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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
3318 BAYOU SOUNDLONGBOAT KEY, FLImmerse yourself in the timeless charm of West Indies-style living with this extraordinary... |
3 beds | 2 baths | 2,675 sq.ft. |
$1,495,000 |
Airbnb cash on cash: 0.87%
|
100 SANDS POINT ROAD #225LONGBOAT KEY, FLPRICING UPDATE! Longboat Key's best kept secret. Sands Point Condominium is everything y... |
2 beds | 2 baths | 1,492 sq.ft. |
$999,995 |
Airbnb cash on cash: 0.89%
|
2450 HARBOURSIDE DRIVE #212LONGBOAT KEY, FLJUMP NOW... $100,000 price reduction!! Indulge in the luxury living experience at Marina ... |
3 beds | 3 baths | 2,830 sq.ft. |
$1,725,000 |
Airbnb cash on cash: -0.7%
|
6330 LAGUNA DRIVELONGBOAT KEY, FLMotivated Seller! Bring offers! Live the ultimate Beach lifestyle! This Raised (16ft.)Hurr... |
3 beds | 3 baths | 2,856 sq.ft. |
$2,195,000 |
Airbnb cash on cash: -0.38%
|
608 SAINT JUDES DRIVELONGBOAT KEY, FLA TRUE FLORIDA DREAM HOME! WALKING DISTANCE TO ONE OF FLORIDA'S MOST BEAUTIFUL BEACH! This... |
4 beds | 3 baths | 2,106 sq.ft. |
$989,000 |
Airbnb cash on cash: 3.4%
|
957 SPANISH DRIVE NLONGBOAT KEY, FLLONGBOAT KEY WATERFRONT CONDO. UNOBSTRUCTED VIEW OF THE BAY. PEACEFUL LOCATION. BEAUTIFU... |
2 beds | 2 baths | 1,399 sq.ft. |
$1,000,000 |
Airbnb cash on cash: -0.05%
|
1065 GULF OF MEXICO DRIVE #601LONGBOAT KEY, FLA rare offering of a penthouse end unit in this Gulf-front complex on southern Longboat Ke... |
2 beds | 2 baths | 1,172 sq.ft. |
$895,000 |
Airbnb cash on cash: 0.21%
|
6800 GULF OF MEXICO DRIVE #203LONGBOAT KEY, FLSerene water views of tranquil Bishops Bayou greet you as you enter this immaculate 2nd fl... |
1 beds | 1 baths | 936 sq.ft. |
$449,000 |
Airbnb cash on cash: 3.8%
|
838 BAYPORT WAY #838LONGBOAT KEY, FLWelcome to this beautifully appointed residence situated in the desirable Longboat Key are... |
2 beds | 2 baths | 1,601 sq.ft. |
$785,000 |
Airbnb cash on cash: 0.79%
|
2055 GULF OF MEXICO DRIVE #G2-214LONGBOAT KEY, FLIsland Living Meets Contemporary Comfort â Gulfside Loft at Seaplace Welcome to your co... |
1 beds | 2 baths | 1,094 sq.ft. |
$399,900 |
Airbnb cash on cash: -0.21%
|
2675 GULF OF MEXICO DRIVE #403LONGBOAT KEY, FLHUGE PRICE CHANGE:Veinte (20 in Spanish) is a luxury condominium community with only twent... |
3 beds | 2 baths | 1,896 sq.ft. |
$1,490,000 |
Airbnb cash on cash: 0.12%
|
705 JUNGLE QUEEN WAYLONGBOAT KEY, FLLONGBOAT KEY CANAL FRONT HOME WITH DEEDED BEACH EASEMENT 2 BLOCKS AWAY. This 4 BED / 3.5 B... |
4 beds | 4 baths | 3,078 sq.ft. |
$2,950,000 |
Airbnb cash on cash: -0.73%
|
3010 GRAND BAY BOULEVARD #472LONGBOAT KEY, FLYour semi-private elevator provides access to the beautiful 7th floor condo with sweeping ... |
3 beds | 3 baths | 2,143 sq.ft. |
$1,725,000 |
Airbnb cash on cash: -1.45%
