124

Longboat Key, FL Homes for Rent with Pool

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  • 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

    $6,500 per month

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

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

    "SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE OF LONGBOAT KEY. BOOKED FOR FEB-APRIL 2026. AVAILABLE NOV 2025 AT $3,500, DEC 2025 AT $5,000 & JAN 2026 AT $6,500. 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 unit, you are met with a

    Chrissie Cummings JENNETTE PROPERTIES INC

    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
  • 435 L Ambiance Dr Unit H402, Longboat Key, FL 34228
    435 L Ambiance Dr Unit H402, Longboat Key, FL 34228
    435 L Ambiance Dr Unit H402, Longboat Key, FL 34228
    /27

    $9,000 per month

    • 2 Beds
    • 2.5 Baths
    • 2,385 Sq Ft
    • Condo for Rent

    435 L Ambiance Dr Unit H402, Longboat Key, FL 34228

    RARELY AVAILABLE! Welcome to L'AMBIANCE! Discover an extraordinary opportunity to rent this luxurious 2-bedroom, 2.5-bathroom condo on the island Longboat Key. Inside the Longboat Key club, this rarely available residence offers 2 car parking spaces (under building garage) private elevator, breathtaking, unobstructed views of the sparkling Gulf of America, complemented by sweeping vistas of lush

    Jose Hugo Martinez KW COASTAL LIVING III

    435 L Ambiance Dr Unit H402, 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

    $7,000 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
  • 1211 Gulf of Mexico Dr Unit 505, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 505, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 505, Longboat Key, FL 34228
    /51

    $13,500 per month

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

    1211 Gulf of Mexico Dr Unit 505, Longboat Key, FL 34228

    Welcome to your beachfront retreat on spectacular Longboat Key, Florida. The owners spared no expense to design and equip their home with the best of everything. This is the first time they've ever offered it for lease; it is available as early as August 1, 2025 thru December (3,4 or 5 month occupancy) and also available for the 4 months of January to April. This is 1600 sq ft of beautiful

    Sharon Whalen COLDWELL BANKER REALTY

    1211 Gulf of Mexico Dr Unit 505, 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
  • 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
    /61

    $12,000 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. Like NEW, this beautifully designed three bedroom luxury residence has just completed a major updating remodeling with all new designer furniture and furnishings, new custom

    Patrice Ivan WAGNER REALTY

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
  • 450 Gulf of Mexico Dr Unit B302, Longboat Key, FL 34228
    450 Gulf of Mexico Dr Unit B302, Longboat Key, FL 34228
    450 Gulf of Mexico Dr Unit B302, Longboat Key, FL 34228
    /29

    $3,400 per month

    • 2 Beds
    • 2 Baths
    • 1,194 Sq Ft
    • Condo for Rent

    450 Gulf of Mexico Dr Unit B302, Longboat Key, FL 34228

    Live Where Others Vacation – Annual Furnished Lease on Longboat Key!Step into island living at its finest in this fully furnished 2 bed / 2 bath condo, available for annual lease only in the prestigious Longboat Harbour community. Enjoy serene water views, tropical breezes, and resort-style amenities—all just minutes from St. Armands Circle, Lido Key Beach, and Downtown

    Benjamin Dietrich ANCHOR DOWN REAL ESTATE

    450 Gulf of Mexico Dr Unit B302, 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

    $2,800 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
  • 842 Bayport Way Unit 842, Longboat Key, FL 34228
    842 Bayport Way Unit 842, Longboat Key, FL 34228
    842 Bayport Way Unit 842, Longboat Key, FL 34228
    /28

    $5,000 per month

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

    842 Bayport Way Unit 842, Longboat Key, FL 34228

    AVAILABLE APRIL 1ST 2025. 6 MONTH STAY $5000 PER MONTH - NO TAX/ PRIME SEASONAL RATES: Jan 1st to April 30th @ $8,500 per month plus 13% sales tax. For shorter off season stay - 3 month minimum - rental rate is $5,000 plus tax. Property may also be rented annually at $5,000 per month - no tax, includes all electricity, shorter terms $75.00 for electric. ***** 1,200 ft. of private beach (with

