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 48 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
3318 BAYOU SOUND LONGBOAT KEY, FL Immerse yourself in the timeless charm of West Indies-style living with this extraordinary...	3 beds \| 2 baths \| 2,675 sq.ft.	$1,495,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.45% Airbnb Rental Income: $4647 Traditional Rental Income: $7257 Airbnb ROI: 0.87% Traditional ROI: 3.45%
6330 LAGUNA DRIVE LONGBOAT KEY, FL Motivated Seller! Bring offers! Live the ultimate Beach lifestyle! This Raised (16ft.)Hurr...	3 beds \| 3 baths \| 2,856 sq.ft.	$2,195,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.36% Airbnb Rental Income: $4647 Traditional Rental Income: $7214 Airbnb ROI: -0.38% Traditional ROI: 1.36%
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%
957 SPANISH DRIVE N LONGBOAT KEY, FL LONGBOAT KEY WATERFRONT CONDO. UNOBSTRUCTED VIEW OF THE BAY. PEACEFUL LOCATION. BEAUTIFU...	2 beds \| 2 baths \| 1,399 sq.ft.	$1,000,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.63% Airbnb Rental Income: $2861 Traditional Rental Income: $2829 Airbnb ROI: -0.05% Traditional ROI: 0.63%
705 JUNGLE QUEEN WAY LONGBOAT KEY, FL LONGBOAT KEY CANAL FRONT HOME WITH DEEDED BEACH EASEMENT 2 BLOCKS AWAY. This 4 BED / 3.5 B...	4 beds \| 4 baths \| 3,078 sq.ft.	$2,950,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.26% Airbnb Rental Income: $6133 Traditional Rental Income: $7637 Airbnb ROI: -0.73% Traditional ROI: 0.26%
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.	$1,282,500	Airbnb cash on cash: 0.99% Traditional cash on cash: 4.18% Airbnb Rental Income: $4647 Traditional Rental Income: $7489 Airbnb ROI: 0.99% Traditional ROI: 4.18%
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%
7147 LA LENAIRE DRIVE LONGBOAT KEY, FL A rare opportunity to own the crown jewel of Floridaâs west coast. Tucked away on the p...	5 beds \| 6 baths \| 3,503 sq.ft.	$5,250,000	Airbnb cash on cash: -0.43% Traditional cash on cash: -0.81% Airbnb Rental Income: $7664 Traditional Rental Income: $4372 Airbnb ROI: -0.43% Traditional ROI: -0.81%
594 SPANISH DRIVE S LONGBOAT KEY, FL Welcome to this 2-bedroom, 2-bath villa located in the highly desirable 55+ community of S...	2 beds \| 2 baths \| 1,427 sq.ft.	$279,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.3% Airbnb Rental Income: $2861 Traditional Rental Income: $2347 Airbnb ROI: -0.28% Traditional ROI: 0.3%
600 FOX STREET LONGBOAT KEY, FL Experience the charm of historic Longboat Key living in this delightful 3-bedroom, 3-bathr...	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%
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 Revel in all the spaciousness and privacy â situated with wide water and golf views in t...	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%
6489 GULFSIDE ROAD LONGBOAT KEY, FL Under Construction. Enjoy the ultimate Longboat Key lifestyle in your very own direct Gulf...	4 beds \| 5 baths \| 6,616 sq.ft.	$16,995,000	Airbnb cash on cash: -0.94% Traditional cash on cash: -0.77% Airbnb Rental Income: $6133 Traditional Rental Income: $7586 Airbnb ROI: -0.94% Traditional ROI: -0.77%
3491 BAYOU SOUND LONGBOAT KEY, FL Welcome to the secure, double-gated Bay Isles Bayou community on Longboat Key. Set on an e...	4 beds \| 6 baths \| 5,730 sq.ft.	$3,849,000	Airbnb cash on cash: -0.19% Traditional cash on cash: -0.21% Airbnb Rental Income: $6133 Traditional Rental Income: $4873 Airbnb ROI: -0.19% Traditional ROI: -0.21%
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%
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.	$3,595,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.55% Airbnb Rental Income: $7664 Traditional Rental Income: $5905 Airbnb ROI: 0.64% Traditional ROI: 0.55%
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%
618 JUNGLE QUEEN WAY LONGBOAT KEY, FL Wow! $75,000 price reduction! Lowest priced Waterfront Single Family Home on Longboat Key!...	3 beds \| 2 baths \| 1,351 sq.ft.	$749,900	Airbnb cash on cash: 3.51% Traditional cash on cash: 2.1% Airbnb Rental Income: $4647 Traditional Rental Income: $2696 Airbnb ROI: 3.51% Traditional ROI: 2.1%
550 DE NARVAEZ DRIVE LONGBOAT KEY, FL ELEVATED LOT \| NO FLOOD DAMAGE \| MOVE-IN READY \| FULLY FURNISHED \| WATERFRONT \| Welcome ...	3 beds \| 2 baths \| 1,758 sq.ft.	$1,298,750	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.03% Airbnb Rental Income: $4647 Traditional Rental Income: $3095 Airbnb ROI: 1.52% Traditional ROI: 1.03%
2065 HARBOUR LINKS DRIVE #5 LONGBOAT KEY, FL Welcome to 2065 Harbour Links Dr, a beautifully maintained 3-bedroom, 3.5-bathroom, 2,865 ...	3 beds \| 4 baths \| 2,865 sq.ft.	$1,849,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 1.41% Airbnb Rental Income: $4647 Traditional Rental Income: $5193 Airbnb ROI: 0.53% Traditional ROI: 1.41%
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.	$5,199,950	Airbnb cash on cash: -0.23% Traditional cash on cash: 0.96% Airbnb Rental Income: $6133 Traditional Rental Income: $10627 Airbnb ROI: -0.23% Traditional ROI: 0.96%
560 SCHOONER LANE LONGBOAT KEY, FL Coastal Elegance on Longboat Key â A Masterpiece of Waterfront Living. Tucked away in t...	4 beds \| 4 baths \| 3,666 sq.ft.	$3,999,999	Airbnb cash on cash: -0.18% Traditional cash on cash: 0.15% Airbnb Rental Income: $6133 Traditional Rental Income: $6140 Airbnb ROI: -0.18% Traditional ROI: 0.15%
600 DE NARVAEZ DRIVE LONGBOAT KEY, FL The Future of Luxury Living on Longboat Key! Discover this newly constructed coastal retre...	3 beds \| 3 baths \| 1,971 sq.ft.	$2,800,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.55% Airbnb Rental Income: $4647 Traditional Rental Income: $3693 Airbnb ROI: -0.55% Traditional ROI: -0.55%
4235 GULF OF MEXICO DRIVE #G203 LONGBOAT KEY, FL REDUCED PRICE!!! SELLER will pay up to $20,000 of Buyers closing cost. Great investor or s...	1 beds \| 1 baths \| 666 sq.ft.	$475,000	Airbnb cash on cash: 0.29% Traditional cash on cash: -2.39% Airbnb Rental Income: $3252 Traditional Rental Income: $1330 Airbnb ROI: 0.29% Traditional ROI: -2.39%
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.	$895,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 1.33% Airbnb Rental Income: $2861 Traditional Rental Income: $2659 Airbnb ROI: 0.78% Traditional ROI: 1.33%
3272 BAYOU ROAD LONGBOAT KEY, FL Under contract-accepting backup offers. Welcome to the exclusive, double-gated Bay Isles B...	3 beds \| 3 baths \| 2,954 sq.ft.	$2,395,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 0.52% Airbnb Rental Income: $4647 Traditional Rental Income: $4587 Airbnb ROI: 0.11% Traditional ROI: 0.52%
3302 SABAL COVE LANE LONGBOAT KEY, FL Just Announced: Major Price Improvement! An incredible opportunity awaits with this newly ...	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%
2944 GULF OF MEXICO DRIVE LONGBOAT KEY, FL Under Construction. Exceptional Custom Home Opportunity with Unobstructed Gulf Views! 2...	4 beds \| 5 baths \| 4,997 sq.ft.	$1,550,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 2.6% Airbnb Rental Income: $6133 Traditional Rental Income: $6042 Airbnb ROI: 1.83% Traditional ROI: 2.6%
540 GULF BAY ROAD LONGBOAT KEY, FL SPECTACULAR LONGBOAT KEY BEACH COMPOUND WITH DEEDED ACCESS TO THE GULF OF MEXICO! This FUL...	3 beds \| 4 baths \| 1,880 sq.ft.	$1,950,000	Airbnb cash on cash: -0.15% Traditional cash on cash: -0.06% Airbnb Rental Income: $4647 Traditional Rental Income: $3853 Airbnb ROI: -0.15% Traditional ROI: -0.06%
6381 GULF OF MEXICO DRIVE LONGBOAT KEY, FL Welcome to a once-in-a-lifetime opportunity to own a sleek, modern coastal estate on one o...	4 beds \| 6 baths \| 4,224 sq.ft.	$7,995,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -1.23% Airbnb Rental Income: $6133 Traditional Rental Income: $7686 Airbnb ROI: -1.6% Traditional ROI: -1.23%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Longboat Key, FL

