147

Longboat Key, FL Homes for Rent

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  • 3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
    /20

    $2,995 per month

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

    3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228

    BAYSIDE CONDO WITH FULL BAY VIEWS – AVAILABLE FOR ANNUAL RENTAL Experience the best of Longboat Key living in this beautifully furnished 2-bedroom, 2-bath second-floor condo (with elevator access) located in the desirable Longboat Arms community. This turnkey residence offers stunning, unobstructed bay views and a well-designed open floor plan. The kitchen flows seamlessly into the dining and

    Heidi Thompson STRINGER MANAGEMENT INC

    3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
  • 747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
    747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
    747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
    /18

    $3,000 per month

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

    747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228

    GORGEOUS BAY VIEWS. Located in a quiet association of only eight units. Annual Unfurnished unit; open kitchen/living and dining area with master bedroom and tub/shower combo in en-suite bath. Canal views with private dock and boat lift (a boater and fisherman's dream). Drop a line outside your back door! Screened lanai with washer/dryer. Exterior parking immediately outside the unit with gas BBQ

    Gregory Koss WAGNER REALTY

    747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
  • 420 Firehouse Ct Unit 10, Longboat Key, FL 34228
    420 Firehouse Ct Unit 10, Longboat Key, FL 34228
    420 Firehouse Ct Unit 10, Longboat Key, FL 34228
    /17

    $4,000 per month

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

    420 Firehouse Ct Unit 10, Longboat Key, FL 34228

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

    Gregory Koss WAGNER REALTY

    420 Firehouse Ct Unit 10, Longboat Key, FL 34228
  • 3240 Gulf of Mexico Dr Unit B504, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit B504, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit B504, Longboat Key, FL 34228
    /52

    $6,500 per month

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

    3240 Gulf of Mexico Dr Unit B504, Longboat Key, FL 34228

    Seasonal / Short-Term Rental on Longboat Key /Vacation 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

    Cody Smith RENT SARASOTA

    3240 Gulf of Mexico Dr Unit B504, Longboat Key, FL 34228
  • 600 Russell St, Longboat Key, FL 34228
    600 Russell St, Longboat Key, FL 34228
    600 Russell St, Longboat Key, FL 34228
    /13

    $4,800 per month

    • 4 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • House for Rent

    600 Russell St, Longboat Key, FL 34228

    Remodeled Single-Family Home in Historic Longbeach Village Available for annual lease on the north end of Longboat Key, this beautifully updated 4-bedroom, 2-bath single-family home is located in the charming and historic Longbeach Village. The home features brand-new appliances, cabinetry, fixtures, and flooring throughout. Lawn maintenance is included in the monthly rent, and the utility room

    Gregory Koss WAGNER REALTY

    600 Russell St, Longboat Key, FL 34228
  • 3330 Gulf of Mexico Dr Unit 206D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 206D, Longboat Key, FL 34228
    3330 Gulf of Mexico Dr Unit 206D, Longboat Key, FL 34228
    /50

    $2,500 per month

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

    3330 Gulf of Mexico Dr Unit 206D, Longboat Key, FL 34228

    BAYSIDE CONDO WITH FULL BAY VIEW AVAILABLE IMMEDIATELY FOR ANNUAL RENTAL. This lovely 2nd floor (elevator access) 2-bedroom, 2-bath Turnkey Furnished condo in a small community with heated pool, tennis court and club house is a boater's Bayside dream! The interior is nicely appointed and the kitchen opens to the dining room and living area. Full length, Spacious enclosed lanai overlooking the Bay

    Teresa Ribaudo JENNETTE PROPERTIES INC

    3330 Gulf of Mexico Dr Unit 206D, Longboat Key, FL 34228
  • 1109 Gulf of Mexico Dr Unit ID1386020P, Longboat Key, FL 34228
    1109 Gulf of Mexico Dr Unit ID1386020P, Longboat Key, FL 34228
    1109 Gulf of Mexico Dr Unit ID1386020P, Longboat Key, FL 34228
    /20

    $9,337 per month

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    1109 Gulf of Mexico Dr Unit ID1386020P, Longboat Key, FL 34228

