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
742 Harms Dr OSPREY, FL ATTENTION NATURE LOVERS: Your Own Private Hide-Away on one-half acre yet conveniently loca...	3 beds \| 2 baths \| 1,293 sq.ft.	$545,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 2.89% Airbnb Rental Income: $3385 Traditional Rental Income: $2206 Airbnb ROI: 3.72% Traditional ROI: 2.89%
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.	$1,197,000	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 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.	$330,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 4.55% Airbnb Rental Income: $2934 Traditional Rental Income: $2223 Airbnb ROI: 4.66% Traditional ROI: 4.55%
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 Blvd 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.	$650,000	Airbnb cash on cash: 7.54% Traditional cash on cash: 4.27% Airbnb Rental Income: $7455 Traditional Rental Income: $4038 Airbnb ROI: 7.54% Traditional ROI: 4.27%
146 Willow Bend Way OSPREY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 2,540 sq.ft.	$699,000	Airbnb cash on cash: 7.29% Traditional cash on cash: 3.7% Airbnb Rental Income: $7455 Traditional Rental Income: $3683 Airbnb ROI: 7.29% Traditional ROI: 3.7%
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%
177 Navigation Cir OSPREY, FL 10K PRICE REDUCTION! NEED A QUICK CLOSE? NO PROBLEM, SELLERS HAVE MOVED TO THEIR NEW HOME!...	3 beds \| 2 baths \| 1,581 sq.ft.	$369,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 3.44% Airbnb Rental Income: $3385 Traditional Rental Income: $2530 Airbnb ROI: 3.73% Traditional ROI: 3.44%
49 Osprey Point Dr OSPREY, FL This 3 bedroom + office, 3.5 bath Oaks Bayside gem offers gorgeous lake views. As you ent...	4 beds \| 3 baths \| 3,953 sq.ft.	$2,500,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 0.23% Airbnb Rental Income: $7455 Traditional Rental Income: $4191 Airbnb ROI: 1.02% Traditional ROI: 0.23%
75 Osprey Point Dr OSPREY, FL STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood on...	4 beds \| 4 baths \| 4,001 sq.ft.	$1,775,000	Airbnb cash on cash: 1.15% Traditional cash on cash: -0.11% Airbnb Rental Income: $7455 Traditional Rental Income: $3945 Airbnb ROI: 1.15% Traditional ROI: -0.11%
140 Sugar Mill Dr 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: 1.39% Traditional cash on cash: 1.11% Airbnb Rental Income: $7455 Traditional Rental Income: $5508 Airbnb ROI: 1.39% Traditional ROI: 1.11%
2043 CORDES STREET OSPREY, FL Charming & Versatile Home Near the Beaches! This cute and cozy, well-maintained 3-bedroom...	3 beds \| 2 baths \| 1,186 sq.ft.	$299,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 6.61% Airbnb Rental Income: $3385 Traditional Rental Income: $2488 Airbnb ROI: 7.12% Traditional ROI: 6.61%
472 Park Trace Blvd OSPREY, FL The gem of a neighborhood that is Park Trace Estates welcomes you, now, and this move in r...	4 beds \| 2 baths \| 2,217 sq.ft.	$645,000	Airbnb cash on cash: 8.18% Traditional cash on cash: 5.36% Airbnb Rental Income: $7455 Traditional Rental Income: $4324 Airbnb ROI: 8.18% Traditional ROI: 5.36%
597 OAK RIVER COURT OSPREY, FL Stunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in ...	4 beds \| 2 baths \| 2,111 sq.ft.	$734,900	Airbnb cash on cash: 6.9% Traditional cash on cash: 2.99% Airbnb Rental Income: $7455 Traditional Rental Income: $3347 Airbnb ROI: 6.9% Traditional ROI: 2.99%
4428 Conchfish Ln 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%
401 Walls Way OSPREY, FL Recently appraised for over 2 million, Seller relocating. Exquisite Executive Home in The...	4 beds \| 3 baths \| 4,387 sq.ft.	$1,800,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 0.92% Airbnb Rental Income: $7455 Traditional Rental Income: $4649 Airbnb ROI: 1.74% Traditional ROI: 0.92%
116 Navigation Cir #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%
312 Yacht Harbor Dr 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%
662 Fernwalk Ln OSPREY, FL **EXCEPTIONAL, FULLY RENOVATED, COUNTRY CLUB ESTATE HOME OFFERING TRANQUIL LAKE AND GARDEN...	4 beds \| 4 baths \| 4,359 sq.ft.	$2,850,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 0.46% Airbnb Rental Income: $7455 Traditional Rental Income: $5371 Airbnb ROI: 0.71% Traditional ROI: 0.46%
362 Pine Run Dr 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: 2.93% Traditional cash on cash: 2.9% Airbnb Rental Income: $2934 Traditional Rental Income: $2248 Airbnb ROI: 2.93% Traditional ROI: 2.9%
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: 3.6% Airbnb Rental Income: $3385 Traditional Rental Income: $2349 Airbnb ROI: 4.3% Traditional ROI: 3.6%
