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.	$1,195,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2504 Airbnb ROI: 1.66% Traditional ROI: 0.29%
38 S Pollard St Oakland, FL 38 S Pollard St, Oakland, FL 34760 \| Single Family Residential	4 beds \| 2 baths \| 1,872 sq.ft.	$659,999	Airbnb cash on cash: 4.51% Traditional cash on cash: 1.99% Airbnb Rental Income: $5064 Traditional Rental Income: $2480 Airbnb ROI: 4.51% Traditional ROI: 1.99%
100 Mather Smith Dr Oakland, FL 100 Mather Smith Dr, Oakland, FL 34760 \| Single Family Residential	3 beds \| 2 baths \| 1,571 sq.ft.	$598,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 2.01% Airbnb Rental Income: $3912 Traditional Rental Income: $2270 Airbnb ROI: 3.45% Traditional ROI: 2.01%
729 Strihal Loop Oakland, FL One or more photo(s) has been virtually staged. Once-in-a-Lifetime Opportunity! *EXTERIO...	4 beds \| 3 baths \| 3,583 sq.ft.	$679,900	Airbnb cash on cash: 4.41% Traditional cash on cash: 4.36% Airbnb Rental Income: $5064 Traditional Rental Income: $4002 Airbnb ROI: 4.41% Traditional ROI: 4.36%
2120 GOPHER TORTOISE TERRACE Oakland, FL Welcome to 2120 Gopher Tortoise Terrace in charming Oakland, Florida, a beautifully mainta...	3 beds \| 3 baths \| 1,620 sq.ft.	$379,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 3.81% Airbnb Rental Income: $3912 Traditional Rental Income: $2653 Airbnb ROI: 4.98% Traditional ROI: 3.81%
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.	$549,900	Airbnb cash on cash: 3.58% Traditional cash on cash: 3.21% Airbnb Rental Income: $3912 Traditional Rental Income: $2879 Airbnb ROI: 3.58% Traditional ROI: 3.21%
624 Hull Island Dr Oakland, FL 624 Hull Island Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 2,708 sq.ft.	$849,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 2.25% Airbnb Rental Income: $5064 Traditional Rental Income: $3361 Airbnb ROI: 3.1% Traditional ROI: 2.25%
6230 Sunny Time Ave Oakland, FL 6230 Sunny Time Ave, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,770 sq.ft.	$496,690	Airbnb cash on cash: 4.53% Traditional cash on cash: 2.46% Airbnb Rental Income: $3912 Traditional Rental Income: $2109 Airbnb ROI: 4.53% Traditional ROI: 2.46%
13861 Easdale Aly Oakland, FL 13861 Easdale Aly, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 2,036 sq.ft.	$559,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.29% Airbnb Rental Income: $3912 Traditional Rental Income: $2274 Airbnb ROI: 3.82% Traditional ROI: 2.29%
13877 Easdale Aly Oakland, FL 13877 Easdale Aly, Oakland, FL 34787 \| Townhouse	4 beds \| 4 baths \| 2,593 sq.ft.	$629,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 3.12% Airbnb Rental Income: $5064 Traditional Rental Income: $3029 Airbnb ROI: 4.82% Traditional ROI: 3.12%
1270 Stationside Drive Dr Oakland, FL 1270 Stationside Drive Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 2,046 sq.ft.	$519,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $2126 Airbnb ROI: 6.17% Traditional ROI: 2.24%
1156 CIVITAS WAY Oakland, FL Motivated seller!! Experience luxury in this immaculate 2022 custom RCB home, featuring hi...	4 beds \| 3 baths \| 2,710 sq.ft.	$1,268,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 0.69% Airbnb Rental Income: $5064 Traditional Rental Income: $3349 Airbnb ROI: 1.27% Traditional ROI: 0.69%
2228 Gopher Tortoise Ter Oakland, FL 2228 Gopher Tortoise Ter, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,620 sq.ft.	$395,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 1.97% Airbnb Rental Income: $3912 Traditional Rental Income: $1994 Airbnb ROI: 4.88% Traditional ROI: 1.97%
2222 GOPHER TORTOISE TERRACE Oakland, FL YOU Must see this absolutely Gorgeous 3BEDS,3 FULL BATH Townhouse in Oakland. located Betw...	3 beds \| 3 baths \| 1,809 sq.ft.	$416,900	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.51% Airbnb Rental Income: $3912 Traditional Rental Income: $2831 Airbnb ROI: 4.13% Traditional ROI: 3.51%
14736 Field Daisy Dr Oakland, FL 14736 Field Daisy Dr, Oakland, FL 34787 \| Single Family Residential	3 beds \| 3 baths \| 2,149 sq.ft.	$550,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.4% Airbnb Rental Income: $3912 Traditional Rental Income: $2549 Airbnb ROI: 3.42% Traditional ROI: 2.4%
14780 Field Daisy Dr Oakland, FL 14780 Field Daisy Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 2,441 sq.ft.	$700,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 2.05% Airbnb Rental Income: $5064 Traditional Rental Income: $2917 Airbnb ROI: 3.76% Traditional ROI: 2.05%
1412 Johns Cove Ln Oakland, FL 1412 Johns Cove Ln, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 3,613 sq.ft.	$1,499,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 0.48% Airbnb Rental Income: $5064 Traditional Rental Income: $3584 Airbnb ROI: 0.81% Traditional ROI: 0.48%
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.	$364,900	Airbnb cash on cash: 3.64% Traditional cash on cash: 2.11% Airbnb Rental Income: $3176 Traditional Rental Income: $1936 Airbnb ROI: 3.64% Traditional ROI: 2.11%
2017 BOSS HEWETT STREET Oakland, FL One or more photo(s) has been virtually staged. This meticulously maintained 2,852 sq ft, ...	4 beds \| 4 baths \| 2,852 sq.ft.	$749,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.54% Airbnb Rental Income: $5064 Traditional Rental Income: $3586 Airbnb ROI: 3.17% Traditional ROI: 2.54%
918 Hull Island Dr Oakland, FL 918 Hull Island Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 3 baths \| 2,268 sq.ft.	$729,900	Airbnb cash on cash: 3.63% Traditional cash on cash: 1.42% Airbnb Rental Income: $5064 Traditional Rental Income: $2527 Airbnb ROI: 3.63% Traditional ROI: 1.42%
14788 Field Daisy Dr Oakland, FL 14788 Field Daisy Dr, Oakland, FL 34787 \| Single Family Residential	3 beds \| 3 baths \| 1,992 sq.ft.	$617,500	Airbnb cash on cash: 2.84% Traditional cash on cash: 1.79% Airbnb Rental Income: $3912 Traditional Rental Income: $2463 Airbnb ROI: 2.84% Traditional ROI: 1.79%
6234 Sunny Time Ave Oakland, FL 6234 Sunny Time Ave, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,553 sq.ft.	$445,490	Airbnb cash on cash: 5.26% Traditional cash on cash: 2.59% Airbnb Rental Income: $3912 Traditional Rental Income: $1958 Airbnb ROI: 5.26% Traditional ROI: 2.59%
6246 Sunny Time Ave Oakland, FL 6246 Sunny Time Ave, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,553 sq.ft.	$446,490	Airbnb cash on cash: 5.24% Traditional cash on cash: 3.46% Airbnb Rental Income: $3912 Traditional Rental Income: $2325 Airbnb ROI: 5.24% Traditional ROI: 3.46%
6238 Sunny Time Ave Oakland, FL 6238 Sunny Time Ave, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,683 sq.ft.	$453,890	Airbnb cash on cash: 5.12% Traditional cash on cash: 2.73% Airbnb Rental Income: $3912 Traditional Rental Income: $2052 Airbnb ROI: 5.12% Traditional ROI: 2.73%
2618 BOBCAT CHASE BOULEVARD Oakland, FL Welcome to this beautiful 3 bedroom, 2 bath home featuring 1,565 square feet of inviting l...	3 beds \| 2 baths \| 1,565 sq.ft.	$519,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 1.44% Airbnb Rental Income: $3912 Traditional Rental Income: $2214 Airbnb ROI: 3.21% Traditional ROI: 1.44%

