Real Estate Investments for Sale in Longboat Key, FL With High ROI

Are you looking for a vacation rental in Longboat Key, FL? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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 107 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
2110 HARBOURSIDE DRIVE #557 LONGBOAT KEY, FL Discover the epitome of waterfront living at Bay Isles Atrium Residences, where Sarasota B...	3 beds \| 2 baths \| 2,039 sq.ft.	$1,349,000	Airbnb cash on cash: -2.31% Traditional cash on cash: -0.47% Airbnb Rental Income: $4814 Traditional Rental Income: $6130 Airbnb ROI: -2.31% Traditional ROI: -0.47%
4370 CHATHAM DRIVE #104 LONGBOAT KEY, FL Beautiful Longboat Key Condo with Water Views from almost every room! Deep water canal rig...	2 beds \| 2 baths \| 1,040 sq.ft.	$530,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 8.91% Airbnb Rental Income: $2726 Traditional Rental Income: $5390 Airbnb ROI: 2.24% Traditional ROI: 8.91%
2016 HARBOURSIDE DRIVE #327 LONGBOAT KEY, FL Nestled in one of the most coveted locations within Fairway Bay, this corner 2BR/2BA haven...	2 beds \| 2 baths \| 1,532 sq.ft.	$899,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 5.27% Airbnb Rental Income: $2726 Traditional Rental Income: $5810 Airbnb ROI: 0.81% Traditional ROI: 5.27%
2109 GULF OF MEXICO DRIVE #1303 LONGBOAT KEY, FL Experience coastal living at its finest in this immaculately renovated 2-bedroom 2 bath be...	2 beds \| 2 baths \| 1,463 sq.ft.	$1,300,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 3.02% Airbnb Rental Income: $2726 Traditional Rental Income: $5800 Airbnb ROI: -0.06% Traditional ROI: 3.02%
455 LONGBOAT CLUB ROAD #305 LONGBOAT KEY, FL As you step into this exquisite Pierre residence, prepare to be captivated by the breathta...	3 beds \| 4 baths \| 2,880 sq.ft.	$2,995,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.95% Airbnb Rental Income: $4814 Traditional Rental Income: $7182 Airbnb ROI: -0.26% Traditional ROI: 0.95%
5231 GULF OF MEXICO DRIVE #104 LONGBOAT KEY, FL This is the gem you have been waiting for. Unique opportunity to own this piece of paradis...	1 beds \| 1 baths \| 720 sq.ft.	$599,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 4.31% Airbnb Rental Income: $3172 Traditional Rental Income: $3706 Airbnb ROI: 2.07% Traditional ROI: 4.31%
2525 GULF OF MEXICO DRIVE #11B LONGBOAT KEY, FL The beachfront life beckons from the 11th floor of this classic 2BR/2BA, 1,491+/- sq.-ft. ...	2 beds \| 2 baths \| 1,491 sq.ft.	$1,499,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.27% Airbnb Rental Income: $2726 Traditional Rental Income: $5774 Airbnb ROI: -0.38% Traditional ROI: 2.27%
6750 GULF OF MEXICO DRIVE #171 LONGBOAT KEY, FL Don't miss out on this immaculate ground floor retreat in a serene waterfront setting read...	2 beds \| 2 baths \| 1,367 sq.ft.	$659,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 7.29% Airbnb Rental Income: $2726 Traditional Rental Income: $5760 Airbnb ROI: 1.32% Traditional ROI: 7.29%
5055 GULF OF MEXICO DRIVE #535 LONGBOAT KEY, FL Welcome to a haven of elegance and style, painstakingly transformed through meticulous ren...	2 beds \| 2 baths \| 1,509 sq.ft.	$1,995,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.44% Airbnb Rental Income: $2726 Traditional Rental Income: $5718 Airbnb ROI: -0.53% Traditional ROI: 1.44%
2105 GULF OF MEXICO DRIVE #3403 LONGBOAT KEY, FL Welcome to this direct Gulf-front, two-bedroom, two-bath condominium at Sunset Beach. The ...	2 beds \| 2 baths \| 1,463 sq.ft.	$1,699,900	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.75% Airbnb Rental Income: $2726 Traditional Rental Income: $5810 Airbnb ROI: -0.61% Traditional ROI: 1.75%
3060 GRAND BAY BOULEVARD #152 LONGBOAT KEY, FL This bayfront Biscayne residence, nestled within the highly sought-after Grand Bay communi...	3 beds \| 4 baths \| 2,250 sq.ft.	$1,395,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.42% Airbnb Rental Income: $4814 Traditional Rental Income: $7092 Airbnb ROI: 0.89% Traditional ROI: 3.42%
4651 GULF OF MEXICO DRIVE #402 LONGBOAT KEY, FL While the photographs and video offer a glimpse of the breathtaking beauty, stepping into ...	4 beds \| 5 baths \| 3,900 sq.ft.	$6,500,000	Airbnb cash on cash: -1.75% Traditional cash on cash: -1.58% Airbnb Rental Income: $5836 Traditional Rental Income: $5673 Airbnb ROI: -1.75% Traditional ROI: -1.58%
860 SPANISH DRIVE N LONGBOAT KEY, FL Calling all boaters! Look no further for magnificent water views! You are home in this gor...	2 beds \| 2 baths \| 1,415 sq.ft.	$995,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 4.03% Airbnb Rental Income: $2726 Traditional Rental Income: $5920 Airbnb ROI: -0.11% Traditional ROI: 4.03%
