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Newest Homes for Rent in Longboat Key, FL

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  • 3465 Gulf of Mexico Dr Unit 223, Longboat Key, FL 34228
    3465 Gulf of Mexico Dr Unit 223, Longboat Key, FL 34228
    3465 Gulf of Mexico Dr Unit 223, Longboat Key, FL 34228
    /53

    $4,995

    Total Monthly Price

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

    3465 Gulf of Mexico Dr Unit 223, Longboat Key, FL 34228

    Welcome to The Beach Resort on Longboat Key. Savor warm Gulf breezes while resting lavishly in this full unobstructed Gulf-front view with your own private balcony. An upscale condominium complex located directly on the Gulf of Mexico providing SPECTACULAR VIEWS AND BREATH TAKING SUNSETS !!This condo is on the 2 nd floor and the interior designs were created using an eclectic mix of

    3465 Gulf of Mexico Dr Unit 223, 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
    • SEASONAL SHORT-TERM 1-BED 1 BATH CONDO ON LONGBOAT KEY. BEACH ACCESS

    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
  • 909 Spanish Dr N Unit 51, Longboat Key, FL 34228
    909 Spanish Dr N Unit 51, Longboat Key, FL 34228
    909 Spanish Dr N Unit 51, Longboat Key, FL 34228
    /86

    $2,950 Per Month

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

    909 Spanish Dr N Unit 51, Longboat Key, FL 34228

    One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. 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 neutral tile plank flooring throughout, a spacious chef’s kitchen with 42-inch wood cabinets, quartz island that seats seven,

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    909 Spanish Dr N Unit 51, 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
  • 1050 Longboat Club Rd Unit 803, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 803, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 803, Longboat Key, FL 34228
    /39

    $6,000 Per Month

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

    1050 Longboat Club Rd Unit 803, Longboat Key, FL 34228

    AVAILABLE 9/1/2026 to 12/31/2026. Oceanfront 2 bed/2 bath luxury condo on the 8th floor with beach and golf course views, two private balconies, and resort-style amenities just steps from the sand.The open-concept living and dining area features a custom bar and stylish decor, creating an inviting space to relax or entertain. A dedicated office makes working remotely effortless, while the sleek

    Melissa Kontny XCELLENCE

    1050 Longboat Club Rd Unit 803, 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

    $7,500 Per Month

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

    3210 Bayou Sound, Longboat Key, FL 34228

    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 plus an office, updated bathrooms, a spacious kitchen with premium appliances, and multiple indoor-outdoor living

    Richard Ivan WAGNER REALTY

    3210 Bayou Sound, Longboat Key, FL 34228
  • 2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
    /78

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft
    • Condo for Rent

    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228

    Now available FOR LEASE at The Islander Club on Longboat Key, this updated 2-bedroom, 2-bath residence offers exceptional value in a true beachfront community.Turnkey and move-in ready, the unit features an open layout with quality finishes, an updated kitchen with stainless steel appliances, wood flooring, refreshed bathrooms, and a spacious 38-foot terrace for outdoor living. The primary

    Richard Ivan WAGNER REALTY

    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
  • 100 Sands Point Rd Unit 317, Longboat Key, FL 34228
    100 Sands Point Rd Unit 317, Longboat Key, FL 34228
    100 Sands Point Rd Unit 317, Longboat Key, FL 34228
    /30

    $10,500 Per Month

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

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

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

    Brenda Cozy COLDWELL BANKER REALTY

    100 Sands Point Rd Unit 317, Longboat Key, FL 34228
  • 3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    /75

    $7,850 Per Month

    • 3 Beds
    • 3 Baths
    • 2,250 Sq Ft
    • Condo for Rent

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228

    LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major

    Patrice Ivan WAGNER REALTY

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
  • 1581 Gulf of Mexico Dr, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr, Longboat Key, FL 34228
    /81

    $15,000 Per Month

    • 1 Bed
    • 2 Baths
    • 1,721 Sq Ft
    • Luxury Furnished Gulf-Front Condo at The St. Regis Residences, Longboat Key, FL

    1581 Gulf of Mexico Dr, Longboat Key, FL 34228

    Annual Furnished Rental Available at The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key,

    1581 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
    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    /26

    $2,500 Per Month

    • 1 Bed
    • 1.5 Baths
    • 761 Sq Ft
    • Beach Harbor Club Beauty

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228

    AVAILABLE FOR ANNUAL OR RENTAL. 3 MONTH MINIMUM. 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 comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find a bright

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr, Longboat Key, FL 34228
    /31

    $15,000 Per Month

    • 1 Bed
    • 2 Baths
    • 1,556 Sq Ft
    • Unfurnished Luxury Rental at The St. Regis Longboat Key

    1591 Gulf of Mexico Dr, Longboat Key, FL 34228

    Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous

    1591 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 601 Longboat Club Rd Unit 1004S, Longboat Key, FL 34228
    601 Longboat Club Rd Unit 1004S, Longboat Key, FL 34228
    601 Longboat Club Rd Unit 1004S, Longboat Key, FL 34228
    /16

