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 |
|---|---|---|---|
1241 GULF OF MEXICO DRIVE #109LONGBOAT KEY, FLLive the lavish lifestyle only found at the Water Club on Longboat Key, an idyllic waterfr... |
2 beds | 3 baths | 2,000 sq.ft. |
$1,525,000 |
Airbnb cash on cash: -0.41%
|
2450 HARBOURSIDE DRIVE #212LONGBOAT KEY, FLJUMP NOW... Price reduction!! Indulge in the luxury living experience at Marina Bay, wher... |
3 beds | 3 baths | 2,830 sq.ft. |
$1,575,000 |
Airbnb cash on cash: -0.67%
|
6330 LAGUNA DRIVELONGBOAT KEY, FLModern Beach Home priced aggressively to sell as the owners are relocating. Ocean Views! P... |
3 beds | 3 baths | 2,856 sq.ft. |
$1,999,999 |
Airbnb cash on cash: -0.32%
|
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%
|
2089 GULF OF MEXICO DRIVE #G1-105LONGBOAT KEY, FLWake up in This Resort-Style Living Condo located on a Barrier Island Paradise! Positioned... |
2 beds | 2 baths | 1,257 sq.ft. |
$880,000 |
Airbnb cash on cash: 0.46%
|
747 MARBURY LANELONGBOAT KEY, FLWelcome to Your Waterfront Paradise! Discover this coastal retreat in the highly desirabl... |
3 beds | 2 baths | 2,353 sq.ft. |
$1,425,000 |
Airbnb cash on cash: 0.65%
|
775 LONGBOAT CLUB ROAD #705LONGBOAT KEY, FLTURN-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: -0.75%
|
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%
|
435 L AMBIANCE DRIVE #K506LONGBOAT KEY, FLOne or more photo(s) has been virtually staged. Sweeping Gulf, bay, and skyline views set ... |
3 beds | 4 baths | 2,820 sq.ft. |
$3,299,000 |
Airbnb cash on cash: -1.1%
|
667 EL CENTROLONGBOAT KEY, FLSpanish Main Yacht Club on Longboat Key is a warm and vital boating community with its pri... |
2 beds | 2 baths | 1,327 sq.ft. |
$380,000 |
Airbnb cash on cash: -0.9%
|
1935 GULF OF MEXICO DRIVE #G7-402LONGBOAT KEY, FLA must-see, this exceptional two-bedroom, two-bath penthouse is the only residence in Seap... |
2 beds | 2 baths | 1,068 sq.ft. |
$649,000 |
Airbnb cash on cash: -1.13%
|
2055 GULF OF MEXICO DRIVE #G2-214LONGBOAT KEY, FLBelow $400,000 Seaplace opportunity ⢠Hurricane shutter & newer AC ⢠Gulf-front commu... |
1 beds | 2 baths | 1,094 sq.ft. |
$399,900 |
Airbnb cash on cash: 0.28%
|
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. |
$1,400,000 |
Airbnb cash on cash: 0.19%
|
3010 GRAND BAY BOULEVARD #472LONGBOAT KEY, FLYour semi-private elevator provides access to the beautiful 7th floor condo with sweeping ... |
3 beds | 3 baths | 2,250 sq.ft. |
$1,725,000 |
Airbnb cash on cash: -1.45%
|
1965 GULF OF MEXICO DRIVE #G5-104LONGBOAT KEY, FLEmbrace 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: 1.12%
|
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. |
$1,168,375 |
Airbnb cash on cash: 1.18%
|
565 SANCTUARY DRIVE #B106LONGBOAT KEY, FLNestled behind the exclusive gates of the Longboat Key Club, The Sanctuary enjoys an envia... |
3 beds | 3 baths | 2,375 sq.ft. |
$1,999,000 |
Airbnb cash on cash: -0.22%
|
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%
|
435 L AMBIANCE DRIVE #J703LONGBOAT KEY, FLExperience unparalleled luxury in this beautifully updated 3-bedroom condo at the highly c... |
3 beds | 3 baths | 2,634 sq.ft. |
$4,795,000 |
