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
410 W Gulley Ave Oakland, FL 410 W Gulley Ave, Oakland, FL 34760 \| Other	N/A beds \| N/A baths \| N/A	$800,000	Airbnb cash on cash: 0.94% Traditional cash on cash: -0.33% Airbnb Rental Income: $2867 Traditional Rental Income: $1250 Airbnb ROI: 0.94% Traditional ROI: -0.33%
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.	$619,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 2.25% Airbnb Rental Income: $5064 Traditional Rental Income: $2480 Airbnb ROI: 4.93% Traditional ROI: 2.25%
137 Petris Ave Oakland, FL 137 Petris Ave, Oakland, FL 34760 \| Single Family Residential	4 beds \| 3 baths \| 3,620 sq.ft.	$1,495,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 0.17% Airbnb Rental Income: $5064 Traditional Rental Income: $2951 Airbnb ROI: 0.95% Traditional ROI: 0.17%
81 Millholland St Oakland, FL 81 Millholland St, Oakland, FL 34760 \| Single Family Residential	3 beds \| 3 baths \| 3,887 sq.ft.	$1,275,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.29% Airbnb Rental Income: $4035 Traditional Rental Income: $2758 Airbnb ROI: 0.64% Traditional ROI: 0.29%
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%
1511 Sweet Apple St Oakland, FL Buyer backed out to allow you an opportunity - Welcome home to this beautiful 3 bed, 2.5 b...	3 beds \| 2 baths \| 1,620 sq.ft.	$364,500	Airbnb cash on cash: 5.69% Traditional cash on cash: 2.67% Airbnb Rental Income: $4035 Traditional Rental Income: $2139 Airbnb ROI: 5.69% Traditional ROI: 2.67%
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: 3.57% Traditional cash on cash: 3.53% Airbnb Rental Income: $5064 Traditional Rental Income: $4006 Airbnb ROI: 3.57% Traditional ROI: 3.53%
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%
13861 Easdale Aly Oakland, FL 13861 Easdale Aly, Oakland, FL 34787 \| Townhouse	4 beds \| 3 baths \| 2,031 sq.ft.	$499,000	Airbnb cash on cash: 6.2% Traditional cash on cash: 2.43% Airbnb Rental Income: $5064 Traditional Rental Income: $2274 Airbnb ROI: 6.2% Traditional ROI: 2.43%
14780 Field Daisy Dr Oakland, FL 14780 Field Daisy Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 2,441 sq.ft.	$653,118	Airbnb cash on cash: 4.16% Traditional cash on cash: 2.33% Airbnb Rental Income: $5064 Traditional Rental Income: $2917 Airbnb ROI: 4.16% Traditional ROI: 2.33%
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.	$679,900	Airbnb cash on cash: 3.6% Traditional cash on cash: 2.9% Airbnb Rental Income: $5064 Traditional Rental Income: $3586 Airbnb ROI: 3.6% Traditional ROI: 2.9%
12788 Sunset Walk Dr Oakland, FL 161 Sunset Walk Dr, Winter Garden, FL 34787 \| Townhouse	4 beds \| 3 baths \| 2,031 sq.ft.	$509,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 2.81% Airbnb Rental Income: $5064 Traditional Rental Income: $2493 Airbnb ROI: 6.04% Traditional ROI: 2.81%
2241 White Feather Loop Oakland, FL 2241 White Feather Loop, Oakland, FL 34787 \| Single Family Residential	3 beds \| 2 baths \| 2,152 sq.ft.	$510,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 2.47% Airbnb Rental Income: $4035 Traditional Rental Income: $2284 Airbnb ROI: 4.33% Traditional ROI: 2.47%
16681 Silver Brook Way Oakland, FL 16681 Silver Brook Way, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 1,896 sq.ft.	$539,790	Airbnb cash on cash: 5.59% Traditional cash on cash: 1.81% Airbnb Rental Income: $5064 Traditional Rental Income: $2125 Airbnb ROI: 5.59% Traditional ROI: 1.81%
7324 Windy Willow St Oakland, FL 7324 Windy Willow St, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,697 sq.ft.	$481,680	Airbnb cash on cash: 4.95% Traditional cash on cash: 2.42% Airbnb Rental Income: $4035 Traditional Rental Income: $2030 Airbnb ROI: 4.95% Traditional ROI: 2.42%
6174 Whispering Gln Oakland, FL 6174 Whispering Gln, Oakland, FL 34787 \| Single Family Residential	3 beds \| 2 baths \| 1,628 sq.ft.	$516,290	Airbnb cash on cash: 4.15% Traditional cash on cash: 1.71% Airbnb Rental Income: $4035 Traditional Rental Income: $1996 Airbnb ROI: 4.15% Traditional ROI: 1.71%
12776 Sunset Walk Dr Oakland, FL 12776 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	4 beds \| 4 baths \| 2,593 sq.ft.	$660,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 2.02% Airbnb Rental Income: $5064 Traditional Rental Income: $2662 Airbnb ROI: 4.24% Traditional ROI: 2.02%
12808 Sunset Walk Dr Oakland, FL 12808 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	4 beds \| 3 baths \| 1,897 sq.ft.	$539,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 2.26% Airbnb Rental Income: $5064 Traditional Rental Income: $2347 Airbnb ROI: 5.6% Traditional ROI: 2.26%
