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
1241 GULF OF MEXICO DRIVE #109 LONGBOAT KEY, FL Live the lavish lifestyle only found at the Water Club on Longboat Key, an idyllic waterfr...	2 beds \| 3 baths \| 2,000 sq.ft.	$1,525,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 0.97% Airbnb Rental Income: $2861 Traditional Rental Income: $4149 Airbnb ROI: -0.41% Traditional ROI: 0.97%
2450 HARBOURSIDE DRIVE #212 LONGBOAT KEY, FL JUMP NOW... $100,000 price reduction!! Indulge in the luxury living experience at Marina ...	3 beds \| 3 baths \| 2,830 sq.ft.	$1,575,000	Airbnb cash on cash: -0.67% Traditional cash on cash: -0.54% Airbnb Rental Income: $4647 Traditional Rental Income: $3879 Airbnb ROI: -0.67% Traditional ROI: -0.54%
608 SAINT JUDES DRIVE LONGBOAT KEY, FL A TRUE FLORIDA DREAM HOME! WALKING DISTANCE TO ONE OF FLORIDA'S MOST BEAUTIFUL BEACH! This...	4 beds \| 3 baths \| 2,106 sq.ft.	$989,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 5.38% Airbnb Rental Income: $6133 Traditional Rental Income: $6745 Airbnb ROI: 3.4% Traditional ROI: 5.38%
1065 GULF OF MEXICO DRIVE #601 LONGBOAT KEY, FL Under contract-accepting backup offers. A rare offering of a penthouse end unit in this Gu...	2 beds \| 2 baths \| 1,172 sq.ft.	$895,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 0.61% Airbnb Rental Income: $2861 Traditional Rental Income: $2531 Airbnb ROI: 0.21% Traditional ROI: 0.61%
6800 GULF OF MEXICO DRIVE #203 LONGBOAT KEY, FL Serene water views of tranquil Bishops Bayou greet you as you enter this immaculate 2nd fl...	1 beds \| 1 baths \| 936 sq.ft.	$449,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 2.03% Airbnb Rental Income: $3252 Traditional Rental Income: $1779 Airbnb ROI: 3.8% Traditional ROI: 2.03%
667 EL CENTRO LONGBOAT KEY, FL Spanish Main Yacht Club on Longboat Key is a warm and vital boating community with its pri...	2 beds \| 2 baths \| 1,327 sq.ft.	$380,000	Airbnb cash on cash: -0.9% Traditional cash on cash: -0.77% Airbnb Rental Income: $2861 Traditional Rental Income: $2240 Airbnb ROI: -0.9% Traditional ROI: -0.77%
1935 GULF OF MEXICO DRIVE #G7-402 LONGBOAT KEY, FL A must-see, this exceptional two-bedroom, two-bath penthouse is the only residence in Seap...	2 beds \| 2 baths \| 1,068 sq.ft.	$649,000	Airbnb cash on cash: -0.81% Traditional cash on cash: -1.26% Airbnb Rental Income: $2861 Traditional Rental Income: $1924 Airbnb ROI: -0.81% Traditional ROI: -1.26%
2055 GULF OF MEXICO DRIVE #G2-214 LONGBOAT KEY, FL Below $400,000 Seaplace opportunity â¢ Hurricane shutter & newer AC â¢ Gulf-front commu...	1 beds \| 2 baths \| 1,094 sq.ft.	$399,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 4.99% Airbnb Rental Income: $3252 Traditional Rental Income: $4287 Airbnb ROI: 0.28% Traditional ROI: 4.99%
575 SANCTUARY DRIVE #A302 LONGBOAT KEY, FL Under contract-accepting backup offers. Renovated in 2023 and perfectly positioned on the ...	3 beds \| 3 baths \| 1,823 sq.ft.	$1,650,000	Airbnb cash on cash: -0.24% Traditional cash on cash: -0.08% Airbnb Rental Income: $4647 Traditional Rental Income: $3916 Airbnb ROI: -0.24% Traditional ROI: -0.08%
2675 GULF OF MEXICO DRIVE #403 LONGBOAT KEY, FL HUGE PRICE CHANGE:Veinte (20 in Spanish) is a luxury condominium community with only twent...	3 beds \| 2 baths \| 1,896 sq.ft.	$1,400,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.07% Airbnb Rental Income: $4647 Traditional Rental Income: $3526 Airbnb ROI: 0.19% Traditional ROI: 0.07%
