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.	$1,125,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 0.42% Airbnb Rental Income: $5064 Traditional Rental Income: $2504 Airbnb ROI: 1.88% Traditional ROI: 0.42%
38 S Pollard St Oakland, FL 38 S Pollard St, Oakland, FL 34760 \| Single Family Residential	4 beds \| 2 baths \| 1,872 sq.ft.	$629,999	Airbnb cash on cash: 4.81% Traditional cash on cash: 2.18% Airbnb Rental Income: $5064 Traditional Rental Income: $2480 Airbnb ROI: 4.81% Traditional ROI: 2.18%
1937 Standing Rock Cir Oakland, FL Oakland Trails is located right on the scenic West Orange Trail and just a bike ride away ...	3 beds \| 2 baths \| 2,069 sq.ft.	$499,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 3.37% Airbnb Rental Income: $4255 Traditional Rental Income: $2779 Airbnb ROI: 4.61% Traditional ROI: 3.37%
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%
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%
529 Johns Landing Way Oakland, FL Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-ba...	4 beds \| 3 baths \| 2,650 sq.ft.	$639,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 4.11% Airbnb Rental Income: $5064 Traditional Rental Income: $3598 Airbnb ROI: 4.84% Traditional ROI: 4.11%
2065 White Feather Loop Oakland, FL Welcome to the highly desirable Oakland Trails community, where this exceptional 2019 Meri...	3 beds \| 2 baths \| 2,089 sq.ft.	$539,900	Airbnb cash on cash: 4.23% Traditional cash on cash: 3.28% Airbnb Rental Income: $4255 Traditional Rental Income: $2879 Airbnb ROI: 4.23% Traditional ROI: 3.28%
13861 Easdale Aly Oakland, FL 13861 Easdale Aly, Oakland, FL 34787 \| Townhouse	4 beds \| 3 baths \| 2,031 sq.ft.	$539,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 2.11% Airbnb Rental Income: $5064 Traditional Rental Income: $2274 Airbnb ROI: 5.6% Traditional ROI: 2.11%
13877 Easdale Aly Oakland, FL 13877 Easdale Aly, Oakland, FL 34787 \| Townhouse	4 beds \| 4 baths \| 2,593 sq.ft.	$615,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 2.94% Airbnb Rental Income: $5064 Traditional Rental Income: $3029 Airbnb ROI: 4.69% Traditional ROI: 2.94%
14780 Field Daisy Dr Oakland, FL 14780 Field Daisy Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 2,441 sq.ft.	$643,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 2.4% Airbnb Rental Income: $5064 Traditional Rental Income: $2917 Airbnb ROI: 4.26% Traditional ROI: 2.4%
1412 Johns Cove Ln Oakland, FL 1412 Johns Cove Ln, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 3,613 sq.ft.	$1,509,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.47% Airbnb Rental Income: $5064 Traditional Rental Income: $3584 Airbnb ROI: 0.79% Traditional ROI: 0.47%
1231 Foltz Loop Oakland, FL 1231 Foltz Loop, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 3,134 sq.ft.	$874,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3036 Airbnb ROI: 2.72% Traditional ROI: 1.5%
2117 Gopher Tortoise Ter Oakland, FL 2117 Gopher Tortoise Ter, Oakland, FL 34787 \| Townhouse	2 beds \| 2 baths \| 1,497 sq.ft.	$350,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 2.28% Airbnb Rental Income: $3127 Traditional Rental Income: $1936 Airbnb ROI: 3.75% Traditional ROI: 2.28%
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.	$699,900	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.79% Airbnb Rental Income: $5064 Traditional Rental Income: $3586 Airbnb ROI: 3.47% Traditional ROI: 2.79%
12788 Sunset Walk Dr Oakland, FL 161 Sunset Walk Dr, Winter Garden, FL 34787 \| Townhouse	4 beds \| 3 baths \| 2,031 sq.ft.	$529,025	Airbnb cash on cash: 5.75% Traditional cash on cash: 2.64% Airbnb Rental Income: $5064 Traditional Rental Income: $2493 Airbnb ROI: 5.75% Traditional ROI: 2.64%
2247 White Feather Loop Oakland, FL Welcome to this exceptional home in the highly sought-after Oakland Trails community! This...	3 beds \| 2 baths \| 1,838 sq.ft.	$457,900	Airbnb cash on cash: 4.86% Traditional cash on cash: 3.07% Airbnb Rental Income: $4255 Traditional Rental Income: $2590 Airbnb ROI: 4.86% Traditional ROI: 3.07%
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: 4.53% Traditional cash on cash: 2.34% Airbnb Rental Income: $4255 Traditional Rental Income: $2284 Airbnb ROI: 4.53% Traditional ROI: 2.34%
17127 Ingram Bluff Dr Oakland, FL Virtually Staged. Under Construction. Sample Images The Anna Maria floor plan is a beautif...	4 beds \| 2 baths \| 2,235 sq.ft.	$721,820	Airbnb cash on cash: 3.72% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $2846 Airbnb ROI: 3.72% Traditional ROI: 1.96%
15997 Honey Harvest St Oakland, FL 15997 Honey Harvest St, Oakland, FL 34787 \| Single Family Residential	4 beds \| 3 baths \| 2,858 sq.ft.	$750,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 1.71% Airbnb Rental Income: $5064 Traditional Rental Income: $2760 Airbnb ROI: 3.53% Traditional ROI: 1.71%
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 \| 1,644 sq.ft.	$484,996	Airbnb cash on cash: 5.31% Traditional cash on cash: 2.39% Airbnb Rental Income: $4255 Traditional Rental Income: $2030 Airbnb ROI: 5.31% Traditional ROI: 2.39%
6174 Whispering Gln Oakland, FL 6174 Whispering Gln, Oakland, FL 34787 \| Single Family Residential	3 beds \| 2 baths \| 1,628 sq.ft.	$518,290	Airbnb cash on cash: 4.5% Traditional cash on cash: 1.7% Airbnb Rental Income: $4255 Traditional Rental Income: $1996 Airbnb ROI: 4.5% Traditional ROI: 1.7%
12776 Sunset Walk Dr Oakland, FL 12776 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	4 beds \| 3 baths \| 2,593 sq.ft.	$593,980	Airbnb cash on cash: 5.22% Traditional cash on cash: 2.75% Airbnb Rental Income: $5064 Traditional Rental Income: $2662 Airbnb ROI: 5.22% Traditional ROI: 2.75%
12808 Sunset Walk Dr Oakland, FL 12808 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	4 beds \| 3 baths \| 1,897 sq.ft.	$495,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 2.63% Airbnb Rental Income: $5064 Traditional Rental Income: $2347 Airbnb ROI: 6.26% Traditional ROI: 2.63%
12732 Sunset Walk Dr Oakland, FL 12732 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	4 beds \| 4 baths \| 2,593 sq.ft.	$649,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.55% Airbnb Rental Income: $5064 Traditional Rental Income: $2942 Airbnb ROI: 4.34% Traditional ROI: 2.55%
7340 Windy Willow St Oakland, FL 7340 Windy Willow St, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,729 sq.ft.	$492,025	Airbnb cash on cash: 5.21% Traditional cash on cash: 2.45% Airbnb Rental Income: $4255 Traditional Rental Income: $2087 Airbnb ROI: 5.21% Traditional ROI: 2.45%
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: 5.14% Traditional cash on cash: 2.41% Airbnb Rental Income: $4255 Traditional Rental Income: $2151 Airbnb ROI: 5.14% Traditional ROI: 2.41%
7332 Windy Willow St Oakland, FL 7332 Windy Willow St, Oakland, FL 34787 \| Townhouse	3 beds \| 3 baths \| 1,715 sq.ft.	$482,819	Airbnb cash on cash: 5.34% Traditional cash on cash: 2.53% Airbnb Rental Income: $4255 Traditional Rental Income: $2086 Airbnb ROI: 5.34% 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.	$690,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.32% Airbnb Rental Income: $5064 Traditional Rental Income: $3056 Airbnb ROI: 3.84% Traditional ROI: 2.32%
12800 Sunset Walk Dr Oakland, FL 12800 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 2,363 sq.ft.	$550,285	Airbnb cash on cash: 4.46% Traditional cash on cash: 2.46% Airbnb Rental Income: $4255 Traditional Rental Income: $2328 Airbnb ROI: 4.46% Traditional ROI: 2.46%
16803 Evermore Aly Oakland, FL 16803 Evermore Aly, Oakland, FL 34787 \| Single Family Residential	3 beds \| 2 baths \| 1,896 sq.ft.	$539,790	Airbnb cash on cash: 4.59% Traditional cash on cash: 2.23% Airbnb Rental Income: $4255 Traditional Rental Income: $2167 Airbnb ROI: 4.59% Traditional ROI: 2.23%
16827 Evermore Aly Oakland, FL 16827 Evermore Aly, Oakland, FL 34787 \| Single Family Residential	3 beds \| 2 baths \| 1,628 sq.ft.	$547,490	Airbnb cash on cash: 4.5% Traditional cash on cash: 1.82% Airbnb Rental Income: $4255 Traditional Rental Income: $1987 Airbnb ROI: 4.5% Traditional ROI: 1.82%
12792 Sunset Walk Dr Oakland, FL 12792 Sunset Walk Dr, Oakland, FL 34787 \| Townhouse	4 beds \| 3 baths \| 1,930 sq.ft.	$527,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 2.37% Airbnb Rental Income: $5064 Traditional Rental Income: $2352 Airbnb ROI: 5.77% Traditional ROI: 2.37%