    The advertised rate of $9,337/month is the lowest available price, based on a 30 day(s) stay with a move-in date of March 31, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1109 Gulf of Mexico Dr Unit ID1386020P, Longboat Key, FL 34228
  • 1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    /45

    $9,000 per month

    • 2 Beds
    • 2.5 Baths
    • 1,569 Sq Ft
    • Condo for Rent

    1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

    Welcome to The Player’s Club on Longboat Key, a guard-gated Gulf-front community offering the ultimate blend of privacy, comfort, and coastal luxury. This fully furnished 2-bedroom, 2.5-bath residence located in building #1 is available for rent with a 3-month minimum per HOA guidelines and features direct Gulf views from the private balcony, perfect for enjoying breathtaking sunsets. Situated

    Rinat Sikdar COLDWELL BANKER REALTY

    1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
  • 730 Fox St, Longboat Key, FL 34228
    730 Fox St, Longboat Key, FL 34228
    730 Fox St, Longboat Key, FL 34228
    /40

    $7,500 per month

    • 3 Beds
    • 3 Baths
    • 1,350 Sq Ft
    • House for Rent

    730 Fox St, Longboat Key, FL 34228

    Serene and cozy home in beautiful Longboat Key Village, place where the old Florida meet the new one. Exquisite dining is couple minutes away (The Shore, Whitney’s or Mar Vista), as well as almost private Whitney Beach. Old times charm slows the time itself and once you enter the home, you will feel like on vacation. Three bedrooms, three bathrooms (two of them are en-suite), nice living room

    Linda Votrubova ENVISION REALTY PARTNERS LLC

    730 Fox St, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228
    /15

    $2,500 per month

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

    3802 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228

    This 1-bedroom, 1.5-bathroom property located at 3802 Gulf of Mexico Dr offers 784 square feet of living space. Beach is steps away from condo. The unit comes fully furnished and includes essential amenities such as air conditioning, a dishwasher, and in-unit washer/dryer. Residents can enjoy access to a fitness center and a pool, enhancing the overall living experience. The living room provides

    3802 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228
  • 2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /20

    $7,000 per month

    • 2 Beds
    • 2 Baths
    • 1,896 Sq Ft
    • Condo for Rent

    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    Absolutely stunning waterfront turnkey furnished rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if you prefer sunrises. This spacious 2/2 split floor plan has been fully renovated and is tastefully furnished. The property boasts amenities such as a beachfront pool, workout room, tennis court, and

    Christian Higgins ANDRE LECLAIR PROPERTIES LLC

    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
    /65

    $85,000 per month

    • 4 Beds
    • 4.5 Baths
    • 5,334 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228

    There are moments in life that stop you mid-thought. Moments so immersive that words struggle to keep up with what you’re feeling. This penthouse is one of those moments. Offered to the public for the first time, this four-bedroom residence sits high above the Gulf of Mexico, where light, water, and horizon become part of everyday life. A private elevator opens directly into the home, setting the

    Inbal August DOUGLAS ELLIMAN

    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
  • 554 Sutton Place, Longboat Key, FL 34228
    554 Sutton Place, Longboat Key, FL 34228
    554 Sutton Place, Longboat Key, FL 34228
    /26

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Condo for Rent

    554 Sutton Place, Longboat Key, FL 34228

    nnual Unfurnished Rental. Now available on beautiful Longboat Key! This spacious second-floor, two-bedroom residence combines comfort with classic coastal living, featuring a screened lanai and a large attached garage with ample storage. Wake up to stunning Bayfront sunrises and end your day with spectacular Gulf sunsets—all from your home in Sutton Place, a sought-after Gulf-to-Bay community

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    554 Sutton Place, Longboat Key, FL 34228
  • 3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228
    3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228
    3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228
    /55

    $3,300 per month

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

    3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228

    Stunning Bayfront and Marina views, this is a rare opportunity for a 1 bedroom, 1 bath, FURNISHED in a 55 + community on Longboat key . This is a beautifully designed and outfitted villa in the community of Twin Shores-located Mid Key(Close to both St. Armand's Circle and Anna Maria Island). Not only are you Sitting within Steps to Panoramic Views of the Bay, you have private DEEDED beach access

