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
2577 Charlan Ct HOLIDAY, FL Come see this amazing town home combining contemporary beauty and practical function and y...	2 beds \| 2 baths \| 1,541 sq.ft.	$267,000	Airbnb cash on cash: 8.75% Traditional cash on cash: 6.62% Airbnb Rental Income: $3690 Traditional Rental Income: $2350 Airbnb ROI: 8.75% Traditional ROI: 6.62%
5226 Forum Blvd HOLIDAY, FL One or more photo(s) has been virtually staged. Why wait for new construction when this 20...	2 beds \| 2 baths \| 1,541 sq.ft.	$269,995	Airbnb cash on cash: 7.95% Traditional cash on cash: 4.97% Airbnb Rental Income: $3690 Traditional Rental Income: $2126 Airbnb ROI: 7.95% Traditional ROI: 4.97%
5311 Boardwalk St HOLIDAY, FL Welcome to 5311 Boardwalk St, a rare opportunity to own a beautifully updated waterfront t...	3 beds \| 2 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%
2627 Charlan Ct HOLIDAY, FL Welcome to effortless living in Holidayâperfectly positioned between the historic charm ...	2 beds \| 2 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%
5199 Forum Blvd HOLIDAY, FL 2% towards closing cost/ rate buy down with preferred lender! Also available for Rent! Wel...	2 beds \| 2 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 Ct HOLIDAY, FL Owner Motivated. $16,000 Under Recent Appraisal! A Truly Unique Property! A Private, Park-...	3 beds \| 2 baths \| 2,284 sq.ft.	$449,000	Airbnb cash on cash: 7.57% Traditional cash on cash: 5.94% Airbnb Rental Income: $4955 Traditional Rental Income: $3256 Airbnb ROI: 7.57% Traditional ROI: 5.94%
3036 Blue Bird Dr HOLIDAY, FL 3036 Blue Bird Dr, HOLIDAY, FL 34690 \| Single Family Residential	2 beds \| 2 baths \| 1,454 sq.ft.	$249,900	Airbnb cash on cash: 9.95% Traditional cash on cash: 6.9% Airbnb Rental Income: $3690 Traditional Rental Income: $2166 Airbnb ROI: 9.95% Traditional ROI: 6.9%
Flotilla HOLIDAY, FL Flotilla, HOLIDAY, FL 34690 \| Other	N/A beds \| N/A baths \| N/A	$799,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.59% Airbnb Rental Income: $2278 Traditional Rental Income: $1356 Airbnb ROI: 3.84% Traditional ROI: 2.59%
1147 Rushmore Dr HOLIDAY, FL Waterfront Retreat with Gulf Access â Turn-Key, RV & Boat Ready! Seller providing mortga...	2 beds \| 2 baths \| 1,161 sq.ft.	$337,000	Airbnb cash on cash: 6.67% Traditional cash on cash: 3.44% Airbnb Rental Income: $3690 Traditional Rental Income: $1862 Airbnb ROI: 6.67% Traditional ROI: 3.44%
1125 Fernwood Dr HOLIDAY, FL 1125 Fernwood Dr, HOLIDAY, FL 34690 \| Single Family Residential	3 beds \| 2 baths \| 1,900 sq.ft.	$499,900	Airbnb cash on cash: 6.35% Traditional cash on cash: 2.55% Airbnb Rental Income: $4955 Traditional Rental Income: $2165 Airbnb ROI: 6.35% Traditional ROI: 2.55%
1326 Flotilla Dr HOLIDAY, FL Waterfront Pool Home with Dock \| Private Preserve Views \| Move-In Ready Welcome to 1326 F...	3 beds \| 2 baths \| 1,399 sq.ft.	$425,000	Airbnb cash on cash: 7.75% Traditional cash on cash: 5.97% Airbnb Rental Income: $4955 Traditional Rental Income: $3229 Airbnb ROI: 7.75% Traditional ROI: 5.97%
5239 Eagle Dr HOLIDAY, FL Welcome to your own private slice of Florida paradise in Colonial Hills. This beautifully ...	2 beds \| 1 baths \| 1,152 sq.ft.	$274,900	Airbnb cash on cash: 8.82% Traditional cash on cash: 4.95% Airbnb Rental Income: $3690 Traditional Rental Income: $1885 Airbnb ROI: 8.82% Traditional ROI: 4.95%
5749 Bacardi Ct HOLIDAY, FL 5749 Bacardi Ct, HOLIDAY, FL 34690 \| Single Family Residential	3 beds \| 2 baths \| 1,660 sq.ft.	$380,000	Airbnb cash on cash: 8.91% Traditional cash on cash: 3.91% Airbnb Rental Income: $4955 Traditional Rental Income: $2160 Airbnb ROI: 8.91% Traditional ROI: 3.91%