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 Dr 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.	$193,000	Airbnb cash on cash: 8.57% Traditional cash on cash: 7.56% Airbnb Rental Income: $2934 Traditional Rental Income: $2072 Airbnb ROI: 8.57% Traditional ROI: 7.56%
133 Osprey Point Dr 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.	$1,350,000	Airbnb cash on cash: 1.47% Traditional cash on cash: -0.29% Airbnb Rental Income: $7455 Traditional Rental Income: $3823 Airbnb ROI: 1.47% Traditional ROI: -0.29%
1602 Southbay Dr OSPREY, FL Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly...	4 beds \| 3 baths \| 2,980 sq.ft.	$974,900	Airbnb cash on cash: 4.27% Traditional cash on cash: 3.54% Airbnb Rental Income: $7455 Traditional Rental Income: $5363 Airbnb ROI: 4.27% Traditional ROI: 3.54%
238 Woodland Dr #238 OSPREY, FL GREAT NEW PRICE to live like you're on vacation every day in this beautiful one bedroom, o...	1 beds \| 1 baths \| 865 sq.ft.	$184,900	Airbnb cash on cash: 6.36% Traditional cash on cash: 3.36% Airbnb Rental Income: $2934 Traditional Rental Income: $1728 Airbnb ROI: 6.36% Traditional ROI: 3.36%
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.	$559,000	Airbnb cash on cash: 9.39% Traditional cash on cash: 3.78% Airbnb Rental Income: $7455 Traditional Rental Income: $3093 Airbnb ROI: 9.39% Traditional ROI: 3.78%
137 Osprey Point Dr 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.	$1,345,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 1.23% Airbnb Rental Income: $7455 Traditional Rental Income: $4192 Airbnb ROI: 2.7% Traditional ROI: 1.23%
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%
20 Bayhead Ln 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: 1.61% Traditional cash on cash: 0.18% Airbnb Rental Income: $7455 Traditional Rental Income: $3933 Airbnb ROI: 1.61% Traditional ROI: 0.18%
362 Macewen Dr OSPREY, FL Experience luxury living in this beautifully appointed traditional home featuring 4 bedroo...	4 beds \| 3 baths \| 4,117 sq.ft.	$2,249,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.96% Airbnb Rental Income: $7455 Traditional Rental Income: $5312 Airbnb ROI: 1.3% Traditional ROI: 0.96%
319 Park Trace Blvd OSPREY, FL Welcome to your dream home in a prime location, positioned near A-rated schools such as Pi...	4 beds \| 3 baths \| 2,551 sq.ft.	$749,900	Airbnb cash on cash: 6.73% Traditional cash on cash: 4.29% Airbnb Rental Income: $7455 Traditional Rental Income: $4318 Airbnb ROI: 6.73% Traditional ROI: 4.29%
51 Macewen Dr #11 OSPREY, FL 51 Macewen Dr #11, OSPREY, FL 34229 \| Condo/Coop	1 beds \| 1 baths \| 623 sq.ft.	$300,000	Airbnb cash on cash: 0.76% Traditional cash on cash: -2.63% Airbnb Rental Income: $2934 Traditional Rental Income: $1300 Airbnb ROI: 0.76% Traditional ROI: -2.63%
919 Tranquility Circle Cir OSPREY, FL 919 Tranquility Circle Cir, OSPREY, FL 34229 \| Single Family Residential	4 beds \| 3 baths \| 2,854 sq.ft.	$825,000	Airbnb cash on cash: 5.61% Traditional cash on cash: 2.09% Airbnb Rental Income: $7455 Traditional Rental Income: $3322 Airbnb ROI: 5.61% Traditional ROI: 2.09%
9681 Crystal Isles Cir OSPREY, FL 9681 Crystal Isles Cir, OSPREY, FL 34241 \| Single Family Residential	4 beds \| 3 baths \| 2,643 sq.ft.	$809,444	Airbnb cash on cash: 5.98% Traditional cash on cash: 2.05% Airbnb Rental Income: $7455 Traditional Rental Income: $3060 Airbnb ROI: 5.98% Traditional ROI: 2.05%
711 Shadow Bay Way OSPREY, FL 711 Shadow Bay Way, OSPREY, FL 34229 \| Single Family Residential	4 beds \| 2 baths \| 2,133 sq.ft.	$600,000	Airbnb cash on cash: 8.47% Traditional cash on cash: 2.22% Airbnb Rental Income: $7455 Traditional Rental Income: $2527 Airbnb ROI: 8.47% Traditional ROI: 2.22%
232 Woodland Dr #232 OSPREY, FL 232 Woodland Dr #232, OSPREY, FL 34229 \| Condo/Coop	2 beds \| 2 baths \| 1,325 sq.ft.	$264,900	Airbnb cash on cash: 3.04% Traditional cash on cash: 1.57% Airbnb Rental Income: $2934 Traditional Rental Income: $1889 Airbnb ROI: 3.04% Traditional ROI: 1.57%
700 Faith Ave OSPREY, FL 700 Faith Ave, OSPREY, FL 34229 \| Single Family Residential	4 beds \| 3 baths \| 2,474 sq.ft.	$1,250,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 0.75% Airbnb Rental Income: $7455 Traditional Rental Income: $3154 Airbnb ROI: 3.22% Traditional ROI: 0.75%
1811 Highland Rd OSPREY, FL 1811 Highland Rd, OSPREY, FL 34229 \| Townhouse	2 beds \| 2 baths \| 1,725 sq.ft.	$433,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 3.03% Airbnb Rental Income: $2934 Traditional Rental Income: $2254 Airbnb ROI: 3.04% Traditional ROI: 3.03%
123 Windward Dr OSPREY, FL 123 Windward Dr, OSPREY, FL 34229 \| Single Family Residential	3 beds \| 2 baths \| 1,894 sq.ft.	$820,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 0.84% Airbnb Rental Income: $3385 Traditional Rental Income: $2419 Airbnb ROI: 1.12% Traditional ROI: 0.84%

