Real Estate Investment Properties for Sale in Longboat Key, FL

Looking for investment property in Longboat Key, FL with high ROI ?

Explore a variety of short-term homes & houses in Longboat Key, FL. Invest wisely with VRBO & Longboat Key, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Longboat Key, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1085 GULF OF MEXICO DRIVE #205 LONGBOAT KEY, FL Spacious 3-Bedroom End-Unit Residence in Sought-After Beachplace Welcome to this beauti...	3 beds \| 2 baths \| 1,819 sq.ft.	$939,000	Airbnb cash on cash: -1.61% Traditional cash on cash: 2.12% Airbnb Rental Income: $2892 Traditional Rental Income: $5489 Airbnb ROI: -1.61% Traditional ROI: 2.12%
1912 HARBOURSIDE DRIVE #604 LONGBOAT KEY, FL Embrace the island life style within the gates of Longboat Key's premier resort community ...	3 beds \| 3 baths \| 2,207 sq.ft.	$835,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -0.61% Airbnb Rental Income: $2892 Traditional Rental Income: $3337 Airbnb ROI: -2.04% Traditional ROI: -0.61%
6700 Gulf OF Mexico Dr #143 LONGBOAT KEY, FL Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story cond...	1 beds \| 1 baths \| 936 sq.ft.	$410,000	Airbnb cash on cash: 1.68% Traditional cash on cash: -0.88% Airbnb Rental Income: $3476 Traditional Rental Income: $1724 Airbnb ROI: 1.68% Traditional ROI: -0.88%
1965 Gulf OF Mexico Dr #G5-103 LONGBOAT KEY, FL Experience coastal living at its finest in this beautifully updated ground-floor residence...	2 beds \| 2 baths \| 933 sq.ft.	$649,000	Airbnb cash on cash: -1.82% Traditional cash on cash: -0.67% Airbnb Rental Income: $2087 Traditional Rental Income: $2248 Airbnb ROI: -1.82% Traditional ROI: -0.67%
793 Jungle Queen Way LONGBOAT KEY, FL Longboat Key Waterfront Home combining Canal frontage & Deeded Beach Access. Key West-styl...	4 beds \| 3 baths \| 2,900 sq.ft.	$1,749,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 1.04% Airbnb Rental Income: $7893 Traditional Rental Income: $4952 Airbnb ROI: 1.92% Traditional ROI: 1.04%
5841 Gulf OF Mexico Dr #244 LONGBOAT KEY, FL REDUCE PRICE- RARE FIND!!! This fully furnished turnkey 1bedroom/1bath end unit has an ope...	1 beds \| 1 baths \| 520 sq.ft.	$505,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 1.05% Airbnb Rental Income: $3476 Traditional Rental Income: $2840 Airbnb ROI: 0.77% Traditional ROI: 1.05%
1935 Gulf OF Mexico Dr #G7-304 LONGBOAT KEY, FL Experience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom...	2 beds \| 1 baths \| 933 sq.ft.	$455,000	Airbnb cash on cash: -2.92% Traditional cash on cash: -2.72% Airbnb Rental Income: $2087 Traditional Rental Income: $1634 Airbnb ROI: -2.92% Traditional ROI: -2.72%
1926 Harbourside Dr #1302 LONGBOAT KEY, FL GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main...	2 beds \| 2 baths \| 2,606 sq.ft.	$769,000	Airbnb cash on cash: -2.86% Traditional cash on cash: 1.45% Airbnb Rental Income: $2087 Traditional Rental Income: $4643 Airbnb ROI: -2.86% Traditional ROI: 1.45%
3806 Gulf OF Mexico Dr #C208 LONGBOAT KEY, FL Discover coastal living at its finest with this charming condominium located on Gulf of Me...	1 beds \| 1 baths \| 712 sq.ft.	$295,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 3.47% Airbnb Rental Income: $3476 Traditional Rental Income: $2689 Airbnb ROI: 3.53% Traditional ROI: 3.47%
4621 Gulf OF Mexico Dr #10D LONGBOAT KEY, FL Huge Price Adjustment! PRICED TO SELL!!! Check out these consistently strong revenue numbe...	2 beds \| 2 baths \| 756 sq.ft.	$625,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.47% Airbnb Rental Income: $2087 Traditional Rental Income: $2884 Airbnb ROI: -0.73% Traditional ROI: 1.47%
1065 Gulf OF Mexico Dr #302 LONGBOAT KEY, FL One of a kind, never rented, ready for a new owner to put their touches on this opportunit...	2 beds \| 2 baths \| 1,392 sq.ft.	$749,000	Airbnb cash on cash: -2.03% Traditional cash on cash: 1.21% Airbnb Rental Income: $2087 Traditional Rental Income: $3809 Airbnb ROI: -2.03% Traditional ROI: 1.21%
