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.	$375,000	Airbnb cash on cash: 6.49% Traditional cash on cash: 4.35% Airbnb Rental Income: $3912 Traditional Rental Income: $2319 Airbnb ROI: 6.49% Traditional ROI: 4.35%
1787 WHITE FEATHER LOOP Oakland, FL Under contract-accepting backup offers. **This home qualifies for loan options with NO DOW...	3 beds \| 3 baths \| 2,152 sq.ft.	$525,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 3.25% Airbnb Rental Income: $3912 Traditional Rental Income: $2839 Airbnb ROI: 3.72% Traditional ROI: 3.25%
610 STRIHAL LOOP Oakland, FL *MOTIVATED SELLERS!!! *Donât Miss This One. Welcome home to Johnâs Landing, one o...	4 beds \| 2 baths \| 2,490 sq.ft.	$555,000	Airbnb cash on cash: 5.87% Traditional cash on cash: 3.19% Airbnb Rental Income: $5064 Traditional Rental Income: $2640 Airbnb ROI: 5.87% Traditional ROI: 3.19%
2755 BOBCAT CHASE BOULEVARD Oakland, FL Live just minutes from the charm of Downtown Winter Garden in the desirable Oakland commun...	3 beds \| 3 baths \| 1,822 sq.ft.	$500,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 2.7% Airbnb Rental Income: $3912 Traditional Rental Income: $2583 Airbnb ROI: 3.74% Traditional ROI: 2.7%
2435 STANDING ROCK CIRCLE Oakland, FL Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and...	4 beds \| 3 baths \| 2,017 sq.ft.	$477,500	Airbnb cash on cash: 6.2% Traditional cash on cash: 3.18% Airbnb Rental Income: $5064 Traditional Rental Income: $2685 Airbnb ROI: 6.2% Traditional ROI: 3.18%
2023 WHITE FEATHER LOOP Oakland, FL One or more photo(s) has been virtually staged. Your dream home is waiting for you! This h...	3 beds \| 3 baths \| 2,089 sq.ft.	$455,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.41% Airbnb Rental Income: $3912 Traditional Rental Income: $2766 Airbnb ROI: 4.13% Traditional ROI: 3.41%
2090 STANDING ROCK CIRCLE Oakland, FL Price reduced to $585,000 on this Stunning Home in Oakland Trails! This immaculate 3-bedr...	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 Welcome to your dream home in the highly sought-after Johns Landing community! This immacu...	4 beds \| 3 baths \| 3,182 sq.ft.	$649,900	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%
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.	$675,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 3.84% Airbnb Rental Income: $5064 Traditional Rental Income: $3592 Airbnb ROI: 4.53% Traditional ROI: 3.84%
2690 BOBCAT CHASE BOULEVARD Oakland, FL Love Where You Live â in Longleaf at Oakland! ? Welcome to Longleaf at Oakland, one o...	3 beds \| 2 baths \| 1,554 sq.ft.	$465,000	Airbnb cash on cash: 4.48% Traditional cash on cash: 2.57% Airbnb Rental Income: $3912 Traditional Rental Income: $2241 Airbnb ROI: 4.48% Traditional ROI: 2.57%
2218 GOPHER TORTOISE TERRACE Oakland, FL Enjoy low-maintenance living in this beautifully kept 2-bedroom, 2.5-bathroom townhome. Th...	2 beds \| 3 baths \| 1,472 sq.ft.	$389,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 3.17% Airbnb Rental Income: $3176 Traditional Rental Income: $2416 Airbnb ROI: 3.29% Traditional ROI: 3.17%

Vacation Rentals in Oakland

There are 11 vacation rental properties available for sale in the city of Oakland . The median list price of Airbnb properties available for sale in Oakland is $570,000 and the average price per square foot is $219. 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 11 Airbnb properties available for sale in Oakland.

In 2025, the best neighborhood to buy short term rental property is Oakland.

In November 2025, 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.

$375,000

Airbnb cash on cash: 6.49%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $3912

Traditional Rental Income: $2319

Airbnb ROI: 6.49%

Traditional ROI: 4.35%

1787 WHITE FEATHER LOOP

Oakland, FL

3 beds | 3 baths | 2,152 sq.ft.

$525,000

Airbnb cash on cash: 3.72%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $3912

Traditional Rental Income: $2839

Airbnb ROI: 3.72%

Traditional ROI: 3.25%

610 STRIHAL LOOP

Oakland, FL

4 beds | 2 baths | 2,490 sq.ft.

$555,000

Airbnb cash on cash: 5.87%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $5064

Traditional Rental Income: $2640

Airbnb ROI: 5.87%

Traditional ROI: 3.19%

2755 BOBCAT CHASE BOULEVARD

Oakland, FL

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

$500,000

Airbnb cash on cash: 3.74%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $3912

Traditional Rental Income: $2583

Airbnb ROI: 3.74%

Traditional ROI: 2.7%

2435 STANDING ROCK CIRCLE

Oakland, FL

4 beds | 3 baths | 2,017 sq.ft.

$477,500

Airbnb cash on cash: 6.2%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $5064

Traditional Rental Income: $2685

Airbnb ROI: 6.2%

Traditional ROI: 3.18%

2023 WHITE FEATHER LOOP

Oakland, FL

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

$455,000

Airbnb cash on cash: 4.13%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $3912

Traditional Rental Income: $2766

Airbnb ROI: 4.13%

Traditional ROI: 3.41%

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.

$649,900

Airbnb cash on cash: 4.05%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $5064

Traditional Rental Income: $3527

Airbnb ROI: 4.05%