5001 Whippoorwill Dr HOLIDAY, FL 5001 Whippoorwill Dr, HOLIDAY, FL 34690 \| Other	N/A beds \| N/A baths \| N/A	$799,000	Airbnb cash on cash: 0.29% Traditional cash on cash: -0.79% Airbnb Rental Income: $2278 Traditional Rental Income: $906 Airbnb ROI: 0.29% Traditional ROI: -0.79%
3236 Madison St HOLIDAY, FL 3236 Madison St, HOLIDAY, FL 34690 \| Other	N/A beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: 0.78% Traditional cash on cash: -0.54% Airbnb Rental Income: $2278 Traditional Rental Income: $906 Airbnb ROI: 0.78% Traditional ROI: -0.54%
5313 BOARDWALK STREET HOLIDAY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 3 baths \| 1,848 sq.ft.	$430,000	Airbnb cash on cash: 7.26% Traditional cash on cash: 4.89% Airbnb Rental Income: $4955 Traditional Rental Income: $2985 Airbnb ROI: 7.26% Traditional ROI: 4.89%
5338 SPANISH TRAIL HOLIDAY, FL Under contract-accepting backup offers. Welcome to this Beautifully maintained 2 bedroom, ...	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%
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%
5844 RIDDLE ROAD HOLIDAY, FL Under contract-accepting backup offers. Situated on an oversized lot, this well-maintained...	2 beds \| 2 baths \| 1,540 sq.ft.	$349,900	Airbnb cash on cash: 7.14% Traditional cash on cash: 5.78% Airbnb Rental Income: $3690 Traditional Rental Income: $2440 Airbnb ROI: 7.14% Traditional ROI: 5.78%
1808 And 1804 HARPOON DRIVE HOLIDAY, FL Under contract-accepting backup offers. Fully renovated DUPLEX located in Flood Zone X in ...	3 beds \| N/A baths \| 1,346 sq.ft.	$379,900	Airbnb cash on cash: 6.69% Traditional cash on cash: 4.47% Airbnb Rental Income: $3690 Traditional Rental Income: $2098 Airbnb ROI: 6.69% Traditional ROI: 4.47%
3345 BLUE BIRD DRIVE HOLIDAY, FL Under contract-accepting backup offers. Welcome to this beautifully maintained 2-bedroom, ...	2 beds \| 2 baths \| 1,430 sq.ft.	$299,000	Airbnb cash on cash: 7.57% Traditional cash on cash: 5.79% Airbnb Rental Income: $3690 Traditional Rental Income: $2385 Airbnb ROI: 7.57% Traditional ROI: 5.79%
3030 SHADOW OAKS DRIVE HOLIDAY, FL Under contract-accepting backup offers. Your next chapter begins now! 3030 Shadow Oaks Dri...	3 beds \| 3 baths \| 2,510 sq.ft.	$375,000	Airbnb cash on cash: 8.07% Traditional cash on cash: 6.94% Airbnb Rental Income: $4955 Traditional Rental Income: $3543 Airbnb ROI: 8.07% Traditional ROI: 6.94%
5130 VICTORIA LANE HOLIDAY, FL Under contract-accepting backup offers. Welcome to this beautifully maintained and spaciou...	2 beds \| 3 baths \| 1,458 sq.ft.	$269,900	Airbnb cash on cash: 9.17% Traditional cash on cash: 6.77% Airbnb Rental Income: $3690 Traditional Rental Income: $2273 Airbnb ROI: 9.17% Traditional ROI: 6.77%
2423 Triggerfish Ct HOLIDAY, FL One or more photo(s) has been virtually staged. Welcome to your turnkey Florida lifestyle ...	4 beds \| 3 baths \| 2,462 sq.ft.	$500,000	Airbnb cash on cash: 9.6% Traditional cash on cash: 3.81% Airbnb Rental Income: $7349 Traditional Rental Income: $3225 Airbnb ROI: 9.6% Traditional ROI: 3.81%
2228 Parrot Fish Dr HOLIDAY, FL Beautiful Must See Home. HIgh & Dry Villa with No Flood, No CDD. The Open Concept with a M...	3 beds \| 2 baths \| 1,876 sq.ft.	$319,900	Airbnb cash on cash: 9.76% Traditional cash on cash: 5.2% Airbnb Rental Income: $4955 Traditional Rental Income: $2570 Airbnb ROI: 9.76% Traditional ROI: 5.2%
3103 Bright Dr HOLIDAY, FL Dreaming of being on Holiday, EVERYDAY? Well your search is over and welcome to your new h...	2 beds \| 2 baths \| 1,457 sq.ft.	$328,950	Airbnb cash on cash: 6.86% Traditional cash on cash: 5.32% Airbnb Rental Income: $3690 Traditional Rental Income: $2410 Airbnb ROI: 6.86% Traditional ROI: 5.32%
