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560 Properties Available
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$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
$9,500
Condo
744 BAYPORT WAY #744, Longboat Key, FL 34228
Delightfully appealing seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 re...
Listed by KELLER WILLIAMS SUBURBAN TAMPA
$6,000
Condo
1050 LONGBOAT CLUB RD #1006, Longboat Key, FL 34228
Available 04/01/2025 THROUGH 05/30/2026 (POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. G...
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
$5,000
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
$13,500
Condo
1211 GULF OF MEXICO DR #302, Longboat Key, FL 34228
Prime location... This absolutely gorgeous condo is located in the Promenade Longboat Key with breathtaking water views ...
Listed by BERKSHIRE HATHAWAY HOMESERVICE
$8,000
Condo
4325 GULF OF MEXICO DR #406, Longboat Key, FL 34228
Don't miss this one! Now available for the Feb 2025 then April forward. February @ $10,000 and April @ $8000/month, May ...
Listed by STERLING REALTY
$5,835
Condo
3806 GULF OF MEXICO DR DR #C210, Longboat Key, FL 34228
Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. <br> <br>W...
Listed by GULF COAST REALTY & MANAGEMENT
$9,500
Condo
517 BAYPORT WAY #517, Longboat Key, FL 34228
Gorgeous Inside! Furnished Rental at the exceptional Bayport Beach and Tennis Club. Single story end unit with private...
Listed by KELLER WILLIAMS SUBURBAN TAMPA
$9,750
Single Family Home
6830 HUGHES ST, Longboat Key, FL 34228
Welcome to Haven on Hughes! This one-of-a-kind 4-bedroom, 2-bath, two-story spacious pool home is located on the Histori...
Listed by GULF COAST REALTY & MANAGEMENT
$7,500
Condo
4540 GULF OF MEXICO DR #PH2, Longboat Key, FL 34228
OPEN FOR SEASON 2026. Also available off season @$3300 per month. Rarely available tranquil 2 bed/2 bath corner unit con...
Listed by JENNETTE PROPERTIES INC
$8,000
Condo
2045 GULF OF MEXICO #313, Longboat Key, FL 34228
OPEN FOR 2026 SEASON. Live your Florida Dream in this 2 bed/2 bath condo on beautiful Longboat Key! Just steps away from...
Listed by JENNETTE PROPERTIES INC
$25,000
Condo
455 LONGBOAT CLUB RD #PH1, Longboat Key, FL 34228
This EXQUISITE 3 bedroom - 3 ½ bath Penthouse has everything you will ever want in a Luxury Beachfront Condo; an open fl...
Listed by JENNETTE PROPERTIES INC
$8,000
Condo
2425 GULF OF MEXICO DR #4E, Longboat Key, FL 34228
LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly cap...
Listed by JENNETTE PROPERTIES INC
$9,000
Condo
775 LONGBOAT CLUB RD #405, Longboat Key, FL 34228
AVAILABLE 2025 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay...
Listed by COLDWELL BANKER REALTY
$11,000
Condo
1125 GULF OF MEXICO DR #403, Longboat Key, FL 34228
Cancellation! 2025! Available March 15th on. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL...
Listed by JENNETTE PROPERTIES, INC.
$7,000
Condo
655 CEDARS CT #655, Longboat Key, FL 34228
AVAILABLE. 2025 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located i...
Listed by COLDWELL BANKER REALTY
$6,500
Condo
3440 GULF OF MEXICO DR #8, Longboat Key, FL 34228
AVAILABLE 2025 SEASON! AVAILABLE OCT. 2024-DEC.2024 This unit has been remodeled with all new furnishings. This is a fir...
Listed by COLDWELL BANKER REALTY
$15,450
Single Family Home
501 CHANNEL LN, Longboat Key, FL 34228
Booked rest of 2024. Booked March through August and Nov 21st-27th. This fabulous newly constructed 4 bedroom 3 bath po...
Listed by PRECISE REALTY CORP
$6,000
Condo
3806 GULF OF MEXICO DR #C111, Longboat Key, FL 34228
Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. <br> <br>S...
Listed by GULF COAST REALTY & MANAGEMENT