143

Longboat Key, FL Homes for Rent

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  • 3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228
    /35

    $5,000 per month

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft
    • Condo for Rent

    3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228

    2-bed, 2-bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community's private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228
  • 1065 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228
    1065 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228
    1065 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228
    /57

    $12,000 per month

    • 2 Beds
    • 2 Baths
    • 1,172 Sq Ft
    • Condo for Rent

    1065 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228

    Presenting a stunning penthouse unit now available for lease!This top-floor, corner residence offers magnificent, panoramic views of the Gulf of Mexico, the Longboat Key Club golf course, and the Intracoastal Waterway. Upon entering, you are welcomed by abundant natural light pouring in through floor-to-ceiling sliding glass doors, which are equipped with electric roller shades. The unit also

    Margaret Young JENNETTE PROPERTIES, INC.

    1065 Gulf of Mexico Dr Unit 601, 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 ($4,600/MONTH). LEASE -3 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
  • 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
    /12

    $5,000 per month

    • 2 Beds
    • 2 Baths
    • 1,032 Sq Ft
    • Condo for Rent

    540 Neptune Ave Unit 7, Longboat Key, FL 34228

    Iconic... Gulf Key.This immaculate, newly renovated two-bedroom, two-bath villa is just a three-minute walk to the beach. Gulf Key invites you to slow down, breathe in the salt air, and truly unwind. It’s classic clay tile roof and stucco exterior reflect understated elegance and the essence of an OLD Florida lifestyle. With only 10 units, Gulf Key offers peace and privacy in a stellar

    Pamala Casey CASEY REALTY CORPORATION

    540 Neptune Ave Unit 7, Longboat Key, FL 34228
  • 1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    /83

    $25,000 per month

    • 1 Bed
    • 1.5 Baths
    • 1,721 Sq Ft
    • Condo for Rent

    1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

    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, Florida. Step inside to beautifully

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1581 Gulf of Mexico Dr Unit 307, 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
  • 690 Old Compass Rd, Longboat Key, FL 34228
    690 Old Compass Rd, Longboat Key, FL 34228
    690 Old Compass Rd, Longboat Key, FL 34228
    /69

    $25,000 per month

    • 3 Beds
    • 3 Baths
    • 3,230 Sq Ft
    • House for Rent

    690 Old Compass Rd, Longboat Key, FL 34228

    Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size

    Teresa Ribaudo JENNETTE PROPERTIES INC

    690 Old Compass Rd, Longboat Key, FL 34228
  • 829 Bayport Way Unit 829 B, Longboat Key, FL 34228
    829 Bayport Way Unit 829 B, Longboat Key, FL 34228
    829 Bayport Way Unit 829 B, Longboat Key, FL 34228
    /58

    $9,000 per month

    • 2 Beds
    • 2 Baths
    • 1,601 Sq Ft
    • Condo for Rent

    829 Bayport Way Unit 829 B, Longboat Key, FL 34228

    Introducing a remarkable opportunity to rent a piece of paradise at 829 Bayport Way in the scenic Longboat Key, Florida. This beautifully situated property offers an exceptional blend of modern living and serene outdoor charm, perfect for those seeking both comfort and a vibrant lifestyle by the coast. As you enter the community, you are greeted by meticulously landscaped grounds that set the

    Agent Photo

    Antonietta Car

    KELLER WILLIAMS SUBURBAN TAMPA

    (941) 239-2327

    829 Bayport Way Unit 829 B, 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
    /52

    $19,975 per month

    • 4 Beds
    • 4 Baths
    • 4,236 Sq Ft
    • House for Rent

    5801 Gulf of Mexico Dr, Longboat Key, FL 34228

    Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. 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

    Kevin Hase KEYRENTER SARASOTA PROPERTY MANAGEMENT

    5801 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 614 Norton St, Longboat Key, FL 34228
    614 Norton St, Longboat Key, FL 34228
    614 Norton St, Longboat Key, FL 34228
    /73

