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 30 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
705 JUNGLE QUEEN Way LONGBOAT KEY, FL Tucked away on the coveted north end of Longboat Key, this custom-designed coastal contemp...	4 beds \| 4 baths \| 3,083 sq.ft.	$2,795,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.55% Airbnb Rental Income: $5769 Traditional Rental Income: $7637 Airbnb ROI: -0.61% Traditional ROI: 0.55%
3530 MISTLETOE Lane LONGBOAT KEY, FL Freshly updated and directly overlooking Sarasota Bay, this four-bedroom waterfront reside...	4 beds \| 4 baths \| 3,102 sq.ft.	$2,675,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.42% Airbnb Rental Income: $5769 Traditional Rental Income: $6723 Airbnb ROI: -0.43% Traditional ROI: 0.42%
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: 0.61% Traditional cash on cash: 1.2% Airbnb Rental Income: $5769 Traditional Rental Income: $6067 Airbnb ROI: 0.61% Traditional ROI: 1.2%
617 WESTON POINTE Court LONGBOAT KEY, FL Welcome to 617 Weston Pointe Court, where timeless elegance meets the Florida waterfro...	4 beds \| 5 baths \| 4,395 sq.ft.	$3,100,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.23% Airbnb Rental Income: $5769 Traditional Rental Income: $7294 Airbnb ROI: -0.7% Traditional ROI: 0.23%
3606 FAIR OAKS Place LONGBOAT KEY, FL Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional fi...	5 beds \| 3 baths \| 3,842 sq.ft.	$4,999,000	Airbnb cash on cash: 1.71% Traditional cash on cash: -0.19% Airbnb Rental Income: $20279 Traditional Rental Income: $7910 Airbnb ROI: 1.71% Traditional ROI: -0.19%
6489 GULFSIDE Road LONGBOAT KEY, FL This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. E...	4 beds \| 5 baths \| 6,616 sq.ft.	$13,995,000	Airbnb cash on cash: -0.95% Traditional cash on cash: -0.4% Airbnb Rental Income: $5769 Traditional Rental Income: $11811 Airbnb ROI: -0.95% Traditional ROI: -0.4%
597 BUTTONWOOD Drive LONGBOAT KEY, FL Completed New Construction - Best-Priced Luxury New Construction on Longboat Key! Gulf & B...	5 beds \| 7 baths \| 4,176 sq.ft.	$4,000,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.44% Airbnb Rental Income: $20279 Traditional Rental Income: $13587 Airbnb ROI: 3.29% Traditional ROI: 2.44%
1600 HARBOR SOUND Drive LONGBOAT KEY, FL Pre-Construction. To be built. Positioned directly across from the iconic St. Regis Longbo...	5 beds \| 6 baths \| 5,689 sq.ft.	$11,900,000	Airbnb cash on cash: 0.21% Traditional cash on cash: -0.61% Airbnb Rental Income: $20279 Traditional Rental Income: $7677 Airbnb ROI: 0.21% Traditional ROI: -0.61%
602 BUTTONWOOD Drive LONGBOAT KEY, FL Expect luxury living and a world of conveniences within the serene enclave of Buttonwood H...	3 beds \| 3 baths \| 2,107 sq.ft.	$1,375,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.9% Airbnb Rental Income: $3137 Traditional Rental Income: $7541 Airbnb ROI: -0.11% Traditional ROI: 3.9%
834 JUNGLE QUEEN Way LONGBOAT KEY, FL Virtually Staged. Situated on an expansive 11,250-square-foot lot, this property offers th...	2 beds \| 2 baths \| 1,346 sq.ft.	$1,050,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.78% Airbnb Rental Income: $2447 Traditional Rental Income: $3146 Airbnb ROI: -0.55% Traditional ROI: 0.78%
550 DE NARVAEZ Drive LONGBOAT KEY, FL One or more photo(s) has been virtually staged. Welcome to 550 De Narvaez Drive, a meticul...	3 beds \| 2 baths \| 1,758 sq.ft.	$1,295,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.97% Airbnb Rental Income: $3137 Traditional Rental Income: $4237 Airbnb ROI: 0.47% Traditional ROI: 1.97%
552 JUAN ANASCO DRIVE LONGBOAT KEY, FL Under contract-accepting backup offers. Imagine living the coastal lifestyle only dreams a...	3 beds \| 4 baths \| 1,846 sq.ft.	$975,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 3.93% Airbnb Rental Income: $3137 Traditional Rental Income: $6180 Airbnb ROI: -0.21% Traditional ROI: 3.93%
720 TARAWITT Drive LONGBOAT KEY, FL Pre-Construction. To be built. Build your dream waterfront home on North Longboat Key! Dis...	3 beds \| 5 baths \| 2,160 sq.ft.	$2,900,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.26% Airbnb Rental Income: $3137 Traditional Rental Income: $6953 Airbnb ROI: -0.42% Traditional ROI: 1.26%