Vacation Rentals in Osprey

There are 49 vacation rental properties available for sale in the city of Osprey . The median list price of Airbnb properties available for sale in Osprey is $749,900 and the average price per square foot is $286. 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 49 Airbnb properties available for sale in Osprey.

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

In February 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

742 Harms Dr

OSPREY, FL

3 beds | 2 baths | 1,293 sq.ft.

$545,000

Airbnb cash on cash: 3.72%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $3385

Traditional Rental Income: $2206

Airbnb ROI: 3.72%

Traditional ROI: 2.89%

403 Longbow Trl

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 Rd

OSPREY, FL

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

$330,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $2934

Traditional Rental Income: $2223

Airbnb ROI: 4.66%

Traditional ROI: 4.55%

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 Blvd

OSPREY, FL

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

$650,000

Airbnb cash on cash: 7.54%

Traditional cash on cash: 4.27%

Airbnb Rental Income: $7455

Traditional Rental Income: $4038

Airbnb ROI: 7.54%

Traditional ROI: 4.27%

146 Willow Bend Way

OSPREY, FL

4 beds | 3 baths | 2,540 sq.ft.

$699,000

Airbnb cash on cash: 7.29%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $7455

Traditional Rental Income: $3683

Airbnb ROI: 7.29%

Traditional ROI: 3.7%

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%

177 Navigation Cir

OSPREY, FL

3 beds | 2 baths | 1,581 sq.ft.

$369,000

Airbnb cash on cash: 3.73%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $3385

Traditional Rental Income: $2530

Airbnb ROI: 3.73%