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
1930 HARBOURSIDE DRIVE #145 LONGBOAT KEY, FL Under contract-accepting backup offers. Set on the 4th floor of Building 1 in Fairway Bay,...	2 beds \| 2 baths \| 1,270 sq.ft.	$549,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 2.25% Airbnb Rental Income: $2861 Traditional Rental Income: $2602 Airbnb ROI: 1.46% Traditional ROI: 2.25%
100 SANDS POINT ROAD #225 LONGBOAT KEY, FL BACK ON THE MARKET with a New Price and Turn Key! Welcome to your slice of paradise, where...	2 beds \| 2 baths \| 1,492 sq.ft.	$899,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 3.11% Airbnb Rental Income: $2861 Traditional Rental Income: $5208 Airbnb ROI: -0.49% Traditional ROI: 3.11%
1085 GULF OF MEXICO DRIVE #205 LONGBOAT KEY, FL Spacious 3-Bedroom End-Unit Residence in Sought-After Beachplace Welcome to this beauti...	3 beds \| 2 baths \| 1,819 sq.ft.	$999,000	Airbnb cash on cash: 0% Traditional cash on cash: 1.94% Airbnb Rental Income: $4647 Traditional Rental Income: $5489 Airbnb ROI: 0% Traditional ROI: 1.94%
1912 HARBOURSIDE DRIVE #604 LONGBOAT KEY, FL Embrace the island life style within the gates of Longboat Key's premier resort community ...	3 beds \| 3 baths \| 2,207 sq.ft.	$835,000	Airbnb cash on cash: -0.16% Traditional cash on cash: -0.61% Airbnb Rental Income: $4647 Traditional Rental Income: $3337 Airbnb ROI: -0.16% Traditional ROI: -0.61%
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.	$1,099,000	Airbnb cash on cash: -3.04% Traditional cash on cash: 0.98% Airbnb Rental Income: $2861 Traditional Rental Income: $6304 Airbnb ROI: -3.04% Traditional ROI: 0.98%
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.	$1,999,979	Airbnb cash on cash: -0.32% Traditional cash on cash: 0.33% Airbnb Rental Income: $4647 Traditional Rental Income: $4883 Airbnb ROI: -0.32% Traditional ROI: 0.33%
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.	$625,000	Airbnb cash on cash: -2.8% Traditional cash on cash: 1.15% Airbnb Rental Income: $2861 Traditional Rental Income: $4498 Airbnb ROI: -2.8% Traditional ROI: 1.15%
1914 HARBOUR LINKS CIRCLE #10 LONGBOAT KEY, FL Tucked behind the gates of Bay Isles in the Emerald Pointe community, this 3BR/3.5BA resid...	3 beds \| 4 baths \| 2,180 sq.ft.	$1,445,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.72% Airbnb Rental Income: $4647 Traditional Rental Income: $8490 Airbnb ROI: 0.14% Traditional ROI: 3.72%
803 BAYPORT WAY #803 LONGBOAT KEY, FL Under contract-accepting backup offers. Welcome to the true tropical oasis of Bayport Beac...	2 beds \| 2 baths \| 1,456 sq.ft.	$775,000	Airbnb cash on cash: -1.87% Traditional cash on cash: 1.86% Airbnb Rental Income: $2861 Traditional Rental Income: $4889 Airbnb ROI: -1.87% Traditional ROI: 1.86%
6800 GULF OF MEXICO DRIVE #184 LONGBOAT KEY, FL Beautifully renovated in 2023, with dazzling views of the Gulf of Mexico and the private b...	2 beds \| 2 baths \| 1,287 sq.ft.	$475,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.92% Airbnb Rental Income: $2861 Traditional Rental Income: $2942 Airbnb ROI: -0.76% Traditional ROI: 0.92%
706 BAYPORT WAY #706 LONGBOAT KEY, FL This stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect...	2 beds \| 2 baths \| 1,601 sq.ft.	$739,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -0.74% Airbnb Rental Income: $2861 Traditional Rental Income: $3093 Airbnb ROI: -2.04% Traditional ROI: -0.74%
667 EL CENTRO LONGBOAT KEY, FL New photos coming on this beautifully updated free-standing villa in Spanish Main Yacht Cl...	2 beds \| 2 baths \| 1,327 sq.ft.	$380,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.6% Airbnb Rental Income: $2861 Traditional Rental Income: $3086 Airbnb ROI: -0.9% Traditional ROI: 1.6%
2089 GULF OF MEXICO DRIVE #G1-108 LONGBOAT KEY, FL Welcome to G1-108, a recently remodeled and fully-furnished residence in Seaplace! Ove...	2 beds \| 2 baths \| 933 sq.ft.	$675,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 1.58% Airbnb Rental Income: $2861 Traditional Rental Income: $3736 Airbnb ROI: -0.87% Traditional ROI: 1.58%