    Shirley Cuddy REALTY SERVICES INC

    842 Bayport Way Unit 842, 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
  • 3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    /30

    $2,500 per month

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

    3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

    Welcome to Beach Harbor Club, a hidden gem on Longboat Key that offers the best of both worlds—spanning from the Gulf of Mexico to Sarasota Bay! This charming one-bedroom, one-bath condo is perfect for seasonal getaways or as an investment property. Located just a 1-minute walk to both the beach and bay, it’s your gateway to coastal living at its finest.Highlights of the Community:Private

    Andrey markov ANMARK REALTY LLC

    3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
  • 3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
    /35

    $2,500 per month

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

    3808 Gulf of Mexico Dr Unit E205, 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

    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
  • 3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    /62

    $8,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228

    Luxury Seasonal or Annual Rental in Luxurious Grand Bay Community – Longboat KeyExperience 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

    Alyssa Cromie NEXTHOME EXCELLENCE

    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
    /20

    $15,500 per month

    • 2 Beds
    • 2.5 Baths
    • 2,135 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228

    Special offer!Get $2000 (total) off for leases of 4+ months.Amazing Gulf front location in Longboat Key (LBK), FloridaThis two bedroom, 2 1/2 Bath condo (plus pull-out couch) is completely renovated and remodeled. All brand-new furnishings, appliances, counters, cabinets, cookware, linens, etc. This ninth-floor unit at the luxurious Promenade offers the best of everything.

    Natasha Shevchuk 1ST PREMIER INTL PROPERTIES

    1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
  • 512 Gunwale Ln, Longboat Key, FL 34228
    512 Gunwale Ln, Longboat Key, FL 34228
    512 Gunwale Ln, Longboat Key, FL 34228
    /48

    $11,000 per month

    • 3 Beds
    • 2 Baths
    • 1,861 Sq Ft
    • House for Rent

    512 Gunwale Ln, Longboat Key, FL 34228

    Location, location, location. This furnished rental offers the perfect blend of convenience and waterfront living. Enjoy direct access to the Gulf of Mexico with a private dock and boat lift, take a walk on the pristine white sand beaches or relax and unwind in the pool. Nestled in a prime location just minutes from St. Armands Circle, you'll have access to the best dining, shopping and

    Marcia Benson Berkshire Hathaway Florida Realty

    512 Gunwale Ln, Longboat Key, FL 34228
  • 5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    /22

    $9,500 per month

    • 2 Beds
    • 2 Baths
    • 1,346 Sq Ft
    • Condo for Rent

    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228

    AVAILABLE MARCH 2025 - APRIL 10 $7,000 30 day lease. Looking for a Beach front vacation in warm sunny Florida in a condo where you walk out onto the deck and directly onto the beach? Stay in this 2 bedroom , 2 bath condo in Salty Acres with 2 parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and is in excellent condition. It must be a monthly rental. $6,950 a

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    5621 Gulf of Mexico Dr Unit 102, 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

    $3,000 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
  • 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

    $5,500 per month

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

    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228

    Experience luxury and tranquility in this stunning unit at 1928 Harbourside Dr, Unit 1402, located within the Bay Isles community on Longboat Key. This residence offers a spacious layout designed for comfort and style, with access to top-tier amenities including a nearby marina, private golf course, swimming pool, and spa. Enjoy the privacy and security of this exclusive gated community, all just

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    1928 Harbourside Dr Unit 1402, 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

    $5,500 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
  • 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
    /32

    $3,975 per month

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

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

    A perfect island getaway. This well appointed and updated Longboat Key condo is available as a six or seven month rental from late June through January. Located Bay side, you'll enjoy a sparkling pool, tennis, kayak launch, fishing pier, grill area and clubhouse, plus deeded beach access is 250ft from your front door. There's plenty of room to spread out with an open, split floor plan and a huge

    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
  • 448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
    448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
    448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
    /30