12732 Sunset Walk Dr Oakland, FL 12732 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	4 beds \| 4 baths \| 2,593 sq.ft.	$569,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 3.16% Airbnb Rental Income: $5064 Traditional Rental Income: $2942 Airbnb ROI: 5.21% Traditional ROI: 3.16%
7340 Windy Willow St Oakland, FL 7340 Windy Willow St, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,772 sq.ft.	$488,920	Airbnb cash on cash: 4.85% Traditional cash on cash: 2.48% Airbnb Rental Income: $4035 Traditional Rental Income: $2087 Airbnb ROI: 4.85% Traditional ROI: 2.48%
12830 Sunset Walk Dr Oakland, FL 12830 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,857 sq.ft.	$471,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 2.41% Airbnb Rental Income: $4035 Traditional Rental Income: $2151 Airbnb ROI: 4.73% Traditional ROI: 2.41%
7332 Windy Willow St Oakland, FL 7332 Windy Willow St, Oakland, FL 34787 \| Townhouse	3 beds \| 3 baths \| 1,764 sq.ft.	$482,453	Airbnb cash on cash: 4.94% Traditional cash on cash: 2.53% Airbnb Rental Income: $4035 Traditional Rental Income: $2086 Airbnb ROI: 4.94% Traditional ROI: 2.53%
14784 Field Daisy Dr Oakland, FL 14784 Field Daisy Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 2,841 sq.ft.	$635,699	Airbnb cash on cash: 4.33% Traditional cash on cash: 2.68% Airbnb Rental Income: $5064 Traditional Rental Income: $3056 Airbnb ROI: 4.33% Traditional ROI: 2.68%
12800 Sunset Walk Dr Oakland, FL 12800 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	3 beds \| 3 baths \| 2,363 sq.ft.	$605,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 1.78% Airbnb Rental Income: $4035 Traditional Rental Income: $2328 Airbnb ROI: 3.27% Traditional ROI: 1.78%
16803 Evermore Aly Oakland, FL 16803 Evermore Aly, Oakland, FL 34787 \| Single Family Residential	3 beds \| 2 baths \| 1,896 sq.ft.	$537,290	Airbnb cash on cash: 3.92% Traditional cash on cash: 1.91% Airbnb Rental Income: $4035 Traditional Rental Income: $2167 Airbnb ROI: 3.92% Traditional ROI: 1.91%
12792 Sunset Walk Dr Oakland, FL 12792 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	4 beds \| 3 baths \| 1,930 sq.ft.	$506,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 2.54% Airbnb Rental Income: $5064 Traditional Rental Income: $2352 Airbnb ROI: 6.09% Traditional ROI: 2.54%
7276 Windy Willow St Oakland, FL Virtually Staged. Under Construction. The Porter floor plan offers a smartly designed two-...	3 beds \| 2 baths \| 1,764 sq.ft.	$456,213	Airbnb cash on cash: 4.75% Traditional cash on cash: 2.25% Airbnb Rental Income: $4035 Traditional Rental Income: $2108 Airbnb ROI: 4.75% Traditional ROI: 2.25%
7272 Windy Willow St Oakland, FL Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-...	3 beds \| 2 baths \| 1,697 sq.ft.	$483,258	Airbnb cash on cash: 4.38% Traditional cash on cash: 2% Airbnb Rental Income: $4035 Traditional Rental Income: $2099 Airbnb ROI: 4.38% Traditional ROI: 2%
523 Walker St Oakland, FL 523 Walker St, Winter Garden, FL 34787 \| Other	N/A beds \| N/A baths \| N/A	$595,000	Airbnb cash on cash: 1.56% Traditional cash on cash: -0.87% Airbnb Rental Income: $2867 Traditional Rental Income: $852 Airbnb ROI: 1.56% Traditional ROI: -0.87%
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: 2.45% Airbnb Rental Income: $5064 Traditional Rental Income: $2475 Airbnb ROI: 5.43% Traditional ROI: 2.45%
226 Hammock Preserve Loop Oakland, FL 226 Hammock Preserve Loop, Oakland, FL 34787 \| Single Family Residential	4 beds \| 3 baths \| 2,239 sq.ft.	$889,900	Airbnb cash on cash: 2.6% Traditional cash on cash: 0.84% Airbnb Rental Income: $5064 Traditional Rental Income: $2573 Airbnb ROI: 2.6% Traditional ROI: 0.84%
1016 Catori Rd Oakland, FL 1016 Catori Rd, Oakland, FL 34787 \| Single Family Residential	4 beds \| 3 baths \| 3,085 sq.ft.	$825,000	Airbnb cash on cash: 3% Traditional cash on cash: 1.44% Airbnb Rental Income: $5064 Traditional Rental Income: $2832 Airbnb ROI: 3% Traditional ROI: 1.44%
2273 Standing Rock Cir Oakland, FL 2273 Standing Rock Cir, Oakland, FL 34787 \| Single Family Residential	3 beds \| 2 baths \| 2,082 sq.ft.	$479,900	Airbnb cash on cash: 4.72% Traditional cash on cash: 2.8% Airbnb Rental Income: $4035 Traditional Rental Income: $2312 Airbnb ROI: 4.72% Traditional ROI: 2.8%
990 Stationside Dr Oakland, FL 990 Stationside Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 2,028 sq.ft.	$525,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $2149 Airbnb ROI: 6.08% Traditional ROI: 2.24%
2470 Standing Rock Cir Oakland, FL 2470 Standing Rock Cir, Oakland, FL 34787 \| Single Family Residential	4 beds \| 3 baths \| 3,430 sq.ft.	$730,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 1.73% Airbnb Rental Income: $5064 Traditional Rental Income: $2671 Airbnb ROI: 3.73% Traditional ROI: 1.73%