2401 Sand Bay Dr HOLIDAY, FL CUSTOM DREAM HOME w/ Fabulous View of Gulf of Mexico! Fully-Updated, Contemporary, w/ Hig...	4 beds \| 3 baths \| 2,451 sq.ft.	$629,999	Airbnb cash on cash: 8.06% Traditional cash on cash: 0.89% Airbnb Rental Income: $7349 Traditional Rental Income: $1720 Airbnb ROI: 8.06% Traditional ROI: 0.89%
2125 Barracuda Ct HOLIDAY, FL Maintenance Free living, 3-Bedrooms 2.5-Bathrooms, Modern Upgrades Galore Step into a h...	3 beds \| 2 baths \| 1,740 sq.ft.	$342,000	Airbnb cash on cash: 8.79% Traditional cash on cash: 3.67% Airbnb Rental Income: $4955 Traditional Rental Income: $2298 Airbnb ROI: 8.79% Traditional ROI: 3.67%
2945 Wood Pointe Dr 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%
2817 Plantain Dr 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%
3249 Merita Dr HOLIDAY, FL Excellent opportunity to own this charming renovated 2 bed 2 full bath home in Holiday Lak...	2 beds \| 2 baths \| 1,120 sq.ft.	$263,000	Airbnb cash on cash: 9.7% Traditional cash on cash: 5.34% Airbnb Rental Income: $3690 Traditional Rental Income: $1803 Airbnb ROI: 9.7% Traditional ROI: 5.34%
4301 Westwood Dr HOLIDAY, FL Adorable 2 bedrooms 2 bathrooms 1 car garage home in Holiday. This true split home has be...	2 beds \| 1 baths \| 1,259 sq.ft.	$299,900	Airbnb cash on cash: 8.72% Traditional cash on cash: 4.48% Airbnb Rental Income: $3690 Traditional Rental Income: $1688 Airbnb ROI: 8.72% Traditional ROI: 4.48%
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.	$369,900	Airbnb cash on cash: 8.45% Traditional cash on cash: 5.51% Airbnb Rental Income: $4955 Traditional Rental Income: $2922 Airbnb ROI: 8.45% Traditional ROI: 5.51%
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: 7.69% Traditional cash on cash: 4.61% Airbnb Rental Income: $3690 Traditional Rental Income: $2018 Airbnb ROI: 7.69% Traditional ROI: 4.61%
3409 Springfield Dr HOLIDAY, FL Beautiful Pool Home in Beacon Square !! Just Reduced by $14,900, Come and See!! Lovely set...	2 beds \| 2 baths \| 1,519 sq.ft.	$335,000	Airbnb cash on cash: 6.61% Traditional cash on cash: 3.73% Airbnb Rental Income: $3690 Traditional Rental Income: $1979 Airbnb ROI: 6.61% Traditional ROI: 3.73%
3000 Jacob Crossing Ln HOLIDAY, FL FLOOD ZONE X (Per FEMA LOMA letter) STUNNING TOWNHOME with soaring ceilings, ample storage...	3 beds \| 2 baths \| 1,813 sq.ft.	$319,000	Airbnb cash on cash: 9.16% Traditional cash on cash: 2.95% Airbnb Rental Income: $4955 Traditional Rental Income: $2078 Airbnb ROI: 9.16% Traditional ROI: 2.95%
2614 Hawk Roost Ct HOLIDAY, FL Under contract-accepting backup offers. (MOTIVATED SELLER) Immaculate Move-In Ready Home i...	3 beds \| 2 baths \| 2,620 sq.ft.	$415,000	Airbnb cash on cash: 6.74% Traditional cash on cash: 4.5% Airbnb Rental Income: $4955 Traditional Rental Income: $3070 Airbnb ROI: 6.74% Traditional ROI: 4.5%
2651 San Luis Rd HOLIDAY, FL This waterfront home on Lake Conley features a spacious custom deck along the water and a ...	3 beds \| 2 baths \| 1,301 sq.ft.	$390,000	Airbnb cash on cash: 9.01% Traditional cash on cash: 5.41% Airbnb Rental Income: $4955 Traditional Rental Income: $2622 Airbnb ROI: 9.01% Traditional ROI: 5.41%
2211 Barracuda Ct 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%
1027 Orca Ct HOLIDAY, FL Experience the best of coastal living in this spacious, maintenance-free villa just minute...	3 beds \| 2 baths \| 1,876 sq.ft.	$330,000	Airbnb cash on cash: 8.6% Traditional cash on cash: 3.41% Airbnb Rental Income: $4955 Traditional Rental Income: $2330 Airbnb ROI: 8.6% Traditional ROI: 3.41%