3318 BAYOU SOUND

LONGBOAT KEY, FL

3 beds | 2 baths | 2,675 sq.ft.

$1,495,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $4647

Traditional Rental Income: $7257

Airbnb ROI: 0.87%

Traditional ROI: 3.45%

6330 LAGUNA DRIVE

LONGBOAT KEY, FL

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

$2,195,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $4647

Traditional Rental Income: $7214

Airbnb ROI: -0.38%

Traditional ROI: 1.36%

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%

957 SPANISH DRIVE N

LONGBOAT KEY, FL

2 beds | 2 baths | 1,399 sq.ft.

$1,000,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $2861

Traditional Rental Income: $2829

Airbnb ROI: -0.05%

Traditional ROI: 0.63%

705 JUNGLE QUEEN WAY

LONGBOAT KEY, FL

4 beds | 4 baths | 3,078 sq.ft.

$2,950,000

Airbnb cash on cash: -0.73%

Traditional cash on cash: 0.26%

Airbnb Rental Income: $6133

Traditional Rental Income: $7637

Airbnb ROI: -0.73%

Traditional ROI: 0.26%

501 DE NARVAEZ DRIVE

LONGBOAT KEY, FL

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

$1,282,500

Airbnb cash on cash: 0.99%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $4647

Traditional Rental Income: $7489

Airbnb ROI: 0.99%

Traditional ROI: 4.18%

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%

7147 LA LENAIRE DRIVE

LONGBOAT KEY, FL

5 beds | 6 baths | 3,503 sq.ft.

$5,250,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: -0.81%

Airbnb Rental Income: $7664

Traditional Rental Income: $4372

Airbnb ROI: -0.43%