2358 HARBOUR OAKS DRIVE LONGBOAT KEY, FL Under contract-accepting backup offers. This expansive villa offers the space and comfort ...	3 beds \| 3 baths \| 2,381 sq.ft.	$985,000	Airbnb cash on cash: -1.97% Traditional cash on cash: 3.04% Airbnb Rental Income: $4647 Traditional Rental Income: $8274 Airbnb ROI: -1.97% Traditional ROI: 3.04%
3010 GRAND BAY BOULEVARD #472 LONGBOAT KEY, FL Your semi-private elevator provides access to the beautiful 7th floor condo with sweeping ...	3 beds \| 3 baths \| 2,250 sq.ft.	$1,725,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 0.52% Airbnb Rental Income: $4647 Traditional Rental Income: $6841 Airbnb ROI: -1.45% Traditional ROI: 0.52%
1932 HARBOURSIDE DRIVE #244 LONGBOAT KEY, FL Welcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in...	2 beds \| 2 baths \| 1,192 sq.ft.	$1,200,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 0.02% Airbnb Rental Income: $2861 Traditional Rental Income: $2440 Airbnb ROI: -0.2% Traditional ROI: 0.02%
501 DE NARVAEZ DRIVE LONGBOAT KEY, FL Some homes whisper. Others make a statement. 501 De Narvaez Drive commands attentionâwit...	3 beds \| 3 baths \| 1,708 sq.ft.	$1,218,375	Airbnb cash on cash: 1.09% Traditional cash on cash: 4.45% Airbnb Rental Income: $4647 Traditional Rental Income: $7489 Airbnb ROI: 1.09% Traditional ROI: 4.45%
565 SANCTUARY DRIVE #B106 LONGBOAT KEY, FL Nestled behind the exclusive gates of the Longboat Key Club, The Sanctuary enjoys an envia...	3 beds \| 3 baths \| 2,375 sq.ft.	$1,999,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 0.23% Airbnb Rental Income: $4647 Traditional Rental Income: $4508 Airbnb ROI: -0.22% Traditional ROI: 0.23%
1281 GULF OF MEXICO DRIVE #404 LONGBOAT KEY, FL Introducing an exceptional beachfront residence that defines luxury living on Longboat Key...	3 beds \| 4 baths \| 3,054 sq.ft.	$2,695,000	Airbnb cash on cash: -0.92% Traditional cash on cash: -0.33% Airbnb Rental Income: $4647 Traditional Rental Income: $5157 Airbnb ROI: -0.92% Traditional ROI: -0.33%
1281 GULF OF MEXICO DRIVE #906 LONGBOAT KEY, FL Welcome to The Water Club on Longboat Key, where refined Gulf-front living meets everyday ...	2 beds \| 3 baths \| 2,655 sq.ft.	$2,495,000	Airbnb cash on cash: -1.22% Traditional cash on cash: -0.22% Airbnb Rental Income: $2861 Traditional Rental Income: $4516 Airbnb ROI: -1.22% Traditional ROI: -0.22%
435 L AMBIANCE DRIVE #J703 LONGBOAT KEY, FL Experience unparalleled luxury in this beautifully updated 3-bedroom condo at the highly c...	3 beds \| 3 baths \| 2,634 sq.ft.	$4,795,000	Airbnb cash on cash: -1.67% Traditional cash on cash: -1.55% Airbnb Rental Income: $4647 Traditional Rental Income: $4230 Airbnb ROI: -1.67% Traditional ROI: -1.55%
619 BUTTONWOOD DRIVE LONGBOAT KEY, FL One or more photo(s) has been virtually staged. Welcome to an exceptional mid-century mode...	3 beds \| 2 baths \| 2,265 sq.ft.	$1,599,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.17% Airbnb Rental Income: $4647 Traditional Rental Income: $7081 Airbnb ROI: 0.88% Traditional ROI: 3.17%
3806 GULF OF MEXICO DRIVE #C-312 LONGBOAT KEY, FL Furnished 2-bedroom, 2-bathroom end unit condo on Longboat Key! Brand New HVAC! This 3rd-...	2 beds \| 2 baths \| 1,062 sq.ft.	$319,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 3.84% Airbnb Rental Income: $2861 Traditional Rental Income: $2007 Airbnb ROI: 4.47% Traditional ROI: 3.84%
