Airbnb Properties for Sale in Holiday, FL

Looking for a vacation rental investment in Holiday, FL with high ROI ?

Explore a range of newly added short-term rental homes in Holiday, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Holiday, FL

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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%
2228 PARROT FISH DRIVE HOLIDAY, FL Beautiful Must See Vylla. HIgh & Dry Villa makes this the Perfect Florida Home. Enter your...	3 beds \| 2 baths \| 1,876 sq.ft.	$319,900	Airbnb cash on cash: 6.92% Traditional cash on cash: 5.87% Airbnb Rental Income: $3690 Traditional Rental Income: $2570 Airbnb ROI: 6.92% Traditional ROI: 5.87%
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%
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%
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%
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%
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%
5311 BOARDWALK STREET HOLIDAY, FL Welcome to 5311 Boardwalk St, a rare opportunity to own a beautifully updated waterfront t...	3 beds \| 3 baths \| 1,848 sq.ft.	$449,900	Airbnb cash on cash: 7.9% Traditional cash on cash: 4.58% Airbnb Rental Income: $4955 Traditional Rental Income: $2540 Airbnb ROI: 7.9% Traditional ROI: 4.58%
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%
2627 CHARLAN COURT HOLIDAY, FL Welcome to effortless living in Holidayâperfectly positioned between the historic charm ...	2 beds \| 3 baths \| 1,541 sq.ft.	$280,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 5.63% Airbnb Rental Income: $3690 Traditional Rental Income: $2463 Airbnb ROI: 7.24% Traditional ROI: 5.63%
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%
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%
1734 RUMAR LANE HOLIDAY, FL Take advantage of a unique opportunity to own an expansive duplex that includes both units...	6 beds \| N/A baths \| 3,384 sq.ft.	$610,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 2.56% Airbnb Rental Income: $3690 Traditional Rental Income: $2727 Airbnb ROI: 2.84% Traditional ROI: 2.56%
5199 FORUM BOULEVARD HOLIDAY, FL 2% towards closing cost/ rate buy down with preferred lender! Also available for Rent! Wel...	2 beds \| 3 baths \| 1,541 sq.ft.	$268,000	Airbnb cash on cash: 7.55% Traditional cash on cash: 5.62% Airbnb Rental Income: $3690 Traditional Rental Income: $2398 Airbnb ROI: 7.55% Traditional ROI: 5.62%
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%
2302 BARRACUDA COURT HOLIDAY, FL EXCEPTIONAL VALUE - SELLER PREPARED TO WORK WITH SERIOUS BUYERS. BRING YOUR OFFER TODAY! W...	3 beds \| 2 baths \| 1,740 sq.ft.	$329,980	Airbnb cash on cash: 9.38% Traditional cash on cash: 4.94% Airbnb Rental Income: $4955 Traditional Rental Income: $2564 Airbnb ROI: 9.38% Traditional ROI: 4.94%
5702 RIDDLE ROAD HOLIDAY, FL Under contract-accepting backup offers. Live the waterfront lifestyle most people only dre...	3 beds \| 2 baths \| 1,622 sq.ft.	$400,000	Airbnb cash on cash: 8.07% Traditional cash on cash: 4.26% Airbnb Rental Income: $4955 Traditional Rental Income: $2514 Airbnb ROI: 8.07% Traditional ROI: 4.26%
1147 RUSHMORE DRIVE HOLIDAY, FL Water view with access to the Gulf and room for your boat and RV in this beautifully updat...	2 beds \| 2 baths \| 1,161 sq.ft.	$347,000	Airbnb cash on cash: 6.45% Traditional cash on cash: 3.31% Airbnb Rental Income: $3690 Traditional Rental Income: $1862 Airbnb ROI: 6.45% Traditional ROI: 3.31%

Vacation Rentals in Holiday

There are 53 vacation rental properties available for sale in the city of Holiday . The median list price of Airbnb properties available for sale in Holiday is $239,900 and the average price per square foot is $177. The cash on cash return on vacation rentals in Holiday is 12.00%. The average monthly short term rental income in Holiday is $3,690.

Holiday, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 53 Airbnb properties available for sale in Holiday.

In April 2026, the average Airbnb occupancy rate in Holiday is N/A%.

Airbnb data on vacation rentals in Holiday, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Holiday, FL market insights, guest information and booking details, seasonality trends and historical Holiday, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb 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%

2228 PARROT FISH DRIVE

HOLIDAY, FL

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

$319,900

Airbnb cash on cash: 6.92%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $3690

Traditional Rental Income: $2570

Airbnb ROI: 6.92%

Traditional ROI: 5.87%

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%

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%

Traditional ROI: 4.54%

2945 WOOD POINTE DRIVE

HOLIDAY, FL

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%