117

Longboat Key, FL Condos for Rent

Section Image
  • 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
  • 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
  • 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
  • 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
    /50

    $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
  • 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

    $8,000 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
  • 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

    $7,000 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

    $12,000 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
  • 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
  • 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

    $6,000 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. 2025 WINTER RENTAL- Not Available 01/21/26-2/21/26. 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

    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

    $12,000 per month

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

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

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

    Teresa Ribaudo JENNETTE PROPERTIES INC

    2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
  • 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
  • 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
  • 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 2026! 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
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /19

    $7,500 per month

    • 2 Beds
    • 2 Baths
    • 1,445 Sq Ft
    • Condo for Rent

    Unlisted Address

    NOW AVAILABLE FOR THE 2026 SEASON: Take a 60 second stroll across the street to the Gulf Beach from this Very Popular and Beautiful Renovated unit with an onsite heated pool and outdoor shower. This is a small community of only 4 units, cozy and intimate seasonal enjoyment. Enjoy Peek-a-views of the gulf beach right from the Living Room Sofa, or Brand New Private Wrap Around Balcony to enjoy

    Monique Holston-Greene COLDWELL BANKER REALTY

    Unlisted Address
  • 1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    /46

    $7,500 per month

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Condo for Rent

    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228

    Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
  • 1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
    1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
    1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
    /23

    $5,000 per month

    • 2 Beds
    • 2.5 Baths
    • 1,590 Sq Ft
    • Condo for Rent

    1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228

    Turnkey Townhouse on Longboat Key – Resort-Style Living!Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy.Enjoy private beach access to the stunning Gulf of Mexico, take

    Victoria Campbell LPT REALTY LLC

    1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
    /44

    $15,000 per month

    • 2 Beds
    • 2.5 Baths
    • 2,135 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

    Gorgeous gulf front vacation rental! Be the first to lease this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the open floor plan with a

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
  • 3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
    /48

    $2,495 per month

    • 2 Beds
    • 2 Baths
    • 1,007 Sq Ft
    • Condo for Rent

    3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228

    GULF to BAY ACCESS! Beach Harbour Club Welcomes you home to Island living. New to the rental market is this second floor condo featuring 2 bedrooms, 2 bathrooms, dining room / family room combination and a full size washer / dryer located in the utility room. Beach Harbour Club is centrally located in the middle of Long Boat Key and this condo is a turn key fully furnished ANNUAL rental. There is

    Edward Whitaker PERLA'S PROPERTIES, LLC

    3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    /47

    $6,000 per month

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

    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    Furnished beachfront vacation rental! This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is located in a smaller building, on an uncrowded segment of beach that can often be enjoyed in complete solitude. The unit was recently upgraded with a new washer/dryer, luxury vinyl flooring in the

    Daniel Goldman COMPASS FLORIDA LLC

    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • 380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
    380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
    380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
    /57

    $7,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,490 Sq Ft
    • Condo for Rent

    380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228

    Available now through the end of the year, off season only. Welcome to coastal elegance at Tangerine Bay Club, where sweeping bay views set the stage for an exceptional lifestyle. This furnished residence captures the charm of a single-family home with its private courtyard entrance while offering all the benefits of resort-style community living. This comfortable three-bedroom retreat features a

    Maureen Plichta STRINGER MANAGEMENT INC

    380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
    /100

    $25,000 per month

    • 1 Bed
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228

    Welcome Serenity Oasis, your paradise at The Residences at the St.?Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat.The expansive living room

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1591 Gulf of Mexico Dr Unit 315, 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
  • 2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    /21

    $45,000 per month

    • 4 Beds
    • 4.5 Baths
    • 3,961 Sq Ft
    • Condo for Rent

    2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

    Step into unparalleled elegance with this stunning 4-bedroom, 4.5-bathroom beachfront condo, where modern sophistication meets coastal serenity. This exclusive residence boasts floor-to-ceiling windows that fill the space with natural light and showcase breathtaking panoramic Gulf views from every angle. Designed for ultimate privacy and comfort, the unit features direct elevator access, a