1241 Gulf OF Mexico Dr #506 LONGBOAT KEY, FL Welcome to coastal luxury redefined at the Water Club on Longboat Key. This fully reimagin...	3 beds \| 3 baths \| 2,650 sq.ft.	$3,850,000	Airbnb cash on cash: -1.92% Traditional cash on cash: -0.69% Airbnb Rental Income: $2892 Traditional Rental Income: $6594 Airbnb ROI: -1.92% Traditional ROI: -0.69%
100 Sands Point Rd #324 LONGBOAT KEY, FL BACK on the market after beautiful renovations!! Unit is impeccably maintained. It has a...	3 beds \| 2 baths \| 1,941 sq.ft.	$980,000	Airbnb cash on cash: -1.77% Traditional cash on cash: 1.52% Airbnb Rental Income: $2892 Traditional Rental Income: $5216 Airbnb ROI: -1.77% Traditional ROI: 1.52%
2945 PYRULA DRIVE LONGBOAT KEY, FL A contemporary masterpiece awaits Your going to love this house !, constructed in 2024 and...	5 beds \| 5 baths \| 4,340 sq.ft.	$3,125,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 0.69% Airbnb Rental Income: $10664 Traditional Rental Income: $8335 Airbnb ROI: 0.81% Traditional ROI: 0.69%
806 Bayport Way #806 LONGBOAT KEY, FL Welcome to this beautifully appointed ground floor residence that combines modern elegance...	2 beds \| 2 baths \| 1,392 sq.ft.	$949,000	Airbnb cash on cash: -2.46% Traditional cash on cash: 1.19% Airbnb Rental Income: $2087 Traditional Rental Income: $4768 Airbnb ROI: -2.46% Traditional ROI: 1.19%
100 Sands Point Rd #323 LONGBOAT KEY, FL Sands Point, a sought-after beachfront community within the gates of the Longboat Key Club...	3 beds \| 2 baths \| 1,941 sq.ft.	$1,395,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.09% Airbnb Rental Income: $2892 Traditional Rental Income: $4383 Airbnb ROI: -1.57% Traditional ROI: 0.09%
2181 HARBOURSIDE DRIVE #1403 LONGBOAT KEY, FL Under contract-accepting backup offers. PRICED TO SELL! Experience the ultimate in island...	3 beds \| 3 baths \| 2,219 sq.ft.	$850,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 3.46% Airbnb Rental Income: $2892 Traditional Rental Income: $6124 Airbnb ROI: -1.46% Traditional ROI: 3.46%
435 L Ambiance Dr #L707 LONGBOAT KEY, FL There are viewsâ¦ and then there is this view! From this desirable seventh-floor corner r...	2 beds \| 2 baths \| 2,525 sq.ft.	$2,890,000	Airbnb cash on cash: -3.47% Traditional cash on cash: -1.27% Airbnb Rental Income: $2087 Traditional Rental Income: $7461 Airbnb ROI: -3.47% Traditional ROI: -1.27%
4440 Exeter Dr LONGBOAT KEY, FL Welcome to Longboat Harbour, a gated waterfront community offering resort-style living on ...	2 beds \| 2 baths \| 1,376 sq.ft.	$649,000	Airbnb cash on cash: -2.94% Traditional cash on cash: 1.06% Airbnb Rental Income: $2087 Traditional Rental Income: $3975 Airbnb ROI: -2.94% Traditional ROI: 1.06%
2819 Gulf OF Mexico Dr LONGBOAT KEY, FL BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on ...	3 beds \| 2 baths \| 1,173 sq.ft.	$3,590,000	Airbnb cash on cash: -1.37% Traditional cash on cash: -0.84% Airbnb Rental Income: $2892 Traditional Rental Income: $4015 Airbnb ROI: -1.37% Traditional ROI: -0.84%
6322 Laguna Dr #1 LONGBOAT KEY, FL Welcome to Laguna Yacht Village on beautiful Longboat Key- a gated waterfront community lo...	4 beds \| 3 baths \| 2,886 sq.ft.	$2,499,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 0.47% Airbnb Rental Income: $7893 Traditional Rental Income: $5222 Airbnb ROI: 0.98% Traditional ROI: 0.47%
4350 Chatham Dr #E-208 LONGBOAT KEY, FL One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! REDUCED $35,000! ...	2 beds \| 2 baths \| 1,316 sq.ft.	$640,000	Airbnb cash on cash: -2.6% Traditional cash on cash: 1.24% Airbnb Rental Income: $2087 Traditional Rental Income: $3844 Airbnb ROI: -2.6% Traditional ROI: 1.24%