Vacation Rentals in Oakland

There are 41 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 $328. The cash on cash return on vacation rentals in Oakland is 2.00%. The average monthly short term rental income in Oakland is $4,035.

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

There are 41 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 40%.

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

410 W Gulley Ave

Oakland, FL

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

$800,000

Airbnb cash on cash: 0.94%

Traditional cash on cash: -0.33%

Airbnb Rental Income: $2867

Traditional Rental Income: $1250

Airbnb ROI: 0.94%

Traditional ROI: -0.33%

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.

$619,000

Airbnb cash on cash: 4.93%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $5064

Traditional Rental Income: $2480

Airbnb ROI: 4.93%

Traditional ROI: 2.25%

137 Petris Ave

Oakland, FL

4 beds | 3 baths | 3,620 sq.ft.

$1,495,000

Airbnb cash on cash: 0.95%

Traditional cash on cash: 0.17%

Airbnb Rental Income: $5064

Traditional Rental Income: $2951

Airbnb ROI: 0.95%

Traditional ROI: 0.17%

81 Millholland St

Oakland, FL

3 beds | 3 baths | 3,887 sq.ft.

$1,275,000

Airbnb cash on cash: 0.64%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $4035

Traditional Rental Income: $2758

Airbnb ROI: 0.64%

Traditional ROI: 0.29%

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%