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Condo for Rent

    601 Longboat Club Rd Unit 1004S, Longboat Key, FL 34228

    Property Id: 2517125This beachfront retreat offers breathtaking panoramic views from its Gulf-front and east-facing balconies, encompassing Lido and Siesta Keys, Longboat Key, and the Sarasota skyline. Inside, a sunlit living room with large windows, a dining area with ocean views, and an updated kitchen with stainless steel appliances and an in-unit washer/dryer provide comfortable

    (629) 207-6561

    601 Longboat Club Rd Unit 1004S, 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
    /58

    $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 starting July 15, 2026! 60 Day Minimum Lease. 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 are perfectly complemented by the beautifully redesigned interior and thoughtfully updated floor plan. The

    Scott Nold TNG PROPERTY MANAGEMENT

    5757 Gulf of Mexico Dr Unit 305, 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

    $5,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,370 Sq Ft
    • Amazing 2BR Condo in Longboat Key

    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.Step inside to find a well-appointed kitchen featuring:- Electric range and stove top-

    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, 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
  • 2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
    /43

    $16,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft
    • Condo for Rent

    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228

    Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms. Step inside to find a thoughtfully updated interior featuring modern finishes, a fully equipped kitchen with

    Michele Conn PREFERRED SHORE LLC

    2301 Gulf of Mexico Dr Unit 102N, 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
    /32

    $6,500 Per Month

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

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

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

    John Schafer, V COLDWELL BANKER REALTY

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

    $2,500 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. 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 comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find

    Brigette Marcus NEXTHOME EXCELLENCE

    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
  • 1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    /48

    $4,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    1000 Longboat Club Rd Unit 406, 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

    Cody Smith RENT SARASOTA

    1000 Longboat Club Rd Unit 406, 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

    $8,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,143 Sq Ft
    • Luxury Seasonal or Annual Rental in the Prestigious Grand Bay Community – Longboat Key

    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
  • 4330 Falmouth Dr, Longboat Key, FL 34228
    4330 Falmouth Dr, Longboat Key, FL 34228
    4330 Falmouth Dr, Longboat Key, FL 34228
    /26

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    4330 Falmouth Dr, Longboat Key, FL 34228

    Longboat Key Beach and Bay Access.2 Bedroom 2 Bathroom First Floor condo in a gated community with tons of amenities.✅ Deepwater channel with docks and slips available up to 34' (on waitlist)✅ Amazing water views & breezes✅ Private deeded beach access (private building on beach with showers + bathrooms, benches and tables!)✅ 4 Pools, clubhouse, gym, sauna,

    4330 Falmouth Dr, 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
    • Seaside Serenity: Luxurious Gulf-Front Retreat on Southern Longboat Key

    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
  • 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
  • 3240 Gulf of Mexico Dr, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr, Longboat Key, FL 34228
    /54

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Seasonal/short term 2/2 condo rental with full water view on Longboat Key.

    3240 Gulf of Mexico Dr, Longboat Key, FL 34228

    Seasonal / Short-Term Rental on Longboat KeyVacation in one of the nation’s most celebrated coastal destinations, where a leading national travel magazine ranked Longboat Key among the Top 5 Best Islands in the United States. Experience the beauty firsthand while enjoying breathtaking water views from nearly every room of this stunning condominium at Portobello. This beautifully renovated and

    3240 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 2013 Harbour Links Dr, Longboat Key, FL 34228
    2013 Harbour Links Dr, Longboat Key, FL 34228
    2013 Harbour Links Dr, Longboat Key, FL 34228
    /77

    $5,950 Per Month

    • 2 Beds
    • 2 Baths
    • 2,369 Sq Ft
    • Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views Remodele...

    2013 Harbour Links Dr, Longboat Key, FL 34228

    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 fully furnished and ready for immediate enjoyment, this home is perfectly positioned on a quiet cul-de-sac with extra guest parking, combining privacy, luxury, and

    2013 Harbour Links Dr, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
    /31

    $15,000 Per Month

    • 1 Bed
    • 2 Baths
    • 1,556 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228

    Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
  • 4805 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    4805 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    4805 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    /20

    $10,100 Per Month

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

    4805 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228

    Property Id: 2484818Available December 1st, 2026! THE OCEAN IS YOUR BACKYARD! Minutes away from world-class golfing, boating, tennis, dining, and shopping. This exclusive, private, and serene Gulf Coast Condominium unit has been a traveler's dream for so many years now. The Property offers steps to the Gulf Coast's richest Beaches. We offer a fully stocked outdoor shed with beach chairs,

