144

Longboat Key, FL Homes for Rent

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  • 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
  • 2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    /21

    $45,000 per month

    • 4 Beds
    • 4.5 Baths
    • 3,961 Sq Ft
    • Condo for Rent

    2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

    Step into unparalleled elegance with this stunning 4-bedroom, 4.5-bathroom beachfront condo, where modern sophistication meets coastal serenity. This exclusive residence boasts floor-to-ceiling windows that fill the space with natural light and showcase breathtaking panoramic Gulf views from every angle. Designed for ultimate privacy and comfort, the unit features direct elevator access, a

    Larry Starr SVN COMMERCIAL ADVISORY GROUP

    2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
  • 2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
    2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
    2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
    /46

    $7,500 per month

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

    2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228

    RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach! Start living the island lifestyle in this beautifully updated, furnished 2-bedroom, 2-bath condo at the Islander Club on South Longboat Key! This turnkey rental is ready for immediate enjoyment—just bring your suitcase. Enjoy a bright, open layout with floor-to-ceiling hurricane

    Michele Conn PREFERRED SHORE LLC

    2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
  • 1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
    /85

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 928 Sq Ft
    • Condo for Rent

    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228

    LONGBOAT KEY "SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE. AVAILABLE DEC 2025 & JAN 2026 AT $3,000/MONTH. UTILITIES INCLUDED. 2 MONTH MINIMUM REQUIRED PER HOA.BOOKED FOR FEB-APRIL 2026. Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the

    Chrissie Cummings JENNETTE PROPERTIES INC

    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    /45

    $6,500 per month

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

    3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228

    2-bed, 2-bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
  • 2339 Harbour Oaks Dr, Longboat Key, FL 34228
    2339 Harbour Oaks Dr, Longboat Key, FL 34228
    2339 Harbour Oaks Dr, Longboat Key, FL 34228
    /45

    $10,995 per month

    • 3 Beds
    • 2.5 Baths
    • 2,396 Sq Ft
    • House for Rent

    2339 Harbour Oaks Dr, Longboat Key, FL 34228

    Seasonal/short term rental on Longboat Key Beautifully renovated 3 bedroom 2 1/2 bathroom villa right on the golf course in prestigious, guard gated, Bay Isles. This spacious light filled delight has vaulted ceilings with sky lights, and new high impact windows and doors. The open floor plan is perfect for family time and entertaining. The kitchen is very large and has solid cherry wood

    Henry Rossi RENT SARASOTA

    2339 Harbour Oaks Dr, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    /33

    $18,000 per month

    • 2 Beds
    • 2.5 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

    The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet kitchen showcases Wolf and Sub-Zero

    Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
  • 531 Birdie Ln, Longboat Key, FL 34228
    531 Birdie Ln, Longboat Key, FL 34228
    531 Birdie Ln, Longboat Key, FL 34228
    /44

    $14,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,268 Sq Ft
    • House for Rent

    531 Birdie Ln, Longboat Key, FL 34228

    Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home

    Karie Gorgone WAGNER REALTY

    531 Birdie Ln, Longboat Key, FL 34228
  • 3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    /60

    $4,000 per month

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

    3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

    1-bed, 1-bath paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community's private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
  • 1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    /12

    $32,000 per month

    • 1 Bed
    • 1.5 Baths
    • 1,684 Sq Ft
    • Condo for Rent

    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

    Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a

    Larry Starr SVN COMMERCIAL ADVISORY GROUP

    1581 Gulf of Mexico Dr Unit 507, 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
  • 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
    /50

    $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
  • 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
  • 3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /34

    $2,500 per month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    2-bed, 2-bath seasonal or annual rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
  • 3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
    /31

    $3,900 per month

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

    3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228

    Open now through end of January. Have your holidays on the Key with HEATED POOL, amazing sunsets, perfect tennis weather and the pristine beach just steps away. This well appointed and updated condo with an open open, split floor plan has plenty of space and a huge screened lanai that spans the entire unit. The primary bedroom has TWO KING SIZED beds, a huge walk-in closet and ensuite bath. The

    Rosemarie McKee COLDWELL BANKER REALTY

    3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
  • 4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /30

    $7,000 per month

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

    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    SEASONAL/VACATION RENTAL! AVAILABLE FOR 2026 SEASON! CALL TODAY! 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, large walk-in closets and

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 202, 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 APRIL 2026** 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 on the beach,

    Norma Mladineo COLDWELL BANKER REALTY

    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
  • 4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    /35

    $6,500 per month

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

    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

    AVAILABLE Jan - Mar 2026!!! : Stunning Gulf views and incredible sunsets await you from this JUST completely renovated 2 bedroom, 2 bath condo on Longboat Key. You’ll fall in love with the contemporary soft-palette, coastal style! The open layout offers a seamless blend of kitchen, dining and living space, perfect for entertaining and relaxing. The gourmet kitchen features state-of-the-art GE

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
  • 1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    /77

    $6,500 per month

    • 2 Beds
    • 2 Baths
    • 928 Sq Ft
    • Condo for Rent

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228

    AVAILABLE ONLY FOR AFTER APRIL 2026 SEASON! MINIMUM 2 MONTH LEASE PLEASE. LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the condo has to give