4485 GULF OF MEXICO DRIVE #804 LONGBOAT KEY, FL Renovated direct Gulf-front 2BR/2BA on Longboat Key. End-unit 8th-floor condo at The Arbom...	2 beds \| 2 baths \| 1,175 sq.ft.	$1,025,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 0.46% Airbnb Rental Income: $2087 Traditional Rental Income: $3534 Airbnb ROI: -1.62% Traditional ROI: 0.46%
2550 Harbourside Dr #333 LONGBOAT KEY, FL Set within a living canopy of mangroves and coastal trees, this BAYFRONT residence invites...	3 beds \| 2 baths \| 3,067 sq.ft.	$1,495,000	Airbnb cash on cash: -2.18% Traditional cash on cash: 1.53% Airbnb Rental Income: $2892 Traditional Rental Income: $7380 Airbnb ROI: -2.18% Traditional ROI: 1.53%
4420 Exeter Dr #303 LONGBOAT KEY, FL Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath...	2 beds \| 2 baths \| 1,152 sq.ft.	$575,000	Airbnb cash on cash: -1.81% Traditional cash on cash: 1.66% Airbnb Rental Income: $2087 Traditional Rental Income: $3490 Airbnb ROI: -1.81% Traditional ROI: 1.66%
1105 Gulf OF Mexico Dr #401 LONGBOAT KEY, FL Direct Ocean view from this Bright Airy corner unit in desirable building five. Catch the ...	2 beds \| 2 baths \| 1,172 sq.ft.	$899,000	Airbnb cash on cash: -2.35% Traditional cash on cash: 1.38% Airbnb Rental Income: $2087 Traditional Rental Income: $4667 Airbnb ROI: -2.35% Traditional ROI: 1.38%
578 Companion Way LONGBOAT KEY, FL Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the u...	4 beds \| 3 baths \| 1,792 sq.ft.	$900,000	Airbnb cash on cash: 5.63% Traditional cash on cash: 2.33% Airbnb Rental Income: $7893 Traditional Rental Income: $3621 Airbnb ROI: 5.63% Traditional ROI: 2.33%
4440 Exeter Dr #106 LONGBOAT KEY, FL Welcome to Longboat Harbour, a gated waterfront community offering resort-style living on ...	2 beds \| 2 baths \| 1,376 sq.ft.	$649,000	Airbnb cash on cash: -2.94% Traditional cash on cash: 1.05% Airbnb Rental Income: $2087 Traditional Rental Income: $3969 Airbnb ROI: -2.94% Traditional ROI: 1.05%
5655 Gulf OF Mexico Dr #D107 LONGBOAT KEY, FL Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bed...	2 beds \| 2 baths \| 1,274 sq.ft.	$799,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 1.72% Airbnb Rental Income: $2087 Traditional Rental Income: $3730 Airbnb ROI: -1.21% Traditional ROI: 1.72%
1925 Gulf OF Mexico Dr #G8-302 LONGBOAT KEY, FL Experience the Best of Gulfside Living at Seaplace on Longboat Key! Welcome to this bea...	2 beds \| 2 baths \| 1,257 sq.ft.	$629,000	Airbnb cash on cash: -2.38% Traditional cash on cash: 3.36% Airbnb Rental Income: $2087 Traditional Rental Income: $4922 Airbnb ROI: -2.38% Traditional ROI: 3.36%
578 - 580 Companion Way LONGBOAT KEY, FL Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the u...	4 beds \| N/A baths \| 1,792 sq.ft.	$900,000	Airbnb cash on cash: 6.51% Traditional cash on cash: 3.06% Airbnb Rental Income: $7893 Traditional Rental Income: $3498 Airbnb ROI: 6.51% Traditional ROI: 3.06%
617 Rountree Dr LONGBOAT KEY, FL Premier waterfront opportunity in Longboat Key Estates, offering direct canal frontage in ...	3 beds \| 2 baths \| 1,972 sq.ft.	$2,350,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.2% Airbnb Rental Income: $2892 Traditional Rental Income: $3705 Airbnb ROI: -0.48% Traditional ROI: 0.2%
1135 GULF OF MEXICO DRIVE #505 LONGBOAT KEY, FL Under contract-accepting backup offers. DIRECT BEACH FRONT VIEWS AND FIFTH FLOOR EXTRORDIN...	2 beds \| 2 baths \| 1,503 sq.ft.	$1,175,000	Airbnb cash on cash: -2.43% Traditional cash on cash: -1.04% Airbnb Rental Income: $2087 Traditional Rental Income: $3064 Airbnb ROI: -2.43% Traditional ROI: -1.04%
3271 BAYOU ROAD LONGBOAT KEY, FL Nestled behind the gates of prestigious Bay Isles on Longboat Key, this exceptional reside...	4 beds \| 4 baths \| 3,059 sq.ft.	$1,995,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 0.12% Airbnb Rental Income: $7893 Traditional Rental Income: $4844 Airbnb ROI: 0.95% Traditional ROI: 0.12%