771 MARBURY Lane LONGBOAT KEY, FL Boaters will love this spacious elevated home in a premier waterfront location on Longboat...	5 beds \| 4 baths \| 3,016 sq.ft.	$2,500,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 1.13% Airbnb Rental Income: $20279 Traditional Rental Income: $7266 Airbnb ROI: 5.21% Traditional ROI: 1.13%
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.	$3,590,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -0.84% Airbnb Rental Income: $3137 Traditional Rental Income: $4015 Airbnb ROI: -1.32% Traditional ROI: -0.84%
560 HARBOR COVE Circle LONGBOAT KEY, FL An exceedingly rare offering within the exclusive Bay Harbour enclave of Bay Isles on Long...	3 beds \| 4 baths \| 3,485 sq.ft.	$7,900,000	Airbnb cash on cash: -1.16% Traditional cash on cash: -0.31% Airbnb Rental Income: $3137 Traditional Rental Income: $8665 Airbnb ROI: -1.16% Traditional ROI: -0.31%
5924 GULF OF MEXICO Drive LONGBOAT KEY, FL Sought after mid-key cottage home with DEEDED BEACH ACCESS on the barrier island of Longbo...	2 beds \| 2 baths \| 1,359 sq.ft.	$849,500	Airbnb cash on cash: -0.15% Traditional cash on cash: 1.38% Airbnb Rental Income: $2447 Traditional Rental Income: $3063 Airbnb ROI: -0.15% Traditional ROI: 1.38%
5920 GULF OF MEXICO Drive LONGBOAT KEY, FL DEEDED BEACH ACCESS AND DEEP WATER CANAL at this beautifully renovated mid-key beach house...	2 beds \| 3 baths \| 2,823 sq.ft.	$1,749,500	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.16% Airbnb Rental Income: $2447 Traditional Rental Income: $4382 Airbnb ROI: -0.4% Traditional ROI: 1.16%
6610 GULF OF MEXICO Drive LONGBOAT KEY, FL Named the House of Columns by world-renowned, award-winning architect Carl Abbott, this pa...	4 beds \| 7 baths \| 6,891 sq.ft.	$22,000,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -0.3% Airbnb Rental Income: $5769 Traditional Rental Income: $18180 Airbnb ROI: -0.96% Traditional ROI: -0.3%
7143 LA LENAIRE Drive LONGBOAT KEY, FL Private island living on Jewfish Key, one of eight homes, accessible by boat only. This ra...	4 beds \| 4 baths \| 2,721 sq.ft.	$5,995,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.03% Airbnb Rental Income: $5769 Traditional Rental Income: $7721 Airbnb ROI: -0.53% Traditional ROI: 0.03%
825 TARAWITT Drive LONGBOAT KEY, FL *Gorgeous Canal Home Featuring A Huge 125x90 Ft.Lot! This Completely Remodeled Waterfront ...	2 beds \| 3 baths \| 1,882 sq.ft.	$1,499,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.92% Airbnb Rental Income: $2447 Traditional Rental Income: $4556 Airbnb ROI: -1.02% Traditional ROI: 0.92%
3040 GULF OF MEXICO Drive #3 LONGBOAT KEY, FL Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destina...	4 beds \| 3 baths \| 3,009 sq.ft.	$1,899,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 0.69% Airbnb Rental Income: $5769 Traditional Rental Income: $4418 Airbnb ROI: 0.8% Traditional ROI: 0.69%
617 ROUNTREE Drive LONGBOAT KEY, FL Discover the perfect canvas for your coastal vision in the prestigious Longboat Key Estate...	3 beds \| 2 baths \| 1,972 sq.ft.	$2,150,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 0.31% Airbnb Rental Income: $3137 Traditional Rental Income: $3705 Airbnb ROI: -0.33% Traditional ROI: 0.31%
791 BROADWAY Street LONGBOAT KEY, FL Welcome home to 791 Broadway, nestled in the heart of historic Longbeach Village on the No...	2 beds \| 2 baths \| 2,236 sq.ft.	$1,625,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 0.35% Airbnb Rental Income: $2447 Traditional Rental Income: $3009 Airbnb ROI: -0.42% Traditional ROI: 0.35%
3301 BAYOU Road LONGBOAT KEY, FL Located within the gated and highly desirable community of Bay Isles on Longboat Key, this...	4 beds \| 3 baths \| 2,827 sq.ft.	$1,250,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.41% Airbnb Rental Income: $5769 Traditional Rental Income: $4379 Airbnb ROI: 1.62% Traditional ROI: 1.41%
549 HALYARD Lane LONGBOAT KEY, FL This is the one * PERFECTLY POSITIONED ON A QUIET CUL DE SAC STREET AT THE PREFERRED SOUTH...	3 beds \| 2 baths \| 1,594 sq.ft.	$2,195,000	Airbnb cash on cash: -0.8% Traditional cash on cash: -0.36% Airbnb Rental Income: $3137 Traditional Rental Income: $3332 Airbnb ROI: -0.8% Traditional ROI: -0.36%