    Larry Starr SVN COMMERCIAL ADVISORY GROUP

    2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
  • 2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
    2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
    2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
    /46

    $7,000 per month

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

    2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228

    RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach! Start living the island lifestyle in this beautifully updated, furnished 2-bedroom, 2-bath condo at the Islander Club on South Longboat Key! This turnkey rental is ready for immediate enjoyment—just bring your suitcase. Enjoy a bright, open layout with floor-to-ceiling hurricane

    Michele Conn PREFERRED SHORE LLC

    2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
  • 1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
    /85

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 928 Sq Ft
    • Condo for Rent

    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228

    LONGBOAT KEY "SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE. AVAILABLE DEC 2025 & JAN 2026 AT $3,000/MONTH. UTILITIES INCLUDED. 2 MONTH MINIMUM REQUIRED PER HOA.BOOKED FOR FEB-APRIL 2026. Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the

    Chrissie Cummings JENNETTE PROPERTIES INC

    1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    /45

    $6,500 per month

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

    3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228

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

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
  • 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
    /56

    $12,000 per month

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

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

    OPEN for 2026 SEASON Reservation. LBK SARASOTA LUXURY RENTAL in Paradise at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY views. Check in and enjoy the spectacular SUNSETS ON THE GULF of MEXICO. Like NEW, this beautifully designed three bedroom luxury residence has just completed a major updating remodeling with all new designer furniture and

    Patrice Ivan WAGNER REALTY

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    /33

    $18,000 per month

    • 2 Beds
    • 2.5 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

    The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet kitchen showcases Wolf and Sub-Zero

    Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
  • 3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    /60

    $4,000 per month

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

    3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

    1-bed, 1-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

    3810 Gulf of Mexico Dr Unit 304, 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

    $32,000 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
  • 840 Bayport Way Unit 840, Longboat Key, FL 34228
    840 Bayport Way Unit 840, Longboat Key, FL 34228
    840 Bayport Way Unit 840, Longboat Key, FL 34228
    /53

    $4,200 per month

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

    840 Bayport Way Unit 840, Longboat Key, FL 34228

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

    Shirley Cuddy REALTY SERVICES INC

    840 Bayport Way Unit 840, Longboat Key, FL 34228
  • 1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
    /45

    $7,000 per month

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

    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228

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

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
    /38

    $4,000 per month

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

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

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

    nicoletta buonaccordo ALTIS REALTY

    3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /34

    $2,500 per month

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

    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

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

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
  • 3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
    /31

    $3,900 per month

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

    3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228

    Open now through end of January. Have your holidays on the Key with HEATED POOL, amazing sunsets, perfect tennis weather and the pristine beach just steps away. This well appointed and updated condo with an open open, split floor plan has plenty of space and a huge screened lanai that spans the entire unit. The primary bedroom has TWO KING SIZED beds, a huge walk-in closet and ensuite bath. The

    Rosemarie McKee COLDWELL BANKER REALTY

    3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
  • 4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /30

    $7,000 per month

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

    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    SEASONAL/VACATION RENTAL! AVAILABLE FOR 2026 SEASON! CALL TODAY! Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, large walk-in closets and

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
  • 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 APRIL 2026** 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 on the beach,

    Norma Mladineo COLDWELL BANKER REALTY

    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
  • 4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    /35

    $6,500 per month

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

    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

    AVAILABLE Jan - Mar 2026!!! : 1 month minimum. Stunning Gulf views and incredible sunsets await you from this JUST completely renovated 2 bedroom, 2 bath condo on Longboat Key. You’ll fall in love with the contemporary soft-palette, coastal style! The open layout offers a seamless blend of kitchen, dining and living space, perfect for entertaining and relaxing. The gourmet kitchen features

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

Showing Results 41 - 80, Page 2 of 3

Florida Manatee County Longboat Key

Condos for Rent in Longboat Key, FL

How to Rent a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group