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451 Properties Available
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$10,000
Condo
2109 GULF OF MEXICO DR #1203, Longboat Key, FL 34228
***NEW VACATION RENTAL LISTING** Rented for Season 2025 February through April 15th.* Welcome to your amazing beachfron...
Listed by PRECISE REALTY CORP
$14,800,000
Single Family Home
6680 GULF OF MEXICO DR, Longboat Key, FL 34228
Expansive, gated, waterfront family estate featuring custom designed main home along with a separate three bedroom guest...
Listed by BARRIER ISLAND REALTY LLC
$1,225,000
Condo
360 GULF OF MEXICO DR #312, Longboat Key, FL 34228
REDUCE $300,000!! SELLER WANT THIS CONDO SOLD! Tangerine Bay Club An Island Resort-style condo located at the premier lo...
Listed by SUNREAL ESTATE INC
$6,950
Condo
4325 GULF OF MEXICO DR #208, Longboat Key, FL 34228
OPEN FOR APRIL 2025!! Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing ...
Listed by PREMIER SOTHEBY'S INTERNATIONAL
$9,000
Condo
720 BAYPORT WAY #720, Longboat Key, FL 34228
Bright and Spacious! This lovely 2 bedroom, 2 bathroom furnished condominium is nestled comfortably in a lush tropical s...
Listed by KELLER WILLIAMS SUBURBAN TAMPA
$5,500
Condo
Longboat Key, FL 34228
SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom co...
Listed by JENNETTE PROPERTIES INC
$5,000
Condo
3240 GULF OF MEXICO DR #603, Longboat Key, FL 34228
VACATION RENTAL!!! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and war...
Listed by GULF COAST RENTAL HOMES&CONDOS
$7,000
Single Family Home
2369 HARBOUR OAKS DR, Longboat Key, FL 34228
LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. O...
Listed by JENNETTE PROPERTIES INC
$7,999,000
Condo
2251 GULF OF MEXICO DR #204, Longboat Key, FL 34228
Exquisite home on the beach. Welcome to ARIA, a modern coastal sanctuary on the Gulf of Mexico, where luxury meets tranq...
Listed by COLDWELL BANKER REALTY
$5,500
Condo
1050 LONGBOAT CLUB RD #804, Longboat Key, FL 34228
AVAILABLE RENTAL JANUARY 1, 2025 1, through MAY 30,2025 31.2025 Located the furthest South Behind The Gates of Longboat ...
Listed by CHROME REALTY LLC
$5,500
Condo
1050 LONGBOAT CLUB RD #502, Longboat Key, FL 34228
Available 10/01/2023 through 05/302024 This residence is gulf and bay views through your hurricane sliding doors and a v...
Listed by CHROME REALTY LLC
$9,000
Condo
1925 GULF OF MEXICO DR #309, Longboat Key, FL 34228
LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDRO...
Listed by JENNETTE PROPERTIES INC
$17,000
Single Family Home
500 SCHOONER LN, Longboat Key, FL 34228
Booked rest of 2024 through Feb 2025, booked May-July, Charming, waterfront Longboat Key surprise! This 2 bedroom 2 ba...
Listed by PRECISE REALTY CORP
$12,000
Condo
2425 GULF OF MEXICO DR #14B, Longboat Key, FL 34228
Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you ...
Listed by ANMARK REALTY LLC
$7,000
Condo
3804 GULF OF MEXICO DR #B307, Longboat Key, FL 34228
Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect locatio...
Listed by GULF COAST REALTY & MANAGEMENT
$30,000
Single Family Home
6925 LONGBOAT DR S, Longboat Key, FL 34228
Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. <br> <br>...
Listed by GULF COAST REALTY & MANAGEMENT
$6,500
Condo
1050 LONGBOAT CLUB RD #1006, Longboat Key, FL 34228
Available 05/01/2024 MONTHS OR MORE until 11/30/2024 The residence has been leased 01/07/2024.through 05/07/2024..Priva...
Listed by CHROME REALTY LLC
$12,369
Condo
2089 GULF OF MEXICO DR #G1-204, Longboat Key, FL 34228
Welcome to Beachfront Paradise! This stunning waterfront second-floor, 2-bedroom, 2.5 bath two-story condo is located in...
Listed by GULF COAST REALTY & MANAGEMENT
$11,000
Condo
1485 GULF OF MEXICO DR #109, Longboat Key, FL 34228
LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players C...
Listed by JENNETTE PROPERTIES INC
$10,900
Condo
2425 GULF OF MEXICO DR #2A, Longboat Key, FL 34228
Available to book 2025 season, 4 month minimum! Sea Gate Club! Direct Gulf Views! This stunning 2nd floor residence fea...
Listed by GULF COAST RENTAL HOMES&CONDOS
$12,000
Condo
4325 GULF OF MEXICO DR #102, Longboat Key, FL 34228
Gorgeous Gulf front, turnkey furnished rental in Tiffany Plaza. Walk out to the beach from this lovely updated and exqui...
Listed by PREMIER SOTHEBY'S INTERNATIONAL
$15,000
Single Family Home
981 LONGBOAT CLUB RD, Longboat Key, FL 34228
Rent is $15,000 monthly off season and $25,000 monthly for the season beginning in December to the end of April. Possibi...
Listed by U.S. INVEST INTERNATIONAL LLC
$4,500
Condo
750 BAYPORT WAY #750, Longboat Key, FL 34228
Seasonal Turnkey Furnished Rental at Bayport Beach and Tennis Club. Availablle in May for a 30 day stay! You will fall i...
Listed by PREMIER SOTHEBY'S INTERNATIONAL
$9,587
Condo
4325 GULF OF MEXICO DR #507, Longboat Key, FL 34228
AVAILABLE FEBRUARY, MARCH 2025!!!" short stories'...THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories i...
Listed by KELLER WILLIAMS ON THE WATER S