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.

Single Family Homes for Sale in Longboat Key, FL

Search for Single Family Residential for Sale in Longboat Key, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 50 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
6330 LAGUNA DRIVE LONGBOAT KEY, FL Modern Beach Home priced aggressively to sell as the owners are relocating. Ocean Views! P...	3 beds \| 3 baths \| 2,856 sq.ft.	$1,999,999	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.58% Airbnb Rental Income: $4647 Traditional Rental Income: $7214 Airbnb ROI: -0.32% Traditional ROI: 1.58%
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%
747 MARBURY LANE LONGBOAT KEY, FL Welcome to Your Waterfront Paradise! Discover this coastal retreat in the highly desirabl...	3 beds \| 2 baths \| 2,353 sq.ft.	$1,425,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 0.9% Airbnb Rental Income: $4647 Traditional Rental Income: $4017 Airbnb ROI: 0.65% Traditional ROI: 0.9%
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%
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.	$1,168,375	Airbnb cash on cash: 1.18% Traditional cash on cash: 4.68% Airbnb Rental Income: $4647 Traditional Rental Income: $7489 Airbnb ROI: 1.18% Traditional ROI: 4.68%
3281 BAYOU SOUND LONGBOAT KEY, FL Under contract-accepting backup offers. Surrounded by tropical landscaping, this 3BR/3Â½BA...	3 beds \| 4 baths \| 3,407 sq.ft.	$2,295,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 1.01% Airbnb Rental Income: $4647 Traditional Rental Income: $5586 Airbnb ROI: 0.12% Traditional ROI: 1.01%
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%
5841 GULF OF MEXICO DRIVE #244 LONGBOAT KEY, FL RARE FIND!!! This fully furnished turnkey 1bedroom/1bath end unit has an open kitchen, din...	1 beds \| 1 baths \| 520 sq.ft.	$575,000	Airbnb cash on cash: 0.21% Traditional cash on cash: -1.52% Airbnb Rental Income: $3252 Traditional Rental Income: $1594 Airbnb ROI: 0.21% Traditional ROI: -1.52%
5840 GULF OF MEXICO DRIVE LONGBOAT KEY, FL Longboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Coon...	4 beds \| 6 baths \| 4,145 sq.ft.	$5,280,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.03% Airbnb Rental Income: $6133 Traditional Rental Income: $9774 Airbnb ROI: -1.02% Traditional ROI: -0.03%
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%
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%
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%
3210 BAYOU SOUND LONGBOAT KEY, FL Welcome to this elevated retreat in the sought-after Bayou section of Bay Islesâa seamle...	2 beds \| 3 baths \| 3,171 sq.ft.	$1,699,999	Airbnb cash on cash: -0.66% Traditional cash on cash: 2.43% Airbnb Rental Income: $2861 Traditional Rental Income: $7079 Airbnb ROI: -0.66% Traditional ROI: 2.43%
3617 FAIR OAKS PLACE LONGBOAT KEY, FL One or more photo(s) has been virtually staged. Situated in the highly sought-after mainte...	3 beds \| 4 baths \| 2,950 sq.ft.	$2,159,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.19% Airbnb Rental Income: $4647 Traditional Rental Income: $9084 Airbnb ROI: -0.51% Traditional ROI: 2.19%
597 BUTTONWOOD DRIVE LONGBOAT KEY, FL GULF AND BAY VIEWS! THREE OUTDOOR PATIOS! Discover an extraordinary coastal contemporary m...	5 beds \| 7 baths \| 4,176 sq.ft.	$4,199,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 0.26% Airbnb Rental Income: $7664 Traditional Rental Income: $5714 Airbnb ROI: 0.38% Traditional ROI: 0.26%
530 DE NARVAEZ DRIVE LONGBOAT KEY, FL New Construction - Discover the epitome of waterfront luxury with this newly built home in...	4 beds \| 6 baths \| 4,106 sq.ft.	$4,995,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 0.4% Airbnb Rental Income: $6133 Traditional Rental Income: $7651 Airbnb ROI: -0.19% Traditional ROI: 0.4%
585 GUNWALE LANE LONGBOAT KEY, FL Welcome to 585 Gunwale Lane, a rare, full-bayfront offering in the desirable community of ...	3 beds \| 4 baths \| 4,733 sq.ft.	$5,225,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 0.36% Airbnb Rental Income: $4647 Traditional Rental Income: $8477 Airbnb ROI: -0.63% Traditional ROI: 0.36%
610 YARDARM LANE LONGBOAT KEY, FL Experience elevated coastal living in this updated, elegantly styled waterfront residence ...	4 beds \| 5 baths \| 4,138 sq.ft.	$4,700,000	Airbnb cash on cash: -0.76% Traditional cash on cash: -0.42% Airbnb Rental Income: $6133 Traditional Rental Income: $6399 Airbnb ROI: -0.76% Traditional ROI: -0.42%
2945 PYRULA DRIVE LONGBOAT KEY, FL Discover unparalleled modern living at this custom contemporary residence nestled on a qui...	5 beds \| 5 baths \| 3,815 sq.ft.	$3,295,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 0.69% Airbnb Rental Income: $7664 Traditional Rental Income: $5905 Airbnb ROI: 0.78% Traditional ROI: 0.69%
501 HARBOR POINT ROAD LONGBOAT KEY, FL Rare opportunity to acquire completely remodeled waterfront residence (Finished in 2023) o...	5 beds \| 6 baths \| 6,125 sq.ft.	$8,500,000	Airbnb cash on cash: -0.74% Traditional cash on cash: -0.59% Airbnb Rental Income: $7664 Traditional Rental Income: $7377 Airbnb ROI: -0.74% Traditional ROI: -0.59%
3408 FAIR OAKS LANE LONGBOAT KEY, FL Elegant 5BR/5BA home in the gated community of Coreyâs Landing within Bay Isles on Longb...	5 beds \| 5 baths \| 4,510 sq.ft.	$2,790,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.39% Airbnb Rental Income: $7664 Traditional Rental Income: $6753 Airbnb ROI: 0.17% Traditional ROI: 0.39%
3540 MISTLETOE LANE LONGBOAT KEY, FL This spectacular direct bayfront three-bedroom plus den home is offered fully furnished an...	4 beds \| 4 baths \| 3,166 sq.ft.	$3,595,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 0.02% Airbnb Rental Income: $6133 Traditional Rental Income: $5686 Airbnb ROI: -0.21% Traditional ROI: 0.02%
