153

Homes for Rent in ZIP Code 34228

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  • 6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    /50

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,367 Sq Ft
    • Condo for Rent

    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228

    Available September 1, 2026 through January 31, 2027 with a one-month minimum rental. Experience the best of Longboat Key in this beautifully renovated and newly furnished 2-bedroom, 2-bathroom condo. Simply pack your flip-flops and beachwear and settle into the relaxed island lifestyle. Residents enjoy an impressive array of resort-style amenities, including two heated swimming pools, tennis and

    Kelly Baldwin COLDWELL BANKER REALTY

    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
  • 1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228
    1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228
    1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228
    /20

    $26,250

    Total Monthly Price

    • 3 Beds
    • 4 Baths
    • 3,272 Sq Ft
    • Condo for Rent

    1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228

    The advertised rate of $26,250/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 9, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228
  • 691 Russell St, Longboat Key, FL 34228
    691 Russell St, Longboat Key, FL 34228
    691 Russell St, Longboat Key, FL 34228
    /35

    $9,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft
    • Luxury Annual Rental with Resort-Style Pool on Longboat Key

    691 Russell St, Longboat Key, FL 34228

    Experience luxury coastal living in this completely renovated annual rental on the desirable north end of Longboat Key. Situated on an oversized double lot just minutes from the pristine Gulf beaches, this exceptional pool home offers the perfect blend of style, comfort, and convenience.Thoughtfully redesigned from top to bottom, the home features a bright, open-concept floor plan with

    691 Russell St, Longboat Key, FL 34228
  • 320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
    320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
    320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
    /20

    $6,345

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 2,131 Sq Ft
    • Condo for Rent

    320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228

    The advertised rate of $6,345/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 4, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
  • 6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228
    6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228
    6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228
    /20

    $4,428

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Condo for Rent

    6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228

    The advertised rate of $4,428/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 13, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228
  • 1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
    1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
    1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
    /20

    $6,191

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,388 Sq Ft
    • Condo for Rent

    1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228

    The advertised rate of $6,192/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 22, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
  • 1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    /20

    $3,019

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,388 Sq Ft
    • Condo for Rent

    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228

    The advertised rate of $3,020/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 5, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
  • 6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228
    /16

    $2,453

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 925 Sq Ft
    • Condo for Rent

    6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228

    The advertised rate of $2,454/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 5, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228
  • 6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
    6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
    6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
    /20

    $5,886

    Total Monthly Price

    • 1 Bed
    • 2 Baths
    • 1,076 Sq Ft
    • Condo for Rent

    6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228

    The advertised rate of $5,886/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 9, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
  • 5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228
    5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228
    5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228
    /20

    $6,570

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,474 Sq Ft
    • Condo for Rent

    5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228

    The advertised rate of $6,570/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 8, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228
  • 1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228
    1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228
    1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228
    /20

    $9,841

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,894 Sq Ft
    • Condo for Rent

    1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228

    The advertised rate of $9,842/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 30, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228
  • 4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
    4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
    4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
    /41

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,314 Sq Ft
    • Condo for Rent

    4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228

    VACATION ALL YEAR ROUND! AVAILABLE FOR AN ANNUAL LEASE! Beautifully updated Gulf-front condo with stunning water views and refined coastal finishes. The chef’s kitchen offers high-end appliances, a center island with beverage chiller, and elegant details throughout. The living area opens to a large lanai with unobstructed Gulf views. The primary suite features a king bed, large flat-screen TV,

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /56

    $11,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,409 Sq Ft
    • Condo for Rent

    Unlisted Address

    Experience the best of Longboat Key living in this beautifully updated, turnkey furnished 2-bedroom, 2-bath residence located behind the gates of the sought after Longboat Key Club. This light-filled condominium features brand-new countertops, new appliances, and an open, inviting floor plan designed for effortless coastal living. Enjoy partial Gulf views and beautiful bay vistas from two private

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    Unlisted Address
  • 706 Spanish Dr S, Longboat Key, FL 34228
    706 Spanish Dr S, Longboat Key, FL 34228
    706 Spanish Dr S, Longboat Key, FL 34228
    /34

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,423 Sq Ft
    • Condo for Rent

    706 Spanish Dr S, Longboat Key, FL 34228

    Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after, active 55+ community of Spanish Main Yacht Club! Ideally situated just steps from the marina, this 2-bedroom, 2-bathroom villa features a bright Florida room and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. It is

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    706 Spanish Dr S, Longboat Key, FL 34228
  • 2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    /34

    $3,500 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,590 Sq Ft
    • Condo for Rent

    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228

    Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
  • 1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
    /32

    $3,500 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,626 Sq Ft
    • Townhouse for Rent

    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228

    Experience furnished island living in this turnkey, two-level Fairway Bay townhome offering 2 bedrooms, 2 full bathrooms, 1 half bathroom and 1,626 square feet of thoughtfully arranged living space. The open living and dining area is enhanced by cathedral and vaulted ceilings and offers views of the tropical landscaping and community pool. A split-bedroom layout provides separation between the

