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.

Single Family Homes for Sale in Holiday, FL

Search for Single Family Residential for Sale in Holiday, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 58 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3520 OVERLAND DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome to your own slice of Gulf Coast waterfront...	2 beds \| 2 baths \| 1,068 sq.ft.	$269,000	Airbnb cash on cash: 9.46% Traditional cash on cash: 7.49% Airbnb Rental Income: $3690 Traditional Rental Income: $2387 Airbnb ROI: 9.46% Traditional ROI: 7.49%
1028 ORCA COURT HOLIDAY, FL Under contract-accepting backup offers. BRAND NEW ROOF (5/2025) \| NEVER FLOODED \| MOVE-IN ...	3 beds \| 2 baths \| 1,740 sq.ft.	$329,900	Airbnb cash on cash: 8.61% Traditional cash on cash: 5.92% Airbnb Rental Income: $4955 Traditional Rental Income: $3106 Airbnb ROI: 8.61% Traditional ROI: 5.92%
1225 GREENLEA DRIVE HOLIDAY, FL Under contract-accepting backup offers. Spacious POOL HOME with a new pump and filter syst...	2 beds \| 2 baths \| 1,525 sq.ft.	$333,000	Airbnb cash on cash: 7.23% Traditional cash on cash: 5.91% Airbnb Rental Income: $3690 Traditional Rental Income: $2474 Airbnb ROI: 7.23% Traditional ROI: 5.91%
5313 BOARDWALK STREET HOLIDAY, FL One or more photo(s) has been virtually staged. Welcome to 5313 Boardwalk Street â a bea...	3 beds \| 3 baths \| 1,848 sq.ft.	$444,000	Airbnb cash on cash: 7% Traditional cash on cash: 4.7% Airbnb Rental Income: $4955 Traditional Rental Income: $2985 Airbnb ROI: 7% Traditional ROI: 4.7%
3645 OVERLAND DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. THIS RESIDENCE IS A 2/3/2 with an oversize...	2 beds \| 3 baths \| 1,416 sq.ft.	$284,900	Airbnb cash on cash: 8.78% Traditional cash on cash: 5.77% Airbnb Rental Income: $3690 Traditional Rental Income: $2078 Airbnb ROI: 8.78% Traditional ROI: 5.77%
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.	$1,295,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 1.85% Airbnb Rental Income: $4955 Traditional Rental Income: $4615 Airbnb ROI: 1.29% Traditional ROI: 1.85%
3309 JACKSON DRIVE HOLIDAY, FL Welcome to 3309 Jackson Dr., Holiday, FL â A Charming Pool Home in the Tahitian Developm...	2 beds \| 1 baths \| 1,140 sq.ft.	$259,999	Airbnb cash on cash: 9.31% Traditional cash on cash: 5.73% Airbnb Rental Income: $3690 Traditional Rental Income: $2008 Airbnb ROI: 9.31% Traditional ROI: 5.73%
3147 MELA COURT HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ne...	3 beds \| 2 baths \| 1,483 sq.ft.	$375,000	Airbnb cash on cash: 8.44% Traditional cash on cash: 4.54% Airbnb Rental Income: $4955 Traditional Rental Income: $2566 Airbnb ROI: 8.44% Traditional ROI: 4.54%
3238 MELA COURT HOLIDAY, FL 5 Bedroom, 3.5 Bath, 2 Story home located in the Gated Community of Vista Lakes, perfectl...	5 beds \| 4 baths \| 3,198 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $3892 Airbnb ROI: N/A Traditional ROI: 4.64%
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: 5.91% Traditional cash on cash: 4% Airbnb Rental Income: $3690 Traditional Rental Income: $2265 Airbnb ROI: 5.91% Traditional ROI: 4%
3228 ROCK VALLEY DRIVE 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: 8.35% Traditional cash on cash: 5.46% Airbnb Rental Income: $3690 Traditional Rental Income: $2073 Airbnb ROI: 8.35% Traditional ROI: 5.46%
5657 OCEANIC ROAD HOLIDAY, FL Welcome to 5657 Oceanic Rd in Holiday, Florida a quiet, well-established neighborhood with...	4 beds \| 4 baths \| 3,553 sq.ft.	$629,900	Airbnb cash on cash: 8.9% Traditional cash on cash: 10.34% Airbnb Rental Income: $7349 Traditional Rental Income: $6777 Airbnb ROI: 8.9% Traditional ROI: 10.34%
2817 PLANTAIN DRIVE HOLIDAY, FL Welcome home to 2817 Plantain Dr! This beautifully maintained home, located inside the gat...	3 beds \| 2 baths \| 1,683 sq.ft.	$415,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 5.29% Airbnb Rental Income: $4955 Traditional Rental Income: $3290 Airbnb ROI: 6.96% Traditional ROI: 5.29%
2216 PARROT FISH DRIVE HOLIDAY, FL Under contract-accepting backup offers. NEW PRICE! This is a great find! This Beautifull...	3 beds \| 2 baths \| 1,740 sq.ft.	$340,000	Airbnb cash on cash: 8.83% Traditional cash on cash: 4.99% Airbnb Rental Income: $4955 Traditional Rental Income: $2713 Airbnb ROI: 8.83% Traditional ROI: 4.99%