552 JUAN ANASCO DRIVE LONGBOAT KEY, FL short stories"...Great opportunity pick cabinets and flooring ..pool is back new air condi...	3 beds \| 4 baths \| 1,846 sq.ft.	$1,397,849	Airbnb cash on cash: 0.52% Traditional cash on cash: 1.07% Airbnb Rental Income: $4647 Traditional Rental Income: $4393 Airbnb ROI: 0.52% Traditional ROI: 1.07%
3151 BAYOU SOUND LONGBOAT KEY, FL Coastal elegance meets island living in Bay Isles Bayou on Longboat Key. Nestled within th...	4 beds \| 4 baths \| 3,263 sq.ft.	$2,295,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.82% Airbnb Rental Income: $6133 Traditional Rental Income: $5850 Airbnb ROI: 0.39% Traditional ROI: 0.82%
569 BAYVIEW DRIVE LONGBOAT KEY, FL Under Construction. New Construction. Experience the pinnacle of waterfront luxury with th...	4 beds \| 6 baths \| 4,106 sq.ft.	$5,049,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.02% Airbnb Rental Income: $6133 Traditional Rental Income: $10627 Airbnb ROI: -0.2% Traditional ROI: 1.02%
560 SCHOONER LANE LONGBOAT KEY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Co...	4 beds \| 4 baths \| 3,666 sq.ft.	$3,500,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 0.31% Airbnb Rental Income: $6133 Traditional Rental Income: $6140 Airbnb ROI: -0.06% Traditional ROI: 0.31%
636 TARAWITT DRIVE LONGBOAT KEY, FL One or more photo(s) has been virtually staged. PRICE IMPROVEMENT!! WATERFRONT GEM ON LONG...	2 beds \| 2 baths \| 1,248 sq.ft.	$885,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.36% Airbnb Rental Income: $2861 Traditional Rental Income: $2659 Airbnb ROI: 0.8% Traditional ROI: 1.36%
2944 GULF OF MEXICO DRIVE LONGBOAT KEY, FL Under Construction. Poised along one of Longboat Keyâs most coveted stretches, this new ...	5 beds \| 6 baths \| 4,826 sq.ft.	$5,299,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.06% Airbnb Rental Income: $7664 Traditional Rental Income: $6042 Airbnb ROI: 0.09% Traditional ROI: 0.06%
510 WEDGE LANE LONGBOAT KEY, FL Welcome to your own piece of paradise in the prestigious Country Club Shores neighborhood ...	4 beds \| 3 baths \| 1,840 sq.ft.	$2,215,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 0.24% Airbnb Rental Income: $6133 Traditional Rental Income: $3998 Airbnb ROI: 0.69% Traditional ROI: 0.24%
5310 GULF OF MEXICO DRIVE #18 LONGBOAT KEY, FL Charming, rarely available beach-to-bay short term vacation rental. This fully furnished 1...	1 beds \| 1 baths \| 711 sq.ft.	$425,000	Airbnb cash on cash: 1.15% Traditional cash on cash: -1.29% Airbnb Rental Income: $3252 Traditional Rental Income: $1550 Airbnb ROI: 1.15% Traditional ROI: -1.29%
701 MARBURY LANE LONGBOAT KEY, FL Welcome to Bougain Villa, your Tropical Island Oasis on a deep water canal leading to secl...	3 beds \| 2 baths \| 2,246 sq.ft.	$1,697,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.8% Airbnb Rental Income: $4647 Traditional Rental Income: $3722 Airbnb ROI: 0.77% Traditional ROI: 0.8%
3310 BAYOU ROAD LONGBOAT KEY, FL Artfully Curated, Fully Reimagined Lakefront Estate in Bay Isles This is not just a hom...	3 beds \| 3 baths \| 2,995 sq.ft.	$2,925,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.19% Airbnb Rental Income: $4647 Traditional Rental Income: $4632 Airbnb ROI: -0.16% Traditional ROI: 0.19%
601 TRITON BEND LONGBOAT KEY, FL Exuding coastal charm, this spacious four bedroom, three full baths, and two half baths Br...	4 beds \| 5 baths \| 3,313 sq.ft.	$3,275,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.27% Airbnb Rental Income: $6133 Traditional Rental Income: $5961 Airbnb ROI: -0.07% Traditional ROI: 0.27%
725 PENFIELD STREET LONGBOAT KEY, FL Experience refined coastal living in this stunning custom canal-front home, where timeless...	4 beds \| 4 baths \| 2,902 sq.ft.	$2,475,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 1.16% Airbnb Rental Income: $6133 Traditional Rental Income: $5871 Airbnb ROI: 0.75% Traditional ROI: 1.16%
569 ROUNTREE DRIVE LONGBOAT KEY, FL STUNNING New Construction WATERFRONT Home in LONGBOAT KEY ESTATES!!! Experience the pinnac...	3 beds \| 4 baths \| 3,428 sq.ft.	$3,190,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 0.16% Airbnb Rental Income: $4647 Traditional Rental Income: $5127 Airbnb ROI: -0.32% Traditional ROI: 0.16%
6601 GULFSIDE ROAD LONGBOAT KEY, FL Discover a truly rare opportunity to own two parcels in a new, beachfront enclave being de...	5 beds \| 3 baths \| 3,492 sq.ft.	$5,000,000	Airbnb cash on cash: -0.83% Traditional cash on cash: -1.21% Airbnb Rental Income: $7664 Traditional Rental Income: $4430 Airbnb ROI: -0.83% Traditional ROI: -1.21%
4325 GULF OF MEXICO DRIVE #102 LONGBOAT KEY, FL Under contract-accepting backup offers. Experience the relaxed Gulf Coast lifestyle at Tif...	2 beds \| 2 baths \| 1,336 sq.ft.	$1,000,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.5% Airbnb Rental Income: $2861 Traditional Rental Income: $2672 Airbnb ROI: -0.01% Traditional ROI: 0.5%
2819 GULF OF MEXICO DRIVE 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.	$4,499,000	Airbnb cash on cash: -0.95% Traditional cash on cash: -1.18% Airbnb Rental Income: $4647 Traditional Rental Income: $2714 Airbnb ROI: -0.95% Traditional ROI: -1.18%
6001 GULF OF MEXICO DRIVE LONGBOAT KEY, FL A Gulf-Front Masterpiece on Longboat Key! This stunning Gulf-front estate is perfectly pla...	5 beds \| 7 baths \| 6,959 sq.ft.	$11,995,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -0.96% Airbnb Rental Income: $7664 Traditional Rental Income: $10221 Airbnb ROI: -1.32% Traditional ROI: -0.96%
3261 BAYOU SOUND LONGBOAT KEY, FL Under contract-accepting backup offers. A boaterâs delight in the heart of Bay Isles on ...	3 beds \| 3 baths \| 2,849 sq.ft.	$2,100,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.06% Airbnb Rental Income: $4647 Traditional Rental Income: $4585 Airbnb ROI: -0.4% Traditional ROI: 0.06%