6700 GULF OF MEXICO DRIVE #143 LONGBOAT KEY, FL Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story cond...	1 beds \| 1 baths \| 936 sq.ft.	$425,000	Airbnb cash on cash: 1.12% Traditional cash on cash: -0.89% Airbnb Rental Income: $3252 Traditional Rental Income: $1724 Airbnb ROI: 1.12% Traditional ROI: -0.89%
1965 GULF OF MEXICO DRIVE #G5-103 LONGBOAT KEY, FL Experience coastal living at its finest in this beautifully updated ground-floor residence...	2 beds \| 3 baths \| 933 sq.ft.	$649,000	Airbnb cash on cash: -0.6% Traditional cash on cash: -0.52% Airbnb Rental Income: $2861 Traditional Rental Income: $2248 Airbnb ROI: -0.6% Traditional ROI: -0.52%
1932 HARBOURSIDE DRIVE #244 LONGBOAT KEY, FL Welcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in...	2 beds \| 2 baths \| 1,192 sq.ft.	$1,200,000	Airbnb cash on cash: -1.86% Traditional cash on cash: -1.65% Airbnb Rental Income: $2861 Traditional Rental Income: $2440 Airbnb ROI: -1.86% Traditional ROI: -1.65%
3427 WINDING OAKS DRIVE #14 LONGBOAT KEY, FL Under contract-accepting backup offers. Privately tucked away within the private Winding O...	3 beds \| 3 baths \| 2,555 sq.ft.	$1,150,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 2.81% Airbnb Rental Income: $4647 Traditional Rental Income: $8117 Airbnb ROI: -1.33% Traditional ROI: 2.81%
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.	$1,018,375	Airbnb cash on cash: 1.5% Traditional cash on cash: 3.19% Airbnb Rental Income: $4647 Traditional Rental Income: $5286 Airbnb ROI: 1.5% Traditional ROI: 3.19%
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.	$1,799,000	Airbnb cash on cash: -1.84% Traditional cash on cash: 0.15% Airbnb Rental Income: $4647 Traditional Rental Income: $6998 Airbnb ROI: -1.84% Traditional ROI: 0.15%
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.	$1,435,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 2.71% Airbnb Rental Income: $4647 Traditional Rental Income: $5826 Airbnb ROI: 1.1% Traditional ROI: 2.71%
5841 GULF OF MEXICO DRIVE #244 LONGBOAT KEY, FL REDUCE PRICE- RARE FIND!!! This fully furnished turnkey 1bedroom/1bath end unit has an ope...	1 beds \| 1 baths \| 520 sq.ft.	$525,500	Airbnb cash on cash: 0.32% Traditional cash on cash: 0.97% Airbnb Rental Income: $3252 Traditional Rental Income: $2840 Airbnb ROI: 0.32% Traditional ROI: 0.97%
3530 MISTLETOE LANE LONGBOAT KEY, FL Located behind the gates of Coreyâs Landing in the sought-after Bay Isles community, thi...	4 beds \| 4 baths \| 3,102 sq.ft.	$2,495,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 0.52% Airbnb Rental Income: $6133 Traditional Rental Income: $6723 Airbnb ROI: -0.25% Traditional ROI: 0.52%
1935 GULF OF MEXICO DRIVE #G7-304 LONGBOAT KEY, FL Under contract-accepting backup offers. Experience the best of coastal living in this beau...	2 beds \| 1 baths \| 933 sq.ft.	$465,000	Airbnb cash on cash: -0.71% Traditional cash on cash: -2% Airbnb Rental Income: $2861 Traditional Rental Income: $1634 Airbnb ROI: -0.71% Traditional ROI: -2%
1050 LONGBOAT CLUB ROAD #901 LONGBOAT KEY, FL Welcome to your beachfront retreat in the sky. Perched on the 9th floor of the highly desi...	2 beds \| 2 baths \| 1,409 sq.ft.	$1,400,000	Airbnb cash on cash: -0.51% Traditional cash on cash: -0.36% Airbnb Rental Income: $2861 Traditional Rental Income: $2389 Airbnb ROI: -0.51% Traditional ROI: -0.36%
1050 LONGBOAT CLUB ROAD #903 LONGBOAT KEY, FL Set on the 9th floor at Privateer North, behind the gates of the Longboat Key Club, this b...	2 beds \| 2 baths \| 1,409 sq.ft.	$995,000	Airbnb cash on cash: -2.22% Traditional cash on cash: 0.64% Airbnb Rental Income: $2861 Traditional Rental Income: $4846 Airbnb ROI: -2.22% Traditional ROI: 0.64%
718 SPANISH DRIVE N LONGBOAT KEY, FL Discover Longboat Key waterfront living at its very best at 718 Spanish Dr N, a beautifull...	2 beds \| 2 baths \| 1,327 sq.ft.	$435,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 0.81% Airbnb Rental Income: $2861 Traditional Rental Income: $2557 Airbnb ROI: -0.08% Traditional ROI: 0.81%
