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2-Bedroom Homes for Rent in Longboat Key, FL

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  • 535 Forest Way, Longboat Key, FL 34228
    535 Forest Way, Longboat Key, FL 34228
    535 Forest Way, Longboat Key, FL 34228
    /60

    $6,900 per month

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

    535 Forest Way, Longboat Key, FL 34228

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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    535 Forest Way, Longboat Key, FL 34228
  • 701 Broadway St, Longboat Key, FL 34228
    701 Broadway St, Longboat Key, FL 34228
    701 Broadway St, Longboat Key, FL 34228
    /33

    $7,850 per month

    • 2 Beds
    • 2 Baths
    • 2,331 Sq Ft
    • House for Rent

    701 Broadway St, Longboat Key, FL 34228

    Newly remodeled bungalow blocks from Whitney Beach & a block from bay. Historic home was once a post office in the 1920's. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! Sleep tight in a quiet neighborhood that allows zero public parking. Very serene, private

    Keith Gordon GETMOREOFFERS

    701 Broadway St, 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
  • 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 FINE PROPERTIES

    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

    $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
  • 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
  • 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
  • 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
  • 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
  • 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

    $5,000 per month

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

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228

    Rented January-April 2026. 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

    Joseph Stephens ONE STEP AHEAD REALTY INC

    4780 Gulf of Mexico Dr, 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
  • 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
  • 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
  • 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

    $9,721 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

    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** Rented for Season 2025 February through April 20th.* Booked Dec1st-March 31st. 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,

    Jennifer LeBlanc PRECISE REALTY CORP

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /18

    $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
  • 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
  • 500 Schooner Ln, Longboat Key, FL 34228
    500 Schooner Ln, Longboat Key, FL 34228
    500 Schooner Ln, Longboat Key, FL 34228
    /75

    $15,750 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. 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 thought out from kitchen to bathrooms. Fun, chic, beach inspired

    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

    $11,900 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
  • 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

    $11,000 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
  • 2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    /34

    $11,500 per month

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

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

    ..."' short stories. ....on the island of longboat key You are on the beach included is swimming pool...and a world class tennis courtf...looking play with others and league Town of Longboat Key tennis three blocks away...fitness gym.. . This is direct Gulf front unit with interior hallways from the balcony ,the kitchen,the living room couch...Your on the water.. Breathtaking view of the

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    /37

    $5,500 per month

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

    4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228

    Gorgeous Gulf front, turnkey furnished rental in Tiffany Plaza. Walk out to the beach from this lovely updated and exquisitely furnished 2 bed/2 bath condo. Coastal inspired decor, king bed in the primary bedroom, full bed and day bed with trundle in the second bedroom. Smart TV's and Wi Fi make this the perfect winter retreat! Tiffany Plaza offers a sparkling heated pool, club room with sauna,

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 102, 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

    $5,000 per month

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

    750 Bayport Way Unit 750, Longboat Key, FL 34228

    Seasonal 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 flooring to the kitchen and baths,

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    750 Bayport Way Unit 750, Longboat Key, FL 34228

Showing Results 41 - 80, Page 2 of 3

Florida Manatee County Longboat Key

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