Vacation Rentals in Holiday

There are 76 vacation rental properties available for sale in the city of Holiday . The median list price of Airbnb properties available for sale in Holiday is $238,750 and the average price per square foot is $176. 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 76 Airbnb properties available for sale in Holiday.

In May 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

2577 Charlan Ct

HOLIDAY, FL

2 beds | 2 baths | 1,541 sq.ft.

$267,000

Airbnb cash on cash: 8.75%

Traditional cash on cash: 6.62%

Airbnb Rental Income: $3690

Traditional Rental Income: $2350

Airbnb ROI: 8.75%

Traditional ROI: 6.62%

5226 Forum Blvd

HOLIDAY, FL

2 beds | 2 baths | 1,541 sq.ft.

$269,995

Airbnb cash on cash: 7.95%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $3690

Traditional Rental Income: $2126

Airbnb ROI: 7.95%

Traditional ROI: 4.97%

5311 Boardwalk St

HOLIDAY, FL

3 beds | 2 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%

2627 Charlan Ct

HOLIDAY, FL

2 beds | 2 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%

5199 Forum Blvd

HOLIDAY, FL

2 beds | 2 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 Ct

HOLIDAY, FL

3 beds | 2 baths | 2,284 sq.ft.

$449,000

Airbnb cash on cash: 7.57%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $4955

Traditional Rental Income: $3256

Airbnb ROI: 7.57%

Traditional ROI: 5.94%

3036 Blue Bird Dr

HOLIDAY, FL

2 beds | 2 baths | 1,454 sq.ft.

$249,900

Airbnb cash on cash: 9.95%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $3690

Traditional Rental Income: $2166

Airbnb ROI: 9.95%

Traditional ROI: 6.9%

Flotilla

HOLIDAY, FL

N/A beds | N/A baths | N/A

$799,000

Airbnb cash on cash: 3.84%

Traditional cash on cash: 2.59%

Airbnb Rental Income: $2278

Traditional Rental Income: $1356

Airbnb ROI: 3.84%