153

Longboat Key, FL Homes for Rent

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  • 420 Firehouse Ct Unit 10, Longboat Key, FL 34228
    420 Firehouse Ct Unit 10, Longboat Key, FL 34228
    420 Firehouse Ct Unit 10, Longboat Key, FL 34228
    /17

    $3,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,015 Sq Ft
    • House for Rent

    420 Firehouse Ct Unit 10, Longboat Key, FL 34228

    Seldom available annual rental on the coveted north end of Longboat Key. This beautifully remodeled 2-bedroom, 2-bath condo boasts new appliances, cabinets, flooring, and modern fixtures throughout. Both bedrooms feature spacious walk-in closets, and a separate utility room includes washer and dryer hookups. Embrace the laid-back coastal lifestyle with quick access to beaches, restaurants,

    Gregory Koss WAGNER REALTY

    420 Firehouse Ct Unit 10, Longboat Key, FL 34228
  • 1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    /34

    $4,048

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,388 Sq Ft
    • Condo for Rent

    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228

    The advertised rate of $4,048/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 9, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
  • 885 Spanish Dr N, Longboat Key, FL 34228
    885 Spanish Dr N, Longboat Key, FL 34228
    885 Spanish Dr N, Longboat Key, FL 34228
    /50

    $2,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,423 Sq Ft
    • Condo for Rent

    885 Spanish Dr N, Longboat Key, FL 34228

    This beautifully updated/unfurnished two-bedroom, two-bath Spanish Main standalone villa with beach access is available for annual lease! The fully remodeled home features tile flooring throughout, a spacious chef’s kitchen, granite island and counters, and new appliances—all opening to a bright living area. The primary suite offers an en-suite bath with new tile shower and granite counter plus a

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    885 Spanish Dr N, Longboat Key, FL 34228
  • 1000 Longboat Club Rd, Longboat Key, FL 34228
    1000 Longboat Club Rd, Longboat Key, FL 34228
    1000 Longboat Club Rd, Longboat Key, FL 34228
    /51

    $4,000 Per Month

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft
    • House for Rent

    1000 Longboat Club Rd, Longboat Key, FL 34228

    Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for

    1000 Longboat Club Rd, Longboat Key, FL 34228
  • 616 Lyons Ln, Longboat Key, FL 34228
    616 Lyons Ln, Longboat Key, FL 34228
    616 Lyons Ln, Longboat Key, FL 34228
    /40

    $4,800 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • House for Rent

    616 Lyons Ln, Longboat Key, FL 34228

    Come and enjoy a little piece of Paradise! This beautiful canal front home is located in the idyllic and picturesque Longboat Key. A charming mid-century style cottage nestled in one of Longboat Key's most private and serene settings. This spacious 2 bedroom + Bonus room, 2.5 bathrooms with outdoor shower residence offers 1,755 square feet of luxurious living space perfect for those seeking a

    Steve Barthelemy ROOST REALTY INC.

    616 Lyons Ln, Longboat Key, FL 34228
  • 537 Outrigger Ln, Longboat Key, FL 34228
    537 Outrigger Ln, Longboat Key, FL 34228
    537 Outrigger Ln, Longboat Key, FL 34228
    /12

    $7,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • House for Rent

    537 Outrigger Ln, Longboat Key, FL 34228

    Welcome boating enthusiasts to this exceptional waterfront residence located in the highly desirable Country Club Shores community on Longboat Key. Situated on a deep-water canal with direct access to the Gulf of America, this beautifully updated two-bedroom, two-bath home with a den offers the ultimate island lifestyle for boaters and beach lovers alike. The property features a brand-new

    537 Outrigger Ln, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /52

    $14,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,498 Sq Ft
    • Condo for Rent

    Unlisted Address

    Pricing: In-Season: $14,500/month (60 Day Minimum) | Off-Season: $9,450/month | All rates include taxes and feesSunset at Banyan Bay is a beautifully appointed 2nd-floor Gulf-front condominium in the coveted Banyan Bay community on Longboat Key — one of Florida's most serene Gulf Coast barrier islands. This 3-bedroom, 3-bathroom residence sleeps up to 8 and offers sweeping views of the

    Dave Holt PMI SOUTHWEST FLORIDA

    Unlisted Address
  • 807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
    /27

    $11,000 Per Month

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

    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228

    Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress. RARELY AVAILABLE FOR 2027 SEASON. LESING NOW FOR DECEMBER 2026 AND JANUARY TRHOUGH APRIL 30TH 2027. MINIMUM

