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
1801 HIGHLAND ROAD OSPREY, FL Enjoy this Key West-style townhome in Towns-End Shores-maintenance-free living at its best...	2 beds \| 2 baths \| 1,165 sq.ft.	$372,500	Airbnb cash on cash: 4.18% Traditional cash on cash: 4.09% Airbnb Rental Income: $2934 Traditional Rental Income: $2223 Airbnb ROI: 4.18% Traditional ROI: 4.09%
519 BAYVIEW AVENUE OSPREY, FL Boating Community, Bay Acres! RV and Boat Parking pad 42'x16' with electric hook-up, and H...	3 beds \| 2 baths \| 1,885 sq.ft.	$495,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 4% Airbnb Rental Income: $3385 Traditional Rental Income: $2623 Airbnb ROI: 4.02% Traditional ROI: 4%
104 PARK TRACE BOULEVARD OSPREY, FL Welcome to your dream home in beautiful Osprey, Florida inside PARK TRACE! This expansive ...	4 beds \| 3 baths \| 2,557 sq.ft.	$647,000	Airbnb cash on cash: 8.11% Traditional cash on cash: 4.82% Airbnb Rental Income: $7455 Traditional Rental Income: $4038 Airbnb ROI: 8.11% Traditional ROI: 4.82%
140 SUGAR MILL DRIVE OSPREY, FL **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landsc...	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%
402 WALLS WAY OSPREY, FL Welcome to timeless elegance and modern comfort in The Oaks Clubside. This stunning 4-bedr...	4 beds \| 4 baths \| 3,464 sq.ft.	$1,500,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 1.3% Airbnb Rental Income: $7455 Traditional Rental Income: $4908 Airbnb ROI: 2.1% Traditional ROI: 1.3%
1484 SEAFARER DRIVE OSPREY, FL Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coastâs most coveted communiti...	4 beds \| 4 baths \| 3,479 sq.ft.	$1,250,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.71% Airbnb Rental Income: $7455 Traditional Rental Income: $5355 Airbnb ROI: 3.29% Traditional ROI: 2.71%
207 WOODLAND DRIVE #207 OSPREY, FL Welcome to this beautifully appointed, well-cared for and fully furnished 2-bedroom, 2-bat...	2 beds \| 2 baths \| 1,325 sq.ft.	$269,999	Airbnb cash on cash: 6.14% Traditional cash on cash: 5.95% Airbnb Rental Income: $2934 Traditional Rental Income: $2210 Airbnb ROI: 6.14% Traditional ROI: 5.95%
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%
758 PINE RUN DRIVE #758 OSPREY, FL This home was professionally inspected by a Contractor following Hurricanes Helene and Mil...	2 beds \| 2 baths \| 1,184 sq.ft.	$256,600	Airbnb cash on cash: 3.56% Traditional cash on cash: 2.96% Airbnb Rental Income: $2934 Traditional Rental Income: $2110 Airbnb ROI: 3.56% Traditional ROI: 2.96%
813 OAK POND DRIVE OSPREY, FL One or more photo(s) has been virtually staged. WELCOME HOME!! THERE HAS BEEN NO FLOODING ...	4 beds \| 2 baths \| 1,981 sq.ft.	$560,000	Airbnb cash on cash: 9.42% Traditional cash on cash: 3.38% Airbnb Rental Income: $7455 Traditional Rental Income: $2867 Airbnb ROI: 9.42% Traditional ROI: 3.38%
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.	$319,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 5.17% Airbnb Rental Income: $3385 Traditional Rental Income: $2550 Airbnb ROI: 5.44% Traditional ROI: 5.17%
191 PALM AIR DRIVE OSPREY, FL Come home to this tastefully-furnished, well-maintained spacious home in a top-of-the-line...	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%
650 CRANE PRAIRIE WAY OSPREY, FL BEST PRICED HOME PER SQ FT in a 3-Mile Radius! Now Offered at $845,000 \| Lease Option/Purc...	4 beds \| 4 baths \| 3,183 sq.ft.	$845,000	Airbnb cash on cash: 5% Traditional cash on cash: 3.19% Airbnb Rental Income: $7455 Traditional Rental Income: $4603 Airbnb ROI: 5% Traditional ROI: 3.19%
662 FERNWALK LANE OSPREY, FL **FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTER...	4 beds \| 4 baths \| 4,359 sq.ft.	$2,995,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 0.39% Airbnb Rental Income: $7455 Traditional Rental Income: $5371 Airbnb ROI: 0.63% Traditional ROI: 0.39%
826 OAK BRIAR LANE OSPREY, FL Under contract-accepting backup offers. Welcome to this MODERN 4-Bedroom, 3-Bath POOL HOME...	4 beds \| 3 baths \| 2,589 sq.ft.	$735,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 3.64% Airbnb Rental Income: $7455 Traditional Rental Income: $3748 Airbnb ROI: 6.96% Traditional ROI: 3.64%
320 TROPIC DRIVE OSPREY, FL A GREAT HOME IN A GREAT PARK AT A GREAT PRICE. Welcome to your new home in the Arbors, Sa...	2 beds \| 2 baths \| 1,199 sq.ft.	$190,000	Airbnb cash on cash: 8.9% Traditional cash on cash: 7.65% Airbnb Rental Income: $2934 Traditional Rental Income: $2029 Airbnb ROI: 8.9% Traditional ROI: 7.65%
750 ANNA HOPE LANE OSPREY, FL Impeccable style and effortless grace define this Rivendell home, which stands as a testam...	4 beds \| 2 baths \| 2,135 sq.ft.	$669,000	Airbnb cash on cash: 7.34% Traditional cash on cash: 3.18% Airbnb Rental Income: $7455 Traditional Rental Income: $3428 Airbnb ROI: 7.34% Traditional ROI: 3.18%
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%
898 MACEWEN DRIVE OSPREY, FL Large 4 bedroom, 4 bath home on over half an acre bordering the 7th fairway of the Heron G...	4 beds \| 4 baths \| 4,132 sq.ft.	$1,950,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 1.07% Airbnb Rental Income: $7455 Traditional Rental Income: $5445 Airbnb ROI: 1.39% Traditional ROI: 1.07%
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.	$199,000	Airbnb cash on cash: 8.29% Traditional cash on cash: 7.31% Airbnb Rental Income: $2934 Traditional Rental Income: $2072 Airbnb ROI: 8.29% Traditional ROI: 7.31%
51 MAC EWEN DRIVE #14 OSPREY, FL This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge...	1 beds \| 1 baths \| 595 sq.ft.	$350,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 2.32% Airbnb Rental Income: $2934 Traditional Rental Income: $1517 Airbnb ROI: 4.57% Traditional ROI: 2.32%

