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 |
|---|---|---|---|
1930 HARBOURSIDE DRIVE #145LONGBOAT KEY, FLSet on the 4th floor of Building 1 in Fairway Bay, this beautifully styled 2BR/2BA residen... |
2 beds | 2 baths | 1,270 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.26%
|
100 SANDS POINT ROAD #225LONGBOAT KEY, FLSELLER IS MOTIVATED AND WILL ENTERTAIN ALL REASONABLE OFFERS! GREAT PRICE REDUCTION !!!! ... |
2 beds | 2 baths | 1,492 sq.ft. |
$950,000 |
Airbnb cash on cash: -0.52%
|
1085 GULF OF MEXICO DRIVE #205LONGBOAT KEY, FLSpacious 3-Bedroom End-Unit Residence in Sought-After Beachplace Welcome to this beauti... |
3 beds | 2 baths | 1,819 sq.ft. |
$999,000 |
Airbnb cash on cash: 0%
|
909 SPANISH DRIVE NLONGBOAT KEY, FLOne or more photo(s) has been virtually staged. This gorgeous two-bedroom, two-bath Spanis... |
2 beds | 2 baths | 1,300 sq.ft. |
$650,000 |
Airbnb cash on cash: -0.77%
|
1912 HARBOURSIDE DRIVE #604LONGBOAT KEY, FLEmbrace the island life style within the gates of Longboat Key's premier resort community ... |
3 beds | 3 baths | 1,316 sq.ft. |
$850,000 |
Airbnb cash on cash: -0.18%
|
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. |
$1,139,000 |
Airbnb cash on cash: -2.97%
|
2450 HARBOURSIDE DRIVE #212LONGBOAT KEY, FLIf you've been waiting for a DEAL... this is it! EXTRAORDINARY OPPORTUNITY!! Indulge in ... |
3 beds | 3 baths | 2,830 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -1.6%
|
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. |
$1,999,989 |
Airbnb cash on cash: -0.32%
|
3030 GRAND BAY BOULEVARD #384LONGBOAT KEY, FLPerched on the eighth floor of Grand Bayâs Building 3, this updated Cayman residence cap... |
3 beds | 3 baths | 2,550 sq.ft. |
$1,699,000 |
Airbnb cash on cash: 0.02%
|
795 MARBURY LANELONGBOAT KEY, FLUnder contract-accepting backup offers. Refined coastal living is waiting for you at 795 M... |
4 beds | 3 baths | 3,355 sq.ft. |
$3,599,000 |
Airbnb cash on cash: -0.44%
|
3080 GRAND BAY BOULEVARD #515LONGBOAT KEY, FLDefined by an exceptional indoorâoutdoor connection, this 2BR/2BA Grand Bay residence of... |
2 beds | 2 baths | 1,276 sq.ft. |
$625,000 |
Airbnb cash on cash: -2.8%
|
1914 HARBOUR LINKS CIRCLE #10LONGBOAT KEY, FLTucked behind the gates of Bay Isles in the Emerald Pointe community, this 3BR/3.5BA resid... |
3 beds | 4 baths | 2,180 sq.ft. |
$1,495,000 |
Airbnb cash on cash: 0.66%
|
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. |
$855,000 |
Airbnb cash on cash: -1.03%
|
803 BAYPORT WAY #803LONGBOAT KEY, FLWelcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to ... |
2 beds | 2 baths | 1,456 sq.ft. |
$775,000 |
Airbnb cash on cash: -1.87%
|
6800 GULF OF MEXICO DRIVE #184LONGBOAT KEY, FLBeautifully renovated in 2023, with dazzling views of the Gulf of Mexico and the private b... |
2 beds | 2 baths | 1,287 sq.ft. |
$475,000 |
Airbnb cash on cash: 2.2%
|
706 BAYPORT WAY #706LONGBOAT KEY, FLThis stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect... |
2 beds | 2 baths | 1,601 sq.ft. |
$739,000 |
Airbnb cash on cash: -2.04%
|
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%
|
4725 GULF OF MEXICO DRIVE #309LONGBOAT KEY, FLUnder contract-accepting backup offers. Welcome to Sand Cay Beach Resortâone of Longboat... |
2 beds | 2 baths | 1,120 sq.ft. |
$819,000 |
Airbnb cash on cash: -1.64%
|
2675 GULF OF MEXICO DRIVE #403LONGBOAT KEY, FLUnder contract-accepting backup offers. A New Year is here and a New Price with gorgeous f... |
