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Fully Furnished Homes for Rent in Longboat Key, FL

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  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
    /66

    $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
  • 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

    $55,000 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
  • 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
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /41

    $11,500 Per Month

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

    Unlisted Address

    Experience the best of Longboat Key living in this beautifully updated, turnkey furnished 2-bedroom, 2-bath residence located behind the gates of the sought after Longboat Key Club. This light-filled condominium features brand-new countertops, new appliances, and an open, inviting floor plan designed for effortless coastal living. Enjoy partial Gulf views and beautiful bay vistas from two private

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    Unlisted Address
  • 6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    /50

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,367 Sq Ft
    • Condo for Rent

    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228

    Available September 1, 2026 through January 31, 2027 with a one-month minimum rental. Experience the best of Longboat Key in this beautifully renovated and newly furnished 2-bedroom, 2-bathroom condo. Simply pack your flip-flops and beachwear and settle into the relaxed island lifestyle. Residents enjoy an impressive array of resort-style amenities, including two heated swimming pools, tennis and

    Kelly Baldwin COLDWELL BANKER REALTY

    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
  • 573 Spanish Dr N, Longboat Key, FL 34228
    573 Spanish Dr N, Longboat Key, FL 34228
    573 Spanish Dr N, Longboat Key, FL 34228
    /40

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • House for Rent

    573 Spanish Dr N, Longboat Key, FL 34228

    NOW AVAILABLE STARTING JUNE 1, 2026 - BRAND NEW RENOVATED and TURNKEY FURNISHED available for ANNUAL LEASE ($3,500/MONTH) OR SEASONAL Jan - April ($5,500/MONTH). 6 MONTH MINUMUM RENTAL (OR INQUIRE ABOUT ANNUAL OPTION). ALL Utilities, Cable and Tax included. Come live the island life in this peaceful, fully detached villa nestled in the vibrant 55+ waterfront community of Spanish Main Yacht Club.

    Norma Mladineo COLDWELL BANKER REALTY

    573 Spanish Dr N, 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

    $6,500 Per Month

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

    655 Cedars Ct, Longboat Key, FL 34228

    AVAILABLE. 2027 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
  • 1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /67

    $13,500 Per Month

    • 2 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    **Prime Location – Luxurious Waterfront Living at Promenade, Longboat Key**This absolutely gorgeous condo is located in the prestigious Promenade on Longboat Key, offering breathtaking water views from every room. The residence features 2 bedrooms plus a den and 2 bathrooms. The spacious master suite includes a king-size bed and an elegant en-suite bathroom with a separate bathtub, walk-in

    Elsie Salazar BERKSHIRE HATHAWAY HOMESERVICE

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • 1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
    1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
    1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
    /38

    $6,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft
    • Condo for Rent

    1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228

    Perched on the top floor with nothing between you & the water, this fully furnished beachfront retreat at Seaplace offers unobstructed Gulf of America views from every room. Living, dining & kitchen face the Gulf; the king primary suite opens to a private beachfront balcony, the second bedroom (two twins) has its own, and a flexible 3rd room with a Murphy bed works as a bedroom, media room, or

    Robert Hildreth THE AGENCY SARASOTA

    1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
  • 2089 Gulf of Mexico Dr Unit G1302, Longboat Key, FL 34228
    2089 Gulf of Mexico Dr Unit G1302, Longboat Key, FL 34228
    2089 Gulf of Mexico Dr Unit G1302, Longboat Key, FL 34228
    /67

    $3,500 Per Month

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

    2089 Gulf of Mexico Dr Unit G1302, Longboat Key, FL 34228

    Why not make every day a vacation? Enjoy year-round paradise in this third-floor, 2-bed, 2-bath condo overlooking the Gulf in the highly sought-after Seaplace community. The location is exceptional, offering resort-style amenities without resort-style prices. Start your mornings with a walk on the beach and end your evenings with sunset cocktails.Seaplace features two pools—one just steps

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    2089 Gulf of Mexico Dr Unit G1302, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    /25

    $5,835 Per Month

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

    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228

    Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Welcome to Seaside Dream! Beautifully furnished and decorated, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. If you enjoy resort-style living, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will

    Andy Moore GULF COAST REALTY & MANAGEMENT

    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
  • 450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    /32

    $4,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,301 Sq Ft
    • Condo for Rent

    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228

    SEASONAL rental: Available for 2026-2027 SEASON!!! Discover the ultimate island lifestyle in this comfortably furnished 2-bedroom, 2 bath, unit located in the highly sought-after community of Bay Harbour on the southern end of Longboat Key. Just minutes from St. Armands Circle, downtown Sarasota, restaurants, shopping, county tennis and pickleball courts, walking trails, parks and of course –

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    /24

    $2,000 Per Month

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

    3802 Gulf of Mexico Dr Unit 204, 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

    Brigette Marcus NEXTHOME EXCELLENCE

    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
  • 1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    /12

    $30,000 Per Month

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

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

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

    Larry Starr SVN COMMERCIAL ADVISORY GROUP

    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
  • 513 Gunwale Ln, Longboat Key, FL 34228
    513 Gunwale Ln, Longboat Key, FL 34228
    513 Gunwale Ln, Longboat Key, FL 34228
    /63