4651 GULF OF MEXICO DRIVE #402 LONGBOAT KEY, FL Experience an unparalleled coastal retreat where the gulf meets impeccable design and tech...	4 beds \| 5 baths \| 3,989 sq.ft.	$5,999,000	Airbnb cash on cash: -2.64% Traditional cash on cash: -1.99% Airbnb Rental Income: $6133 Traditional Rental Income: $8527 Airbnb ROI: -2.64% Traditional ROI: -1.99%
3806 GULF OF MEXICO DRIVE #C311 LONGBOAT KEY, FL Priced to sell! Discover the perfect blend of comfort and coastal living in this beautiful...	2 beds \| 2 baths \| 1,062 sq.ft.	$325,000	Airbnb cash on cash: -0.13% Traditional cash on cash: -1.01% Airbnb Rental Income: $2861 Traditional Rental Income: $1926 Airbnb ROI: -0.13% Traditional ROI: -1.01%
1935 GULF OF MEXICO DRIVE #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.	$510,000	Airbnb cash on cash: -0.72% Traditional cash on cash: -1.89% Airbnb Rental Income: $2861 Traditional Rental Income: $1634 Airbnb ROI: -0.72% Traditional ROI: -1.89%
6701 GULF OF MEXICO DRIVE #311 LONGBOAT KEY, FL COASTAL ELEGANCE ON LONGBOAT KEY - DIRECT GULF FRONT PROPERTY: Welcome to a rare opportun...	1 beds \| 1 baths \| 936 sq.ft.	$849,900	Airbnb cash on cash: -1.57% Traditional cash on cash: -2.5% Airbnb Rental Income: $3252 Traditional Rental Income: $1782 Airbnb ROI: -1.57% Traditional ROI: -2.5%
3060 GRAND BAY BOULEVARD #154 LONGBOAT KEY, FL Beautifully renovated and offered turnkey furnished, this 3BR/3.5BA residence is perfectly...	3 beds \| 4 baths \| 2,550 sq.ft.	$1,695,000	Airbnb cash on cash: -1.83% Traditional cash on cash: -0.39% Airbnb Rental Income: $4647 Traditional Rental Income: $5935 Airbnb ROI: -1.83% Traditional ROI: -0.39%
1050 LONGBOAT CLUB ROAD #903 LONGBOAT KEY, FL SIGNIFICANT PRICE REDUCTON - This TOTALLY RENOVATED ISLAND BEAUTY will charm the most soph...	2 beds \| 2 baths \| 1,409 sq.ft.	$1,250,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.11% Airbnb Rental Income: $2861 Traditional Rental Income: $2876 Airbnb ROI: -0.48% Traditional ROI: 0.11%
3030 GRAND BAY BOULEVARD #381 LONGBOAT KEY, FL Under contract-accepting backup offers. Experience luxury coastal living at its finest in ...	3 beds \| 4 baths \| 2,925 sq.ft.	$2,795,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.13% Airbnb Rental Income: $4647 Traditional Rental Income: $5059 Airbnb ROI: -0.4% Traditional ROI: 0.13%
600 FOX STREET LONGBOAT KEY, FL Under contract-accepting backup offers. Experience the charm of historic Longboat Key livi...	3 beds \| 3 baths \| 1,427 sq.ft.	$899,999	Airbnb cash on cash: 2.07% Traditional cash on cash: 0.87% Airbnb Rental Income: $4647 Traditional Rental Income: $2674 Airbnb ROI: 2.07% Traditional ROI: 0.87%
509 SPANISH DRIVE N LONGBOAT KEY, FL Welcome to your slice of paradise on Longboat Key! Just steps from the white sandy beaches...	2 beds \| 2 baths \| 1,357 sq.ft.	$395,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 1.54% Airbnb Rental Income: $2861 Traditional Rental Income: $3124 Airbnb ROI: -0.97% Traditional ROI: 1.54%
1926 HARBOURSIDE DRIVE #1302 LONGBOAT KEY, FL GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main...	2 beds \| 3 baths \| 2,606 sq.ft.	$949,000	Airbnb cash on cash: -1.78% Traditional cash on cash: -0.53% Airbnb Rental Income: $2861 Traditional Rental Income: $3300 Airbnb ROI: -1.78% Traditional ROI: -0.53%
