Airbnb Properties for Sale in Osprey, FL

Looking for a vacation rental investment in Osprey, FL with high ROI ?

Explore a range of newly added short-term rental homes in Osprey, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Osprey, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
403 LONGBOW TRAIL OSPREY, FL Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in o...	4 beds \| 3 baths \| 2,770 sq.ft.	$1,095,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 2.88% Airbnb Rental Income: $7455 Traditional Rental Income: $4922 Airbnb ROI: 3.96% Traditional ROI: 2.88%
1801 HIGHLAND ROAD OSPREY, FL One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhom...	2 beds \| 2 baths \| 1,165 sq.ft.	$299,900	Airbnb cash on cash: 5.22% Traditional cash on cash: 5.06% Airbnb Rental Income: $2934 Traditional Rental Income: $2212 Airbnb ROI: 5.22% Traditional ROI: 5.06%
1019 SCHERER WAY OSPREY, FL Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community o...	4 beds \| 3 baths \| 2,498 sq.ft.	$735,000	Airbnb cash on cash: 6.64% Traditional cash on cash: 3.21% Airbnb Rental Income: $7455 Traditional Rental Income: $3677 Airbnb ROI: 6.64% Traditional ROI: 3.21%
104 PARK TRACE BOULEVARD OSPREY, FL Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of r...	4 beds \| 3 baths \| 2,557 sq.ft.	$595,000	Airbnb cash on cash: 8.32% Traditional cash on cash: 5.13% Airbnb Rental Income: $7455 Traditional Rental Income: $4254 Airbnb ROI: 8.32% Traditional ROI: 5.13%
1211 LOST CREEK COURT OSPREY, FL Under contract-accepting backup offers. **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPAC...	4 beds \| 3 baths \| 2,876 sq.ft.	$829,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 5.47% Airbnb Rental Income: $7455 Traditional Rental Income: $5303 Airbnb ROI: 6.4% Traditional ROI: 5.47%
597 OAK RIVER COURT OSPREY, FL Under contract-accepting backup offers. Stunning, fully remodeled 4-bedroom, 2-bathroom ho...	4 beds \| 2 baths \| 2,111 sq.ft.	$699,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 3.79% Airbnb Rental Income: $7455 Traditional Rental Income: $3733 Airbnb ROI: 7.3% Traditional ROI: 3.79%
4428 CONCHFISH LANE OSPREY, FL Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located ...	4 beds \| 2 baths \| 1,861 sq.ft.	$548,000	Airbnb cash on cash: 9.19% Traditional cash on cash: 3.03% Airbnb Rental Income: $7455 Traditional Rental Income: $2870 Airbnb ROI: 9.19% Traditional ROI: 3.03%
554 DOVE POINTE OSPREY, FL Located on a quiet cul-de-sac within the gates of The Oaks Clubside, this custom-built res...	4 beds \| 4 baths \| 3,501 sq.ft.	$1,495,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 0.75% Airbnb Rental Income: $7455 Traditional Rental Income: $4093 Airbnb ROI: 2.14% Traditional ROI: 0.75%
401 WALLS WAY OSPREY, FL Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously ...	4 beds \| 4 baths \| 4,387 sq.ft.	$1,800,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 1.16% Airbnb Rental Income: $7455 Traditional Rental Income: $5053 Airbnb ROI: 1.74% Traditional ROI: 1.16%
819 SHADOW BAY WAY OSPREY, FL Welcome to this stunning 2,145 square foot pool home in the premier community of Rivendell...	4 beds \| 2 baths \| 2,145 sq.ft.	$615,000	Airbnb cash on cash: 7.99% Traditional cash on cash: 3.7% Airbnb Rental Income: $7455 Traditional Rental Income: $3564 Airbnb ROI: 7.99% Traditional ROI: 3.7%
352 GLENWOOD AVE OSPREY, FL Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this ...	3 beds \| 2 baths \| 1,300 sq.ft.	$429,500	Airbnb cash on cash: 4.3% Traditional cash on cash: 4.14% Airbnb Rental Income: $3385 Traditional Rental Income: $2566 Airbnb ROI: 4.3% Traditional ROI: 4.14%
238 PALM AIR DRIVE OSPREY, FL Fall in love with this beautifully maintained and upgraded 2 Bedroom, 2 Bathroom home loca...	2 beds \| 2 baths \| 1,152 sq.ft.	$179,900	Airbnb cash on cash: 9.38% Traditional cash on cash: 8.47% Airbnb Rental Income: $2934 Traditional Rental Income: $2100 Airbnb ROI: 9.38% Traditional ROI: 8.47%
1602 SOUTHBAY DRIVE OSPREY, FL Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly...	4 beds \| 4 baths \| 2,980 sq.ft.	$974,900	Airbnb cash on cash: 4.27% Traditional cash on cash: 3.2% Airbnb Rental Income: $7455 Traditional Rental Income: $5051 Airbnb ROI: 4.27% Traditional ROI: 3.2%
20 BAYHEAD LANE OSPREY, FL A rare opportunity to own a significantly newer, custom-built residence inside the exclusi...	4 beds \| 3 baths \| 3,486 sq.ft.	$1,575,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 1.73% Airbnb Rental Income: $7455 Traditional Rental Income: $5751 Airbnb ROI: 1.91% Traditional ROI: 1.73%
362 MACEWEN DRIVE OSPREY, FL Experience luxury living in this beautifully appointed traditional home featuring 4 bedroo...	4 beds \| 4 baths \| 4,117 sq.ft.	$2,249,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 0.77% Airbnb Rental Income: $7455 Traditional Rental Income: $4926 Airbnb ROI: 1.29% Traditional ROI: 0.77%
1471 SHOAL WAY OSPREY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	4 beds \| 3 baths \| 2,798 sq.ft.	$1,499,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 1.52% Airbnb Rental Income: $7455 Traditional Rental Income: $4399 Airbnb ROI: 2.69% Traditional ROI: 1.52%
665 CRANE PRAIRIE WAY OSPREY, FL Discover a blend of comfort and sophistication in this meticulously maintained home in the...	4 beds \| 3 baths \| 2,306 sq.ft.	$719,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 3.49% Airbnb Rental Income: $7455 Traditional Rental Income: $3990 Airbnb ROI: 6.53% Traditional ROI: 3.49%
1016 SCHERER WAY OSPREY, FL Under contract-accepting backup offers. BEAUTIFUL INSIDE and exceptionally well maintained...	4 beds \| 3 baths \| 2,921 sq.ft.	$950,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 2.56% Airbnb Rental Income: $7455 Traditional Rental Income: $3872 Airbnb ROI: 4.99% Traditional ROI: 2.56%