    $10,000 per month

    • 6 Beds
    • 5.5 Baths
    • 4,676 Sq Ft
    • House for Rent

    614 Norton St, Longboat Key, FL 34228

    Experience the ultimate in coastal luxury with this exceptional residence on Longboat Key. Nestled along a canal with direct access to the Gulf, this expansive home is a dream for boating enthusiasts and those seeking a serene, upscale lifestyle.Key Features:-Prime Location: Situated on a canal with private dock and direct Gulf access—perfect for boating, fishing, or simply enjoying the

    Miranda Platt, PA RELAX REALTY GROUP INC

    614 Norton St, Longboat Key, FL 34228
  • 595 Bowsprit Ln, Longboat Key, FL 34228
    595 Bowsprit Ln, Longboat Key, FL 34228
    /2

    $14,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft
    • House for Rent

    595 Bowsprit Ln, Longboat Key, FL 34228

    Longboat Key Waterfront Perfection! Experience the ultimate coastal lifestyle in this turn-key furnished 3-bedroom, 2.5-bath home in the prestigious Country Club Shores community—just three homes from Sarasota Bay with quick access to the Gulf of Mexico. Boater’s paradise with two boat lifts (20,000 lb and 7,000 lb), a new seawall, and private dock complete with a custom fish cleaning station

    Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    595 Bowsprit Ln, Longboat Key, FL 34228
  • 4360 Chatham Dr Unit 108, Longboat Key, FL 34228
    4360 Chatham Dr Unit 108, Longboat Key, FL 34228
    4360 Chatham Dr Unit 108, Longboat Key, FL 34228
    /56

    $6,000 per month

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Condo for Rent

    4360 Chatham Dr Unit 108, Longboat Key, FL 34228

    Newly renovated and elegantly designed 2-bedroom, 2-bathroom condo in the highly desirable Longboat Harbour Condominiums, located just 600 feet from the shore and a 3-minute walk to the beach. This fully furnished ground floor unit offers a modern open layout with scenic views, access to Sarasota Bay, and resort-style community amenities including four swimming pools (one located right behind the

    Jorge Perez ROI AVE LLC

    4360 Chatham Dr Unit 108, 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
    /67

    $6,500 per month

    • 2 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • House for Rent

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228

    Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January and February 2026! An opportunity that won’t last long. 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. Appreciate

    Debby McCaig COLDWELL BANKER REALTY

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 615 Dream Island Place Unit 201, Longboat Key, FL 34228
    615 Dream Island Place Unit 201, Longboat Key, FL 34228
    615 Dream Island Place Unit 201, Longboat Key, FL 34228
    /40

    $9,000 per month

    • 2 Beds
    • 2 Baths
    • 1,514 Sq Ft
    • Condo for Rent

    615 Dream Island Place Unit 201, Longboat Key, FL 34228

    Picturesque Water view of Sarasota Bay . The Harbour Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boatramp, kayak launch/storage, 3 tennis courts, covered parking and 400' of boat slips and bayfront. Features include over 1500 sq ft of livingspace in this end unit, high ceilings, Waterview available in all rooms, open floor plan, large enclosed balcony

    Agent Photo

    William Glade

    WILLIAM GLADE LIC. REAL ESTATE BROKER

    (941) 279-2178

    615 Dream Island Place Unit 201, Longboat Key, FL 34228
  • 3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228
    3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228
    3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228
    /35

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • 1,612 Sq Ft
    • Condo for Rent

    3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228

    AVAILABLE Dec. 2025-April 2026, 2 mos. min. This is a second floor walk up, two bedroom and den, two bathroom unit with over 1,600 square feet of interior living space. There is a private screened balcony/lanai and aa staircase entrance to the front door of the unit. The unit has partial water views from the living room, dining room, den, and the screened balcony and exterior open balcony/lanai