Your search for investment property begins and ends here

Single Family Homes for Sale in Longboat Key, FL

705 JUNGLE QUEEN Way

LONGBOAT KEY, FL

4 beds | 4 baths | 3,083 sq.ft.

$2,795,000

Airbnb cash on cash: -0.61%

Traditional cash on cash: 0.55%

Airbnb Rental Income: $5769

Traditional Rental Income: $7637

Airbnb ROI: -0.61%

Traditional ROI: 0.55%

3530 MISTLETOE Lane

LONGBOAT KEY, FL

4 beds | 4 baths | 3,102 sq.ft.

$2,675,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $5769

Traditional Rental Income: $6723

Airbnb ROI: -0.43%

Traditional ROI: 0.42%

610 HIBISCUS Way

LONGBOAT KEY, FL

4 beds | 5 baths | 2,788 sq.ft.

$2,650,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $5769

Traditional Rental Income: $6067

Airbnb ROI: 0.61%

Traditional ROI: 1.2%

617 WESTON POINTE Court

LONGBOAT KEY, FL

4 beds | 5 baths | 4,395 sq.ft.

$3,100,000

Airbnb cash on cash: -0.7%

Traditional cash on cash: 0.23%

Airbnb Rental Income: $5769

Traditional Rental Income: $7294

Airbnb ROI: -0.7%

Traditional ROI: 0.23%

3606 FAIR OAKS Place

LONGBOAT KEY, FL

5 beds | 3 baths | 3,842 sq.ft.

$4,999,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: -0.19%

Airbnb Rental Income: $20279

Traditional Rental Income: $7910

Airbnb ROI: 1.71%

Traditional ROI: -0.19%

6489 GULFSIDE Road

LONGBOAT KEY, FL

4 beds | 5 baths | 6,616 sq.ft.

$13,995,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: -0.4%

Airbnb Rental Income: $5769

Traditional Rental Income: $11811

Airbnb ROI: -0.95%

Traditional ROI: -0.4%

597 BUTTONWOOD Drive

LONGBOAT KEY, FL

5 beds | 7 baths | 4,176 sq.ft.

$4,000,000

Airbnb cash on cash: 3.29%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $20279

Traditional Rental Income: $13587

Airbnb ROI: 3.29%

Traditional ROI: 2.44%

1600 HARBOR SOUND Drive

LONGBOAT KEY, FL

5 beds | 6 baths | 5,689 sq.ft.

$11,900,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: -0.61%

Airbnb Rental Income: $20279

Traditional Rental Income: $7677

Airbnb ROI: 0.21%