    $11,700 per month

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

    448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228

    LONGBOAT KEY SOUTH...This is a 3 bedroom, 2 bathroom, end unit on the main floor which makes this unit light & bright with extra windows. The interior is decorated tastefully with warm neutral colors. Beautiful views of Sarasota Bay. Fully equipped kitchen which features stainless appliances, granite countertops and wood cabinets. There is a king size bed in the main bedroom and a queen bed in

    Teresa Ribaudo JENNETTE PROPERTIES INC

    448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
  • 2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /20

    $10,000 per month

    • 2 Beds
    • 2 Baths
    • 1,896 Sq Ft
    • Condo for Rent

    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    Available Now! Absolutely stunning waterfront turnkey furnished short term rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if you prefer sunrises. This spacious 2/2 split floor plan has been fully renovated and is tastefully furnished. The property boasts amenities such as a beachfront pool,

    Christian Higgins ANDRE LECLAIR PROPERTIES LLC

    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 7F, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7F, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7F, Longboat Key, FL 34228
    /50

    $10,500 per month

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

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

    No damage to unit after storms. Call for rates and availability. Available December - April. One month minimum. Tremendous view of the Gulf from this Gulfside/Beachside 2 BR/2 B condo. Direct Gulf front unit. Breathtaking view of the pristine waters of the Gulf of Mexico. Sit on the balcony to your 7th floor unit. Take in the sunsets with your loved ones and friends. Just a couple minutes and

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    2425 Gulf of Mexico Dr Unit 7F, Longboat Key, FL 34228
  • 4780 Gulf of Mexico Dr, Longboat Key, FL 34228
    4780 Gulf of Mexico Dr, Longboat Key, FL 34228
    4780 Gulf of Mexico Dr, Longboat Key, FL 34228
    /38

    $4,500 per month

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft
    • House for Rent

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228

    This immaculate 2-bedroom, 2-bath ground-floor villa located in the highly sought-out community of Windward Bay has peek-a-boo views of the Gulf. Turnkey furnished with one carport at your front door. The community of Windward Bay is pristine. There is private deeded beach access just across the street, two public beach access, two marinas BBQ grills, 1/2 mile of walking trails, two heated pools,

    Joseph Stephens ONE STEP AHEAD REALTY INC

    4780 Gulf of Mexico Dr, 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 JANUARY and FEBRUARY 2026 with the option to include 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

    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

    $8,500 per month

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

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

    BEAUTIFULLY RENOVATED VACATION RENTAL: 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

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
  • 3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    /49

    $3,750 per month

    • 2 Beds
    • 2 Baths
    • 1,175 Sq Ft
    • Condo for Rent

    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

    Escape to this 2-bed, 2-bath penthouse paradise at Beach Harbor Club. The penthouse features more spacious living and dining areas with stunning Gulf views. The unit includes an outside patio, as well as a washer/dryer. Beach Harbor Club is a beach to bay community and has a bundle of awesome amenities. Enjoy exclusive beach access, complete with grills, showers, and beach/lounge chairs. Take a

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3804 Gulf of Mexico Dr Unit 402, 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 FOR 2026 SEASON! MINIMUM 3 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 with the natural

    Brigette Marcus NEXTHOME EXCELLENCE

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
  • 3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    /14

    $6,000 per month

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

    3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

    PORTOBELLO - SHORT TERM RENTAL - 2 Bedrooms, 2 Baths in the #1 Beach of Florida, white quartz sand and dreamy sunsets Ample and chic apartment fully furnished to enjoy vacation time. 2 Parking spots

    Valeria Fucaraccio Benesch Brokers, LLC

    3240 Gulf of Mexico Dr Unit 307, 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
  • 5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228
    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228
    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228
    /39

    $14,000 per month

    • 3 Beds
    • 2 Baths
    • 1,675 Sq Ft
    • Condo for Rent

    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228

    DIRECTLY on the GULF. WITH PRIVATE BEACH .Be Prepared for style, relaxation and Longboat luxury. This stunning boutique condominium renovated in 2024 and located on Longboat Key's Gulf of Mexico Beach. Its newly designed layout emphasizes the magnificent ocean view throughout its open floor plan that is visible from the time you walk in the door, through the beautiful dining area, upscale

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    5611 Gulf of Mexico Dr Unit 1, 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

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