|
1932 HARBOURSIDE DRIVE #244LONGBOAT KEY, FLWelcome 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: -0.2%
|
501 DE NARVAEZ DRIVELONGBOAT KEY, FLSome homes whisper. Others make a statement. 501 De Narvaez Drive commands attentionâwit... |
3 beds | 3 baths | 1,708 sq.ft. |
$1,282,500 |
Airbnb cash on cash: 0.99%
|
1281 GULF OF MEXICO DRIVE #404LONGBOAT KEY, FLIntroducing an exceptional beachfront residence that defines luxury living on Longboat Key... |
3 beds | 4 baths | 3,054 sq.ft. |
$2,695,000 |
Airbnb cash on cash: -0.92%
|
1281 GULF OF MEXICO DRIVE #906LONGBOAT KEY, FLWelcome to The Water Club on Longboat Key, where refined Gulf-front living meets everyday ... |
2 beds | 3 baths | 2,655 sq.ft. |
$2,495,000 |
Airbnb cash on cash: -1.22%
|
619 BUTTONWOOD DRIVELONGBOAT KEY, FLOne or more photo(s) has been virtually staged. Welcome to an exceptional mid-century mode... |
3 beds | 2 baths | 2,265 sq.ft. |
$1,599,000 |
Airbnb cash on cash: 0.88%
|
3806 GULF OF MEXICO DRIVE #C-312LONGBOAT KEY, FLFurnished 2-bedroom, 2-bathroom end unit condo on Longboat Key! Brand New HVAC! This 3rd-... |
2 beds | 2 baths | 1,062 sq.ft. |
$319,000 |
Airbnb cash on cash: 4.47%
|
4651 GULF OF MEXICO DRIVE #402LONGBOAT KEY, FLExperience an unparalleled coastal retreat where the gulf meets impeccable design and tech... |
4 beds | 5 baths | 3,989 sq.ft. |
$5,999,000 |
Airbnb cash on cash: -2.64%
|
7147 LA LENAIRE DRIVELONGBOAT KEY, FLA rare opportunity to own the crown jewel of Floridaâs west coast. Tucked away on the p... |
5 beds | 6 baths | 3,503 sq.ft. |
$5,250,000 |
Airbnb cash on cash: -0.43%
|
3806 GULF OF MEXICO DRIVE #C311LONGBOAT KEY, FLPriced to sell! Discover the perfect blend of comfort and coastal living in this beautiful... |
2 beds | 2 baths | 1,062 sq.ft. |
$325,000 |
Airbnb cash on cash: -0.13%
|
1935 GULF OF MEXICO DRIVE #G7-304LONGBOAT KEY, FLExperience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom... |
2 beds | 1 baths | 933 sq.ft. |
$525,000 |
Airbnb cash on cash: -0.73%
|
594 SPANISH DRIVE SLONGBOAT KEY, FLWelcome to this 2-bedroom, 2-bath villa located in the highly desirable 55+ community of S... |
2 beds | 2 baths | 1,427 sq.ft. |
$279,000 |
Airbnb cash on cash: -0.28%
|
6701 GULF OF MEXICO DRIVE #311LONGBOAT KEY, FLCOASTAL ELEGANCE ON LONGBOAT KEY - DIRECT GULF FRONT PROPERTY: Welcome to a rare opportun... |
1 beds | 1 baths | 936 sq.ft. |
$849,900 |
Airbnb cash on cash: -1.57%
|
1050 LONGBOAT CLUB ROAD #903LONGBOAT KEY, FLThis TOTALLY RENOVATED ISLAND BEAUTY will charm the most sophisticated Buyers and the spec... |
2 beds | 2 baths | 1,409 sq.ft. |
$1,349,000 |
Airbnb cash on cash: -0.51%
|
600 FOX STREETLONGBOAT KEY, FLExperience the charm of historic Longboat Key living in this delightful 3-bedroom, 3-bathr... |
3 beds | 3 baths | 1,427 sq.ft. |
$899,999 |
