156

Longboat Key, FL Homes for Rent

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  • 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
  • 2020 Harbourside Dr Unit 446, Longboat Key, FL 34228
    2020 Harbourside Dr Unit 446, Longboat Key, FL 34228
    2020 Harbourside Dr Unit 446, Longboat Key, FL 34228
    /25

    $5,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft
    • Condo for Rent

    2020 Harbourside Dr Unit 446, Longboat Key, FL 34228

    Experience luxury island living in this beautifully fully remodeled 2-bedroom, 2-bath residence located in the Bay Isles community on Longboat Key. Situated within the highly desirable Bay Harbour community, this modern coastal retreat is ready for immediate occupancy with flexible lease terms available from 6 to 12 months.Step inside to discover a bright and open floor plan featuring upscale

    Jeffrey Swanson VIVE REALTY

    2020 Harbourside Dr Unit 446, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr, Longboat Key, FL 34228
    /31

    $15,000 Per Month

    • 1 Bed
    • 2 Baths
    • 1,556 Sq Ft
    • Unfurnished Luxury Rental at The St. Regis Longboat Key

    1591 Gulf of Mexico Dr, Longboat Key, FL 34228

    Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous

    1591 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    /42

    $10,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,698 Sq Ft
    • Condo for Rent

    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228

    LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle

    Jane Hunter JENNETTE PROPERTIES INC

    1925 Gulf of Mexico Dr Unit 309, 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,

    4330 Falmouth Dr, Longboat Key, FL 34228
  • 3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    /55

    $7,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,133 Sq Ft
    • Condo for Rent

    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

    Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You

    Andy Moore GULF COAST REALTY & MANAGEMENT

    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
  • 2013 Harbour Links Dr, Longboat Key, FL 34228
    2013 Harbour Links Dr, Longboat Key, FL 34228
    2013 Harbour Links Dr, Longboat Key, FL 34228
    /77

    $5,950 Per Month

    • 2 Beds
    • 2 Baths
    • 2,369 Sq Ft
    • Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views Remodele...

    2013 Harbour Links Dr, Longboat Key, FL 34228

    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 fully furnished and ready for immediate enjoyment, this home is perfectly positioned on a quiet cul-de-sac with extra guest parking, combining privacy, luxury, and

    2013 Harbour Links Dr, 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

    $7,500 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
  • 3240 Gulf of Mexico Dr, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr, Longboat Key, FL 34228
    /54

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Seasonal/short term 2/2 condo rental with full water view on Longboat Key.

    3240 Gulf of Mexico Dr, Longboat Key, FL 34228

    Seasonal / Short-Term Rental on Longboat KeyVacation in one of the nation’s most celebrated coastal destinations, where a leading national travel magazine ranked Longboat Key among the Top 5 Best Islands in the United States. Experience the beauty firsthand while enjoying breathtaking water views from nearly every room of this stunning condominium at Portobello. This beautifully renovated and

    3240 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    /40

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

    Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 208, 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
  • 4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
    /39

    $10,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Condo for Rent

    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

    **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease DECEMBER 2026 and APRIL 2027** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly

    Norma Mladineo COLDWELL BANKER REALTY

    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
  • 6979 Longboat Dr S, Longboat Key, FL 34228
    6979 Longboat Dr S, Longboat Key, FL 34228
    6979 Longboat Dr S, Longboat Key, FL 34228
    /39

    $10,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,454 Sq Ft
    • House for Rent

    6979 Longboat Dr S, Longboat Key, FL 34228

    Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room

    Rinat Sikdar COLDWELL BANKER REALTY

    6979 Longboat Dr S, 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
    /44

    $4,000 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.

