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.	$1,197,000	Airbnb cash on cash: 3.54% Traditional cash on cash: 2.09% Airbnb Rental Income: $7455 Traditional Rental Income: $4413 Airbnb ROI: 3.54% Traditional ROI: 2.09%
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.	$340,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 4.46% Airbnb Rental Income: $2934 Traditional Rental Income: $2223 Airbnb ROI: 4.56% Traditional ROI: 4.46%
392 PARK TRACE BOULEVARD OSPREY, FL Under contract-accepting backup offers. Set on a premier lakefront lot in Osprey, 392 Park...	4 beds \| 3 baths \| 2,802 sq.ft.	$939,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 3.1% Airbnb Rental Income: $7455 Traditional Rental Income: $4526 Airbnb ROI: 4.81% Traditional ROI: 3.1%
75 OSPREY POINT DRIVE OSPREY, FL STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood on...	4 beds \| 4 baths \| 4,001 sq.ft.	$1,975,000	Airbnb cash on cash: 0.94% Traditional cash on cash: -0.19% Airbnb Rental Income: $7455 Traditional Rental Income: $3945 Airbnb ROI: 0.94% Traditional ROI: -0.19%
140 SUGAR MILL DRIVE OSPREY, FL **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE RESIDENCE with Lush Garden Lan...	4 beds \| 4 baths \| 3,286 sq.ft.	$1,970,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 1.11% Airbnb Rental Income: $7455 Traditional Rental Income: $5508 Airbnb ROI: 1.4% Traditional ROI: 1.11%
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.	$599,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 2.4% Airbnb Rental Income: $7455 Traditional Rental Income: $2711 Airbnb ROI: 8.33% Traditional ROI: 2.4%
819 SHADOW BAY WAY OSPREY, FL A new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of ...	4 beds \| 2 baths \| 2,145 sq.ft.	$689,000	Airbnb cash on cash: 6.94% Traditional cash on cash: 3.3% Airbnb Rental Income: $7455 Traditional Rental Income: $3687 Airbnb ROI: 6.94% Traditional ROI: 3.3%
116 NAVIGATION CIRCLE #106 OSPREY, FL Location, Lifestyle, and Peace of Mind â All in One! Welcome home to this beautifully...	3 beds \| 2 baths \| 1,430 sq.ft.	$325,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 5.06% Airbnb Rental Income: $3385 Traditional Rental Income: $2550 Airbnb ROI: 5.32% Traditional ROI: 5.06%
191 PALM AIR DRIVE OSPREY, FL Under contract-accepting backup offers. Come home to this tastefully-furnished, well-maint...	2 beds \| 2 baths \| 1,376 sq.ft.	$185,000	Airbnb cash on cash: 9.13% Traditional cash on cash: 8.99% Airbnb Rental Income: $2934 Traditional Rental Income: $2232 Airbnb ROI: 9.13% Traditional ROI: 8.99%
523 HABITAT BOULEVARD OSPREY, FL In the Lee Wetherington-built community of Willowbend is a stunning home. This enchanting ...	4 beds \| 3 baths \| 2,314 sq.ft.	$785,500	Airbnb cash on cash: 5.98% Traditional cash on cash: 3.06% Airbnb Rental Income: $7455 Traditional Rental Income: $3885 Airbnb ROI: 5.98% Traditional ROI: 3.06%
312 YACHT HARBOR DRIVE OSPREY, FL One or more photo(s) has been virtually staged. Considered one of the finest community-own...	4 beds \| 4 baths \| 2,572 sq.ft.	$2,299,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 0.52% Airbnb Rental Income: $7455 Traditional Rental Income: $4850 Airbnb ROI: 1.07% Traditional ROI: 0.52%
362 PINE RUN DRIVE OSPREY, FL One or more photo(s) has been virtually staged. Welcome to 362 Pine Run Drive, a move-in r...	2 beds \| 2 baths \| 1,224 sq.ft.	$235,000	Airbnb cash on cash: 7.5% Traditional cash on cash: 7.47% Airbnb Rental Income: $2934 Traditional Rental Income: $2248 Airbnb ROI: 7.5% Traditional ROI: 7.47%
218 PALM AIR DRIVE OSPREY, FL Youâll be impressed with this delightful double wide from the moment you enter featuring...	2 beds \| 2 baths \| 1,120 sq.ft.	$189,000	Airbnb cash on cash: 8.93% Traditional cash on cash: 7.51% Airbnb Rental Income: $2934 Traditional Rental Income: $2001 Airbnb ROI: 8.93% Traditional ROI: 7.51%
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.	$444,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.45% Airbnb Rental Income: $3385 Traditional Rental Income: $2349 Airbnb ROI: 4.13% Traditional ROI: 3.45%
471 PARK TRACE BOULEVARD OSPREY, FL SIGNIFICANT PRICE IMPROVEMENT!! Welcome to your dream home! This stunning, custom-built 4...	4 beds \| 3 baths \| 2,267 sq.ft.	$699,000	Airbnb cash on cash: 7.61% Traditional cash on cash: 4.49% Airbnb Rental Income: $7455 Traditional Rental Income: $3990 Airbnb ROI: 7.61% Traditional ROI: 4.49%
238 PALM AIR DRIVE OSPREY, FL AN ARBORS BEAUTY in one of Floridaâs most-sought-after 55+ parks. You wonât believe h...	2 beds \| 2 baths \| 1,152 sq.ft.	$198,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 7.35% Airbnb Rental Income: $2934 Traditional Rental Income: $2072 Airbnb ROI: 8.33% Traditional ROI: 7.35%
133 OSPREY POINT DRIVE OSPREY, FL One or more photo(s) has been virtually staged. Custom Home located in the exclusive gated...	4 beds \| 3 baths \| 3,679 sq.ft.	$1,500,000	Airbnb cash on cash: 1.4% Traditional cash on cash: -0.18% Airbnb Rental Income: $7455 Traditional Rental Income: $3823 Airbnb ROI: 1.4% Traditional ROI: -0.18%
447 OAK POINT ROAD OSPREY, FL Prepare to be impressed as you enter this bright and spacious maintenance-free townhome wi...	4 beds \| 3 baths \| 2,688 sq.ft.	$545,000	Airbnb cash on cash: 8.16% Traditional cash on cash: 4.24% Airbnb Rental Income: $7455 Traditional Rental Income: $4025 Airbnb ROI: 8.16% Traditional ROI: 4.24%
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.	$995,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 3.45% Airbnb Rental Income: $7455 Traditional Rental Income: $5363 Airbnb ROI: 4.17% Traditional ROI: 3.45%
453 E MACEWEN DRIVE OSPREY, FL Under contract-accepting backup offers. Set an appointment to experience this thoughtfully...	4 beds \| 4 baths \| 4,191 sq.ft.	$1,899,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 1.39% Airbnb Rental Income: $7455 Traditional Rental Income: $5394 Airbnb ROI: 1.75% Traditional ROI: 1.39%
1036 OAK MEADOW LN OSPREY, FL Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rive...	4 beds \| 2 baths \| 2,186 sq.ft.	$585,000	Airbnb cash on cash: 8.97% Traditional cash on cash: 3.61% Airbnb Rental Income: $7455 Traditional Rental Income: $3093 Airbnb ROI: 8.97% Traditional ROI: 3.61%
137 OSPREY POINT DRIVE OSPREY, FL Although built in the 20th century, this home looks as authentic as the French manor house...	4 beds \| 3 baths \| 3,303 sq.ft.	$1,425,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 1.11% Airbnb Rental Income: $7455 Traditional Rental Income: $4192 Airbnb ROI: 2.49% Traditional ROI: 1.11%
216 GLENWOOD AVENUE OSPREY, FL Nestled in the quietly coveted, underrated gem of Osprey, FL, this charming property offer...	2 beds \| 1 baths \| 732 sq.ft.	$250,000	Airbnb cash on cash: 7.86% Traditional cash on cash: 5.49% Airbnb Rental Income: $2934 Traditional Rental Income: $1697 Airbnb ROI: 7.86% Traditional ROI: 5.49%