    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
  • 820 Spanish Dr S, Longboat Key, FL 34228
    820 Spanish Dr S, Longboat Key, FL 34228
    820 Spanish Dr S, Longboat Key, FL 34228
    /31

    $3,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • Condo for Rent

    820 Spanish Dr S, Longboat Key, FL 34228

    Coastal Living at Its Finest in the Spanish Main Yacht Club! Discover your perfect Florida retreat in this beautifully maintained, free-standing 2-bedroom, 2-bathroom villa located on the highly coveted southern end of Longboat Key at 820 Spanish Dr S. Offering 1,390 square feet of bright, open living space, this single-story residence perfectly blends maintenance-free comfort with an active,

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    820 Spanish Dr S, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    /44

    $12,000 Per Month

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

    2425 Gulf of Mexico Dr, Longboat Key, FL 34228

    Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath

    2425 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 706 Spanish Dr S, Longboat Key, FL 34228
    706 Spanish Dr S, Longboat Key, FL 34228
    706 Spanish Dr S, Longboat Key, FL 34228
    /34

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,423 Sq Ft
    • Condo for Rent

    706 Spanish Dr S, Longboat Key, FL 34228

    Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after, active 55+ community of Spanish Main Yacht Club! Ideally situated just steps from the marina, this 2-bedroom, 2-bathroom villa features a bright Florida room and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. It is

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    706 Spanish Dr S, Longboat Key, FL 34228
  • 3040 Grand Bay Blvd, Longboat Key, FL 34228
    3040 Grand Bay Blvd, Longboat Key, FL 34228
    3040 Grand Bay Blvd, Longboat Key, FL 34228
    /49

    $10,500 Per Month

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

    3040 Grand Bay Blvd, Longboat Key, FL 34228

    Experience 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 sophistication, this residence offers the elegance of a luxury waterfront home with the

    3040 Grand Bay Blvd, Longboat Key, FL 34228
  • 1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    /42

    $10,000 Per Month

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

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

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

    Jane Hunter JENNETTE PROPERTIES INC

    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
  • 5801 Gulf of Mexico Dr, Longboat Key, FL 34228
    5801 Gulf of Mexico Dr, Longboat Key, FL 34228
    5801 Gulf of Mexico Dr, Longboat Key, FL 34228
    /39

    $19,975 Per Month

    • 4 Beds
    • 3 Baths
    • 4,000 Sq Ft
    • House for Rent

    5801 Gulf of Mexico Dr, Longboat Key, FL 34228

    Welcome to your own Gulf-front retreat on Longboat Key!This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views.Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows that bring in natural light and frame the Gulf.The

    5801 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    /55

    $7,000 Per Month

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

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

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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    /26

    $2,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 761 Sq Ft
    • House for Rent

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228

    AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. $2000 PRICE LISTED IS FOR SEPTEMBER-DECEMBER ONLY. REACH OUT FOR SEASONAL RENTAL PRICE. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 3210 Bayou Sound, Longboat Key, FL 34228
    3210 Bayou Sound, Longboat Key, FL 34228
    3210 Bayou Sound, Longboat Key, FL 34228
    /38

    $11,900 Per Month

    • 3 Beds
    • 2 Baths
    • 2,091 Sq Ft
    • House for Rent

    3210 Bayou Sound, Longboat Key, FL 34228

    AVAILABLE HIGH-SEASON January - April, $11,900/month. LOW SEASON May - December, $7,000/month. 3 Month Minimum Stay. Experience the best of Longboat Key living in this beautifully updated Bay Isles pool home, offered TURNKEY furnished FOR LEASE and available for both short-term and long-term reservations. This furnished coastal retreat features an open floor plan with vaulted ceilings, 2 bedrooms

    Richard Ivan WAGNER REALTY

    3210 Bayou Sound, Longboat Key, FL 34228
  • 691 Russell St, Longboat Key, FL 34228
    691 Russell St, Longboat Key, FL 34228
    691 Russell St, Longboat Key, FL 34228
    /35

    $9,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft
    • House for Rent

    691 Russell St, Longboat Key, FL 34228

    Experience luxury coastal living in this completely renovated annual rental on the desirable north end of Longboat Key. Situated on an oversized double lot just minutes from the pristine Gulf beaches, this exceptional pool home offers the perfect blend of style, comfort, and convenience.Thoughtfully redesigned from top to bottom, the home features a bright, open-concept floor plan with

