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.

Condos for Sale in Longboat Key, FL

Search for Condo for Sale in Longboat Key, Florida. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 265 Condo 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
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%
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%
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%
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.	$1,799,000	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%
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%
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%
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%
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%
1445 Gulf OF Mexico Dr #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: -1.35% Traditional cash on cash: -1.17% Airbnb Rental Income: $4647 Traditional Rental Income: $3926 Airbnb ROI: -1.35% Traditional ROI: -1.17%
1211 Gulf OF Mexico Dr #403 LONGBOAT KEY, FL Escape to Elegance on Longboat Key Welcome to this fully renovated, fourth-floor reside...	2 beds \| 2 baths \| 1,585 sq.ft.	$1,695,000	Airbnb cash on cash: -0.63% Traditional cash on cash: -0.12% Airbnb Rental Income: $2861 Traditional Rental Income: $3053 Airbnb ROI: -0.63% Traditional ROI: -0.12%
2525 Gulf OF Mexico Dr #6B LONGBOAT KEY, FL Ultra-luxury, fully remodeled Gulf-front residence on Longboat Key. This sixth-floor, move...	2 beds \| 2 baths \| 1,491 sq.ft.	$1,425,000	Airbnb cash on cash: -1.8% Traditional cash on cash: 0.57% Airbnb Rental Income: $2861 Traditional Rental Income: $5615 Airbnb ROI: -1.8% Traditional ROI: 0.57%
2045 GULF OF MEXICO DRIVE #M1-505 LONGBOAT KEY, FL Under contract-accepting backup offers. Fully RE-DESIGNED and RENOVATED 2-bedroom, 2-bath ...	2 beds \| 2 baths \| 1,265 sq.ft.	$879,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 3.56% Airbnb Rental Income: $2861 Traditional Rental Income: $6295 Airbnb ROI: -1.45% Traditional ROI: 3.56%
1485 Gulf OF Mexico Dr #303 LONGBOAT KEY, FL Coastal elegance meets effortless island living at The Playerâs Club on Longboat Key. Th...	2 beds \| 2 baths \| 1,569 sq.ft.	$1,395,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.69% Airbnb Rental Income: $2861 Traditional Rental Income: $5978 Airbnb ROI: -0.22% Traditional ROI: 2.69%
4540 Gulf OF Mexico Dr #204 LONGBOAT KEY, FL Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offeri...	2 beds \| 2 baths \| 1,312 sq.ft.	$625,000	Airbnb cash on cash: -1.9% Traditional cash on cash: 4.16% Airbnb Rental Income: $2861 Traditional Rental Income: $5867 Airbnb ROI: -1.9% Traditional ROI: 4.16%
1125 Gulf OF Mexico Dr #101 LONGBOAT KEY, FL Step into a bright, inviting coastal retreat just moments from the sand at Beachplace on L...	2 beds \| 2 baths \| 1,172 sq.ft.	$849,000	Airbnb cash on cash: -1.72% Traditional cash on cash: 1.31% Airbnb Rental Income: $2861 Traditional Rental Income: $4726 Airbnb ROI: -1.72% Traditional ROI: 1.31%
3060 GRAND BAY BOULEVARD #182 LONGBOAT KEY, FL Soaring Sarasota Bay and Gulf of Mexico views from every room of this 8th floor residence ...	2 beds \| 4 baths \| 2,143 sq.ft.	$1,595,000	Airbnb cash on cash: -2.49% Traditional cash on cash: 0.79% Airbnb Rental Income: $2861 Traditional Rental Income: $7065 Airbnb ROI: -2.49% Traditional ROI: 0.79%
4976 Gulf OF Mexico Dr #Villa 18 LONGBOAT KEY, FL This spacious waterfront villa lives like a single-family home yet offers the ease of mai...	3 beds \| 2 baths \| 1,900 sq.ft.	$699,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 5.5% Airbnb Rental Income: $4647 Traditional Rental Income: $6408 Airbnb ROI: 1.42% Traditional ROI: 5.5%
4370 Chatham Dr #104 LONGBOAT KEY, FL Turnkey two-bedroom, two-bath residence in a first-floor, walkout location. Freshly painte...	2 beds \| 2 baths \| 1,072 sq.ft.	$470,000	Airbnb cash on cash: -0.77% Traditional cash on cash: -1.13% Airbnb Rental Income: $2861 Traditional Rental Income: $2031 Airbnb ROI: -0.77% Traditional ROI: -1.13%
1065 Gulf OF Mexico Dr #302 LONGBOAT KEY, FL One of a kind, never rented, ready for a new owner to put their touches on this opportunit...	2 beds \| 2 baths \| 1,392 sq.ft.	$639,000	Airbnb cash on cash: -1.12% Traditional cash on cash: -0.91% Airbnb Rental Income: $2861 Traditional Rental Income: $2322 Airbnb ROI: -1.12% Traditional ROI: -0.91%
2109 Gulf OF Mexico Dr #1303 LONGBOAT KEY, FL Discover effortless beachfront living in this beautifully renovated 2-bedroom, 2-bath resi...	2 beds \| 2 baths \| 1,463 sq.ft.	$1,125,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -0.77% Airbnb Rental Income: $2861 Traditional Rental Income: $2933 Airbnb ROI: -1.47% Traditional ROI: -0.77%
5311 GULF OF MEXICO DRIVE #3 LONGBOAT KEY, FL Turnkey furnished and positioned directly on the sandy shores of the Gulf of Mexico, this ...	2 beds \| 2 baths \| 1,028 sq.ft.	$995,000	Airbnb cash on cash: -1.61% Traditional cash on cash: -1.68% Airbnb Rental Income: $2861 Traditional Rental Income: $2128 Airbnb ROI: -1.61% Traditional ROI: -1.68%
2295 Gulf OF Mexico Dr #64S LONGBOAT KEY, FL PRICE REDUCED! Donât miss this opportunity, schedule your showing today! Beachfront Livi...	2 beds \| 2 baths \| 1,235 sq.ft.	$625,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 4.04% Airbnb Rental Income: $2861 Traditional Rental Income: $5596 Airbnb ROI: -1.79% Traditional ROI: 4.04%
2675 GULF OF MEXICO DRIVE #204 LONGBOAT KEY, FL Under contract-accepting backup offers. This exclusive corner unit at Veinte presents a ra...	3 beds \| 3 baths \| 2,180 sq.ft.	$1,495,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 0.33% Airbnb Rental Income: $4647 Traditional Rental Income: $3666 Airbnb ROI: 0.34% Traditional ROI: 0.33%
360 Gulf OF Mexico Dr #322 LONGBOAT KEY, FL This is your perfect tropical Happy Place! Elevator access takes you directly to your very...	2 beds \| 2 baths \| 2,276 sq.ft.	$1,195,000	Airbnb cash on cash: -3.34% Traditional cash on cash: -1.16% Airbnb Rental Income: $2861 Traditional Rental Income: $4613 Airbnb ROI: -3.34% Traditional ROI: -1.16%

Your search for investment property begins and ends here

Condos 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%

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%

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%

Traditional ROI: -1.59%

1145 Gulf OF Mexico Dr #301

LONGBOAT KEY, FL

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%

2675 Gulf OF Mexico Dr #403

LONGBOAT KEY, FL

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

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%