Vacation Rentals in Oakland

There are 26 vacation rental properties available for sale in the city of Oakland . The median list price of Airbnb properties available for sale in Oakland is $675,000 and the average price per square foot is $380. The cash on cash return on vacation rentals in Oakland is 4.00%. The average monthly short term rental income in Oakland is $3,912.

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

There are 26 Airbnb properties available for sale in Oakland.

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

In May 2026, the average Airbnb occupancy rate in Oakland is 72%.

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.

$1,195,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $5064

Traditional Rental Income: $2504

Airbnb ROI: 1.66%

Traditional ROI: 0.29%

38 S Pollard St

Oakland, FL

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

$659,999

Airbnb cash on cash: 4.51%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $5064

Traditional Rental Income: $2480

Airbnb ROI: 4.51%

Traditional ROI: 1.99%

100 Mather Smith Dr

Oakland, FL

3 beds | 2 baths | 1,571 sq.ft.

$598,000

Airbnb cash on cash: 3.45%

Traditional cash on cash: 2.01%

Airbnb Rental Income: $3912

Traditional Rental Income: $2270

Airbnb ROI: 3.45%

Traditional ROI: 2.01%

729 Strihal Loop

Oakland, FL

4 beds | 3 baths | 3,583 sq.ft.

$679,900

Airbnb cash on cash: 4.41%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $5064

Traditional Rental Income: $4002

Airbnb ROI: 4.41%

Traditional ROI: 4.36%

2120 GOPHER TORTOISE TERRACE

Oakland, FL

3 beds | 3 baths | 1,620 sq.ft.

$379,900

Airbnb cash on cash: 4.98%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $3912

Traditional Rental Income: $2653

Airbnb ROI: 4.98%

Traditional ROI: 3.81%

2065 White Feather Loop

Oakland, FL

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

$549,900

Airbnb cash on cash: 3.58%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $3912

Traditional Rental Income: $2879

Airbnb ROI: 3.58%

Traditional ROI: 3.21%

624 Hull Island Dr

Oakland, FL

4 beds | 2 baths | 2,708 sq.ft.

$849,000

Airbnb cash on cash: 3.1%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $5064

Traditional Rental Income: $3361

Airbnb ROI: 3.1%

Traditional ROI: 2.25%

6230 Sunny Time Ave

Oakland, FL

3 beds | 2 baths | 1,770 sq.ft.

$496,690

Airbnb cash on cash: 4.53%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $3912

Traditional Rental Income: $2109

Airbnb ROI: 4.53%