Vacation Rentals in Oakland

There are 33 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 $344. The cash on cash return on vacation rentals in Oakland is 4.00%. The average monthly short term rental income in Oakland is $5,064.

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

There are 33 Airbnb properties available for sale in Oakland.

In July 2026, the average Airbnb occupancy rate in Oakland is N/A%.

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.

$1,125,000

Airbnb cash on cash: 1.88%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $5064

Traditional Rental Income: $2504

Airbnb ROI: 1.88%

Traditional ROI: 0.42%

38 S Pollard St

Oakland, FL

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

$629,999

Airbnb cash on cash: 4.81%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $5064

Traditional Rental Income: $2480

Airbnb ROI: 4.81%

Traditional ROI: 2.18%

1937 Standing Rock Cir

Oakland, FL

3 beds | 2 baths | 2,069 sq.ft.

$499,000

Airbnb cash on cash: 4.61%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $4255

Traditional Rental Income: $2779

Airbnb ROI: 4.61%

Traditional ROI: 3.37%

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%

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%

Traditional ROI: 2.75%

529 Johns Landing Way

Oakland, FL

4 beds | 3 baths | 2,650 sq.ft.

$639,000

Airbnb cash on cash: 4.84%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $5064

Traditional Rental Income: $3598

Airbnb ROI: 4.84%

Traditional ROI: 4.11%

2065 White Feather Loop

Oakland, FL

3 beds | 2 baths | 2,089 sq.ft.

$539,900

Airbnb cash on cash: 4.23%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $4255

Traditional Rental Income: $2879

Airbnb ROI: 4.23%

Traditional ROI: 3.28%

13861 Easdale Aly

Oakland, FL

4 beds | 3 baths | 2,031 sq.ft.

$539,000

Airbnb cash on cash: 5.6%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $5064

Traditional Rental Income: $2274

Airbnb ROI: 5.6%