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 Trl 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: 3.94% Traditional cash on cash: 2.88% Airbnb Rental Income: $7428 Traditional Rental Income: $4922 Airbnb ROI: 3.94% Traditional ROI: 2.88%
103 Bishops Court Rd OSPREY, FL LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY this Charming and Coz...	3 beds \| 2 baths \| 2,034 sq.ft.	$749,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 2% Airbnb Rental Income: $5858 Traditional Rental Income: $3003 Airbnb ROI: 4.42% Traditional ROI: 2%
1801 Highland Rd 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.	$289,900	Airbnb cash on cash: 9.63% Traditional cash on cash: 5.27% Airbnb Rental Income: $4310 Traditional Rental Income: $2212 Airbnb ROI: 9.63% Traditional ROI: 5.27%
764 Sarabay Rd #8 OSPREY, FL Virtually Staged. Live the Florida dream on the water! Wake up to shimmering bay views, sp...	2 beds \| 2 baths \| 1,392 sq.ft.	$399,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 1.61% Airbnb Rental Income: $4310 Traditional Rental Income: $3203 Airbnb ROI: 2.11% Traditional ROI: 1.61%
14021 Bellagio Way #404 OSPREY, FL This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comf...	3 beds \| 3 baths \| 2,187 sq.ft.	$1,100,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 0.66% Airbnb Rental Income: $5858 Traditional Rental Income: $4250 Airbnb ROI: 1.06% Traditional ROI: 0.66%
1361 New Forest Ln OSPREY, FL PRICE TO SELL. One or more photo(s) has been virtually staged. Exceptional opportunity in ...	3 beds \| 2 baths \| 2,074 sq.ft.	$535,000	Airbnb cash on cash: 7.63% Traditional cash on cash: 3.93% Airbnb Rental Income: $5858 Traditional Rental Income: $2842 Airbnb ROI: 7.63% Traditional ROI: 3.93%
754 Pine Run Dr #754 OSPREY, FL Virtually Staged. Rarely available and truly one-of-a-kind, this beautifully updated groun...	2 beds \| 2 baths \| 1,379 sq.ft.	$259,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 3.36% Airbnb Rental Income: $4310 Traditional Rental Income: $2411 Airbnb ROI: 7.42% Traditional ROI: 3.36%
409 N Point Rd #502 OSPREY, FL **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The cov...	3 beds \| 3 baths \| 2,055 sq.ft.	$599,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 4.96% Airbnb Rental Income: $5858 Traditional Rental Income: $4276 Airbnb ROI: 5.71% Traditional ROI: 4.96%
110 Pine Ave OSPREY, FL Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your...	3 beds \| 2 baths \| 2,058 sq.ft.	$649,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 4.86% Airbnb Rental Income: $5858 Traditional Rental Income: $4189 Airbnb ROI: 5.69% Traditional ROI: 4.86%
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: 6.37% Traditional cash on cash: 5.47% Airbnb Rental Income: $7428 Traditional Rental Income: $5303 Airbnb ROI: 6.37% Traditional ROI: 5.47%
365 S SHORE DRIVE OSPREY, FL Wake up to ever-changing INTRACOASTAL VIEWS â SUNSETS dancing across the water, BOATS gl...	3 beds \| 2 baths \| 1,824 sq.ft.	$1,349,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 1.25% Airbnb Rental Income: $5858 Traditional Rental Income: $3647 Airbnb ROI: 2.09% Traditional ROI: 1.25%
759 Fordingbridge Way OSPREY, FL Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layou...	4 beds \| 3 baths \| 2,950 sq.ft.	$715,000	Airbnb cash on cash: 6.43% Traditional cash on cash: 5.59% Airbnb Rental Income: $7428 Traditional Rental Income: $5418 Airbnb ROI: 6.43% Traditional ROI: 5.59%
293 Turquoise Ln OSPREY, FL **STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure ...	3 beds \| 2 baths \| 2,271 sq.ft.	$875,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 1.72% Airbnb Rental Income: $5858 Traditional Rental Income: $3448 Airbnb ROI: 3.25% Traditional ROI: 1.72%
385 N Point Rd #402 OSPREY, FL BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW features 3-BEDS and 3-FULL BATH, Open Fl...	3 beds \| 3 baths \| 2,055 sq.ft.	$615,000	Airbnb cash on cash: 4.86% Traditional cash on cash: 4.42% Airbnb Rental Income: $5858 Traditional Rental Income: $4422 Airbnb ROI: 4.86% Traditional ROI: 4.42%
13 Bayhead Ln OSPREY, FL **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANC...	3 beds \| 2 baths \| 2,310 sq.ft.	$799,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 2.95% Airbnb Rental Income: $5858 Traditional Rental Income: $3842 Airbnb ROI: 4.09% Traditional ROI: 2.95%
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.	$417,000	Airbnb cash on cash: 9.74% Traditional cash on cash: 4.29% Airbnb Rental Income: $5858 Traditional Rental Income: $2566 Airbnb ROI: 9.74% Traditional ROI: 4.29%
1527 Buoy Ln OSPREY, FL Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet...	3 beds \| 2 baths \| 2,830 sq.ft.	$1,165,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 1.91% Airbnb Rental Income: $5858 Traditional Rental Income: $4259 Airbnb ROI: 2.31% Traditional ROI: 1.91%
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: 4.25% Traditional cash on cash: 3.2% Airbnb Rental Income: $7428 Traditional Rental Income: $5051 Airbnb ROI: 4.25% Traditional ROI: 3.2%
33 Bishops Court Rd #118 OSPREY, FL **EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIE...	2 beds \| 2 baths \| 1,890 sq.ft.	$679,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 2.89% Airbnb Rental Income: $4310 Traditional Rental Income: $3348 Airbnb ROI: 2.98% Traditional ROI: 2.89%
107 Sorrento Dr OSPREY, FL This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an...	2 beds \| 2 baths \| 1,284 sq.ft.	$425,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 4.1% Airbnb Rental Income: $4310 Traditional Rental Income: $2375 Airbnb ROI: 6.68% Traditional ROI: 4.1%
113 BURNEY ROAD OSPREY, FL Under contract-accepting backup offers. **DONâT WAIT TO BUILD!! NEWER, CUSTOM-BUILT HOM...	3 beds \| 3 baths \| 2,502 sq.ft.	$999,500	Airbnb cash on cash: 2.91% Traditional cash on cash: 1.94% Airbnb Rental Income: $5858 Traditional Rental Income: $3797 Airbnb ROI: 2.91% Traditional ROI: 1.94%
184 Explorer Dr OSPREY, FL Luxury Corner Residence in Osprey \| Top-Rated Pine View School District. Welcome to an ex...	2 beds \| 2 baths \| 1,244 sq.ft.	$294,900	Airbnb cash on cash: 7.85% Traditional cash on cash: 4.24% Airbnb Rental Income: $4310 Traditional Rental Income: $2400 Airbnb ROI: 7.85% Traditional ROI: 4.24%
314 S Shore Dr OSPREY, FL Rare Gulf-access waterfront opportunity in desirable Sorrento Shores in Osprey. This spaci...	4 beds \| 3 baths \| 3,853 sq.ft.	$1,495,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 1.53% Airbnb Rental Income: $7428 Traditional Rental Income: $4433 Airbnb ROI: 2.66% Traditional ROI: 1.53%
206 Four Knot Ln OSPREY, FL Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living r...	3 beds \| 2 baths \| 2,411 sq.ft.	$1,790,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 0.32% Airbnb Rental Income: $5858 Traditional Rental Income: $3475 Airbnb ROI: 1.03% Traditional ROI: 0.32%