510 PUTTER LANE LONGBOAT KEY, FL Welcome to 510 Putter Lane, a stunning canal-front retreat nestled in the coveted Country ...	3 beds \| 2 baths \| 2,253 sq.ft.	$3,250,000	Airbnb cash on cash: -0.34% Traditional cash on cash: -0.24% Airbnb Rental Income: $4647 Traditional Rental Income: $4000 Airbnb ROI: -0.34% Traditional ROI: -0.24%
3806 GULF OF MEXICO DRIVE #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.	$305,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 6.13% Airbnb Rental Income: $3252 Traditional Rental Income: $3495 Airbnb ROI: 2.74% Traditional ROI: 6.13%
610 HIBISCUS WAY LONGBOAT KEY, FL Pre-Construction. To be built. Welcome to a luxurious modern retreat in The Preserve on Lo...	4 beds \| 5 baths \| 2,788 sq.ft.	$2,650,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 1.23% Airbnb Rental Income: $6133 Traditional Rental Income: $6152 Airbnb ROI: 0.73% Traditional ROI: 1.23%
3467 BYRON LANE LONGBOAT KEY, FL Under contract-accepting backup offers. Revel in all the spaciousness and privacy â situ...	3 beds \| 3 baths \| 2,227 sq.ft.	$1,149,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 0.41% Airbnb Rental Income: $4647 Traditional Rental Income: $3801 Airbnb ROI: 0.3% Traditional ROI: 0.41%
1445 GULF OF MEXICO DRIVE #304 LONGBOAT KEY, FL Timeless sophistication meets resort-style elegance in this fully renovated 3-bedroom resi...	3 beds \| 3 baths \| 1,859 sq.ft.	$1,500,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 0.32% Airbnb Rental Income: $4647 Traditional Rental Income: $3926 Airbnb ROI: 0.14% Traditional ROI: 0.32%
651 JUNGLE QUEEN WAY LONGBOAT KEY, FL * * DO NOT MISS OUT ON THIS LONGBOAT SPECIAL * * MULTIPLE USES ARE AVAILABLE TO YOU * * Pr...	4 beds \| 3 baths \| 2,242 sq.ft.	$950,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 0.84% Airbnb Rental Income: $6133 Traditional Rental Income: $3457 Airbnb ROI: 2.49% Traditional ROI: 0.84%
1211 GULF OF MEXICO DRIVE #403 LONGBOAT KEY, FL Escape to Elegance on Longboat Key Welcome to this fully renovated, fourth-floor reside...	2 beds \| 2 baths \| 1,585 sq.ft.	$1,795,000	Airbnb cash on cash: -0.63% Traditional cash on cash: -0.12% Airbnb Rental Income: $2861 Traditional Rental Income: $3053 Airbnb ROI: -0.63% Traditional ROI: -0.12%
2013 HARBOUR LINKS DRIVE #2013 LONGBOAT KEY, FL Step into easy, worry-free condo living behind the double gates of Bay Isles. Set within a...	2 beds \| 3 baths \| 2,369 sq.ft.	$899,999	Airbnb cash on cash: -1.21% Traditional cash on cash: 7.06% Airbnb Rental Income: $2861 Traditional Rental Income: $9123 Airbnb ROI: -1.21% Traditional ROI: 7.06%
3802 GULF OF MEXICO DRIVE #A203 LONGBOAT KEY, FL Beach Harbor Club is a beautifully maintained Gulf-to-bay community offering boat slips on...	2 beds \| 2 baths \| 1,007 sq.ft.	$419,900	Airbnb cash on cash: 3.69% Traditional cash on cash: 9.24% Airbnb Rental Income: $2861 Traditional Rental Income: $4379 Airbnb ROI: 3.69% Traditional ROI: 9.24%
2045 GULF OF MEXICO DRIVE #M1-502 LONGBOAT KEY, FL PARADISE AWAITS! Wake up to breathtaking sunrise views from your private lanai and unwind ...	2 beds \| 1 baths \| 928 sq.ft.	$509,000	Airbnb cash on cash: -3.83% Traditional cash on cash: -0.3% Airbnb Rental Income: $2861 Traditional Rental Income: $3877 Airbnb ROI: -3.83% Traditional ROI: -0.3%

