Airbnb Properties for Sale in Oakland, FL

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

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

Airbnb For Sale in Oakland, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
250 N Walker St Oakland, FL 250 N Walker St, Oakland, FL 34760 \| Single Family Residential	4 beds \| 2 baths \| 2,469 sq.ft.	$1,049,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 0.59% Airbnb Rental Income: $5064 Traditional Rental Income: $2504 Airbnb ROI: 2.15% Traditional ROI: 0.59%
38 S Pollard St Oakland, FL 38 S Pollard St, Oakland, FL 34760 \| Single Family Residential	4 beds \| 2 baths \| 1,872 sq.ft.	$619,999	Airbnb cash on cash: 4.92% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $2480 Airbnb ROI: 4.92% Traditional ROI: 2.24%
521 W Herriott Ave Oakland, FL Virtually Staged. Welcome to this brand-new construction home in the heart of Oakland! Thi...	3 beds \| 2 baths \| 1,170 sq.ft.	$415,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 3.82% Airbnb Rental Income: $3781 Traditional Rental Income: $2046 Airbnb ROI: 6.17% Traditional ROI: 3.82%
239 Largovista Dr Oakland, FL MASSIVE PRICE PRICE ADJUSTMENT. SELLER VERY MOTIVATED. They are ready to negotiate Today!....	4 beds \| 2 baths \| 3,652 sq.ft.	$675,900	Airbnb cash on cash: 4.55% Traditional cash on cash: 2.21% Airbnb Rental Income: $5064 Traditional Rental Income: $2557 Airbnb ROI: 4.55% Traditional ROI: 2.21%
1750 Standing Rock Cir Oakland, FL Welcome to this energy efficient two story home built in 2020, ideally located in the high...	4 beds \| 2 baths \| 2,614 sq.ft.	$640,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $2921 Airbnb ROI: 4.1% Traditional ROI: 2.24%
2259 White Feather Loop Oakland, FL ABSOLUTELY STUNNING 4/2.5 PLUS LOFT HOME LOCATED ON A CORNER LOT IN OAKLAND TRAILS. UPON E...	4 beds \| 2 baths \| 2,204 sq.ft.	$515,000	Airbnb cash on cash: 6.14% Traditional cash on cash: 2.75% Airbnb Rental Income: $5064 Traditional Rental Income: $2402 Airbnb ROI: 6.14% Traditional ROI: 2.75%
166 Hammock Preserve Loop Oakland, FL Pre-Construction. To be built. To be built. AR Homes (Arthur Rutenberg Homes) , a renowned...	4 beds \| 4 baths \| 3,186 sq.ft.	$850,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 3.55% Airbnb Rental Income: $5064 Traditional Rental Income: $4006 Airbnb ROI: 3.58% Traditional ROI: 3.55%
223 Largovista Dr Oakland, FL This beautiful 4-bedroom, 2.5-bath home offers plenty of space, both inside and out, makin...	4 beds \| 2 baths \| 2,486 sq.ft.	$540,000	Airbnb cash on cash: 5.4% Traditional cash on cash: 2.75% Airbnb Rental Income: $5064 Traditional Rental Income: $2698 Airbnb ROI: 5.4% Traditional ROI: 2.75%
2017 Boss Hewett St Oakland, FL Virtually Staged. Enjoy single-level living in lakefront Hull Island in this meticulously ...	4 beds \| 4 baths \| 2,852 sq.ft.	$689,900	Airbnb cash on cash: 3.53% Traditional cash on cash: 2.84% Airbnb Rental Income: $5064 Traditional Rental Income: $3586 Airbnb ROI: 3.53% Traditional ROI: 2.84%
2241 White Feather Loop Oakland, FL 2241 White Feather Loop, Oakland, FL 34787 \| Single Family Residential	3 beds \| 2 baths \| 2,152 sq.ft.	$525,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 2.34% Airbnb Rental Income: $3781 Traditional Rental Income: $2284 Airbnb ROI: 3.73% Traditional ROI: 2.34%
2471 Sky Stone Ct Oakland, FL 2471 Sky Stone Ct, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 2,854 sq.ft.	$559,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 4.88% Airbnb Rental Income: $5064 Traditional Rental Income: $3742 Airbnb ROI: 5.43% Traditional ROI: 4.88%
1808 WESTERN TRAILWAY Drive Oakland, FL JUST REDUCED $30,000! EXCEPTIONAL VALUE in the Sought-After Hull Island Community! If you'...	3 beds \| 2 baths \| 1,860 sq.ft.	$559,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 1.12% Airbnb Rental Income: $3781 Traditional Rental Income: $2163 Airbnb ROI: 2.65% Traditional ROI: 1.12%

Vacation Rentals in Oakland

There are 13 vacation rental properties available for sale in the city of Oakland . The median list price of Airbnb properties available for sale in Oakland is $682,592 and the average price per square foot is $334. The cash on cash return on vacation rentals in Oakland is -1.00%. The average monthly short term rental income in Oakland is $1,240.

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

There are 13 Airbnb properties available for sale in Oakland.

In 2026, the best neighborhood to buy short term rental property is Oakland.

In September 2026, the average Airbnb occupancy rate in Oakland is 32%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Oakland, FL

250 N Walker St

Oakland, FL

4 beds | 2 baths | 2,469 sq.ft.

$1,049,000

Airbnb cash on cash: 2.15%

Traditional cash on cash: 0.59%

Airbnb Rental Income: $5064

Traditional Rental Income: $2504

Airbnb ROI: 2.15%

Traditional ROI: 0.59%

38 S Pollard St

Oakland, FL

4 beds | 2 baths | 1,872 sq.ft.

$619,999

Airbnb cash on cash: 4.92%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $5064

Traditional Rental Income: $2480

Airbnb ROI: 4.92%

Traditional ROI: 2.24%

521 W Herriott Ave

Oakland, FL

3 beds | 2 baths | 1,170 sq.ft.

$415,000

Airbnb cash on cash: 6.17%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $3781

Traditional Rental Income: $2046

Airbnb ROI: 6.17%

Traditional ROI: 3.82%

239 Largovista Dr

Oakland, FL

4 beds | 2 baths | 3,652 sq.ft.

$675,900

Airbnb cash on cash: 4.55%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $5064

Traditional Rental Income: $2557

Airbnb ROI: 4.55%

Traditional ROI: 2.21%

1750 Standing Rock Cir

Oakland, FL

4 beds | 2 baths | 2,614 sq.ft.

$640,000

Airbnb cash on cash: 4.1%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $5064

Traditional Rental Income: $2921

Airbnb ROI: 4.1%

Traditional ROI: 2.24%

2259 White Feather Loop

Oakland, FL

4 beds | 2 baths | 2,204 sq.ft.

$515,000

Airbnb cash on cash: 6.14%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $5064

Traditional Rental Income: $2402

Airbnb ROI: 6.14%

Traditional ROI: 2.75%

166 Hammock Preserve Loop

Oakland, FL

4 beds | 4 baths | 3,186 sq.ft.

$850,000

Airbnb cash on cash: 3.58%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $5064

Traditional Rental Income: $4006

Airbnb ROI: 3.58%

Traditional ROI: 3.55%

223 Largovista Dr

Oakland, FL

4 beds | 2 baths | 2,486 sq.ft.

$540,000

Airbnb cash on cash: 5.4%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $5064

Traditional Rental Income: $2698

Airbnb ROI: 5.4%