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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
101 N Starr St Oakland, FL 101 N Starr St, Oakland, FL 34760 \| Single Family Residential	3 beds \| 3 baths \| 2,502 sq.ft.	$1,450,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 0.25% Airbnb Rental Income: $3912 Traditional Rental Income: $2965 Airbnb ROI: 0.33% Traditional ROI: 0.25%
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%
847 Cura Ct Oakland, FL Welcome Home to this highly desirable gated, waterfront community of John's Landing. This ...	4 beds \| 3 baths \| 3,000 sq.ft.	$645,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 2.93% Airbnb Rental Income: $5064 Traditional Rental Income: $2790 Airbnb ROI: 4.99% Traditional ROI: 2.93%
2029 White Feather Loop Oakland, FL Looking for a "like new" home with the pros of new construction, but without the con of ha...	3 beds \| 2 baths \| 1,909 sq.ft.	$489,900	Airbnb cash on cash: 4.41% Traditional cash on cash: 2.73% Airbnb Rental Income: $3912 Traditional Rental Income: $2301 Airbnb ROI: 4.41% Traditional ROI: 2.73%
2139 Bay Line Rd Oakland, FL This new home is a single-story, 3-way split plan with 4 bedrooms and 3 baths. Off the foy...	4 beds \| 3 baths \| 2,281 sq.ft.	$649,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 2.9% Airbnb Rental Income: $5064 Traditional Rental Income: $2753 Airbnb ROI: 5.01% Traditional ROI: 2.9%
2755 BOBCAT CHASE BOULEVARD Oakland, FL Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, bu...	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%
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.	$471,900	Airbnb cash on cash: 6.28% Traditional cash on cash: 3.23% Airbnb Rental Income: $5064 Traditional Rental Income: $2685 Airbnb ROI: 6.28% Traditional ROI: 3.23%
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.	$655,000	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 \| 3 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 CIRCLE Oakland, FL ASSUMABLE 2.4% Interest Rate. Welcome to this beautifully appointed single-family home ...	3 beds \| 3 baths \| 2,078 sq.ft.	$494,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 3.54% Airbnb Rental Income: $3912 Traditional Rental Income: $2746 Airbnb ROI: 4.24% Traditional ROI: 3.54%
624 Hull Island Dr Oakland, FL 624 Hull Island Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 2,708 sq.ft.	$1,000,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 0.47% Airbnb Rental Income: $5064 Traditional Rental Income: $2281 Airbnb ROI: 2.35% Traditional ROI: 0.47%
1161 Prado Ln Oakland, FL 1161 Prado Ln, Oakland, FL 34787 \| Other	N/A beds \| N/A baths \| N/A	$420,000	Airbnb cash on cash: 0.49% Traditional cash on cash: -0.73% Airbnb Rental Income: $1662 Traditional Rental Income: $714 Airbnb ROI: 0.49% Traditional ROI: -0.73%
1215 Ridge Lake Way Oakland, FL 1215 Ridge Lake Way, Oakland, FL 34787 \| Other	N/A beds \| N/A baths \| N/A	$374,900	Airbnb cash on cash: 0.62% Traditional cash on cash: -0.75% Airbnb Rental Income: $1662 Traditional Rental Income: $714 Airbnb ROI: 0.62% Traditional ROI: -0.75%
610 STRIHAL LOOP Oakland, FL Under contract-accepting backup offers. Welcome to 610 Strihal Loop, a beautifully updated...	4 beds \| 2 baths \| 2,490 sq.ft.	$535,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 3.35% Airbnb Rental Income: $5064 Traditional Rental Income: $2640 Airbnb ROI: 6.13% Traditional ROI: 3.35%
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%
2690 BOBCAT CHASE BOULEVARD Oakland, FL Under contract-accepting backup offers. Love Where You Live â in Longleaf at Oakland! ? ...	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%
1185 WILDER OAKS WAY Oakland, FL BETTER THAN BRAND NEW! Welcome home to 1185 Wilder Oaks Way, ideally located in the covete...	4 beds \| 4 baths \| 2,789 sq.ft.	$995,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.8% Airbnb Rental Income: $5064 Traditional Rental Income: $3589 Airbnb ROI: 2.28% Traditional ROI: 1.8%

Vacation Rentals in Oakland

There are 19 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 $357. The cash on cash return on vacation rentals in Oakland is 3.00%. 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 19 Airbnb properties available for sale in Oakland.

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

In January 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

101 N Starr St

Oakland, FL

3 beds | 3 baths | 2,502 sq.ft.

$1,450,000

Airbnb cash on cash: 0.33%

Traditional cash on cash: 0.25%

Airbnb Rental Income: $3912

Traditional Rental Income: $2965

Airbnb ROI: 0.33%

Traditional ROI: 0.25%

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%

847 Cura Ct

Oakland, FL

4 beds | 3 baths | 3,000 sq.ft.

$645,000

Airbnb cash on cash: 4.99%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $5064

Traditional Rental Income: $2790

Airbnb ROI: 4.99%

Traditional ROI: 2.93%

2029 White Feather Loop

Oakland, FL

3 beds | 2 baths | 1,909 sq.ft.

$489,900

Airbnb cash on cash: 4.41%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $3912

Traditional Rental Income: $2301

Airbnb ROI: 4.41%

Traditional ROI: 2.73%

2139 Bay Line Rd

Oakland, FL

4 beds | 3 baths | 2,281 sq.ft.

$649,000

Airbnb cash on cash: 5.01%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $5064

Traditional Rental Income: $2753

Airbnb ROI: 5.01%

Traditional ROI: 2.9%

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%

2435 STANDING ROCK CIRCLE

Oakland, FL

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

$471,900

Airbnb cash on cash: 6.28%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $5064

Traditional Rental Income: $2685

Airbnb ROI: 6.28%

Traditional ROI: 3.23%

529 JOHNS LANDING WAY

Oakland, FL

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

$655,000

Airbnb cash on cash: 4.7%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $5064

Traditional Rental Income: $3592

Airbnb ROI: 4.7%