Real Estate investment in Longboat-key, FL

There are 140 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,286,880 and the average price per square foot is $618. In October 2025, the average monthly cash on cash return in Longboat Key is N/A%. The average monthly rental income in Longboat Key is $2,548.

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

There are 140 investment properties available for sale in Longboat-key.

In 2025, 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 $2,861.

Your search for investment property begins and ends here

Investment Property for Sale in Longboat Key, FL

1241 GULF OF MEXICO DRIVE #109

LONGBOAT KEY, FL

2 beds | 3 baths | 2,000 sq.ft.

$1,525,000

Airbnb cash on cash: -0.41%

Traditional cash on cash: 0.97%

Airbnb Rental Income: $2861

Traditional Rental Income: $4149

Airbnb ROI: -0.41%

Traditional ROI: 0.97%

2450 HARBOURSIDE DRIVE #212

LONGBOAT KEY, FL

3 beds | 3 baths | 2,830 sq.ft.

$1,575,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: -0.54%

Airbnb Rental Income: $4647

Traditional Rental Income: $3879

Airbnb ROI: -0.67%

Traditional ROI: -0.54%

608 SAINT JUDES DRIVE

LONGBOAT KEY, FL

4 beds | 3 baths | 2,106 sq.ft.

$989,000

Airbnb cash on cash: 3.4%

Traditional cash on cash: 5.38%

Airbnb Rental Income: $6133

Traditional Rental Income: $6745

Airbnb ROI: 3.4%

Traditional ROI: 5.38%

1065 GULF OF MEXICO DRIVE #601

LONGBOAT KEY, FL

2 beds | 2 baths | 1,172 sq.ft.

$895,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $2861

Traditional Rental Income: $2531

Airbnb ROI: 0.21%

Traditional ROI: 0.61%

6800 GULF OF MEXICO DRIVE #203

LONGBOAT KEY, FL

1 beds | 1 baths | 936 sq.ft.

$449,000

Airbnb cash on cash: 3.8%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $3252

Traditional Rental Income: $1779

Airbnb ROI: 3.8%

Traditional ROI: 2.03%

667 EL CENTRO

LONGBOAT KEY, FL

2 beds | 2 baths | 1,327 sq.ft.

$380,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: -0.77%

Airbnb Rental Income: $2861

Traditional Rental Income: $2240

Airbnb ROI: -0.9%

Traditional ROI: -0.77%

1935 GULF OF MEXICO DRIVE #G7-402

LONGBOAT KEY, FL

2 beds | 2 baths | 1,068 sq.ft.

$649,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: -1.26%

Airbnb Rental Income: $2861

Traditional Rental Income: $1924

Airbnb ROI: -0.81%

Traditional ROI: -1.26%

2055 GULF OF MEXICO DRIVE #G2-214

LONGBOAT KEY, FL

1 beds | 2 baths | 1,094 sq.ft.

$399,900

Airbnb cash on cash: 0.28%

Traditional cash on cash: 4.99%

Airbnb Rental Income: $3252

Traditional Rental Income: $4287

Airbnb ROI: 0.28%