    Brenda Cozy COLDWELL BANKER REALTY

    3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228
  • 5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
    5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
    5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
    /30

    $7,750 per month

    • 3 Beds
    • 3 Baths
    • 1,672 Sq Ft
    • Condo for Rent

    5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

    Available Dec 20- April .Steps to the Sand – 3BR/3BA Beachfront Condo with Heated Pool & Spa | Longboat KeyEnjoy the best of beachfront living at 5611 Gulf of Mexico Drive, Unit 105 — a beautifully appointed three-bedroom, three-bath condo located in a boutique community directly on the beach. You’re just steps away from the soft sand and turquoise waters of the Gulf of Mexico.This

    Agent Photo

    William Glade

    WILLIAM GLADE LIC. REAL ESTATE BROKER

    (941) 207-4034

    5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
  • 806 Bayport Way Unit 806, Longboat Key, FL 34228
    806 Bayport Way Unit 806, Longboat Key, FL 34228
    806 Bayport Way Unit 806, Longboat Key, FL 34228
    /81

    $13,000 per month

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

    806 Bayport Way Unit 806, Longboat Key, FL 34228

    Discover a tranquil retreat at 806 Bayport Way, where coastal living meets sophisticated design. This exceptional property is ideally located near a private beach, providing residents with exclusive access to sun-soaked shores and beautiful ocean views.Upon entering, you’ll be greeted by a thoughtfully designed space that emphasizes both comfort and functionality. The kitchen features

    Agent Photo

    Antonietta Car

    KELLER WILLIAMS SUBURBAN TAMPA

    (941) 390-2885

    806 Bayport Way Unit 806, Longboat Key, FL 34228
  • 609 Bayport Way Unit 609, Longboat Key, FL 34228
    609 Bayport Way Unit 609, Longboat Key, FL 34228
    609 Bayport Way Unit 609, Longboat Key, FL 34228
    /79

    $13,000 per month

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

    609 Bayport Way Unit 609, Longboat Key, FL 34228

    ELEGANTLY PRESENTED! This bright and spacious property located just steps away from a private deeded beach is perfect for those who appreciate easy access to sun and sand. This residence boasts modern features and well-thought-out design, making it an ideal retreat for relaxation and comfort.The living area is characterized by an open layout that seamlessly connects to the kitchen,

    Agent Photo

    Antonietta Car

    KELLER WILLIAMS SUBURBAN TAMPA

    (941) 214-7905

    609 Bayport Way Unit 609, Longboat Key, FL 34228
  • 618 Bayport Way Unit 618, Longboat Key, FL 34228
    618 Bayport Way Unit 618, Longboat Key, FL 34228
    618 Bayport Way Unit 618, Longboat Key, FL 34228
    /66

    $6,050 per month

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

    618 Bayport Way Unit 618, Longboat Key, FL 34228

    Escape to paradise with a stay in this newly renovated 2-bedroom, 2-bath second floor condominium at Bayport Beach & Tennis Club on Longboat Key. Perfectly positioned for your dream beach getaway, this condo blends comfort, style and unbeatable amenities. Bright, modern, and welcoming, this condo has been thoughtfully updated with all the comforts of home, including a king-size bed in the primary

    Alzira Meierling KELLER WILLIAMS ON THE WATER S

    618 Bayport Way Unit 618, 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
    /42

    $10,000 per month

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

    2823 Gulf of Mexico Dr, Longboat Key, FL 34228

    Available beginning June 1st, 2026. Welcome to beachfront paradise on Longboat Key! This outstanding location offers a rare opportunity to enjoy coastal living with breathtaking views of the shoreline. Nestled along the pristine shores of Longboat Key, this three-bedroom, three-bathroom home invites you to experience the ultimate beachfront lifestyle. Relax under the sun, unwind to the sound of

