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 Rd #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: -0.53% Traditional cash on cash: 0.85% Airbnb Rental Income: $2861 Traditional Rental Income: $3450 Airbnb ROI: -0.53% Traditional ROI: 0.85%
1241 Gulf OF Mexico Dr #109 LONGBOAT KEY, FL Live the lavish lifestyle only found at the Water Club on Longboat Key, an idyllic waterfr...	2 beds \| 2 baths \| 2,000 sq.ft.	$1,139,000	Airbnb cash on cash: -2.73% Traditional cash on cash: -1.11% Airbnb Rental Income: $2861 Traditional Rental Income: $4149 Airbnb ROI: -2.73% Traditional ROI: -1.11%
6330 Laguna Dr 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.	$1,999,989	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%
3080 Grand Bay Blvd #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: -2.7% Traditional cash on cash: -2% Airbnb Rental Income: $2861 Traditional Rental Income: $2627 Airbnb ROI: -2.7% Traditional ROI: -2%
2089 Gulf OF Mexico Dr #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.	$855,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.44% Airbnb Rental Income: $2861 Traditional Rental Income: $2669 Airbnb ROI: -1.03% Traditional ROI: -0.44%
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: -0.36% Traditional cash on cash: -0.1% Airbnb Rental Income: $2861 Traditional Rental Income: $2276 Airbnb ROI: -0.36% Traditional ROI: -0.1%
747 MARBURY LANE LONGBOAT KEY, FL Under contract-accepting backup offers. Welcome to Your Waterfront Paradise! This beautif...	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 Rd #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: -2.26% Traditional cash on cash: -1.59% Airbnb Rental Income: $2861 Traditional Rental Income: $3122 Airbnb ROI: -2.26% Traditional ROI: -1.59%
1145 Gulf OF Mexico Dr #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: -1.76% Traditional cash on cash: -1.49% Airbnb Rental Income: $2861 Traditional Rental Income: $2494 Airbnb ROI: -1.76% Traditional ROI: -1.49%
1935 Gulf Of Mexico Dr #G7-402 Sarasota, 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: -2.24% Traditional cash on cash: -1.61% Airbnb Rental Income: $2088 Traditional Rental Income: $1924 Airbnb ROI: -2.24% Traditional ROI: -1.61%
2055 Gulf Of Mexico Dr #G2-214 Sarasota, 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: -2.66% Traditional cash on cash: 5% Airbnb Rental Income: $1926 Traditional Rental Income: $4287 Airbnb ROI: -2.66% Traditional ROI: 5%
2675 Gulf OF Mexico Dr #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: -1.18% Traditional cash on cash: -1.33% Airbnb Rental Income: $4647 Traditional Rental Income: $3526 Airbnb ROI: -1.18% Traditional ROI: -1.33%
1975 Gulf OF Mexico Dr #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: -1.35% Traditional cash on cash: -1.94% Airbnb Rental Income: $2861 Traditional Rental Income: $1782 Airbnb ROI: -1.35% Traditional ROI: -1.94%
4600 Gulf OF Mexico Dr #206 LONGBOAT KEY, FL Experience elevated Longboat Key bayfront living in this BEAUTIFULLY UPDATED and impeccabl...	2 beds \| 2 baths \| 1,523 sq.ft.	$750,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 3.24% Airbnb Rental Income: $2861 Traditional Rental Income: $5402 Airbnb ROI: -1.17% Traditional ROI: 3.24%
3010 Grand Bay Blvd #472 LONGBOAT KEY, FL Your semi-private elevator provides access to the beautiful 7th floor condo with sweeping ...	3 beds \| 2 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: -0.76% Traditional cash on cash: -0.85% Airbnb Rental Income: $2861 Traditional Rental Income: $2154 Airbnb ROI: -0.76% Traditional ROI: -0.85%
775 Longboat Club Rd #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.	$895,000	Airbnb cash on cash: -2.64% Traditional cash on cash: -1.72% Airbnb Rental Income: $2861 Traditional Rental Income: $3049 Airbnb ROI: -2.64% Traditional ROI: -1.72%
565 Sanctuary Dr #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: -1.79% Traditional cash on cash: -1.33% Airbnb Rental Income: $4647 Traditional Rental Income: $4508 Airbnb ROI: -1.79% Traditional ROI: -1.33%
1920 Harbourside Dr #1003 LONGBOAT KEY, FL Start your day with glowing sunrise views across Sarasota Bay from the living room, primar...	2 beds \| 2 baths \| 1,590 sq.ft.	$684,500	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 Dr #J703 LONGBOAT KEY, FL Experience unparalleled luxury in this beautifully updated 3-bedroom condo at the highly c...	3 beds \| 2 baths \| 2,820 sq.ft.	$4,495,000	Airbnb cash on cash: -2.18% Traditional cash on cash: -2.05% Airbnb Rental Income: $4647 Traditional Rental Income: $4230 Airbnb ROI: -2.18% Traditional ROI: -2.05%
5841 Gulf OF Mexico Dr #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.	$525,500	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 Dr #505 LONGBOAT KEY, FL No matter where you 'summer' you belong in sunny Sarasota for the 'winter'. Feast your ey...	2 beds \| 2 baths \| 1,598 sq.ft.	$1,575,000	Airbnb cash on cash: -2.1% Traditional cash on cash: -1.47% Airbnb Rental Income: $2861 Traditional Rental Income: $3120 Airbnb ROI: -2.1% Traditional ROI: -1.47%
1095 Gulf OF Mexico Dr #502 LONGBOAT KEY, FL Stunning Beachplace Condo with Gulf Views. Perfectly suited for investors, seasonal res...	2 beds \| 2 baths \| 1,392 sq.ft.	$999,000	Airbnb cash on cash: -1.78% Traditional cash on cash: -1.11% Airbnb Rental Income: $2861 Traditional Rental Income: $2825 Airbnb ROI: -1.78% Traditional ROI: -1.11%
6701 Gulf OF Mexico Dr #311 LONGBOAT KEY, FL LARGE PRICE REDUCTION - COASTAL ELEGANCE ON LONGBOAT KEY - DIRECT GULF FRONT PROPERTY: We...	1 beds \| 1 baths \| 936 sq.ft.	$699,900	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 Rd #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: -2.24% Traditional cash on cash: -1.58% Airbnb Rental Income: $2861 Traditional Rental Income: $2876 Airbnb ROI: -2.24% Traditional ROI: -1.58%
2110 Harbourside Dr #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.	$750,000	Airbnb cash on cash: -1.72% Traditional cash on cash: 1.69% Airbnb Rental Income: $4647 Traditional Rental Income: $6149 Airbnb ROI: -1.72% Traditional ROI: 1.69%
1926 Harbourside Dr #1302 LONGBOAT KEY, FL GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main...	2 beds \| 2 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 Rd #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: -0.95% Traditional cash on cash: -1.9% Airbnb Rental Income: $3252 Traditional Rental Income: $1641 Airbnb ROI: -0.95% Traditional ROI: -1.9%
510 Putter Ln 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 Dr #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 \| 4 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 Dr #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%