    Janette Schafer COLDWELL BANKER REALTY

    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
  • 775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
    /37

    $9,000 Per Month

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

    775 Longboat Club Rd Unit 405, Longboat Key, FL 34228

    AVAILABLE 2026 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay views. This 1600 sq. ft. two bedroom two bath condo is located directly on the sugary beach of Longboat Key with lounge chairs and umbrellas provided. Wrap around balcony with partial Gulf of Mexico and Longboat Key Club golf views. Washer/dryer in the unit, pool, fitness

    Brenda Cozy COLDWELL BANKER REALTY

    775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
  • 535 Forest Way, Longboat Key, FL 34228
    535 Forest Way, Longboat Key, FL 34228
    535 Forest Way, Longboat Key, FL 34228
    /60

    $6,900 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • House for Rent

    535 Forest Way, Longboat Key, FL 34228

    Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.Step

    Andy Moore GULF COAST REALTY & MANAGEMENT

    535 Forest Way, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
    /100

    $25,000 Per Month

    • 1 Bed
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228

    Welcome Serenity Oasis, your paradise at The Residences at the St.Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat. The expansive living room is

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1591 Gulf of Mexico Dr Unit 315, 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
  • 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
  • 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
    /32

    $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
  • 1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    /51

    $11,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,642 Sq Ft
    • Condo for Rent

    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

    Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. Relax on the lanai and take in the beautiful gulf views at sunset. The

    Margaret Young JENNETTE PROPERTIES, INC.

    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
  • 3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
    /68

    $5,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Condo for Rent

    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

    VACATION RENTAL!!! AVAILABLE JAN - MARCH 2027! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    /37

    $14,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,598 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

    Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
  • 1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
    /45

    $7,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • Condo for Rent

    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228

    GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought-after Bay Isles community. The spacious Kitchen had been updated along with the both baths, with Quartz counter-tops and new cabinetry, the Primary suite offers a King bed, views of the bay and the Primary bath has dual sinks, new vanity, new

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
  • 591 Putting Green Ln, Longboat Key, FL 34228
    591 Putting Green Ln, Longboat Key, FL 34228
    591 Putting Green Ln, Longboat Key, FL 34228
    /68

    $29,000 Per Month

    • 5 Beds
    • 5.5 Baths
    • 4,858 Sq Ft
    • House for Rent

    591 Putting Green Ln, Longboat Key, FL 34228

    LONGBOAT KEY...If you're looking for a Luxury winter vacation home, stop searching. You have just found the perfect house located on a private & peaceful cul-de-sac. This beautiful 5 bedroom, 5.1 bathrooms has everything you would want and more with all the comforts of home. All new furniture throughout in every room. Primary, 1st & 2nd bedrooms all have king size beds. Bedrooms 3 & 4 have twin

    Teresa Ribaudo JENNETTE PROPERTIES INC

    591 Putting Green Ln, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
    /34

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,513 Sq Ft
    • Condo for Rent

    2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228

    ELEGANT BEACH FRONT CONDO ON LONGBOAT KEY. This exquisite 2 bedroom, 2 bathroom condo has been totally updated. The kitchen has top of the line, state of the art appliances. Induction stove top, touchless kitchen sink faucet, cooking island, breakfast bar. From the moment you enter this property you are greeted with a wide open floor plan. Incredible views of the Gulf of Mexico and Sarasota Bay.

    Teresa Ribaudo JENNETTE PROPERTIES INC

    2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    /23

    $9,587 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,336 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

    THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean breezes flow through the unit and the peaceful sound of

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
  • 3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
    /20

    $2,795 Per Month

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

    3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228

    BAYSIDE CONDO WITH FULL BAY VIEWS – AVAILABLE FOR ANNUAL RENTAL Experience the best of Longboat Key living in this beautifully furnished 2-bedroom, 2-bath second-floor condo (with elevator access) located in the desirable Longboat Arms community. This turnkey residence offers stunning, unobstructed bay views and a well-designed open floor plan. The kitchen flows seamlessly into the dining and

    Heidi Thompson STRINGER MANAGEMENT INC

    3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
  • 2823 Gulf of Mexico Dr, Longboat Key, FL 34228
    2823 Gulf of Mexico Dr, Longboat Key, FL 34228
    2823 Gulf of Mexico Dr, Longboat Key, FL 34228
    /42

    $10,000 Per Month

    • 3 Beds
    • 3 Baths
    • 1,744 Sq Ft
    • House for Rent

    2823 Gulf of Mexico Dr, Longboat Key, FL 34228

    Summer 2026 is approaching! We still have the month of August available but it won't last long! Welcome to BEACHFRONT PARADISE on Longboat Key! This outstanding location offers a RARE OPPORTUNITY to enjoy coastal living with BREATHTAKING VIEWS of the shoreline. Nestled along the PRISTINE SHORES of Longboat Key, this three-bedroom, three-bathroom single family home invites you to experience the