    Michael Cella CELLA'S REAL ESTATE INC

    2823 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 100 Sands Point Rd Unit 223, Longboat Key, FL 34228
    100 Sands Point Rd Unit 223, Longboat Key, FL 34228
    100 Sands Point Rd Unit 223, Longboat Key, FL 34228
    /16

    $9,000 per month

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

    100 Sands Point Rd Unit 223, Longboat Key, FL 34228

    Location! Location! Location for Winter 2026 Rental Season!Gulf-front condominium complex “Sands Point” sits on the southernmost tip of Longboat Key. This location allows you to save time in traffic. Nestled adjacent to the iconic Longboat Key Resort, this Mid-Century modern 77-unit complex boosts impeccable views, gorgeous landscaping, a full-time maintenance crew and your own covered

    Diane Smith KELLER WILLIAMS ON THE WATER S

    100 Sands Point Rd Unit 223, 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
  • 5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    /71

    $9,000 per month

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

    5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

    Beautiful completely remodeled 2-bedroom, 2-bathroom Tropical Oasis on Longboat Key. Relax and enjoy the Florida lifestyle at its best with stunning gulf views from this gorgeous second floor retreat. Just steps to the beautiful white sand and warm gulf waters. Upgrades include new open floor plan with spacious rooms decorated in a soothing coastal color palette. Heightened ceilings, hardwood

    Roxanne Klopp JENNETTE PROPERTIES, INC.

    5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
  • 1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
    /40

    $12,500 per month

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

    1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228

    Available for 2026 and 2027 Season!! Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
  • 3390 Bayou Sound, Longboat Key, FL 34228
    3390 Bayou Sound, Longboat Key, FL 34228
    3390 Bayou Sound, Longboat Key, FL 34228
    /59

    $11,000 per month

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • House for Rent

    3390 Bayou Sound, Longboat Key, FL 34228

    **This is a 2 month minimum vacation rental**Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou section of Bay Isles, this

    Jennifer LeBlanc PRECISE REALTY CORP

    3390 Bayou Sound, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    /13

    $3,000 per month

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

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

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

    Teresa Ribaudo JENNETTE PROPERTIES INC

    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
  • 737 Bayport Way Unit D, Longboat Key, FL 34228
    737 Bayport Way Unit D, Longboat Key, FL 34228
    737 Bayport Way Unit D, Longboat Key, FL 34228
    /34

    $7,000 per month

    • 3 Beds
    • 2 Baths
    • 1,909 Sq Ft
    • Condo for Rent

    737 Bayport Way Unit D, Longboat Key, FL 34228

    BAYPORT TENNIS AND RAQUET CLUB has all the amenities including direct GULF Access. This tastefully furnished, one floor, three bedroom, two bathroom condo in the Bayport Beach and Tennis Club offers spacious living areas; Wonderful views of the Gulf of Mexico; and beautiful outdoor space. Large patios with tropical Gulf of Mexico views - perfect for morning coffee and sunset cocktails. Two

    Agent Photo

    Marianne LeBar

    ROSEBAY INTERNATIONAL REALTY, INC

    (941) 946-6594

    737 Bayport Way Unit D, 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
  • 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

    $4,500 per month

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

    4420 Exeter Dr Unit 208, Longboat Key, FL 34228

    2025 WINTER RENTAL- Available Oct 1, 2025- May 24, 2026. 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 slips MAY be available so you

    Armando Gonzalez AG REALTY SERVICES LLC

    4420 Exeter Dr Unit 208, 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

    $15,000 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
  • 825 Tarawitt Dr, Longboat Key, FL 34228
    825 Tarawitt Dr, Longboat Key, FL 34228
    825 Tarawitt Dr, Longboat Key, FL 34228
    /43

    $10,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,882 Sq Ft
    • House for Rent