    Joseph Patoray FINE PROPERTIES

    3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228
  • 7147 La Lenaire Dr, Longboat Key, FL 34228
    7147 La Lenaire Dr, Longboat Key, FL 34228
    7147 La Lenaire Dr, Longboat Key, FL 34228
    /100

    $40,000 per month

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

    7147 La Lenaire Dr, Longboat Key, FL 34228

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

    Chase Moore SIGHT REAL ESTATE, LLC

    7147 La Lenaire Dr, Longboat Key, FL 34228
  • 700 Lands End Dr Unit 2, Longboat Key, FL 34228
    700 Lands End Dr Unit 2, Longboat Key, FL 34228
    700 Lands End Dr Unit 2, Longboat Key, FL 34228
    /70

    $10,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    700 Lands End Dr Unit 2, Longboat Key, FL 34228

    Experience refined coastal living in this fully furnished 4-bedroom, 4-bath residence ideally positioned within a private, gated enclave on Longboat Key, tucked beneath majestic banyan trees for exceptional privacy and tranquility. Designed to embrace Florida’s indoor-outdoor lifestyle, the home welcomes you through a stunning atrium entry, where natural light filters through lush tropical

    Jenn Spinelli THE AGENCY FL

    700 Lands End Dr Unit 2, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    /69

    $40,000 per month

    • 2 Beds
    • 2.5 Baths
    • 3,130 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228

    An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
  • 3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
    /28

    $2,500 per month

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

    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228

    1-bed, 1-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 E205, Longboat Key, FL 34228
  • 3111 Bayou Sound, Longboat Key, FL 34228
    3111 Bayou Sound, Longboat Key, FL 34228
    3111 Bayou Sound, Longboat Key, FL 34228
    /59

    $10,000 per month

    • 3 Beds
    • 5 Baths
    • 2,908 Sq Ft
    • House for Rent

    3111 Bayou Sound, Longboat Key, FL 34228

    LOCATION, LOCATION, LOCATION. BEAUTIFUL TURNKEY FURNISHED SINGLE FAMILY HOME available in the sought after community of Bay Isles is available to rent. This lovely light, bright 3 bedroom plus 3 bathroom, two half bathroom home boasts 2,908 square feet, double primary bedrooms, living room/dining room combination, loft/den space and much much more. The home has been fully painted and newly

    C. Alison Hunter JENNETTE PROPERTIES INC

    3111 Bayou Sound, Longboat Key, FL 34228
  • 2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228
    2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228
    2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228
    /24

    $10,500 per month

    • 2 Beds
    • 2 Baths
    • 1,651 Sq Ft
    • Condo for Rent

    2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228

    Stunning Gulf-Front Condo with Breathtaking Views at Islands West! Experience the epitome of coastal living in this exquisite 2-bedroom, 2-bathroom condominium on the 12th floor of Islands West, where full Gulf views become a part of your daily life. This beautifully furnished unit is not just a rental; it’s a lifestyle choice that offers you the chance to wake up to the soothing sounds of waves

    Jane Hunter JENNETTE PROPERTIES INC

    2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228
  • 601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228
    601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228
    601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228
    /65

    $9,000 per month

    • 2 Beds
    • 2 Baths
    • 1,458 Sq Ft
    • Condo for Rent

    601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228

    Your winter on the Gulf begins here. This is a rare opportunity to enjoy direct Gulf front living in a fully furnished seasonal residence, available January through March 2026. Tucked behind the private gates of Longboat Key, this premium condo blends the ease of coastal condo living with the comfort of generous, well-designed interiors. Mornings begin with soft sunrise views over the golf course

    Agent Photo

    Irma Scherer

    COMPASS FLORIDA LLC

    (941) 401-1756

    601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228
  • 513 Gunwale Ln, Longboat Key, FL 34228
    513 Gunwale Ln, Longboat Key, FL 34228
    513 Gunwale Ln, Longboat Key, FL 34228
    /61