Real Estate investment in Longboat-key, FL

There are 444 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,150,000 and the average price per square foot is $582. In March 2026, the average monthly cash on cash return in Longboat Key is N/A%. The average monthly rental income in Longboat Key is $2,480.

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

There are 444 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 Rd #225

LONGBOAT KEY, FL

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

$975,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 0.85%

Airbnb Rental Income: $2861

Traditional Rental Income: $3450

Airbnb ROI: -0.53%

Traditional ROI: 0.85%

1241 Gulf OF Mexico Dr #109

LONGBOAT KEY, FL

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

$1,139,000

Airbnb cash on cash: -2.73%

Traditional cash on cash: -1.11%

Airbnb Rental Income: $2861

Traditional Rental Income: $4149

Airbnb ROI: -2.73%

Traditional ROI: -1.11%

6330 Laguna Dr

LONGBOAT KEY, FL

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

$1,999,989

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%

3080 Grand Bay Blvd #515

LONGBOAT KEY, FL

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

$659,000

Airbnb cash on cash: -2.7%

Traditional cash on cash: -2%

Airbnb Rental Income: $2861

Traditional Rental Income: $2627

Airbnb ROI: -2.7%

Traditional ROI: -2%

2089 Gulf OF Mexico Dr #G1-105

LONGBOAT KEY, FL

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

$855,000

Airbnb cash on cash: -1.03%

Traditional cash on cash: -0.44%

Airbnb Rental Income: $2861

Traditional Rental Income: $2669

Airbnb ROI: -1.03%

Traditional ROI: -0.44%

738 EL Centro

LONGBOAT KEY, FL

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

$329,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: -0.1%

Airbnb Rental Income: $2861

Traditional Rental Income: $2276

Airbnb ROI: -0.36%

Traditional ROI: -0.1%

747 MARBURY LANE

LONGBOAT KEY, FL

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 Rd #705

LONGBOAT KEY, FL

2 beds | 2 baths | 1,602 sq.ft.

$1,499,000

Airbnb cash on cash: -2.26%

Traditional cash on cash: -1.59%

Airbnb Rental Income: $2861

Traditional Rental Income: $3122

Airbnb ROI: -2.26%