    825 Tarawitt Dr, Longboat Key, FL 34228

    Welcome To 825 Tarawitt Drive! This Beautifully Renovated Waterfront Home Features 3 Bedrooms & 3 Washrooms. Located In The Quiet Community of Sleepy Lagoon. An Open Concept Floor Plan With Gorgeous Bay Views, Perfect For Entertaining! 125 Ft of Canal Frontage. Direct Access To Sarasota Bay. A Jet Ski Lift, Docking For Up To 30 Ft Boat, Outdoor Shower, Above Ground Spa, Spacious Outdoor Area For

    Ian Greenberg BRISTA REALTY LLC

    825 Tarawitt Dr, Longboat Key, FL 34228
  • 535 Sanctuary Dr Unit A102, Longboat Key, FL 34228
    535 Sanctuary Dr Unit A102, Longboat Key, FL 34228
    535 Sanctuary Dr Unit A102, Longboat Key, FL 34228
    /44

    $6,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,580 Sq Ft
    • Condo for Rent

    535 Sanctuary Dr Unit A102, Longboat Key, FL 34228

    Welcome to the Sanctuary. This beach front community is located inside the private gates of The Longboat Key Club. This 1st floor walk out residence that feels like a beach house will impress you with the space and tasteful decor/furnishings. Spend your time walking the private beach with the turquoise blue waters of the Gulf of Mexico along with a game of tennis, private fitness center, Olympic

    Jose Hugo Martinez KW COASTAL LIVING III

    535 Sanctuary Dr Unit A102, Longboat Key, FL 34228
  • 601 Longboat Club Rd, Longboat Key, FL 34228
    601 Longboat Club Rd, Longboat Key, FL 34228
    601 Longboat Club Rd, Longboat Key, FL 34228
    /11

    $15,500 per month

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

    601 Longboat Club Rd, Longboat Key, FL 34228

    Welcome to your serene escape in Longboat Key, Florida! This charming property offers an ideal location for those seeking a beachside lifestyle while still being close to essential amenities.Key property features include spacious bedrooms and bathrooms, providing ample space for relaxation and comfort. With several delightful restaurants nearby, you can easily enjoy the local cuisine.

    601 Longboat Club Rd, Longboat Key, FL 34228
  • 957 Spanish Dr N, Longboat Key, FL 34228
    957 Spanish Dr N, Longboat Key, FL 34228
    957 Spanish Dr N, Longboat Key, FL 34228
    /37

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • 1,399 Sq Ft
    • House for Rent

    957 Spanish Dr N, Longboat Key, FL 34228

    AVAILABLE STARTING MAY 1, 2026. WITH 3 MONTH MINUMUM RENTAL. FULL WATERFRONT NEWLY RENOVATED (internal new photos coming soon) and TURNKEY FURNISHED VILLA for SEASONAL OR ANNUAL LEASE. Seasonal Lease December to April is $7,000 per month (OR inquire about annual/off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Panoramic Bay Views - Spanish Main Yacht

    Norma Mladineo COLDWELL BANKER REALTY

    957 Spanish Dr N, Longboat Key, FL 34228
  • 534 Sutton Place, Longboat Key, FL 34228
    534 Sutton Place, Longboat Key, FL 34228
    534 Sutton Place, Longboat Key, FL 34228
    /47

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,278 Sq Ft
    • Condo for Rent

    534 Sutton Place, Longboat Key, FL 34228

    Available for immediate occupancy and incredible deal on leases through the end of 2025! GULF BEACH and BAY ACCESS! This single story end unit is the perfect place to escape the cold winter months and experience Island living on Longboat Key. This 2 bedroom, 2 bathroom condo has a spacious living and dining room combo, which opens to a bright and airy Florida room, perfect for relaxing or

    Tanner Frey KELLER WILLIAMS ON THE WATER S

    534 Sutton Place, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr Unit 107, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 107, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 107, Longboat Key, FL 34228
    /41