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 $742,000 and the average price per square foot is $289. The cash on cash return on vacation rentals in Osprey is 2.00%. 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 September 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

1801 HIGHLAND ROAD

OSPREY, FL

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

$372,500

Airbnb cash on cash: 4.18%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $2934

Traditional Rental Income: $2223

Airbnb ROI: 4.18%

Traditional ROI: 4.09%

519 BAYVIEW AVENUE

OSPREY, FL

3 beds | 2 baths | 1,885 sq.ft.

$495,000

Airbnb cash on cash: 4.02%

Traditional cash on cash: 4%

Airbnb Rental Income: $3385

Traditional Rental Income: $2623

Airbnb ROI: 4.02%

Traditional ROI: 4%

104 PARK TRACE BOULEVARD

OSPREY, FL

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

$647,000

Airbnb cash on cash: 8.11%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $7455

Traditional Rental Income: $4038

Airbnb ROI: 8.11%

Traditional ROI: 4.82%

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%

402 WALLS WAY

OSPREY, FL

4 beds | 4 baths | 3,464 sq.ft.

$1,500,000

Airbnb cash on cash: 2.1%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $7455

Traditional Rental Income: $4908

Airbnb ROI: 2.1%

Traditional ROI: 1.3%

1484 SEAFARER DRIVE

OSPREY, FL

4 beds | 4 baths | 3,479 sq.ft.

$1,250,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $7455

Traditional Rental Income: $5355

Airbnb ROI: 3.29%

Traditional ROI: 2.71%

207 WOODLAND DRIVE #207

OSPREY, FL

2 beds | 2 baths | 1,325 sq.ft.

$269,999

Airbnb cash on cash: 6.14%

Traditional cash on cash: 5.95%

Airbnb Rental Income: $2934

Traditional Rental Income: $2210

Airbnb ROI: 6.14%

Traditional ROI: 5.95%

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%