1932 HARBOURSIDE DRIVE #242 LONGBOAT KEY, FL Fourth floor full Bay front unit in much sought after Fairway Bay inside the 24/7 guarded ...	2 beds \| 2 baths \| 1,192 sq.ft.	$850,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 5.23% Airbnb Rental Income: $2726 Traditional Rental Income: $5652 Airbnb ROI: 0.72% Traditional ROI: 5.23%
563 SPANISH DRIVE S #127 LONGBOAT KEY, FL Dream Villa Awaits in Spanish Main Yacht Club â A Rare Find with Luxurious Comforts! ...	3 beds \| 2 baths \| 1,516 sq.ft.	$715,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 6.42% Airbnb Rental Income: $4814 Traditional Rental Income: $5757 Airbnb ROI: 3.52% Traditional ROI: 6.42%
3040 GRAND BAY BOULEVARD #244 LONGBOAT KEY, FL $120,000 Price Improvement!! Enjoy panoramic views of sunrise and sunset! Across Sarasot...	2 beds \| 4 baths \| 2,550 sq.ft.	$1,775,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 2.48% Airbnb Rental Income: $2726 Traditional Rental Income: $7091 Airbnb ROI: -0.56% Traditional ROI: 2.48%
1465 GULF OF MEXICO DRIVE #303 LONGBOAT KEY, FL Significant New Price! Come look at this beautiful condo with magnificent Gulf views!! W...	2 beds \| 3 baths \| 1,548 sq.ft.	$1,150,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 4.1% Airbnb Rental Income: $2726 Traditional Rental Income: $6269 Airbnb ROI: 0.19% Traditional ROI: 4.1%
660 CEDARS COURT LONGBOAT KEY, FL EXCEPTIONAL LONGBOAT KEY TURNKEY INVESTMENT OPPORTUNITY. 14-DAY RENTAL PROPERTY. RESORT SE...	2 beds \| 2 baths \| 1,440 sq.ft.	$760,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 5.99% Airbnb Rental Income: $2726 Traditional Rental Income: $5838 Airbnb ROI: 0.69% Traditional ROI: 5.99%
1125 GULF OF MEXICO DRIVE #402 LONGBOAT KEY, FL This beautifully renovated and meticulously maintained residence is ready for immediate oc...	2 beds \| 2 baths \| 1,392 sq.ft.	$1,250,000	Airbnb cash on cash: 0% Traditional cash on cash: 3.14% Airbnb Rental Income: $2726 Traditional Rental Income: $5733 Airbnb ROI: 0% Traditional ROI: 3.14%
1241 GULF OF MEXICO DRIVE #708 LONGBOAT KEY, FL Imagine the feeling of stepping into your new home where the beauty of sea and sky surroun...	3 beds \| 4 baths \| 2,965 sq.ft.	$3,575,000	Airbnb cash on cash: -1.65% Traditional cash on cash: -0.68% Airbnb Rental Income: $4814 Traditional Rental Income: $7033 Airbnb ROI: -1.65% Traditional ROI: -0.68%
3070 GRAND BAY BOULEVARD #625 LONGBOAT KEY, FL Views, views, and more views await in this spectacular panoramic setting. Upon entering fr...	2 beds \| 2 baths \| 1,276 sq.ft.	$850,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 5.2% Airbnb Rental Income: $2726 Traditional Rental Income: $5751 Airbnb ROI: 0.56% Traditional ROI: 5.2%
4540 GULF OF MEXICO DRIVE #205 LONGBOAT KEY, FL Entering this cheery and bright water view condo, you are greeted by a gorgeous, unique op...	2 beds \| 2 baths \| 1,325 sq.ft.	$860,000	Airbnb cash on cash: -2.55% Traditional cash on cash: 0.04% Airbnb Rental Income: $2726 Traditional Rental Income: $4162 Airbnb ROI: -2.55% Traditional ROI: 0.04%
679 SPANISH DRIVE S LONGBOAT KEY, FL Wow! Walk into this Spanish Main villa and that will be your thought. Every detail has bee...	2 beds \| 2 baths \| 1,361 sq.ft.	$695,000	Airbnb cash on cash: -2.83% Traditional cash on cash: 3.03% Airbnb Rental Income: $2726 Traditional Rental Income: $5877 Airbnb ROI: -2.83% Traditional ROI: 3.03%
5757 GULF OF MEXICO DRIVE #102 LONGBOAT KEY, FL The epitome of direct beachfront living awaits you in this 2BR/2BA, 1,561+/- sq. ft. retre...	2 beds \| 2 baths \| 1,561 sq.ft.	$895,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 4.9% Airbnb Rental Income: $2726 Traditional Rental Income: $5863 Airbnb ROI: 0.36% Traditional ROI: 4.9%
4241 GULF OF MEXICO DRIVE #502 LONGBOAT KEY, FL PRICED TO SELL! Don't let this ocean front condo with full sunset views get away! Wake u...	3 beds \| 3 baths \| 1,660 sq.ft.	$1,995,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 1.11% Airbnb Rental Income: $4814 Traditional Rental Income: $6094 Airbnb ROI: -0.12% Traditional ROI: 1.11%
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.	$1,125,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 3.53% Airbnb Rental Income: $4814 Traditional Rental Income: $6149 Airbnb ROI: 1.3% Traditional ROI: 3.53%