    $3,900 per month

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft
    • Condo for Rent

    3802 Gulf of Mexico Dr Unit 107, Longboat Key, FL 34228

    2-bed, 2-bath paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3802 Gulf of Mexico Dr Unit 107, Longboat Key, FL 34228
  • 601 Longboat Club Rd Unit 404S, Longboat Key, FL 34228
    601 Longboat Club Rd Unit 404S, Longboat Key, FL 34228
    601 Longboat Club Rd Unit 404S, Longboat Key, FL 34228
    /28

    $15,500 per month

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

    601 Longboat Club Rd Unit 404S, Longboat Key, FL 34228

    Experience refined coastal luxury in this exclusive beachfront residence, available for the 2026 season. Gulf views greet you in nearly every room, with designer finishes, a chef’s kitchen, spa-style primary suite, and private beach access. With bespoke interiors and elevated design, this privately released residence redefines coastal sophistication. Longboat Key Towers offers amenities including

    Agent Photo

    Irma Scherer

    COMPASS FLORIDA LLC

    (941) 206-3611

    601 Longboat Club Rd Unit 404S, Longboat Key, FL 34228
  • 640 Broadway St, Longboat Key, FL 34228
    640 Broadway St, Longboat Key, FL 34228
    640 Broadway St, Longboat Key, FL 34228
    /35

    $6,850 per month

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    640 Broadway St, Longboat Key, FL 34228

    Experience tranquility in this 2025 hurricane-rebuilt Longboat Key retreat, featuring 2 bedrooms, 2 bathrooms, and a versatile home office that doubles as a guest bedroom. Situated on a peaceful corner lot surrounded by lush tropical landscaping, this home combines modern luxury with relaxing coastal charm. Enter an open-concept layout with a spacious living room flowing into a modern kitchen

    Keith Gordon ADDVANTAGE

    640 Broadway St, Longboat Key, FL 34228
  • 2377 Harbour Oaks Dr, Longboat Key, FL 34228
    2377 Harbour Oaks Dr, Longboat Key, FL 34228
    2377 Harbour Oaks Dr, Longboat Key, FL 34228
    /64

    $8,000 per month

    • 3 Beds
    • 3 Baths
    • 2,487 Sq Ft
    • House for Rent

    2377 Harbour Oaks Dr, Longboat Key, FL 34228

    AVAILABLE - APRIL 2026 - ANNUAL RENTAL - Welcome home! Enjoy the serenity of this 3 bed, 3 bath, 2 car garage residence, located in Harbour Oaks within the gated community of Bay Isles in the heart of Longboat Key. This tastefully appointed home with open concept floor plan features vaulted ceilings and skylights which create an abundance of natural light throughout the home. The amazing gourmet

    Agent Photo

    Antonietta Car

    KELLER WILLIAMS SUBURBAN TAMPA

    (941) 336-7031

    2377 Harbour Oaks Dr, 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
    /25

    $11,000 per month

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

    1000 Longboat Club Rd, Longboat Key, FL 34228

    Welcome to your elevated coastal retreat on Longboat Key, located behind the gate of the prestigious Longboat Key Club. Available annually at $9,000/month or seasonally from November through April at $11,500/month, this fully renovated upper-floor residence offers refined living with sweeping Gulf and Bay views from two private balconies. Set within one of the island’s most exclusive beachfront

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    1000 Longboat Club Rd, Longboat Key, FL 34228

Showing Results 1 - 40, Page 1 of 4

Florida Manatee County Longboat Key

Homes for Rent in Longboat Key, FL

Frequently Asked Questions

What are the most popular neighborhoods in Longboat Key, FL for renters?
The most popular neighborhoods in Longboat Key, FL for renters are West Bradenton, El Conquistador, Indian Beach-Sapphire Shores, South Bradenton and Bayou Oaks.
What are the most popular zip codes in Longboat Key, FL for renters?
The most popular zip codes in Longboat Key, FL for renters include 34228, 34210, 34207, 34243 and 34234.
How to Rent a Home

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