOCK, SCREENED POOL & NO HOA! Too ...	2 beds \| 2 baths \| 1,292 sq.ft.	$340,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.05% Airbnb Rental Income: $1371 Traditional Rental Income: $1686 Airbnb ROI: 0.76% Traditional ROI: 3.05%
1652 Marengo Dr HOLIDAY, FL Welcome to this charming, move-in-ready block home tucked away on a quiet street. Sale fel...	2 beds \| 1 baths \| 816 sq.ft.	$232,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 5.49% Airbnb Rental Income: $1371 Traditional Rental Income: $1822 Airbnb ROI: 1.54% Traditional ROI: 5.49%

Real Estate investment in Holiday, FL

There are 216 properties for sale in the city of Holiday . The median list price in Holiday is $224,865 and the average price per square foot is $167. In July 2026, the average monthly cash on cash return in Holiday is 6.00%. The average monthly rental income in Holiday is $2,063.

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

There are 216 investment properties available for sale in Holiday.

In 2026, the best neighborhood to buy investment property is HOLIDAY.

The ROI for Long-Term is higher than the Short-Term in Holiday with average rental income of $2,063.

Your search for investment property begins and ends here

Investment Property for Sale in Holiday, FL

1414 WHITEHALL LANE

HOLIDAY, FL

3 beds | 2 baths | 1,636 sq.ft.

$288,900

Airbnb cash on cash: 4.11%

Traditional cash on cash: 6.78%

Airbnb Rental Income: $2239

Traditional Rental Income: $2402

Airbnb ROI: 4.11%

Traditional ROI: 6.78%

2423 TRIGGERFISH COURT

HOLIDAY, FL

4 beds | 3 baths | 2,462 sq.ft.

$500,000

Airbnb cash on cash: -1.43%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $1156

Traditional Rental Income: $3225

Airbnb ROI: -1.43%

Traditional ROI: 3.81%

2228 Parrot Fish Dr

HOLIDAY, FL

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

$319,900

Airbnb cash on cash: 2.16%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $2239

Traditional Rental Income: $2570

Airbnb ROI: 2.16%

Traditional ROI: 5.13%

3325 HONEYMOON LANE

HOLIDAY, FL

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

$250,000

Airbnb cash on cash: 1.95%

Traditional cash on cash: 8.62%

Airbnb Rental Income: $1371

Traditional Rental Income: $2529

Airbnb ROI: 1.95%

Traditional ROI: 8.62%

3401 Supreme Dr

HOLIDAY, FL

2 beds | 2 baths | 1,442 sq.ft.

$254,999

Airbnb cash on cash: 1.64%

Traditional cash on cash: 6.78%

Airbnb Rental Income: $1371

Traditional Rental Income: $2215

Airbnb ROI: 1.64%

Traditional ROI: 6.78%

2128 SHANNON DRIVE

HOLIDAY, FL

2 beds | 1 baths | 1,200 sq.ft.

$217,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 6.59%

Airbnb Rental Income: $1371

Traditional Rental Income: $1756

Airbnb ROI: 2.69%

Traditional ROI: 6.59%

3114 BLUFF BOULEVARD

HOLIDAY, FL

3 beds | 3 baths | 3,234 sq.ft.

$1,265,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $2239

Traditional Rental Income: $4615

Airbnb ROI: -0.58%

Traditional ROI: 1.92%

2216 OAK WIND DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,128 sq.ft.

$169,900

Airbnb cash on cash: 2.53%

Traditional cash on cash: 9.35%

Airbnb Rental Income: $1371

Traditional Rental Income: $2059

Airbnb ROI: 2.53%