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Longboat Key, FL Condos for Rent with Community Pool

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  • 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
    /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
  • 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
  • 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

    $2,995 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
  • 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
  • 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
    /25

    $11,000 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
  • 100 Sands Point Rd Unit 317, Longboat Key, FL 34228
    100 Sands Point Rd Unit 317, Longboat Key, FL 34228
    100 Sands Point Rd Unit 317, Longboat Key, FL 34228
    /30

    $10,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,941 Sq Ft
    • Condo for Rent

    100 Sands Point Rd Unit 317, Longboat Key, FL 34228

    AVAILABLE 2027 SEASON! RARE FIND on south LONGBOAT KEY. Absolutely gorgeous tranquil Gulf of Mexico views from most rooms in this lovely 1900 sq. ft. 3 bedroom 2 bath plus den. 3rd floor condo in elevator bldg. 1 carport. Relax in the fabulous pool overlooking the pass and beautiful sandy beach. Boat dock!!! Situated behind the gates of the Longboat Key Club and a short drive or bike ride to St.

    Brenda Cozy COLDWELL BANKER REALTY

    100 Sands Point Rd Unit 317, 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
  • 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
  • 1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    /46

    $7,500 Per Month

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

    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228

    Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
  • 3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
    /33

    $2,500 Per Month

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

    3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228

    1-bed, 1-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 the community’s private beach access 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 105, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
    /39

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,401 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228

    Available for season 2027! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by

    Maureen Plichta STRINGER MANAGEMENT INC

    3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
  • 1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    /31

    $10,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,957 Sq Ft
    • Condo for Rent

    1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with

    Brad Wilson M&M PROPERTY MANAGEMENT GROUP

    1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • 4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    /34

    $7,200 Per Month

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

    4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

    This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views. This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can’t be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    4825 Gulf of Mexico Dr Unit 605, 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
  • 3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
    /23

    $4,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,046 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228

    Lease/Option - Owner looking to lease up to 6 Months $4300 a Month of Longboat's Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seeds oats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly

    Len Scavron LEN SCAVRON

    3806 Gulf of Mexico Dr Unit C310, 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
  • 1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
    /44

    $15,000 Per Month

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

    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

    Gorgeous gulf front vacation rental! Be the first to lease this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the open floor plan with a

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1211 Gulf of Mexico Dr Unit 1005, 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

    Booked Dec 1st 2026-March 31st 2027. 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 beach chairs along the private

    Jennifer Le Blanc PRECISE REALTY CORP

    2109 Gulf of Mexico Dr Unit 1203, 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
    /28

    $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 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

    3808 Gulf of Mexico Dr Unit E205, 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
    /48

    $3,975 Per Month

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

    842 Bayport Way Unit 842, Longboat Key, FL 34228

    Available June through December. This first-floor corner condo means extra privacy, added natural light and the convenience of a walk-out patio. Nicely furnished and move-in ready for a comfortable stay. A spacious dining and living area opens out to a screened lanai and large west facing outdoor patio overlooking landscaped grounds. A patio gate allows easy access to a path out to the beach

    Rosemarie McKee COLDWELL BANKER REALTY

    842 Bayport Way Unit 842, Longboat Key, FL 34228
  • 1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    /35

    $2,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,503 Sq Ft
    • Condo for Rent

    1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

    FURNISHED CONDO ON THE BEACH ! AVAILABLE MAY 1ST! SORRY JAN 1- MARCH 2027 IS NOT AVAILABLE . May - November are AVAILABLE MONTHS. This wonderful Condo 2 bed/2 bath and den is now available. Beach Place is one of the most sought out places on Longboat Key. Located mid-island, this association has a FANTASTIC beach, large heated pool, spa and his/hers fitness areas, EV charging station, tennis,

    Annabelle Newland STOCKTON REALTY ADVISORS LLC

    1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    /13

    $2,500 Per Month

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

    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228

    LONGBOAT KEY...Lovely 2 bedroom 2 bath condo directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile. Split floor plan, master suite with a king size bed and the guest room has bunk beds with one single bed and one full size bed. Spacious, open, light and bright. Very well maintained GULF TO BAY complex with lush

    Teresa Ribaudo JENNETTE PROPERTIES INC

    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    /47

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,336 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    Furnished beachfront vacation rental! This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is located in a smaller building, on an uncrowded segment of beach that can often be enjoyed in complete solitude. The unit was recently upgraded with a new washer/dryer, luxury vinyl flooring in the

    Daniel Goldman COMPASS FLORIDA LLC

    4325 Gulf of Mexico Dr Unit 305, 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
  • 1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    /32

    $5,000 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228

    Beachfront Longboat Key Luxury Living. Wake up every day to sweeping **Gulf views** from this beautifully renovated **5th-floor beachfront residence**. Designed for comfort, tranquility, and effortless coastal living, this 12-month annual rental places you steps from the sand and moments from the world-class dining and boutique shopping of **St. Armands Circle**. Property Highlights*Direct

    Donna Channey WAGNER REALTY

    1050 Longboat Club Rd Unit 506, 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 AND SEASONAL. RENTAL MAY 1, 2026 THROUGH November 30, 2026 AT $5000 A MONTH AND SEASONAL JANUARY 1, 2027 THROUGH APRIL 30, 2027 for $7500. 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

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
    /31

    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,336 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228

    Available March 2026. Experience unparalleled Gulf-front living in this beautifully renovated 2-bedroom, 2-bathroom condo at Tiffany Plaza. Spanning 1,336 sq ft, this fully furnished residence boasts luxury vinyl flooring, a modern kitchen with marble countertops, and a spacious lanai offering breathtaking views of the turquoise waters of the Gulf of Mexico . The master suite features a

    Shaun Cumston STERLING REALTY

    4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
  • 914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    /31

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,341 Sq Ft
    • Condo for Rent

    914 Spanish Dr S Unit 76, Longboat Key, FL 34228

    Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the sought-after community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bath residence features all brand-new furnishings and is ideally situated just steps from the marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
  • 5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    /28

    $6,000 Per Month

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

    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

    Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
  • 655 Cedars Ct, Longboat Key, FL 34228
    655 Cedars Ct, Longboat Key, FL 34228
    655 Cedars Ct, Longboat Key, FL 34228
    /22

    $7,000 Per Month

    • 1 Bed
    • 2 Baths
    • 1,244 Sq Ft
    • Condo for Rent

    655 Cedars Ct, Longboat Key, FL 34228

    AVAILABLE. 2026 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay views

    Brenda Cozy COLDWELL BANKER REALTY

    655 Cedars Ct, Longboat Key, FL 34228
  • 750 Bayport Way Unit 750, Longboat Key, FL 34228
    750 Bayport Way Unit 750, Longboat Key, FL 34228
    750 Bayport Way Unit 750, Longboat Key, FL 34228
    /45

    $4,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,370 Sq Ft
    • Condo for Rent

    750 Bayport Way Unit 750, Longboat Key, FL 34228

    AVAILABLE IN JUNE FOR 6-MONTHS OR MORE! Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat Key Community, featuring one of the most beautiful beach fronts, and Bay front locations on Longboat Key. This well-appointed and tastefully furnished, updated home welcomes you with its understated elegance. Everything inside is new, from the

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    750 Bayport Way Unit 750, 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

Showing Results 41 - 80, Page 2 of 3

Florida Manatee County Longboat Key

Condos for Rent with Community Pool in Longboat Key, FL

How to Rent a Home

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