    691 Russell St, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    /40

    $5,500 Per Month

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

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

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

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

    $10,500 Per Month

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

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

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

    Norma Mladineo COLDWELL BANKER REALTY

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

    $3,500 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
  • 6979 Longboat Dr S, Longboat Key, FL 34228
    6979 Longboat Dr S, Longboat Key, FL 34228
    6979 Longboat Dr S, Longboat Key, FL 34228
    /39

    $10,000 Per Month

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

    6979 Longboat Dr S, Longboat Key, FL 34228

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

    Rinat Sikdar COLDWELL BANKER REALTY

    6979 Longboat Dr S, Longboat Key, FL 34228
  • 3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
    /44

    $4,000 Per Month

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

    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228

    Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease.

    Janette Schafer COLDWELL BANKER REALTY

    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
  • 535 Forest Way, Longboat Key, FL 34228
    535 Forest Way, Longboat Key, FL 34228
    535 Forest Way, Longboat Key, FL 34228
    /60

    $6,900 Per Month

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

    535 Forest Way, Longboat Key, FL 34228

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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    535 Forest Way, Longboat Key, FL 34228
  • 840 Bayport Way Unit 840, Longboat Key, FL 34228
    840 Bayport Way Unit 840, Longboat Key, FL 34228
    840 Bayport Way Unit 840, Longboat Key, FL 34228
    /53

    $4,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • Condo for Rent

    840 Bayport Way Unit 840, Longboat Key, FL 34228

    This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The

    Shirley Cuddy REALTY SERVICES INC

    840 Bayport Way Unit 840, Longboat Key, FL 34228
  • 5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    /46

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,561 Sq Ft
    • Condo for Rent

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    A little slice of Gulf-front heaven. Seasonal rental only, available July 15 through December 31, 2026! 60 Day Minimum Lease, not available Jan 1, 2027-March 31, 2027. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches

    Scott Nold TNG PROPERTY MANAGEMENT

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • 1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    /51

    $11,000 Per Month

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

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

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

    Margaret Young JENNETTE PROPERTIES, INC.

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

    $5,700 Per Month

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

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

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

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

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

    $14,000 Per Month

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

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

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

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

    $7,000 Per Month

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

    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228

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

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

    $29,000 Per Month

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

    591 Putting Green Ln, Longboat Key, FL 34228

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

    Teresa Ribaudo JENNETTE PROPERTIES INC

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

    $12,000 Per Month

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

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

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

    Teresa Ribaudo JENNETTE PROPERTIES INC

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

    $9,587 Per Month

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

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

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

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
  • 2823 Gulf of Mexico Dr, Longboat Key, FL 34228
    2823 Gulf of Mexico Dr, Longboat Key, FL 34228
    2823 Gulf of Mexico Dr, Longboat Key, FL 34228
    /46

    $12,500 Per Month

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

    2823 Gulf of Mexico Dr, Longboat Key, FL 34228

    AVAILABLE: November 2026 $12,500/month and December 2026 $15,000/month. This availability won't last long. Call today and book your stay! Also, we are now accepting reservations for the summer of 2027- Call for special pricing. Welcome to BEACHFRONT PARADISE on Longboat Key! This outstanding location offers a RARE OPPORTUNITY to enjoy coastal living with BREATHTAKING VIEWS of the shoreline.

    Michael Cella CELLA'S REAL ESTATE INC

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

    $3,000 Per Month

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

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

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

    nicoletta buonaccordo ALTIS REALTY

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

    $6,000 Per Month

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

    Unlisted Address

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

    Jane Hunter JENNETTE PROPERTIES INC

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

    $13,000 Per Month

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

    501 Channel Ln, Longboat Key, FL 34228

    Booked all of July, September, Novemeber 2026, and all of 2027Experience elevated island living in this stunning coastal retreat featuring 4 bedrooms, 3 bathrooms, a private pool, and exceptional indoor-outdoor entertaining spaces.Designed with comfort and style in mind, the bright open-concept living area features soaring ceilings, designer finishes, and large sliding glass doors

    Jennifer Le Blanc PRECISE REALTY CORP

    501 Channel Ln, 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
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    $12,000 Per Month

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

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

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

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

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

    $35,000 Per Month

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

    7147 La Lenaire Dr, Longboat Key, FL 34228

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

    Chase Moore SIGHT REAL ESTATE, LLC

    7147 La Lenaire Dr, Longboat Key, FL 34228

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