Vacation Rentals in Osprey

There are 18 vacation rental properties available for sale in the city of Osprey . The median list price of Airbnb properties available for sale in Osprey is $829,000 and the average price per square foot is $315. The cash on cash return on vacation rentals in Osprey is 1.00%. The average monthly short term rental income in Osprey is $3,385.

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

There are 18 Airbnb properties available for sale in Osprey.

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

In April 2026, the average Airbnb occupancy rate in Osprey is 48%.

Airbnb data on vacation rentals in Osprey, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Osprey, FL market insights, guest information and booking details, seasonality trends and historical Osprey, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Osprey, FL

403 LONGBOW TRAIL

OSPREY, FL

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

$1,095,000

Airbnb cash on cash: 3.96%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $7455

Traditional Rental Income: $4922

Airbnb ROI: 3.96%

Traditional ROI: 2.88%

1801 HIGHLAND ROAD

OSPREY, FL

2 beds | 2 baths | 1,165 sq.ft.

$299,900

Airbnb cash on cash: 5.22%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $2934

Traditional Rental Income: $2212

Airbnb ROI: 5.22%

Traditional ROI: 5.06%

1019 SCHERER WAY

OSPREY, FL

4 beds | 3 baths | 2,498 sq.ft.

$735,000

Airbnb cash on cash: 6.64%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $7455

Traditional Rental Income: $3677

Airbnb ROI: 6.64%

Traditional ROI: 3.21%

104 PARK TRACE BOULEVARD

OSPREY, FL

4 beds | 3 baths | 2,557 sq.ft.

$595,000

Airbnb cash on cash: 8.32%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $7455

Traditional Rental Income: $4254

Airbnb ROI: 8.32%

Traditional ROI: 5.13%

1211 LOST CREEK COURT

OSPREY, FL

4 beds | 3 baths | 2,876 sq.ft.

$829,000

Airbnb cash on cash: 6.4%

Traditional cash on cash: 5.47%

Airbnb Rental Income: $7455

Traditional Rental Income: $5303

Airbnb ROI: 6.4%

Traditional ROI: 5.47%

597 OAK RIVER COURT

OSPREY, FL

4 beds | 2 baths | 2,111 sq.ft.

$699,000

Airbnb cash on cash: 7.3%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $7455

Traditional Rental Income: $3733

Airbnb ROI: 7.3%

Traditional ROI: 3.79%

4428 CONCHFISH LANE

OSPREY, FL

4 beds | 2 baths | 1,861 sq.ft.

$548,000

Airbnb cash on cash: 9.19%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $7455

Traditional Rental Income: $2870

Airbnb ROI: 9.19%

Traditional ROI: 3.03%

554 DOVE POINTE

OSPREY, FL

4 beds | 4 baths | 3,501 sq.ft.

$1,495,000

Airbnb cash on cash: 2.14%

Traditional cash on cash: 0.75%

Airbnb Rental Income: $7455

Traditional Rental Income: $4093

Airbnb ROI: 2.14%