2906 WINDRIDGE DRIVE 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.	$375,000	Airbnb cash on cash: 8.32% Traditional cash on cash: 5.42% Airbnb Rental Income: $4955 Traditional Rental Income: $2922 Airbnb ROI: 8.32% Traditional ROI: 5.42%
3127 DOLE STREET 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: 7.69% Traditional cash on cash: 4.61% Airbnb Rental Income: $3690 Traditional Rental Income: $2018 Airbnb ROI: 7.69% Traditional ROI: 4.61%
3406 PALOMA DRIVE HOLIDAY, FL Welcome home to this beautifully updated 2-bedroom, 2-bath home offering comfort, style, a...	2 beds \| 2 baths \| 1,310 sq.ft.	$255,000	Airbnb cash on cash: 9.03% Traditional cash on cash: 5.62% Airbnb Rental Income: $3690 Traditional Rental Income: $2066 Airbnb ROI: 9.03% Traditional ROI: 5.62%
2012 FERN RIDGE COURT HOLIDAY, FL Under contract-accepting backup offers. Located in the gated community of Key Vista, this ...	4 beds \| 3 baths \| 2,768 sq.ft.	$490,000	Airbnb cash on cash: 9.73% Traditional cash on cash: 11.68% Airbnb Rental Income: $7349 Traditional Rental Income: $6831 Airbnb ROI: 9.73% Traditional ROI: 11.68%
3409 SPRINGFIELD DRIVE HOLIDAY, FL Lovely setting on a spring-fed lake. Enjoy the spectacular sunsets and cool evening breeze...	2 beds \| 2 baths \| 1,519 sq.ft.	$349,900	Airbnb cash on cash: 6.29% Traditional cash on cash: 3.53% Airbnb Rental Income: $3690 Traditional Rental Income: $1979 Airbnb ROI: 6.29% Traditional ROI: 3.53%
2126 PARROT FISH DRIVE HOLIDAY, FL Welcome home to this exceptional 3 bedroom, 2 bath villa with a 2 car garage, located in t...	3 beds \| 2 baths \| 1,740 sq.ft.	$353,999	Airbnb cash on cash: 8.41% Traditional cash on cash: 4.41% Airbnb Rental Income: $4955 Traditional Rental Income: $2611 Airbnb ROI: 8.41% Traditional ROI: 4.41%
2211 BARRACUDA COURT HOLIDAY, FL Welcome to 2211 Barracuda Ct, Holiday, FL 34691 â a beautifully maintained turn-key home...	3 beds \| 2 baths \| 1,876 sq.ft.	$320,000	Airbnb cash on cash: 8.75% Traditional cash on cash: 4.52% Airbnb Rental Income: $4955 Traditional Rental Income: $2668 Airbnb ROI: 8.75% Traditional ROI: 4.52%
2529 SANDY HILL COURT HOLIDAY, FL Where else can you find a like-new home in a gated community just a short walk from the Gu...	2 beds \| 2 baths \| 1,555 sq.ft.	$379,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.82% Airbnb Rental Income: $3690 Traditional Rental Income: $2518 Airbnb ROI: 4.85% Traditional ROI: 3.82%
5930 DELLA DRIVE HOLIDAY, FL Under contract-accepting backup offers. Tucked away in a quiet, peaceful neighborhood, thi...	2 beds \| 2 baths \| 1,125 sq.ft.	$265,000	Airbnb cash on cash: 9.12% Traditional cash on cash: 4.94% Airbnb Rental Income: $3690 Traditional Rental Income: $1840 Airbnb ROI: 9.12% Traditional ROI: 4.94%
1414 GRAND BOULEVARD HOLIDAY, FL NEW ROOF JUST PUT ON AUGUST 2025,NEW FANS, AND THE INSIDE PAINTED! NEWER ELECTRIC, WINDOWS...	2 beds \| 2 baths \| 2,278 sq.ft.	$349,999	Airbnb cash on cash: 6.86% Traditional cash on cash: 7.99% Airbnb Rental Income: $3690 Traditional Rental Income: $3255 Airbnb ROI: 6.86% Traditional ROI: 7.99%
1102 SPRINGTIME DRIVE HOLIDAY, FL Under contract-accepting backup offers. Pool Home Under $400K The One Buyers Have Been Wai...	3 beds \| 2 baths \| 1,930 sq.ft.	$379,900	Airbnb cash on cash: 9.04% Traditional cash on cash: 5.95% Airbnb Rental Income: $4955 Traditional Rental Income: $2838 Airbnb ROI: 9.04% Traditional ROI: 5.95%
3257 MASONVILLE LOOP HOLIDAY, FL Welcome to this beautifully updated 2 bedroom, 1-bathroom, single-family home, offering bo...	2 beds \| 1 baths \| 1,134 sq.ft.	$259,000	Airbnb cash on cash: 9.08% Traditional cash on cash: 5.12% Airbnb Rental Income: $3690 Traditional Rental Income: $1919 Airbnb ROI: 9.08% Traditional ROI: 5.12%
3222 JACKSON DRIVE HOLIDAY, FL Imagine waking up to the gentle sounds of nature and enjoying a stunning lake view every m...	2 beds \| 2 baths \| 1,126 sq.ft.	$339,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 4.98% Airbnb Rental Income: $3690 Traditional Rental Income: $2378 Airbnb ROI: 6.57% Traditional ROI: 4.98%