509 SPANISH DRIVE N LONGBOAT KEY, FL STEPS FROM THE BEACH.....WATERFRONT COMMUNITY......DEEDED BEACH ACCESS......FULLY RENOVATE...	2 beds \| 2 baths \| 1,357 sq.ft.	$369,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 1.59% Airbnb Rental Income: $2861 Traditional Rental Income: $3124 Airbnb ROI: -1.09% Traditional ROI: 1.59%
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.	$769,000	Airbnb cash on cash: -1.96% Traditional cash on cash: 1.45% Airbnb Rental Income: $2861 Traditional Rental Income: $4643 Airbnb ROI: -1.96% Traditional ROI: 1.45%
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: -0.49% Traditional cash on cash: 0.11% Airbnb Rental Income: $3252 Traditional Rental Income: $3069 Airbnb ROI: -0.49% Traditional ROI: 0.11%
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.	$2,875,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.76% Airbnb Rental Income: $4647 Traditional Rental Income: $6400 Airbnb ROI: -0.26% Traditional ROI: 0.76%
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: 3.47% Airbnb Rental Income: $3252 Traditional Rental Income: $2689 Airbnb ROI: 2.86% Traditional ROI: 3.47%
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: 1.2% Airbnb Rental Income: $6133 Traditional Rental Income: $6067 Airbnb ROI: 0.73% Traditional ROI: 1.2%
4621 GULF OF MEXICO DRIVE #10D LONGBOAT KEY, FL Huge Price Adjustment! PRICED TO SELL!!! Check out these consistently strong revenue numbe...	2 beds \| 2 baths \| 756 sq.ft.	$649,900	Airbnb cash on cash: 0.33% Traditional cash on cash: 1.47% Airbnb Rental Income: $2861 Traditional Rental Income: $2884 Airbnb ROI: 0.33% Traditional ROI: 1.47%
828 BAYPORT WAY LONGBOAT KEY, FL Bayport Beach & Tennis Club is a true Longboat Key Gulf-to-Bay community, set across 27 ac...	2 beds \| 2 baths \| 1,456 sq.ft.	$900,000	Airbnb cash on cash: -1.76% Traditional cash on cash: -0.88% Airbnb Rental Income: $2861 Traditional Rental Income: $2934 Airbnb ROI: -1.76% Traditional ROI: -0.88%
1918 HARBOURSIDE DRIVE #902 LONGBOAT KEY, FL Under contract-accepting backup offers. Welcome to a masterfully reimagined two-bedroom, 2...	2 beds \| 3 baths \| 1,748 sq.ft.	$1,299,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.84% Airbnb Rental Income: $2861 Traditional Rental Income: $4751 Airbnb ROI: -0.28% Traditional ROI: 1.84%
1211 GULF OF MEXICO DRIVE #403 LONGBOAT KEY, FL Escape to elegance in this tastefully renovated, fully furnished fourth-floor residence at...	2 beds \| 2 baths \| 1,585 sq.ft.	$1,695,000	Airbnb cash on cash: -1.88% Traditional cash on cash: -0.15% Airbnb Rental Income: $2861 Traditional Rental Income: $4931 Airbnb ROI: -1.88% Traditional ROI: -0.15%
775 LONGBOAT CLUB ROAD #401 LONGBOAT KEY, FL Discover Coastal Elegance at The Beaches of Longboat Key! Nestled behind the renowned gate...	2 beds \| 2 baths \| 1,510 sq.ft.	$1,595,000	Airbnb cash on cash: -2.62% Traditional cash on cash: -0.66% Airbnb Rental Income: $2861 Traditional Rental Income: $5106 Airbnb ROI: -2.62% Traditional ROI: -0.66%
535 SANCTUARY DRIVE #C807 LONGBOAT KEY, FL Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Saras...	3 beds \| 3 baths \| 2,580 sq.ft.	$3,750,000	Airbnb cash on cash: -1.65% Traditional cash on cash: -0.66% Airbnb Rental Income: $4647 Traditional Rental Income: $7152 Airbnb ROI: -1.65% Traditional ROI: -0.66%
519 ROUNTREE DRIVE LONGBOAT KEY, FL BUILT TO LAST. 519 Rountree is new construction built entirely of concrete block (CBS) acr...	4 beds \| 5 baths \| 3,554 sq.ft.	$6,488,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 0.31% Airbnb Rental Income: $6133 Traditional Rental Income: $9088 Airbnb ROI: -0.38% Traditional ROI: 0.31%
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: -0.47% Traditional cash on cash: -0.1% Airbnb Rental Income: $7664 Traditional Rental Income: $7910 Airbnb ROI: -0.47% Traditional ROI: -0.1%