    Brigette Marcus NEXTHOME EXCELLENCE

    1945 Gulf of Mexico Dr Unit M2414, 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
    /51

    $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

    Available rental for July 15, 2025-October 2025 ONLY! 60 Day Minimum Lease. Fully remodeled and impeccably furnished with Gulf views on Longboat. Situated on the top floor, this 2 bedroom, and 2 bath residence presents coveted views of the beach and Gulf of Mexico! Take note, that the clear, Caribbean blue waters and white sand beaches are not upstaged by the finishes in this redesigned floor

    Scott Nold TNG PROPERTY MANAGEMENT

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • 1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    /76

    $15,000 per month

    • 3 Beds
    • 3 Baths
    • 1,710 Sq Ft
    • Condo for Rent

    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

    LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room

    C. Alison Hunter JENNETTE PROPERTIES INC

    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    /39

    $12,000 per month

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

    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228

    Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 408, 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
    /14

    $11,250 per month

    • 3 Beds
    • 3 Baths
    • 3,171 Sq Ft
    • House for Rent

    3210 Bayou Sound, Longboat Key, FL 34228

    Unique 3 bedrooms and 3 bathrooms property in Longboat Key ready for immediate occupancy, all repairs are done. Bay Isles community has a lot to offer to prospective long term renters. Set in The Bayou behind 2 security gates. House was remodeled in the last couple of years. Fully furnished with contemporary decoration and furniture. Kitchen equipped with high end stainless steel appliances and

    Gary Dontsov LONDON FOSTER REALTY

    3210 Bayou Sound, Longboat Key, FL 34228
  • 1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    /46

    $11,250 per month

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Condo for Rent

    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

    Available May-rest of 2025. Booked for Season 2026 February 1st to April 30th. Direct Beachfront, Longboat Key remodeled 2/2 Condo in Beachplace. Beautiful Beachplace is a gated community located on the southern end of Longboat Key, FL. Our unit is located in building nine, 4th floor, with a green belt area just to the north, the beach to the west, tennis courts to the East and few steps to the

    Jennifer LeBlanc PRECISE REALTY CORP

    1045 Gulf of Mexico Dr Unit 402, 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
  • 2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    /30

    $8,721 per month

    • 2 Beds
    • 2 Baths
    • 1,461 Sq Ft
    • Condo for Rent

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228

    short stories AVAILABLE NOW... Stunning 2 bedroom 2 bath Longboat Key Gulf front condo with direct sweeping view of the Gulf of Mexico. Every evening enjoy breathtaking sunsets on your private balcony. Start your day with a leisurely stroll on the soft sand beach or take a refreshing dip in the pool. This condo is beautifully furnished and professionally decorated. King size bed in both bedrooms.

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
  • 2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    /63

    $10,000 per month

    • 2 Beds
    • 2 Baths
    • 1,463 Sq Ft
    • Condo for Rent

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228

    ***NEW VACATION RENTAL LISTING** * Booked Dec1st-March 31st 2026. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to

    Jennifer LeBlanc PRECISE REALTY CORP

    2109 Gulf of Mexico Dr Unit 1203, 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

    • 3 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
  • 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
  • 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
    /47

    $4,800 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 2026! 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
  • 2369 Harbour Oaks Dr, Longboat Key, FL 34228
    2369 Harbour Oaks Dr, Longboat Key, FL 34228
    2369 Harbour Oaks Dr, Longboat Key, FL 34228
    /100

    $8,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,424 Sq Ft
    • House for Rent

    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. Open floor plan, with vaulted ceilings, hardwood floors throughout. Private screened in pool with a view of the golf course and evening sunsets with plenty of space for entertaining. Kitchen is equipped with everything a cook would need including a separate wet bar with a

    Teresa Ribaudo JENNETTE PROPERTIES INC

    2369 Harbour Oaks Dr, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    /31

    $5,000 per month

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

    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228

    AVAILABLE OFF SEASON RENTAL JULY 1, 2025 THROUGH NOVEMBER 30, 2025 AT $5000 A MONTH AND SEASONAL JANUARY 2026 THROUGH APRIL 30, 2026 through MAY 30, 2026 Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 804, 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 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. 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 private lanais,

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 502, 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
  • 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 1st- June 16th, July13th-July 27th, Nov 14th-rest of 2025. Booked January, May, October, and Dec 2026 through February 2027, Must be a one month minimum stay during seasonal months and 2 week minimum stay out of season. 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

    Jennifer LeBlanc PRECISE REALTY CORP

    500 Schooner Ln, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    /55

    $11,950 per month

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

    2425 Gulf of Mexico Dr Unit 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 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,

    Andrey markov ANMARK REALTY LLC

    2425 Gulf of Mexico Dr Unit 14B, 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
  • 6925 Longboat Dr S, Longboat Key, FL 34228
    6925 Longboat Dr S, Longboat Key, FL 34228
    6925 Longboat Dr S, Longboat Key, FL 34228
    /39

    $30,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,230 Sq Ft
    • House for Rent

    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. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your family to enjoy your home away from home! This three-story 3-bedroom, 3.5-bath home boasts top of the line features, Smart Home technology, and beautiful decor

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    6925 Longboat Dr S, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
    /41

    $6,000 per month

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

    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228

    Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
  • 1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    /72

    $10,000 per month

    • 2 Beds
    • 2 Baths
    • 1,839 Sq Ft
    • Condo for Rent

    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228

    LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and

    C. Alison Hunter JENNETTE PROPERTIES INC

    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228

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