3237 SANFORD DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welome to 3237 Sanford Drive in Holiday, Florida â...	2 beds \| 2 baths \| 1,246 sq.ft.	$259,998	Airbnb cash on cash: 9.57% Traditional cash on cash: 5.82% Airbnb Rental Income: $3690 Traditional Rental Income: $1966 Airbnb ROI: 9.57% Traditional ROI: 5.82%
3143 PINEVIEW DRIVE HOLIDAY, FL Welcome to your dream waterfront estate in the sought-after Baileys Bluff community! This ...	4 beds \| 4 baths \| 4,204 sq.ft.	$1,449,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.91% Airbnb Rental Income: $7349 Traditional Rental Income: $5990 Airbnb ROI: 2.87% Traditional ROI: 2.91%
2211 PLEASANT HILL LANE HOLIDAY, FL Welcome to Key Vista, one of Holidayâs most desirable 55+ gated communities, where comfo...	2 beds \| 2 baths \| 1,500 sq.ft.	$315,000	Airbnb cash on cash: 7.15% Traditional cash on cash: 5.44% Airbnb Rental Income: $3690 Traditional Rental Income: $2378 Airbnb ROI: 7.15% Traditional ROI: 5.44%
2743 BIG PINE DRIVE HOLIDAY, FL Welcome to this beautifully maintained three bedroom, two bath, plus a den, pool home in t...	3 beds \| 2 baths \| 1,758 sq.ft.	$415,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 5.51% Airbnb Rental Income: $4955 Traditional Rental Income: $3016 Airbnb ROI: 7.89% Traditional ROI: 5.51%
2453 PLEASANT HILL LANE HOLIDAY, FL Welcome to one of Holidayâs most sought after 55+ gated communities, where privacy, comf...	2 beds \| 2 baths \| 1,555 sq.ft.	$300,000	Airbnb cash on cash: 7.56% Traditional cash on cash: 6.04% Airbnb Rental Income: $3690 Traditional Rental Income: $2459 Airbnb ROI: 7.56% Traditional ROI: 6.04%
3149 ROCK VALLEY DRIVE HOLIDAY, FL This property truly stands out from the rest! Boasting rich, bold colors, gorgeous styling...	2 beds \| 2 baths \| 1,519 sq.ft.	$309,500	Airbnb cash on cash: 8.24% Traditional cash on cash: 6.99% Airbnb Rental Income: $3690 Traditional Rental Income: $2522 Airbnb ROI: 8.24% Traditional ROI: 6.99%
5904 SPRINGRUN COURT HOLIDAY, FL A Private, Park-Like Oasis with Unmatched Amenities Awaits! Discover an unparalleled ret...	3 beds \| 2 baths \| 2,284 sq.ft.	$463,000	Airbnb cash on cash: 7.32% Traditional cash on cash: 5.74% Airbnb Rental Income: $4955 Traditional Rental Income: $3256 Airbnb ROI: 7.32% Traditional ROI: 5.74%
3340 WILSON DRIVE HOLIDAY, FL One or more photo(s) has been virtually staged. HUGE PRICE ADJUSTMENT. This charming 2-bed...	2 beds \| 2 baths \| 1,268 sq.ft.	$264,900	Airbnb cash on cash: 9.27% Traditional cash on cash: 8.05% Airbnb Rental Income: $3690 Traditional Rental Income: $2582 Airbnb ROI: 9.27% Traditional ROI: 8.05%
2153 BARRACUDA COURT HOLIDAY, FL Now priced at $329,900, this 3-bedroom, 2-bath, 2-car garage, single-story home offers 1,7...	3 beds \| 2 baths \| 1,740 sq.ft.	$329,900	Airbnb cash on cash: 9.31% Traditional cash on cash: 4.91% Airbnb Rental Income: $4955 Traditional Rental Income: $2576 Airbnb ROI: 9.31% Traditional ROI: 4.91%
2003 BARRACUDA COURT HOLIDAY, FL WOW WOW WOW - A piece of paradise awaits you .... Tucked away at the end of a quiet cul-de...	3 beds \| 2 baths \| 1,876 sq.ft.	$342,000	Airbnb cash on cash: 9.16% Traditional cash on cash: 5.01% Airbnb Rental Income: $4955 Traditional Rental Income: $2606 Airbnb ROI: 9.16% Traditional ROI: 5.01%
5338 SPANISH TRAIL HOLIDAY, FL Welcome to this Beautifully maintained 2 bedroom, 2 bathroom Single Family Home. This hom...	2 beds \| 2 baths \| 1,212 sq.ft.	$299,900	Airbnb cash on cash: 7.73% Traditional cash on cash: 4.75% Airbnb Rental Income: $3690 Traditional Rental Income: $2044 Airbnb ROI: 7.73% Traditional ROI: 4.75%
4149 DARLINGTON ROAD HOLIDAY, FL Welcome to this fully renovated, move-in-ready home in the Tahitian Homes community! Virtu...	2 beds \| 2 baths \| 1,032 sq.ft.	$249,900	Airbnb cash on cash: 9.76% Traditional cash on cash: 5.73% Airbnb Rental Income: $3690 Traditional Rental Income: $1934 Airbnb ROI: 9.76% Traditional ROI: 5.73%
2700 SIERRA VISTA WAY HOLIDAY, FL PRICE ADJUSTMENT !! Totally renovated 3bedroom 2 bathroom 2 car garage home in quiet commu...	3 beds \| 2 baths \| 1,526 sq.ft.	$444,000	Airbnb cash on cash: 6.61% Traditional cash on cash: 3.28% Airbnb Rental Income: $4955 Traditional Rental Income: $2554 Airbnb ROI: 6.61% Traditional ROI: 3.28%