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /67

    $13,500 Per Month

    • 2 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    **Prime Location – Luxurious Waterfront Living at Promenade, Longboat Key**This absolutely gorgeous condo is located in the prestigious Promenade on Longboat Key, offering breathtaking water views from every room. The residence features 2 bedrooms plus a den and 2 bathrooms. The spacious master suite includes a king-size bed and an elegant en-suite bathroom with a separate bathtub, walk-in

    Elsie Salazar BERKSHIRE HATHAWAY HOMESERVICE

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • 775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    /36

    $11,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,602 Sq Ft
    • Condo for Rent

    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228

    AVAILABLE DEC. '26 THROUGH FEB.'27. Beautiful 9th floor, 1600 sq. ft. 2 bedroom 2 bath at the sort after Beaches condominium which is within the gates of the Longboat Key Club. Updated kitchen and bathrooms. Fabulous bay, and Longboat Key Club golf views. Wrap around balcony with partial Gulf view. Washer/dryer in the unit, pool, fitness center and tennis courts plus 24 hr. Concierge and garage

    Brenda Cozy COLDWELL BANKER REALTY

    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
  • 4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
    4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
    4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
    /20

    $19,798

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,065 Sq Ft
    • Condo for Rent

    4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228

    The advertised rate of $19,799/month is the lowest available price, based on a 1 month(s) and 1 day(s) stay with a move-in date of February 4, 2028.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed

    4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
  • 5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
    5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
    5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
    /20

    $7,932

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,184 Sq Ft
    • Condo for Rent

    5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228

    The advertised rate of $7,932/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 26, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
  • 1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
    1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
    1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
    /38

    $6,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft
    • Condo for Rent

    1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228

    Perched on the top floor with nothing between you & the water, this fully furnished beachfront retreat at Seaplace offers unobstructed Gulf of America views from every room. Living, dining & kitchen face the Gulf; the king primary suite opens to a private beachfront balcony, the second bedroom (two twins) has its own, and a flexible 3rd room with a Murphy bed works as a bedroom, media room, or

    Robert Hildreth THE AGENCY SARASOTA

    1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
    /100

    $65,000 Per Month

    • 4 Beds
    • 4.5 Baths
    • 5,334 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228

    Imagine taking in this view from your private balcony pool! An exceptionally rare opportunity to lease one of the most exclusive waterfront residences ever offered on Florida’s Gulf Coast. Positioned within the iconic St. Regis Residences on Longboat Key, this extraordinary four-bedroom, four-and-a-half-bath condominium redefines annual luxury living with an unrivaled level of privacy,

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
  • 820 Spanish Dr S, Longboat Key, FL 34228
    820 Spanish Dr S, Longboat Key, FL 34228
    820 Spanish Dr S, Longboat Key, FL 34228
    /31

    $3,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • Condo for Rent

    820 Spanish Dr S, Longboat Key, FL 34228

    Coastal Living at Its Finest in the Spanish Main Yacht Club! Discover your perfect Florida retreat in this beautifully maintained, free-standing 2-bedroom, 2-bathroom villa located on the highly coveted southern end of Longboat Key at 820 Spanish Dr S. Offering 1,390 square feet of bright, open living space, this single-story residence perfectly blends maintenance-free comfort with an active,

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    820 Spanish Dr S, Longboat Key, FL 34228
  • 450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    /32

    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,301 Sq Ft
    • Condo for Rent

    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228

    Annual furnished rental: Discover the ultimate island lifestyle in this comfortably furnished 2-bedroom, 2 bath, unit located in the highly sought-after community of Bay Harbour on the southern end of Longboat Key. Just minutes from St. Armands Circle, downtown Sarasota, restaurants, shopping, county tennis and pickleball courts, walking trails, parks and of course – Longboat Key public beach

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
  • 1000 Longboat Club Rd, Longboat Key, FL 34228
    1000 Longboat Club Rd, Longboat Key, FL 34228
    1000 Longboat Club Rd, Longboat Key, FL 34228
    /51

    $4,000 Per Month

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft
    • SEASONAL SHORT-TERM 1-BED 1 BATH CONDO ON LONGBOAT KEY. BEACH ACCESS

    1000 Longboat Club Rd, Longboat Key, FL 34228

    Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for

    1000 Longboat Club Rd, Longboat Key, FL 34228
  • 909 Spanish Dr N Unit 51, Longboat Key, FL 34228
    909 Spanish Dr N Unit 51, Longboat Key, FL 34228
    909 Spanish Dr N Unit 51, Longboat Key, FL 34228
    /86

    $2,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    909 Spanish Dr N Unit 51, Longboat Key, FL 34228

    Virtually Staged. Virtually Staged. This beautifully updated/unfurnished two-bedroom, two-bath Spanish Main standalone villa with beach access is available for annual lease! The fully remodeled home features neutral tile plank flooring throughout, a spacious chef’s kitchen with 42-inch wood cabinets, quartz island that seats seven, slow-close drawers, and new appliances—all opening to a bright