3500 GULF OF MEXICO DRIVE #301 LONGBOAT KEY, FL Gulf and Bay Views from third level in Buttonwood Cove!!! This highly sought after Furnish...	3 beds \| 2 baths \| 1,486 sq.ft.	$899,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 4.79% Airbnb Rental Income: $4814 Traditional Rental Income: $5741 Airbnb ROI: 2.5% Traditional ROI: 4.79%
415 L AMBIANCE DRIVE #D206 LONGBOAT KEY, FL Embrace the allure of beachfront living in this exclusive residence at LâAmbiance. Here,...	3 beds \| 4 baths \| 2,820 sq.ft.	$2,695,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 2.19% Airbnb Rental Income: $4814 Traditional Rental Income: $9728 Airbnb ROI: -0.17% Traditional ROI: 2.19%
2120 HARBOURSIDE DRIVE #623 LONGBOAT KEY, FL OVER $200,000 FULL ARCHITECTURE REBUILD BY JESSE BALAITY . . . HIGHEST QUALITY FIXTURES AN...	2 beds \| 2 baths \| 2,031 sq.ft.	$1,250,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.52% Airbnb Rental Income: $2726 Traditional Rental Income: $6094 Airbnb ROI: 0.07% Traditional ROI: 3.52%
3453 WINDING OAKS DRIVE #27 LONGBOAT KEY, FL Location, Location, Location! This three bedroom, three bath villa/condo, located on the ...	3 beds \| 3 baths \| 2,608 sq.ft.	$1,299,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 3.52% Airbnb Rental Income: $4814 Traditional Rental Income: $6627 Airbnb ROI: 1.19% Traditional ROI: 3.52%
3040 GRAND BAY BOULEVARD #252 LONGBOAT KEY, FL Indulge in the epitome of luxury living in this 3 bedroom (all en-suite), 3.5 bathroom, ex...	3 beds \| 4 baths \| 2,250 sq.ft.	$1,750,000	Airbnb cash on cash: -3.02% Traditional cash on cash: -1.01% Airbnb Rental Income: $4814 Traditional Rental Income: $7081 Airbnb ROI: -3.02% Traditional ROI: -1.01%
1211 GULF OF MEXICO DRIVE #408 LONGBOAT KEY, FL Newly reduced association fees and all Milestone requirements met at this building, Discov...	2 beds \| 2 baths \| 1,827 sq.ft.	$1,850,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 1.95% Airbnb Rental Income: $2726 Traditional Rental Income: $5925 Airbnb ROI: -0.29% Traditional ROI: 1.95%
1085 GULF OF MEXICO DRIVE #101 LONGBOAT KEY, FL * Best Value in Beachplace for this sun filled corner 2 bedroom 2 bath condo in this beach...	2 beds \| 2 baths \| 1,172 sq.ft.	$729,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 6.59% Airbnb Rental Income: $2726 Traditional Rental Income: $5559 Airbnb ROI: 1.47% Traditional ROI: 6.59%
2295 GULF OF MEXICO DRIVE #83s LONGBOAT KEY, FL If youâve ever dreamt of awakening to the sound of surf and forever views of the Gulf of...	2 beds \| 2 baths \| 1,235 sq.ft.	$1,550,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.16% Airbnb Rental Income: $2726 Traditional Rental Income: $5619 Airbnb ROI: -0.29% Traditional ROI: 2.16%
706 SPANISH DRIVE S LONGBOAT KEY, FL Tranquil, serene and lush are the only words to describe the lovely backdrop of this compl...	2 beds \| 2 baths \| 1,423 sq.ft.	$695,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 7.46% Airbnb Rental Income: $2726 Traditional Rental Income: $5938 Airbnb ROI: 1.51% Traditional ROI: 7.46%
3320 GULF OF MEXICO DRIVE #204C LONGBOAT KEY, FL Enjoy the year-round salt air surrounded by streaming sunlight in this modern and inviting...	2 beds \| 2 baths \| 1,080 sq.ft.	$599,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 8.12% Airbnb Rental Income: $2726 Traditional Rental Income: $5410 Airbnb ROI: 2.17% Traditional ROI: 8.12%
1241 GULF OF MEXICO DRIVE #401 LONGBOAT KEY, FL Discover the delight of living in a direct Gulf front 3BR/5BA, 3,400+/- sq.-ft. residence ...	3 beds \| 5 baths \| 3,400 sq.ft.	$4,649,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.05% Airbnb Rental Income: $4814 Traditional Rental Income: $8280 Airbnb ROI: -0.98% Traditional ROI: 0.05%
1065 GULF OF MEXICO DRIVE #302 LONGBOAT KEY, FL Coveted Southern exposure offering morning sun with a very tropical feel there palm trees ...	2 beds \| 2 baths \| 1,392 sq.ft.	$850,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 5.59% Airbnb Rental Income: $2726 Traditional Rental Income: $5730 Airbnb ROI: 0.98% Traditional ROI: 5.59%
4380 EXETER DRIVE #204 LONGBOAT KEY, FL Call this gorgeous waterfront condominium home! This beautifully updated home is light and...	2 beds \| 2 baths \| 992 sq.ft.	$475,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 10.13% Airbnb Rental Income: $2726 Traditional Rental Income: $5371 Airbnb ROI: 2.73% Traditional ROI: 10.13%
4239 GULF OF MEXICO DRIVE #MH1 LONGBOAT KEY, FL Experience the pinnacle of coastal living in Longboat Key. Located mid-key, Pelican Harbou...	2 beds \| 2 baths \| 1,241 sq.ft.	$1,250,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.4% Airbnb Rental Income: $2726 Traditional Rental Income: $5658 Airbnb ROI: -0.68% Traditional ROI: 2.4%