Your search for investment property begins and ends here

Single Family Homes for Sale in Holiday, FL

3520 OVERLAND DRIVE

HOLIDAY, FL

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

$269,000

Airbnb cash on cash: 9.46%

Traditional cash on cash: 7.49%

Airbnb Rental Income: $3690

Traditional Rental Income: $2387

Airbnb ROI: 9.46%

Traditional ROI: 7.49%

1028 ORCA COURT

HOLIDAY, FL

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

$329,900

Airbnb cash on cash: 8.61%

Traditional cash on cash: 5.92%

Airbnb Rental Income: $4955

Traditional Rental Income: $3106

Airbnb ROI: 8.61%

Traditional ROI: 5.92%

1225 GREENLEA DRIVE

HOLIDAY, FL

2 beds | 2 baths | 1,525 sq.ft.

$333,000

Airbnb cash on cash: 7.23%

Traditional cash on cash: 5.91%

Airbnb Rental Income: $3690

Traditional Rental Income: $2474

Airbnb ROI: 7.23%

Traditional ROI: 5.91%

5313 BOARDWALK STREET

HOLIDAY, FL

3 beds | 3 baths | 1,848 sq.ft.

$444,000

Airbnb cash on cash: 7%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $4955

Traditional Rental Income: $2985

Airbnb ROI: 7%

Traditional ROI: 4.7%

3645 OVERLAND DRIVE

HOLIDAY, FL

2 beds | 3 baths | 1,416 sq.ft.

$284,900

Airbnb cash on cash: 8.78%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $3690

Traditional Rental Income: $2078

Airbnb ROI: 8.78%

Traditional ROI: 5.77%

3114 BLUFF BOULEVARD

HOLIDAY, FL

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

$1,295,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $4955

Traditional Rental Income: $4615

Airbnb ROI: 1.29%

Traditional ROI: 1.85%

3309 JACKSON DRIVE

HOLIDAY, FL

2 beds | 1 baths | 1,140 sq.ft.

$259,999

Airbnb cash on cash: 9.31%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $3690

Traditional Rental Income: $2008

Airbnb ROI: 9.31%

Traditional ROI: 5.73%

3147 MELA COURT

HOLIDAY, FL

3 beds | 2 baths | 1,483 sq.ft.

$375,000

Airbnb cash on cash: 8.44%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $4955

Traditional Rental Income: $2566

Airbnb ROI: 8.44%