Airbnb cash on cash: 2.07%
|
250 SANDS POINT ROAD #5101LONGBOAT KEY, FLA 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: 0.52%
|
510 PUTTER LANELONGBOAT KEY, FLWelcome to 510 Putter Lane, a stunning canal-front retreat nestled in the coveted Country ... |
3 beds | 2 baths | 2,253 sq.ft. |
$3,250,000 |
Airbnb cash on cash: -0.34%
|
3806 GULF OF MEXICO DRIVE #C211LONGBOAT KEY, FLLovely, spacious 2/2 second floor corner unit in a Gulf-to-Bay community on Longboat Key. ... |
2 beds | 2 baths | 1,062 sq.ft. |
$319,000 |
Airbnb cash on cash: 4.06%
|
610 HIBISCUS WAYLONGBOAT KEY, FLPre-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%
|
3467 BYRON LANELONGBOAT KEY, FLRevel in all the spaciousness and privacy â situated with wide water and golf views in t... |
3 beds | 3 baths | 2,227 sq.ft. |
$1,149,000 |
Airbnb cash on cash: 0.3%
|
1445 GULF OF MEXICO DRIVE #304LONGBOAT KEY, FLTimeless sophistication meets resort-style elegance in this fully renovated 3-bedroom resi... |
3 beds | 3 baths | 1,859 sq.ft. |
$1,500,000 |
Airbnb cash on cash: 0.14%
|
651 JUNGLE QUEEN WAYLONGBOAT KEY, FL* * DO NOT MISS OUT ON THIS LONGBOAT SPECIAL * * MULTIPLE USES ARE AVAILABLE TO YOU * * Pr... |
4 beds | 3 baths | 2,242 sq.ft. |
$950,000 |
Airbnb cash on cash: 2.49%
|
1211 GULF OF MEXICO DRIVE #403LONGBOAT KEY, FLEscape to Elegance on Longboat Key Welcome to this fully renovated, fourth-floor reside... |
2 beds | 2 baths | 1,585 sq.ft. |
$1,795,000 |
Airbnb cash on cash: -0.63%
|
826 BAYPORT WAY #826LONGBOAT KEY, FLUnder contract-accepting backup offers. Imagine owning a stunning second-floor end-unit ne... |
2 beds | 2 baths | 1,676 sq.ft. |
$695,000 |
Airbnb cash on cash: -3.84%
|
2410 HARBOURSIDE DRIVE #142LONGBOAT KEY, FLA 4th Floor Waterfront Sanctuary Where Every Detail Feels Like Home and with a new price p... |
3 beds | 4 baths | 3,382 sq.ft. |
$2,995,000 |
Airbnb cash on cash: -0.54%
|
4651 GULF OF MEXICO DRIVE #304LONGBOAT KEY, FLPerched above the Gulf, Beach and Bay this home is a rare blend of modern luxury and untou... |
3 beds | 5 baths | 4,012 sq.ft. |
$6,995,000 |
Airbnb cash on cash: -2.79%
|
6489 GULFSIDE ROADLONGBOAT KEY, FLUnder Construction. Enjoy the ultimate Longboat Key lifestyle in your very own direct Gulf... |
4 beds | 5 baths | 6,616 sq.ft. |
$16,995,000 |
Airbnb cash on cash: -0.94%
|
3491 BAYOU SOUNDLONGBOAT KEY, FLWelcome to the secure, double-gated Bay Isles Bayou community on Longboat Key. Set on an e... |
4 beds | 6 baths | 5,730 sq.ft. |
$3,849,000 |
Airbnb cash on cash: -0.19%
|
Real Estate investment in Longboat-key, FL
There are 137 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,296,880 and the average price per square foot is $604. In September 2025, the average monthly cash on cash return in Longboat Key is N/A%. The average monthly rental income in Longboat Key is $2,983.