Your search for investment property begins and ends here

Condos for Sale in Longboat Key, FL

2110 HARBOURSIDE DRIVE #557

LONGBOAT KEY, FL

3 beds | 2 baths | 2,039 sq.ft.

$1,349,000

Airbnb cash on cash: -2.31%

Traditional cash on cash: -0.47%

Airbnb Rental Income: $4814

Traditional Rental Income: $6130

Airbnb ROI: -2.31%

Traditional ROI: -0.47%

4370 CHATHAM DRIVE #104

LONGBOAT KEY, FL

2 beds | 2 baths | 1,040 sq.ft.

$530,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 8.91%

Airbnb Rental Income: $2726

Traditional Rental Income: $5390

Airbnb ROI: 2.24%

Traditional ROI: 8.91%

2016 HARBOURSIDE DRIVE #327

LONGBOAT KEY, FL

2 beds | 2 baths | 1,532 sq.ft.

$899,000

Airbnb cash on cash: 0.81%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $2726

Traditional Rental Income: $5810

Airbnb ROI: 0.81%

Traditional ROI: 5.27%

2109 GULF OF MEXICO DRIVE #1303

LONGBOAT KEY, FL

2 beds | 2 baths | 1,463 sq.ft.

$1,300,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $2726

Traditional Rental Income: $5800

Airbnb ROI: -0.06%

Traditional ROI: 3.02%

455 LONGBOAT CLUB ROAD #305

LONGBOAT KEY, FL

3 beds | 4 baths | 2,880 sq.ft.

$2,995,000

Airbnb cash on cash: -0.26%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $4814

Traditional Rental Income: $7182

Airbnb ROI: -0.26%

Traditional ROI: 0.95%

5231 GULF OF MEXICO DRIVE #104

LONGBOAT KEY, FL

1 beds | 1 baths | 720 sq.ft.

$599,000

Airbnb cash on cash: 2.07%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $3172

Traditional Rental Income: $3706

Airbnb ROI: 2.07%

Traditional ROI: 4.31%

2525 GULF OF MEXICO DRIVE #11B

LONGBOAT KEY, FL

2 beds | 2 baths | 1,491 sq.ft.

$1,499,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 2.27%

Airbnb Rental Income: $2726

Traditional Rental Income: $5774

Airbnb ROI: -0.38%

Traditional ROI: 2.27%

6750 GULF OF MEXICO DRIVE #171

LONGBOAT KEY, FL

2 beds | 2 baths | 1,367 sq.ft.

$659,900

Airbnb cash on cash: 1.32%

Traditional cash on cash: 7.29%

Airbnb Rental Income: $2726

Traditional Rental Income: $5760

Airbnb ROI: 1.32%