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
100 SANDS POINT ROAD #225 LONGBOAT KEY, FL MUST SEE ARCHITECTURAL GEM on Longboat Key! Sands Point Condominium is a best kept secret...	2 beds \| 2 baths \| 1,492 sq.ft.	$975,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 2.3% Airbnb Rental Income: $2861 Traditional Rental Income: $3450 Airbnb ROI: 0.92% Traditional ROI: 2.3%
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.	$1,295,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.25% Airbnb Rental Income: $2861 Traditional Rental Income: $4149 Airbnb ROI: -0.38% Traditional ROI: 1.25%
2450 HARBOURSIDE DRIVE #212 LONGBOAT KEY, FL JUMP NOW... Price reduction!! Indulge in the luxury living experience at Marina Bay, wher...	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%
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%
795 MARBURY LANE LONGBOAT KEY, FL Refined coastal living is waiting for you at 795 Marbury Lane in Longboat Key. Perfectly p...	4 beds \| 3 baths \| 3,355 sq.ft.	$3,999,990	Airbnb cash on cash: -0.49% Traditional cash on cash: -0.68% Airbnb Rental Income: $6133 Traditional Rental Income: $4246 Airbnb ROI: -0.49% Traditional ROI: -0.68%
3080 GRAND BAY BOULEVARD #515 LONGBOAT KEY, FL Defined by an exceptional indoorâoutdoor connection, this 2BR/2BA Grand Bay residence of...	2 beds \| 2 baths \| 1,276 sq.ft.	$659,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.4% Airbnb Rental Income: $2861 Traditional Rental Income: $2627 Airbnb ROI: -1.1% Traditional ROI: -0.4%
2089 GULF OF MEXICO DRIVE #G1-105 LONGBOAT KEY, FL Wake up in This Resort-Style Living Condo located on a Barrier Island Paradise! Positioned...	2 beds \| 2 baths \| 1,257 sq.ft.	$880,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.04% Airbnb Rental Income: $2861 Traditional Rental Income: $2669 Airbnb ROI: 0.46% Traditional ROI: 1.04%
738 EL CENTRO LONGBOAT KEY, FL Calling all boaters, investors, paradise seekers and people who are looking for incredible...	2 beds \| 2 baths \| 1,299 sq.ft.	$329,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 4.51% Airbnb Rental Income: $2861 Traditional Rental Income: $2276 Airbnb ROI: 4.25% Traditional ROI: 4.51%
747 MARBURY LANE LONGBOAT KEY, FL Welcome to Your Waterfront Paradise! This beautiful home even includes the Boat! This be...	3 beds \| 2 baths \| 2,353 sq.ft.	$1,369,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 0.98% Airbnb Rental Income: $4647 Traditional Rental Income: $4017 Airbnb ROI: 0.72% Traditional ROI: 0.98%
775 LONGBOAT CLUB ROAD #705 LONGBOAT KEY, FL TURN-KEY FURNISHED beach-to-bay corner residence offering 2 bedrooms, 2 ensuite baths, and...	2 beds \| 2 baths \| 1,602 sq.ft.	$1,499,000	Airbnb cash on cash: -0.75% Traditional cash on cash: -0.09% Airbnb Rental Income: $2861 Traditional Rental Income: $3122 Airbnb ROI: -0.75% Traditional ROI: -0.09%
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%
1145 GULF OF MEXICO DRIVE #301 LONGBOAT KEY, FL Elegance meets comfort in this rarely available, Turnkey Furnished, Gulf-front corner unit...	2 beds \| 2 baths \| 1,172 sq.ft.	$1,195,000	Airbnb cash on cash: -1.15% Traditional cash on cash: -0.88% Airbnb Rental Income: $2861 Traditional Rental Income: $2494 Airbnb ROI: -1.15% Traditional ROI: -0.88%
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.	$625,000	Airbnb cash on cash: -1.14% Traditional cash on cash: -1.61% Airbnb Rental Income: $2861 Traditional Rental Income: $1924 Airbnb ROI: -1.14% Traditional ROI: -1.61%
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%
2675 GULF OF MEXICO DRIVE #403 LONGBOAT KEY, FL A New Year is here and a New Price with gorgeous full gulf views on Longboat Key. Veinte (...	3 beds \| 2 baths \| 1,896 sq.ft.	$1,200,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.25% Airbnb Rental Income: $4647 Traditional Rental Income: $3526 Airbnb ROI: 0.39% Traditional ROI: 0.25%
1975 GULF OF MEXICO DRIVE #G4-309 LONGBOAT KEY, FL Rarely available with unobstructed and direct Gulf views unit in the desirable G4 building...	2 beds \| 2 baths \| 933 sq.ft.	$749,500	Airbnb cash on cash: 0.7% Traditional cash on cash: 0.11% Airbnb Rental Income: $2861 Traditional Rental Income: $1782 Airbnb ROI: 0.7% Traditional ROI: 0.11%
4600 GULF OF MEXICO DRIVE #206 LONGBOAT KEY, FL Experience elevated Longboat Key bayfront living in this BEAUTIFULLY UPDATED and impeccabl...	2 beds \| 2 baths \| 1,523 sq.ft.	$800,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 3.14% Airbnb Rental Income: $2861 Traditional Rental Income: $5402 Airbnb ROI: -1.17% Traditional ROI: 3.14%
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%
1965 GULF OF MEXICO DRIVE #G5-104 LONGBOAT KEY, FL Embrace an extraordinary coastal lifestyle where fun water adventures fill your days and p...	2 beds \| 2 baths \| 933 sq.ft.	$495,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 1.03% Airbnb Rental Income: $2861 Traditional Rental Income: $2154 Airbnb ROI: 1.12% Traditional ROI: 1.03%