    Michael Cella CELLA'S REAL ESTATE INC

    2823 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
    /38

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,031 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228

    Steps from the Sand – Luxury Beach Condo with Pool Access!Leave the snow behind and soak up the sun! This stunningly turnkey renovated 2-bedroom, 2-bathroom condo has everything you need for a carefree beach living– including a washer and dryer for sandy swimsuits!Enjoy private access to the shimmering Gulf beaches, relax by the heated pool, or paddle your cares away in the community

    nicoletta buonaccordo ALTIS REALTY

    3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /53

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,257 Sq Ft
    • Condo for Rent

    Unlisted Address

    SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST

    Jane Hunter JENNETTE PROPERTIES INC

    Unlisted Address
  • 501 Channel Ln, Longboat Key, FL 34228
    501 Channel Ln, Longboat Key, FL 34228
    501 Channel Ln, Longboat Key, FL 34228
    /53

    $13,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,349 Sq Ft
    • House for Rent

    501 Channel Ln, Longboat Key, FL 34228

    Booked May-July, September, and November 2026. Looking for a 3 month rental for January-March 2027. Booked April-December 2027. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floor plan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous

    Jennifer Le Blanc PRECISE REALTY CORP

    501 Channel Ln, Longboat Key, FL 34228
  • 1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
    /40

    $10,000 Per Month

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

    1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228

    Available for 2027 Season. Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each offering a

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    /41

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Condo for Rent

    2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228

    SEASONAL: 90 day minimum. No damages sustained in Hurricane. Beautiful unit from floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
  • 7147 La Lenaire Dr, Longboat Key, FL 34228
    7147 La Lenaire Dr, Longboat Key, FL 34228
    7147 La Lenaire Dr, Longboat Key, FL 34228
    /100

    $35,000 Per Month

    • 5 Beds
    • 5.5 Baths
    • 3,503 Sq Ft
    • House for Rent

    7147 La Lenaire Dr, Longboat Key, FL 34228

    A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian

    Chase Moore SIGHT REAL ESTATE, LLC

    7147 La Lenaire Dr, Longboat Key, FL 34228
  • 500 Schooner Ln, Longboat Key, FL 34228
    500 Schooner Ln, Longboat Key, FL 34228
    500 Schooner Ln, Longboat Key, FL 34228
    /75

    $11,550 Per Month

    • 2 Beds
    • 2 Baths
    • 1,657 Sq Ft
    • House for Rent

    500 Schooner Ln, Longboat Key, FL 34228

    Booked May-June 8th, October, and Dec 2026 through April 15th 2027, May 2027. There is 2 week minimum stay required. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathrooms. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to

    Jennifer Le Blanc PRECISE REALTY CORP

    500 Schooner Ln, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    /24

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Condo for Rent

    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228

    Available 05/01/2026 through 12/30/2026 FOR $5000. LEASED SEASON JAN, 2026 THROUGH MARCH, 2027. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    /69

    $40,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 3,130 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228

    An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
  • 957 Spanish Dr N, Longboat Key, FL 34228
    957 Spanish Dr N, Longboat Key, FL 34228
    957 Spanish Dr N, Longboat Key, FL 34228
    /37

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,399 Sq Ft
    • House for Rent

    957 Spanish Dr N, Longboat Key, FL 34228

    AVAILABLE STARTING MAY 1, 2026. WITH 4 MONTH MINUMUM RENTAL DURING SEASON and 3 MONTHS OFF SEASON. FULL WATERFRONT NEWLY RENOVATED and TURNKEY FURNISHED VILLA for SEASONAL OR ANNUAL LEASE. Seasonal Lease December to April is $7,000 per month (OR inquire about annual/off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Panoramic Bay Views - Spanish Main

    Norma Mladineo COLDWELL BANKER REALTY

    957 Spanish Dr N, Longboat Key, FL 34228
  • 4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
    /42

    $7,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • Condo for Rent

    4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

    SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

Showing Results 41 - 80, Page 2 of 4

Florida Manatee County Longboat Key

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