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    909 Spanish Dr N Unit 51, Longboat Key, FL 34228
  • 840 Bayport Way Unit 840, Longboat Key, FL 34228
    840 Bayport Way Unit 840, Longboat Key, FL 34228
    840 Bayport Way Unit 840, Longboat Key, FL 34228
    /53

    $4,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • Condo for Rent

    840 Bayport Way Unit 840, Longboat Key, FL 34228

    This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The

    Shirley Cuddy REALTY SERVICES INC

    840 Bayport Way Unit 840, Longboat Key, FL 34228
  • 3210 Bayou Sound, Longboat Key, FL 34228
    3210 Bayou Sound, Longboat Key, FL 34228
    3210 Bayou Sound, Longboat Key, FL 34228
    /38

    $7,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,091 Sq Ft
    • House for Rent

    3210 Bayou Sound, Longboat Key, FL 34228

    Experience the best of Longboat Key living in this beautifully updated Bay Isles pool home, offered turnkey furnished FOR LEASE and available for both short-term and long-term reservations. This furnished coastal retreat features an open floor plan with vaulted ceilings, 2 bedrooms plus an office, updated bathrooms, a spacious kitchen with premium appliances, and multiple indoor-outdoor living

    Richard Ivan WAGNER REALTY

    3210 Bayou Sound, Longboat Key, FL 34228
  • 3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    /75

    $7,850 Per Month

    • 3 Beds
    • 3 Baths
    • 2,250 Sq Ft
    • Condo for Rent

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228

    LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major

    Patrice Ivan WAGNER REALTY

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    /26

    $2,500 Per Month

    • 1 Bed
    • 1.5 Baths
    • 761 Sq Ft
    • Beach Harbor Club Beauty

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228

    AVAILABLE FOR ANNUAL OR RENTAL. 3 MONTH MINIMUM. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find a bright

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    /46

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,561 Sq Ft
    • Condo for Rent

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    A little slice of Gulf-front heaven. Seasonal rental only, available July 15 through December 31, 2026! 60 Day Minimum Lease, not available Jan 1, 2027-March 31, 2027. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches

    Scott Nold TNG PROPERTY MANAGEMENT

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • 807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
    /27

    $11,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,370 Sq Ft
    • Amazing 2BR Condo in Longboat Key

    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228

    Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress. RARELY AVAILABLE FOR 2027 SEASON. LESING NOW FOR DECEMBER 2026 AND JANUARY TRHOUGH APRIL 30TH 2027. MINIMUM

    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
  • 2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    /72

    $6,950 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,369 Sq Ft
    • Condo for Rent

    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228

    Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered

    Andrew Clark SECURE DOOR PROPERTY MANAGEMENT

    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
  • 2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
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    $16,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft
    • Condo for Rent

    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228

    Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms. Rental dates are fully flexible to suit your needs — unlike most units that require a three-month minimum, this

    Michele Conn PREFERRED SHORE LLC

    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
  • 3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
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    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,106 Sq Ft
    • Condo for Rent

    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228

    Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease.

    John Schafer, V COLDWELL BANKER REALTY

    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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    $2,500 Per Month

    • 1 Bed
    • 1.5 Baths
    • 761 Sq Ft
    • Condo for Rent

    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

    AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find

    Brigette Marcus NEXTHOME EXCELLENCE

    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
  • 1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    /48

    $4,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228

    Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for

    Cody Smith RENT SARASOTA

    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
  • 3040 Grand Bay Blvd, Longboat Key, FL 34228
    3040 Grand Bay Blvd, Longboat Key, FL 34228
    3040 Grand Bay Blvd, Longboat Key, FL 34228
    /49

    $8,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,143 Sq Ft
    • Luxury Seasonal or Annual Rental in the Prestigious Grand Bay Community – Longboat Key

    3040 Grand Bay Blvd, Longboat Key, FL 34228

    Experience unparalleled luxury and breathtaking views from this stunning 9th-floor condominium at Grand Bay. From sunrise to sunset, enjoy panoramic vistas from your private wraparound balcony or through the floor-to-ceiling sliding glass doors that frame the living room. Designed for both relaxation and sophistication, this residence offers the elegance of a luxury waterfront home with the

    3040 Grand Bay Blvd, Longboat Key, FL 34228
  • 4330 Falmouth Dr, Longboat Key, FL 34228
    4330 Falmouth Dr, Longboat Key, FL 34228
    4330 Falmouth Dr, Longboat Key, FL 34228
    /26

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    4330 Falmouth Dr, Longboat Key, FL 34228

    Longboat Key Beach and Bay Access.2 Bedroom 2 Bathroom First Floor condo in a gated community with tons of amenities.? Deepwater channel with docks and slips available up to 34' (on waitlist)? Amazing water views & breezes? Private deeded beach access (private building on beach with showers + bathrooms, benches and tables!)? 4 Pools, clubhouse, gym, sauna, game room, pool table & cards room, BBQ

    4330 Falmouth Dr, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    /44

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Seaside Serenity: Luxurious Gulf-Front Retreat on Southern Longboat Key

    2425 Gulf of Mexico Dr, Longboat Key, FL 34228

    Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath

    2425 Gulf of Mexico Dr, Longboat Key, FL 34228

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