Vacation Rentals in Osprey

There are 23 vacation rental properties available for sale in the city of Osprey . The median list price of Airbnb properties available for sale in Osprey is $879,000 and the average price per square foot is $332. 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 23 Airbnb properties available for sale in Osprey.

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

In November 2025, 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.

$1,197,000

Airbnb cash on cash: 3.54%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $7455

Traditional Rental Income: $4413

Airbnb ROI: 3.54%

Traditional ROI: 2.09%

1801 HIGHLAND ROAD

OSPREY, FL

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

$340,000

Airbnb cash on cash: 4.56%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $2934

Traditional Rental Income: $2223

Airbnb ROI: 4.56%

Traditional ROI: 4.46%

392 PARK TRACE BOULEVARD

OSPREY, FL

4 beds | 3 baths | 2,802 sq.ft.

$939,000

Airbnb cash on cash: 4.81%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $7455

Traditional Rental Income: $4526

Airbnb ROI: 4.81%

Traditional ROI: 3.1%

75 OSPREY POINT DRIVE

OSPREY, FL

4 beds | 4 baths | 4,001 sq.ft.

$1,975,000

Airbnb cash on cash: 0.94%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $7455

Traditional Rental Income: $3945

Airbnb ROI: 0.94%

Traditional ROI: -0.19%

140 SUGAR MILL DRIVE

OSPREY, FL

4 beds | 4 baths | 3,286 sq.ft.

$1,970,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $7455

Traditional Rental Income: $5508

Airbnb ROI: 1.4%

Traditional ROI: 1.11%

4428 CONCHFISH LANE

OSPREY, FL

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

$599,000

Airbnb cash on cash: 8.33%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $7455

Traditional Rental Income: $2711

Airbnb ROI: 8.33%

Traditional ROI: 2.4%

819 SHADOW BAY WAY

OSPREY, FL

4 beds | 2 baths | 2,145 sq.ft.

$689,000

Airbnb cash on cash: 6.94%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $7455

Traditional Rental Income: $3687

Airbnb ROI: 6.94%

Traditional ROI: 3.3%

116 NAVIGATION CIRCLE #106

OSPREY, FL

3 beds | 2 baths | 1,430 sq.ft.

$325,000

Airbnb cash on cash: 5.32%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $3385

Traditional Rental Income: $2550

Airbnb ROI: 5.32%