775 LONGBOAT CLUB ROAD #204 LONGBOAT KEY, FL Located behind the gates of the Longboat Key Club, this updated residence at The Beaches o...	2 beds \| 2 baths \| 1,602 sq.ft.	$1,089,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 0.56% Airbnb Rental Income: $2861 Traditional Rental Income: $3049 Airbnb ROI: -0.29% Traditional ROI: 0.56%
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.	$1,118,375	Airbnb cash on cash: 1.28% Traditional cash on cash: 4.93% Airbnb Rental Income: $4647 Traditional Rental Income: $7489 Airbnb ROI: 1.28% Traditional ROI: 4.93%
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.	$1,899,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 0.29% Airbnb Rental Income: $4647 Traditional Rental Income: $4508 Airbnb ROI: -0.18% Traditional ROI: 0.29%
1920 HARBOURSIDE DRIVE #1003 LONGBOAT KEY, FL Start your day with glowing sunrise views across Sarasota Bay from the living room, primar...	2 beds \| 3 baths \| 1,590 sq.ft.	$729,900	Airbnb cash on cash: -1.73% Traditional cash on cash: -1.4% Airbnb Rental Income: $2861 Traditional Rental Income: $2416 Airbnb ROI: -1.73% Traditional ROI: -1.4%
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 \| 2,820 sq.ft.	$4,495,000	Airbnb cash on cash: -1.71% Traditional cash on cash: -1.58% Airbnb Rental Income: $4647 Traditional Rental Income: $4230 Airbnb ROI: -1.71% Traditional ROI: -1.58%
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.	$1,575,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.24% Airbnb Rental Income: $4647 Traditional Rental Income: $7081 Airbnb ROI: 0.92% Traditional ROI: 3.24%
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%
1211 GULF OF MEXICO DRIVE #505 LONGBOAT KEY, FL Turn-key furnished, beach-front and available for a quick close! This lovely Longboat Key...	2 beds \| 2 baths \| 1,598 sq.ft.	$1,595,000	Airbnb cash on cash: -0.73% Traditional cash on cash: -0.1% Airbnb Rental Income: $2861 Traditional Rental Income: $3120 Airbnb ROI: -0.73% Traditional ROI: -0.1%
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%
1095 GULF OF MEXICO DRIVE #502 LONGBOAT KEY, FL Stunning Beachplace Condo with Gulf Views + Seller Incentive! Your opportunity on Longboa...	2 beds \| 2 baths \| 1,392 sq.ft.	$1,099,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 0.4% Airbnb Rental Income: $2861 Traditional Rental Income: $2825 Airbnb ROI: -0.22% Traditional ROI: 0.4%
6701 GULF OF MEXICO DRIVE #311 LONGBOAT KEY, FL LARGE PRICE REDUCTION - COASTAL ELEGANCE ON LONGBOAT KEY - DIRECT GULF FRONT PROPERTY: We...	1 beds \| 1 baths \| 936 sq.ft.	$748,000	Airbnb cash on cash: -1.64% Traditional cash on cash: -2.7% Airbnb Rental Income: $3252 Traditional Rental Income: $1782 Airbnb ROI: -1.64% Traditional ROI: -2.7%
3060 GRAND BAY BOULEVARD #154 LONGBOAT KEY, FL Under contract-accepting backup offers. Beautifully renovated and offered turnkey furnishe...	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.	$1,100,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 0.26% Airbnb Rental Income: $2861 Traditional Rental Income: $2876 Airbnb ROI: -0.41% Traditional ROI: 0.26%
2110 HARBOURSIDE DRIVE #526 LONGBOAT KEY, FL Carefree living awaits you with beautiful panoramic views of Sarasota Bay in this beautifu...	3 beds \| 2 baths \| 2,031 sq.ft.	$795,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 5.45% Airbnb Rental Income: $4647 Traditional Rental Income: $6149 Airbnb ROI: 2.12% Traditional ROI: 5.45%
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.	$859,000	Airbnb cash on cash: -1.86% Traditional cash on cash: -0.48% Airbnb Rental Income: $2861 Traditional Rental Income: $3300 Airbnb ROI: -1.86% Traditional ROI: -0.48%
250 SANDS POINT ROAD #5101 LONGBOAT KEY, FL A corner A+ junior suite with a walk-down rarely becomes available. It offers quiet and pr...	1 beds \| 1 baths \| 716 sq.ft.	$995,000	Airbnb cash on cash: 0.48% Traditional cash on cash: -0.47% Airbnb Rental Income: $3252 Traditional Rental Income: $1641 Airbnb ROI: 0.48% Traditional ROI: -0.47%
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.	$2,999,000	Airbnb cash on cash: -0.29% Traditional cash on cash: -0.18% Airbnb Rental Income: $4647 Traditional Rental Income: $4000 Airbnb ROI: -0.29% Traditional ROI: -0.18%
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.	$295,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 6.37% Airbnb Rental Income: $3252 Traditional Rental Income: $3495 Airbnb ROI: 2.86% Traditional ROI: 6.37%
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%
4621 GULF OF MEXICO DRIVE #10D LONGBOAT KEY, FL Under contract-accepting backup offers. Whether you choose resort style living or just wan...	2 beds \| 2 baths \| 756 sq.ft.	$675,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 0.56% Airbnb Rental Income: $2861 Traditional Rental Income: $1968 Airbnb ROI: 0.92% Traditional ROI: 0.56%
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.	$1,475,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 0.34% Airbnb Rental Income: $4647 Traditional Rental Income: $3926 Airbnb ROI: 0.16% Traditional ROI: 0.34%