Real Estate investment in Longboat-key, FL

There are 211 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,000,000 and the average price per square foot is $499. In June 2026, the average monthly cash on cash return in Longboat Key is N/A%. The average monthly rental income in Longboat Key is $2,422.

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

There are 211 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

1930 HARBOURSIDE DRIVE #145

LONGBOAT KEY, FL

2 beds | 2 baths | 1,270 sq.ft.

$549,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $2861

Traditional Rental Income: $2602

Airbnb ROI: 1.46%

Traditional ROI: 2.25%

100 SANDS POINT ROAD #225

LONGBOAT KEY, FL

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

$899,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $2861

Traditional Rental Income: $5208

Airbnb ROI: -0.49%

Traditional ROI: 3.11%

1085 GULF OF MEXICO DRIVE #205

LONGBOAT KEY, FL

3 beds | 2 baths | 1,819 sq.ft.

$999,000

Airbnb cash on cash: 0%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $4647

Traditional Rental Income: $5489

Airbnb ROI: 0%

Traditional ROI: 1.94%

1912 HARBOURSIDE DRIVE #604

LONGBOAT KEY, FL

3 beds | 3 baths | 2,207 sq.ft.

$835,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: -0.61%

Airbnb Rental Income: $4647

Traditional Rental Income: $3337

Airbnb ROI: -0.16%

Traditional ROI: -0.61%

1241 GULF OF MEXICO DRIVE #109

LONGBOAT KEY, FL

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

$1,099,000

Airbnb cash on cash: -3.04%

Traditional cash on cash: 0.98%

Airbnb Rental Income: $2861

Traditional Rental Income: $6304

Airbnb ROI: -3.04%

Traditional ROI: 0.98%

6330 LAGUNA DRIVE

LONGBOAT KEY, FL

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

$1,999,979

Airbnb cash on cash: -0.32%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $4647

Traditional Rental Income: $4883

Airbnb ROI: -0.32%

Traditional ROI: 0.33%

3080 GRAND BAY BOULEVARD #515

LONGBOAT KEY, FL

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

$625,000

Airbnb cash on cash: -2.8%

Traditional cash on cash: 1.15%

Airbnb Rental Income: $2861

Traditional Rental Income: $4498

Airbnb ROI: -2.8%

Traditional ROI: 1.15%

1914 HARBOUR LINKS CIRCLE #10

LONGBOAT KEY, FL

3 beds | 4 baths | 2,180 sq.ft.

$1,445,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $4647

Traditional Rental Income: $8490

Airbnb ROI: 0.14%