Your search for investment property begins and ends here

Single Family Homes for Sale in Longboat Key, FL

6330 LAGUNA DRIVE

LONGBOAT KEY, FL

3 beds | 3 baths | 2,856 sq.ft.

$1,999,999

Airbnb cash on cash: -0.32%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $4647

Traditional Rental Income: $7214

Airbnb ROI: -0.32%

Traditional ROI: 1.58%

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%

747 MARBURY LANE

LONGBOAT KEY, FL

3 beds | 2 baths | 2,353 sq.ft.

$1,425,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 0.9%

Airbnb Rental Income: $4647

Traditional Rental Income: $4017

Airbnb ROI: 0.65%

Traditional ROI: 0.9%

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%

501 DE NARVAEZ DRIVE

LONGBOAT KEY, FL

3 beds | 3 baths | 1,708 sq.ft.

$1,168,375

Airbnb cash on cash: 1.18%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $4647

Traditional Rental Income: $7489

Airbnb ROI: 1.18%

Traditional ROI: 4.68%

3281 BAYOU SOUND

LONGBOAT KEY, FL

3 beds | 4 baths | 3,407 sq.ft.

$2,295,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 1.01%

Airbnb Rental Income: $4647

Traditional Rental Income: $5586

Airbnb ROI: 0.12%

Traditional ROI: 1.01%

619 BUTTONWOOD DRIVE

LONGBOAT KEY, FL

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%

5841 GULF OF MEXICO DRIVE #244

LONGBOAT KEY, FL

1 beds | 1 baths | 520 sq.ft.

$575,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: -1.52%

Airbnb Rental Income: $3252

Traditional Rental Income: $1594

Airbnb ROI: 0.21%