    $14,750 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,292 Sq Ft
    • House for Rent

    513 Gunwale Ln, Longboat Key, FL 34228

    Welcome to Beach & Boaters Paradise located on Longboat Key. Enjoy immediate access access to beautiful Sarasota Bay, the Gulf of Mexico and Longboat Key’s sugar white sand beaches and emerald green waters. Fish off the dock or walk to the beach! Or enjoy the large heated pool in this 4 bedroom, 3.5 bath luxury waterfront home designed to provide you and your family a lifetime of vacation

    Marcia Benson Berkshire Hathaway Florida Realty

    513 Gunwale Ln, 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
    /30

    $11,769 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
  • 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

    2027 Season Rental Rate will be $24,000. 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

    Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
  • 540 Neptune Ave Unit 7, Longboat Key, FL 34228
    540 Neptune Ave Unit 7, Longboat Key, FL 34228
    540 Neptune Ave Unit 7, Longboat Key, FL 34228
    /25

    $5,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • Condo for Rent

    540 Neptune Ave Unit 7, Longboat Key, FL 34228

    ****Enchanting, Iconic...Gulf Key****~Discover Relaxation and Island Charm Just Steps from the Beach~Unwind at Gulf KeyWelcome to Gulf Key, a truly iconic villa community where the spirit of “old Florida” meets modern comfort. This immaculate, newly renovated 2-bedroom, 2-bath villa is perfectly situated just a 5-minute walk from the beach, making it an ideal destination for

    Pamala Casey CASEY REALTY CORPORATION

    540 Neptune Ave Unit 7, Longboat Key, FL 34228
  • 6980 Poinsetta Ave, Longboat Key, FL 34228
    6980 Poinsetta Ave, Longboat Key, FL 34228
    6980 Poinsetta Ave, Longboat Key, FL 34228
    /18

    $4,250 Per Month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • House for Rent

    6980 Poinsetta Ave, Longboat Key, FL 34228

    Tucked away in a quiet fisherman’s village on Longboat Key, this elegant one-bedroom cottage blends classic island charm with modern luxury.The bright, open living space features soaring vaulted ceilings and a sleek, contemporary kitchen. Premium comforts include high-speed internet, in-unit laundry, a reverse osmosis water filtration system, and UV air purification.Perfect for couples

    Christina Vescovo LPT REALTY, LLC

    6980 Poinsetta Ave, Longboat Key, FL 34228
  • 5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /23

    $5,500 Per Month

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

    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    Pristine Gulf Beachfront on Longboat Key Welcome to this beautifully updated 2-bedroom, 2-bathroom luxury beachside retreat located in The Shore on mid-Longboat Key. This inviting second-floor condo offers stunning Gulf views and is just steps from the powdery white sand and crystal-clear waters—an ideal setting for a relaxed island getaway. Highlights-Sweeping Gulf views from living room and

    Matt Darak DARAK GROUP INCORPORATED

    5757 Gulf of Mexico Dr Unit 202, 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
    /41

    $5,850 Per Month

    • 2 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • House for Rent

    701 Broadway St, Longboat Key, FL 34228

    August & Sept Summer special rate! This charming single-story residence is a meticulous rebuild with an open-concept great room featuring high ceilings, abundant natural light, and a gourmet kitchen equipped with stainless steel appliances and a gas range. The private, fully fenced backyard offers a lagoon style heated swimming pool, separate hot tub, lush tropical landscaping, and the soothing

    Christina Vescovo LPT REALTY, LLC

    701 Broadway St, Longboat Key, FL 34228
  • 2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    /72

    $6,950 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,369 Sq Ft
    • Condo for Rent

    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228

    Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered

    Andrew Clark SECURE DOOR PROPERTY MANAGEMENT

    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
  • 4420 Exeter Dr Unit 208, Longboat Key, FL 34228
    4420 Exeter Dr Unit 208, Longboat Key, FL 34228
    4420 Exeter Dr Unit 208, Longboat Key, FL 34228
    /28

    $4,900 Per Month

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

    4420 Exeter Dr Unit 208, Longboat Key, FL 34228

    Must read entirely. 2026-2027 RENTAL- Not Available until Nov 2026 or Jan 15-Mar 30. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina

    Armando Gonzalez AG REALTY SERVICES LLC

    4420 Exeter Dr Unit 208, 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
    /69

    $7,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • House for Rent

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228

    Booking Now for Summer 2027! Booked for January-June 30, 2027. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access.

    Debby McCaig COLDWELL BANKER REALTY

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 2254 Harbour Court Dr, Longboat Key, FL 34228
    2254 Harbour Court Dr, Longboat Key, FL 34228
    2254 Harbour Court Dr, Longboat Key, FL 34228
    /57

    $11,500 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,101 Sq Ft
    • House for Rent

    2254 Harbour Court Dr, Longboat Key, FL 34228

    Nestled on the tranquil waterfront of Longboat Key, this stunning residence offers the ultimate coastal lifestyle. With direct water access and a private dock, boating and jet skiing are right at your doorstep. Two floating jet ski docks can also accommodate dinghies, making this property a boater’s dream. The home is ideally situated beside the golf course, blending serene water views with lush

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    2254 Harbour Court Dr, Longboat Key, FL 34228

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