    (941) 207-7562

    4805 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
    /23

    $4,300 Per Month

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

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

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

    Len Scavron LEN SCAVRON

    3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
  • 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
  • 842 Bayport Way Unit 842, Longboat Key, FL 34228
    842 Bayport Way Unit 842, Longboat Key, FL 34228
    842 Bayport Way Unit 842, Longboat Key, FL 34228
    /48

    $3,975 Per Month

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

    842 Bayport Way Unit 842, Longboat Key, FL 34228

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

    Rosemarie McKee COLDWELL BANKER REALTY

    842 Bayport Way Unit 842, Longboat Key, FL 34228
  • 5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
    5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
    5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
    /44

    $5,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft
    • Condo for Rent

    5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228

    Experience true beachfront living at 5611 Gulf of Mexico Drive, Unit 3103. This beautifully kept 3-bedroom, 2-bath residence is in excellent condition and offers stunning views of the Gulf of Mexico in a setting that is hard to beat. Located directly on the beach with no road to cross, this property gives you effortless access to the shoreline just steps from your door. Guests can enjoy the

    Agent Photo

    William Glade

    WILLIAM GLADE LIC. REAL ESTATE BROKER

    (941) 279-2310

    5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
  • 615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    /20

    $12,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,293 Sq Ft
    • Condo for Rent

    615 Dream Island Rd Unit 107, Longboat Key, FL 34228

    Welcome to one of the most sought-after condo units in the Harbour Villa Club. This magnificent unit is for rent fully furnished. Opening the front door, you will enjoy a beautiful view of the serene intracoastal waterway and stunning Florida palm trees. No need to mess with an elevator, this first floor unit opens directly to the swimming pool and is only steps away from a 40’ deeded boat slip

    Jerome Henin HENIN REALTY

    615 Dream Island Rd Unit 107, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /65

    $12,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,396 Sq Ft
    • House for Rent

    Unlisted Address

    Enjoy resort-style living on prestigious Longboat Key in this completely updated and renovated 3-bedroom, 2.5-bathroom villa. Located in Harbour Circle, an enclave of 42 villas in the guard-gated, maintenance-free, community of Bay Isles, this 2,396 SF open floorplan has soaring ceilings and an abundance of natural light through the new high-impact doors and windows that uplifts and illuminates.

    Teresa Ribaudo JENNETTE PROPERTIES INC

    Unlisted Address
  • 914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    /31

    $6,500 Per Month

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

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

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

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
  • 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
  • 360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    /78

    $6,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,298 Sq Ft
    • Condo for Rent

    360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228

    WILL CONSIDER A 6 TO 12 MONTH LEASE AND WILL FURNISH FOR $7750 PER MONTH.Welcome to Tangerine Bay Club An Island Resort-style condo located at the premier location on Longboat Key. This professionally painted 2 bedroom, 2.5 bath with office/den features views of Sarasota Bay. It is in close proximity to New Pass and the pristine beaches of the Gulf of Mexico. Upgraded Ergon Fall White stone

    Karl Helbig SUNREAL ESTATE INC

    360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    /32

    $5,000 Per Month

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

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

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

    Donna Channey WAGNER REALTY

    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
  • 603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228
    603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228
    603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228
    /74

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Condo for Rent

    603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228

    LONGBOAT KEY CLUB – GULF FRONT LUXURY RENTAL Enter the private, gated community of Longboat Key Club and experience true coastal paradise with breathtaking Gulf-front views. This completely remodeled 2-bedroom, 2-bath condominium showcases elegant, high-end finishes throughout. The bright and open living area features stunning marble flooring and walls, with expansive windows and a large private

    Agent Photo

    Lily Behrends

    RE/MAX ALLIANCE GROUP

    (941) 299-8853

    603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228

Showing Results 1 - 40, Page 1 of 4

Florida Manatee County Longboat Key

Newest Homes for Rent in Longboat Key, FL

Frequently Asked Questions

How much does it cost to rent a home in Longboat Key, FL?
The median rent for a home in Longboat Key, FL is $7,000 per month, though prices vary by neighborhood, size, and property type. As of May 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Longboat Key, FL?
To comfortably afford the median rent in Longboat Key, FL, a household needs to earn roughly $280,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $7,000 per month in Longboat Key, FL, renters typically need to show $21,000 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Longboat Key, FL?
In Longboat Key, FL, the price-to-rent ratio is 12.6, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Longboat Key, FL are best for renting a home?
The best neighborhood for renting in Longboat Key, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include West Bradenton, El Conquistador, Indian Beach-Sapphire Shores, South Bradenton and Bayou Oaks, each with its own character and price range.

Rental Home Trends in Longboat Key, FL

There are currently 159 homes available for rent in Longboat Key, FL. The median rent is $7,000 per month, with single-family homes renting at $10,000, townhouses at $8,500 and condos at $6,700.

Rental Home Trends

Number of Homes for Rent
159
Median Rent
$7,000
Median Single Family Home Rent
$10,000
Median Townhouse Rent
$8,500
Median Condo Rent
$6,700
How to Rent a Home

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