3 beds | 2 baths | 1,896 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -1.18%
|
2089 GULF OF MEXICO DRIVE #G1-108LONGBOAT KEY, FLWelcome to G1-108, a recently remodeled and fully-furnished residence in Seaplace! Ove... |
2 beds | 2 baths | 933 sq.ft. |
$675,000 |
Airbnb cash on cash: -0.87%
|
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%
|
3427 WINDING OAKS DRIVE #14LONGBOAT KEY, FLPrivately tucked away within the private Winding Oaks community on Longboat Key, this beau... |
3 beds | 3 baths | 2,555 sq.ft. |
$1,150,000 |
Airbnb cash on cash: -1.33%
|
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. |
$1,068,375 |
Airbnb cash on cash: 1.38%
|
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. |
$1,799,000 |
Airbnb cash on cash: -1.84%
|
435 L AMBIANCE DRIVE #J703LONGBOAT KEY, FLUnder contract-accepting backup offers. Experience unparalleled luxury in this beautifully... |
3 beds | 3 baths | 2,820 sq.ft. |
$4,495,000 |
Airbnb cash on cash: -2.18%
|
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. |
$1,475,000 |
Airbnb cash on cash: 1.05%
|
5841 GULF OF MEXICO DRIVE #244LONGBOAT KEY, FLREDUCE PRICE- RARE FIND!!! This fully furnished turnkey 1bedroom/1bath end unit has an ope... |
1 beds | 1 baths | 520 sq.ft. |
$525,500 |
Airbnb cash on cash: 0.32%
|
1211 GULF OF MEXICO DRIVE #505LONGBOAT KEY, FLUnder contract-accepting backup offers. No matter where you 'summer' you belong in sunny S... |
2 beds | 2 baths | 1,598 sq.ft. |
$1,499,000 |
Airbnb cash on cash: -2.16%
|
1965 GULF OF MEXICO DRIVE #G5-406LONGBOAT KEY, FLExperience the Ultimate Gulf-Front Lifestyle at Seaplace Wake up to breathtaking, unobs... |
3 beds | 2 baths | 1,804 sq.ft. |
$1,900,000 |
Airbnb cash on cash: -0.39%
|
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. |
$4,950,000 |
Airbnb cash on cash: -1.02%
|
3530 MISTLETOE LANELONGBOAT KEY, FLLocated behind the gates of Coreyâs Landing in the sought-after Bay Isles community, thi... |
4 beds | 4 baths | 3,102 sq.ft. |
$2,695,000 |
Airbnb cash on cash: -0.31%
|
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. |
$465,000 |
Airbnb cash on cash: -0.71%
|
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. |
$995,000 |
Airbnb cash on cash: -2.38%
|
509 SPANISH DRIVE NLONGBOAT KEY, FLSTEPS FROM THE BEACH.....WATERFRONT COMMUNITY......DEEDED BEACH ACCESS......FULLY RENOVATE... |
2 beds | 2 baths | 1,357 sq.ft. |
$369,000 |
Airbnb cash on cash: -0.97%
|
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. |
$700,000 |
Airbnb cash on cash: -1.8%
|
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. |
$859,000 |
Airbnb cash on cash: -1.86%
|
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: -0.49%
|
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. |
$2,999,000 |
Airbnb cash on cash: -0.29%
|
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. |
$295,000 |
Airbnb cash on cash: 2.86%
|
4621 GULF OF MEXICO DRIVE #10DLONGBOAT KEY, FLWhether you choose resort style living or just want to enjoy vacationing at the beach whil... |
2 beds | 2 baths | 756 sq.ft. |
$675,000 |
Airbnb cash on cash: 0.28%
|
Real Estate investment in Longboat-key, FL
There are 237 properties for sale in the city of Longboat Key . The median list price in Longboat Key is $1,068,380 and the average price per square foot is $533. In April 2026, the average monthly cash on cash return in Longboat Key is N/A%. The average monthly rental income in Longboat Key is $3,093.