Vacation Rentals in Osprey

There are 36 vacation rental properties available for sale in the city of Osprey . The median list price of Airbnb properties available for sale in Osprey is $580,653 and the average price per square foot is $237. The cash on cash return on vacation rentals in Osprey is 4.00%. The average monthly short term rental income in Osprey is $5,858.

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

There are 36 Airbnb properties available for sale in Osprey.

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

In August 2026, the average Airbnb occupancy rate in Osprey is N/A%.

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 Trl

OSPREY, FL

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

$1,095,000

Airbnb cash on cash: 3.94%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $7428

Traditional Rental Income: $4922

Airbnb ROI: 3.94%

Traditional ROI: 2.88%

103 Bishops Court Rd

OSPREY, FL

3 beds | 2 baths | 2,034 sq.ft.

$749,000

Airbnb cash on cash: 4.42%

Traditional cash on cash: 2%

Airbnb Rental Income: $5858

Traditional Rental Income: $3003

Airbnb ROI: 4.42%

Traditional ROI: 2%

1801 Highland Rd

OSPREY, FL

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

$289,900

Airbnb cash on cash: 9.63%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $4310

Traditional Rental Income: $2212

Airbnb ROI: 9.63%

Traditional ROI: 5.27%

764 Sarabay Rd #8

OSPREY, FL

2 beds | 2 baths | 1,392 sq.ft.

$399,000

Airbnb cash on cash: 2.11%

Traditional cash on cash: 1.61%

Airbnb Rental Income: $4310

Traditional Rental Income: $3203

Airbnb ROI: 2.11%

Traditional ROI: 1.61%

14021 Bellagio Way #404

OSPREY, FL

3 beds | 3 baths | 2,187 sq.ft.

$1,100,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $5858

Traditional Rental Income: $4250

Airbnb ROI: 1.06%

Traditional ROI: 0.66%

1361 New Forest Ln

OSPREY, FL

3 beds | 2 baths | 2,074 sq.ft.

$535,000

Airbnb cash on cash: 7.63%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $5858

Traditional Rental Income: $2842

Airbnb ROI: 7.63%

Traditional ROI: 3.93%

754 Pine Run Dr #754

OSPREY, FL

2 beds | 2 baths | 1,379 sq.ft.

$259,000

Airbnb cash on cash: 7.42%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $4310

Traditional Rental Income: $2411

Airbnb ROI: 7.42%

Traditional ROI: 3.36%

409 N Point Rd #502

OSPREY, FL

3 beds | 3 baths | 2,055 sq.ft.

$599,000

Airbnb cash on cash: 5.71%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $5858

Traditional Rental Income: $4276

Airbnb ROI: 5.71%