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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
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%
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%
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%
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%
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%
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%
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%
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.	$4,249,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 0.24% Airbnb Rental Income: $7664 Traditional Rental Income: $5714 Airbnb ROI: 0.37% Traditional ROI: 0.24%
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.	$5,425,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.31% Airbnb Rental Income: $4647 Traditional Rental Income: $8477 Airbnb ROI: -0.64% Traditional ROI: 0.31%
531 RANGER LANE LONGBOAT KEY, FL Nestled in the sought-after Country Club Shores on Longboat Key, this exquisite waterfront...	4 beds \| 4 baths \| 3,436 sq.ft.	$3,795,500	Airbnb cash on cash: -0.29% Traditional cash on cash: -0.26% Airbnb Rental Income: $6133 Traditional Rental Income: $5029 Airbnb ROI: -0.29% Traditional ROI: -0.26%
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.	$3,495,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.59% Airbnb Rental Income: $7664 Traditional Rental Income: $5905 Airbnb ROI: 0.68% Traditional ROI: 0.59%
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%
834 JUNGLE QUEEN WAY LONGBOAT KEY, FL LOCATION LOCATION LOCATION! JUST 3 LOTS IN FROM SARASOTA BAY!!! Imagine living in highly ...	2 beds \| 2 baths \| 1,346 sq.ft.	$1,100,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 0.44% Airbnb Rental Income: $2861 Traditional Rental Income: $2752 Airbnb ROI: -0.11% Traditional ROI: 0.44%
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%
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 One or more photo(s) has been virtually staged. Coastal Elegance on Longboat Key â A Mas...	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%
3302 SABAL COVE LANE LONGBOAT KEY, FL Under contract-accepting backup offers. Just Announced: Major Price Improvement! An incred...	5 beds \| 4 baths \| 3,993 sq.ft.	$2,999,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 0.22% Airbnb Rental Income: $7664 Traditional Rental Income: $6082 Airbnb ROI: 0.26% Traditional ROI: 0.22%
588 BAYVIEW DRIVE LONGBOAT KEY, FL It is time to build your dream home in the best location in Longboat Key. This 100 ft of w...	4 beds \| 3 baths \| 2,248 sq.ft.	$1,890,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 0.13% Airbnb Rental Income: $6133 Traditional Rental Income: $3910 Airbnb ROI: 0.7% Traditional ROI: 0.13%
4968 GULF OF MEXICO DRIVE #Villa 22 LONGBOAT KEY, FL Breathtaking Sarasota Bay views can be yours! This rare to find 3BR/2BA waterfront villa o...	3 beds \| 2 baths \| 1,422 sq.ft.	$1,200,000	Airbnb cash on cash: 0.28% Traditional cash on cash: -0.19% Airbnb Rental Income: $4647 Traditional Rental Income: $3157 Airbnb ROI: 0.28% Traditional ROI: -0.19%
4 WINSLOW PLACE LONGBOAT KEY, FL Welcome to an extraordinary coastal retreat in the coveted enclave of Buttonwood Harbor on...	4 beds \| 3 baths \| 3,288 sq.ft.	$2,000,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 0.38% Airbnb Rental Income: $6133 Traditional Rental Income: $4634 Airbnb ROI: 0.54% Traditional ROI: 0.38%
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%
590 DE NARVAEZ DRIVE LONGBOAT KEY, FL Step into a new era of coastal modern living with this breathtaking, newly constructed wat...	4 beds \| 4 baths \| 3,243 sq.ft.	$4,340,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 0.09% Airbnb Rental Income: $6133 Traditional Rental Income: $5053 Airbnb ROI: 0.05% Traditional ROI: 0.09%
571 BIRDIE LANE LONGBOAT KEY, FL Under contract-accepting backup offers. Country Club Shores at its finest. Three homes in ...	3 beds \| 3 baths \| 2,626 sq.ft.	$2,995,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 0.11% Airbnb Rental Income: $4647 Traditional Rental Income: $4850 Airbnb ROI: -0.31% Traditional ROI: 0.11%
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.	$3,450,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 0.21% Airbnb Rental Income: $6133 Traditional Rental Income: $5961 Airbnb ROI: -0.12% Traditional ROI: 0.21%
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%
210 SANDS POINT ROAD #2405 LONGBOAT KEY, FL Located behind the gates of the highly desirable Longboat Key Club, this 1BR/1BA Club Suit...	1 beds \| 1 baths \| 650 sq.ft.	$1,175,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -0.49% Airbnb Rental Income: $3252 Traditional Rental Income: $1560 Airbnb ROI: 0.39% Traditional ROI: -0.49%
569 ROUNTREE DRIVE LONGBOAT KEY, FL Welcome to Elegant Shores, the newest construction in the highly sought after, rarely avai...	3 beds \| 4 baths \| 3,428 sq.ft.	$3,299,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.13% Airbnb Rental Income: $4647 Traditional Rental Income: $5127 Airbnb ROI: -0.34% Traditional ROI: 0.13%
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 Experience the relaxed Gulf Coast lifestyle at Tiffany Plaza - direct Gulf-front, accessib...	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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Longboat Key, FL

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%

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%

2358 HARBOUR OAKS DRIVE

LONGBOAT KEY, FL

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%

501 DE NARVAEZ DRIVE

LONGBOAT KEY, FL

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%

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%

600 FOX STREET

LONGBOAT KEY, FL

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

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%

510 PUTTER LANE

LONGBOAT KEY, FL

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%