Airbnb cash on cash: -1.67%
|
3281 BAYOU SOUNDLONGBOAT KEY, FLUnder contract-accepting backup offers. Surrounded by tropical landscaping, this 3BR/3½BA... |
3 beds | 4 baths | 3,407 sq.ft. |
$2,295,000 |
Airbnb cash on cash: 0.12%
|
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%
|
5841 GULF OF MEXICO DRIVE #244LONGBOAT KEY, FLRARE FIND!!! This fully furnished turnkey 1bedroom/1bath end unit has an open kitchen, din... |
1 beds | 1 baths | 520 sq.ft. |
$575,000 |
Airbnb cash on cash: 0.21%
|
1211 GULF OF MEXICO DRIVE #505LONGBOAT KEY, FLNew price for this exceptional condo on the beach! Unit 505 at Longboat Key's popular Pro... |
2 beds | 2 baths | 1,598 sq.ft. |
$1,595,000 |
Airbnb cash on cash: -0.73%
|
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. |
$309,000 |
Airbnb cash on cash: 4.65%
|
4651 GULF OF MEXICO DRIVE #402LONGBOAT KEY, FLUnder contract-accepting backup offers. Experience an unparalleled coastal retreat where t... |
4 beds | 5 baths | 3,989 sq.ft. |
$5,999,000 |
Airbnb cash on cash: -2.64%
|
5840 GULF OF MEXICO DRIVELONGBOAT KEY, FLLongboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Coon... |
4 beds | 6 baths | 4,145 sq.ft. |
$5,280,000 |
Airbnb cash on cash: -1.02%
|
1930 HARBOURSIDE DRIVE #136LONGBOAT KEY, FLUnder contract-accepting backup offers. Sweeping bay views and refined comfort define this... |
2 beds | 2 baths | 1,270 sq.ft. |
$679,000 |
Airbnb cash on cash: -2.13%
|
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. |
$495,000 |
Airbnb cash on cash: -0.71%
|
6701 GULF OF MEXICO DRIVE #311LONGBOAT KEY, FLLARGE PRICE REDUCTION - COASTAL ELEGANCE ON LONGBOAT KEY - DIRECT GULF FRONT PROPERTY: We... |
1 beds | 1 baths | 936 sq.ft. |
$798,000 |
Airbnb cash on cash: -1.6%
|
3060 GRAND BAY BOULEVARD #154LONGBOAT KEY, FLBeautifully renovated and offered turnkey furnished, this 3BR/3.5BA residence is perfectly... |
3 beds | 4 baths | 2,550 sq.ft. |
$1,695,000 |
Airbnb cash on cash: -1.83%
|
1050 LONGBOAT CLUB ROAD #903LONGBOAT KEY, FLSIGNIFICANT 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: -0.41%
|
2110 HARBOURSIDE DRIVE #526LONGBOAT KEY, FLCarefree living awaits you with beautiful panoramic views of Sarasota Bay in this beautifu... |
3 beds | 2 baths | 2,031 sq.ft. |
$795,000 |
Airbnb cash on cash: 2.12%
|
1926 HARBOURSIDE DRIVE #1302LONGBOAT KEY, FLGATED, 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. |
$899,000 |
Airbnb cash on cash: -1.82%
|
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 #C208LONGBOAT KEY, FLDiscover coastal living at its finest with this charming condominium located on Gulf of Me... |
1 beds | 1 baths | 712 sq.ft. |
$305,000 |
Airbnb cash on cash: 2.74%
|
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%
|
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. |
$1,475,000 |
Airbnb cash on cash: 0.16%
|
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%
|
Real Estate investment in Longboat-key, FL
There are 181 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,292,000 and the average price per square foot is $628. In November 2025, the average monthly cash on cash return in Longboat Key is N/A%. The average monthly rental income in Longboat Key is $2,553.