Real Estate investment in Longboat-key, FL

There are 198 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,149,000 and the average price per square foot is $581. In January 2026, the average monthly cash on cash return in Longboat Key is N/A%. The average monthly rental income in Longboat Key is $2,492.

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

There are 198 investment properties available for sale in Longboat-key.

In 2026, 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

100 SANDS POINT ROAD #225

LONGBOAT KEY, FL

2 beds | 2 baths | 1,492 sq.ft.

$975,000

Airbnb cash on cash: 0.92%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $2861

Traditional Rental Income: $3450

Airbnb ROI: 0.92%

Traditional ROI: 2.3%

1241 GULF OF MEXICO DRIVE #109

LONGBOAT KEY, FL

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

$1,295,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $2861

Traditional Rental Income: $4149

Airbnb ROI: -0.38%

Traditional ROI: 1.25%

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%

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%

795 MARBURY LANE

LONGBOAT KEY, FL

4 beds | 3 baths | 3,355 sq.ft.

$3,999,990

Airbnb cash on cash: -0.49%

Traditional cash on cash: -0.68%

Airbnb Rental Income: $6133

Traditional Rental Income: $4246

Airbnb ROI: -0.49%

Traditional ROI: -0.68%

3080 GRAND BAY BOULEVARD #515

LONGBOAT KEY, FL

2 beds | 2 baths | 1,276 sq.ft.

$659,000

Airbnb cash on cash: -1.1%

Traditional cash on cash: -0.4%

Airbnb Rental Income: $2861

Traditional Rental Income: $2627

Airbnb ROI: -1.1%

Traditional ROI: -0.4%

2089 GULF OF MEXICO DRIVE #G1-105

LONGBOAT KEY, FL

2 beds | 2 baths | 1,257 sq.ft.

$880,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $2861

Traditional Rental Income: $2669

Airbnb ROI: 0.46%

Traditional ROI: 1.04%

738 EL CENTRO

LONGBOAT KEY, FL

2 beds | 2 baths | 1,299 sq.ft.

$329,000

Airbnb cash on cash: 4.25%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $2861

Traditional Rental Income: $2276

Airbnb ROI: 4.25%