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
507 W OAKLAND AVENUE Oakland, FL One or more photo(s) has been virtually staged. One or more photo(s) has been virtually st...	3 beds \| 2 baths \| 1,338 sq.ft.	$364,900	Airbnb cash on cash: 6.69% Traditional cash on cash: 4.49% Airbnb Rental Income: $3912 Traditional Rental Income: $2319 Airbnb ROI: 6.69% Traditional ROI: 4.49%
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.	$649,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 3.98% Airbnb Rental Income: $5064 Traditional Rental Income: $3592 Airbnb ROI: 4.7% Traditional ROI: 3.98%
717 Strihal Loop Oakland, FL Welcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath resi...	4 beds \| 2 baths \| 2,065 sq.ft.	$480,000	Airbnb cash on cash: 7.01% Traditional cash on cash: 3.74% Airbnb Rental Income: $5064 Traditional Rental Income: $2561 Airbnb ROI: 7.01% Traditional ROI: 3.74%
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.	$560,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 3.06% Airbnb Rental Income: $3912 Traditional Rental Income: $2844 Airbnb ROI: 3.5% Traditional ROI: 3.06%
2135 Standing Rock Cir Oakland, FL ASSUMABLE 2.4% Interest Rate. Welcome to this beautifully appointed single-family home ...	3 beds \| 2 baths \| 2,078 sq.ft.	$474,990	Airbnb cash on cash: 4.45% Traditional cash on cash: 3.72% Airbnb Rental Income: $3912 Traditional Rental Income: $2746 Airbnb ROI: 4.45% Traditional ROI: 3.72%
2755 BOBCAT CHASE BOULEVARD Oakland, FL Under contract-accepting backup offers. Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedr...	3 beds \| 3 baths \| 1,822 sq.ft.	$495,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 2.73% Airbnb Rental Income: $3912 Traditional Rental Income: $2583 Airbnb ROI: 3.79% Traditional ROI: 2.73%
2090 STANDING ROCK CIRCLE Oakland, FL Under contract-accepting backup offers. Price reduced to $585,000 on this Stunning Home in...	3 beds \| 3 baths \| 2,010 sq.ft.	$585,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 3.06% Airbnb Rental Income: $3912 Traditional Rental Income: $2777 Airbnb ROI: 3.6% Traditional ROI: 3.06%
326 LARGOVISTA DRIVE Oakland, FL Under contract-accepting backup offers. Welcome to your dream home in the highly sought-af...	4 beds \| 3 baths \| 3,182 sq.ft.	$649,600	Airbnb cash on cash: 4.05% Traditional cash on cash: 3.22% Airbnb Rental Income: $5064 Traditional Rental Income: $3527 Airbnb ROI: 4.05% Traditional ROI: 3.22%

Vacation Rentals in Oakland

There are 21 vacation rental properties available for sale in the city of Oakland . The median list price of Airbnb properties available for sale in Oakland is $667,500 and the average price per square foot is $399. 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 21 Airbnb properties available for sale in Oakland.

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

In February 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

507 W OAKLAND AVENUE

Oakland, FL

3 beds | 2 baths | 1,338 sq.ft.

$364,900

Airbnb cash on cash: 6.69%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $3912

Traditional Rental Income: $2319

Airbnb ROI: 6.69%

Traditional ROI: 4.49%

529 Johns Landing Way

Oakland, FL

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

$649,000

Airbnb cash on cash: 4.7%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $5064

Traditional Rental Income: $3592

Airbnb ROI: 4.7%

Traditional ROI: 3.98%

717 Strihal Loop

Oakland, FL

4 beds | 2 baths | 2,065 sq.ft.

$480,000

Airbnb cash on cash: 7.01%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $5064

Traditional Rental Income: $2561

Airbnb ROI: 7.01%

Traditional ROI: 3.74%

2065 White Feather Loop

Oakland, FL

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

$560,000

Airbnb cash on cash: 3.5%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3912

Traditional Rental Income: $2844

Airbnb ROI: 3.5%

Traditional ROI: 3.06%

2135 Standing Rock Cir

Oakland, FL

3 beds | 2 baths | 2,078 sq.ft.

$474,990

Airbnb cash on cash: 4.45%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $3912

Traditional Rental Income: $2746

Airbnb ROI: 4.45%

Traditional ROI: 3.72%

2755 BOBCAT CHASE BOULEVARD

Oakland, FL

3 beds | 3 baths | 1,822 sq.ft.

$495,000

Airbnb cash on cash: 3.79%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $3912

Traditional Rental Income: $2583

Airbnb ROI: 3.79%

Traditional ROI: 2.73%

2090 STANDING ROCK CIRCLE

Oakland, FL

3 beds | 3 baths | 2,010 sq.ft.

$585,000

Airbnb cash on cash: 3.6%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3912

Traditional Rental Income: $2777

Airbnb ROI: 3.6%

Traditional ROI: 3.06%

326 LARGOVISTA DRIVE

Oakland, FL

4 beds | 3 baths | 3,182 sq.ft.

$649,600

Airbnb cash on cash: 4.05%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $5064

Traditional Rental Income: $3527

Airbnb ROI: 4.05%