Real Estate investment in Longboat-key, FL

There are 306 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,114,333 and the average price per square foot is $633. In July 2026, the average monthly cash on cash return in Longboat Key is N/A%. The average monthly rental income in Longboat Key is $2,121.

Longboat-key, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 306 investment properties available for sale in Longboat-key.

In 2026, the best neighborhood to buy investment property is LONGBOAT KEY.

The ROI for Short-Term is higher than the Long-Term in Longboat-key with average rental income of $2,087.

Your search for investment property begins and ends here

Investment Property for Sale in Longboat Key, FL

1085 GULF OF MEXICO DRIVE #205

LONGBOAT KEY, FL

3 beds | 2 baths | 1,819 sq.ft.

$939,000

Airbnb cash on cash: -1.61%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $2892

Traditional Rental Income: $5489

Airbnb ROI: -1.61%

Traditional ROI: 2.12%

1912 HARBOURSIDE DRIVE #604

LONGBOAT KEY, FL

3 beds | 3 baths | 2,207 sq.ft.

$835,000

Airbnb cash on cash: -2.04%

Traditional cash on cash: -0.61%

Airbnb Rental Income: $2892

Traditional Rental Income: $3337

Airbnb ROI: -2.04%

Traditional ROI: -0.61%

6700 Gulf OF Mexico Dr #143

LONGBOAT KEY, FL

1 beds | 1 baths | 936 sq.ft.

$410,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: -0.88%

Airbnb Rental Income: $3476

Traditional Rental Income: $1724

Airbnb ROI: 1.68%

Traditional ROI: -0.88%

1965 Gulf OF Mexico Dr #G5-103

LONGBOAT KEY, FL

2 beds | 2 baths | 933 sq.ft.

$649,000

Airbnb cash on cash: -1.82%

Traditional cash on cash: -0.67%

Airbnb Rental Income: $2087

Traditional Rental Income: $2248

Airbnb ROI: -1.82%

Traditional ROI: -0.67%

793 Jungle Queen Way

LONGBOAT KEY, FL

4 beds | 3 baths | 2,900 sq.ft.

$1,749,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $7893

Traditional Rental Income: $4952

Airbnb ROI: 1.92%

Traditional ROI: 1.04%

5841 Gulf OF Mexico Dr #244

LONGBOAT KEY, FL

1 beds | 1 baths | 520 sq.ft.

$505,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 1.05%

Airbnb Rental Income: $3476

Traditional Rental Income: $2840

Airbnb ROI: 0.77%

Traditional ROI: 1.05%

1935 Gulf OF Mexico Dr #G7-304

LONGBOAT KEY, FL

2 beds | 1 baths | 933 sq.ft.

$455,000

Airbnb cash on cash: -2.92%

Traditional cash on cash: -2.72%

Airbnb Rental Income: $2087

Traditional Rental Income: $1634

Airbnb ROI: -2.92%

Traditional ROI: -2.72%

1926 Harbourside Dr #1302

LONGBOAT KEY, FL

2 beds | 2 baths | 2,606 sq.ft.

$769,000

Airbnb cash on cash: -2.86%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $2087

Traditional Rental Income: $4643

Airbnb ROI: -2.86%