    $14,750 per month

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

    513 Gunwale Ln, Longboat Key, FL 34228

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

    Marcia Benson Berkshire Hathaway Florida Realty

    513 Gunwale Ln, Longboat Key, FL 34228
  • 3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228
    /15

    $7,500 per month

    • 2 Beds
    • 2 Baths
    • 1,505 Sq Ft
    • Condo for Rent

    3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228

    Charming turnkey-furnished 2BR/2BA condo on the beautiful island of Longboat Key. Enjoy magnificent ocean views and spectacular sunsets from the private balcony. This well-appointed unit offers an ideal winter escape with comfortable living spaces and a serene coastal atmosphere. Building amenities include an in-ground heated pool, docking station, fish cleaning station, kayak/paddleboard rack,

    Juliana Brando Perez BROKER & BAKER INTERNATIONAL REALTY

    3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228
  • 4473 Gulf of Mexico Dr, Longboat Key, FL 34228
    4473 Gulf of Mexico Dr, Longboat Key, FL 34228
    4473 Gulf of Mexico Dr, Longboat Key, FL 34228
    /50

    $20,000 per month

    • 4 Beds
    • 4 Baths
    • 2,943 Sq Ft
    • Condo for Rent

    4473 Gulf of Mexico Dr, Longboat Key, FL 34228

    Experience Gulf-front living at its finest on the pristine shores of Longboat Key. This exceptional 4-bedroom, 4-bathroom coastal retreat spans nearly 3,000 sq. ft. and sits on over half an acre of direct beachfront property. Thoughtfully furnished with a mix of modern and timeless design, this two-story residence offers stunning water views from almost every room. ( Available FEB 11, 1 Month

    Agent Photo

    Curtis Andrews

    BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

    (941) 294-4305

    4473 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228
    3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228
    3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228
    /42

    $2,999 per month

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228

    LONGBOAT ARMS - This beautiful and professionally decorated apartment is ready to enjoy good times with zero afford. Ideal for work from home people, and those who value the benefit of have a prime space in front of the most panoramic surroundings. Live in the place where people takes vacation!

    Valeria Fucaraccio Benesch Brokers, LLC

    3320 Gulf of Mexico Dr Unit 208C, 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
    /26

    $9,800 per month

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

    640 Broadway St, Longboat Key, FL 34228

    Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024

    Christina Vescovo LPT REALTY, LLC

    640 Broadway St, Longboat Key, FL 34228
  • 701 Broadway St, Longboat Key, FL 34228
    701 Broadway St, Longboat Key, FL 34228
    701 Broadway St, Longboat Key, FL 34228
    /33

    $14,400 per month

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

    701 Broadway St, Longboat Key, FL 34228

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

    Christina Vescovo LPT REALTY, LLC

    701 Broadway St, Longboat Key, FL 34228
  • 4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228
    4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228
    4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228
    /23

    $5,000 per month

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

    4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228

    Desirable Furnished One Bedroom 1 1/2 Bathroom Condo on Longboat Key. It is on the 7th floor with a 20 ft lanai that has an outstanding view of the beach and the Gulf of America. The building is one of the closest to the beach with access within few feet of the building, is well managed, has a salt water heated pool & recreational area with gas grill. There is an exercise center, public kitchen,

    David Gardner PINEBROOK IRONWOOD REALTY

    4401 Gulf of Mexico Dr Unit 703, 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
    /77

    $4,650 per month

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

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

    AVAILABLE NOW!!Longboat Key vacation rental! You will love this wonderfully updated and tastefully furnished two-bedroom, two-bath third-floor condominium at the Beach Harbor Club. Located mid-key, this is a great resort-style community with deeded beach access just across the Gulf of Mexico, a beautiful heated community pool, access to the Bay for fishing and kayaking, and community grills and

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    3806 Gulf of Mexico Dr Unit C310, 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
    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
  • 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
  • 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
  • 4780 Gulf of Mexico Dr, Longboat Key, FL 34228
    4780 Gulf of Mexico Dr, Longboat Key, FL 34228
    4780 Gulf of Mexico Dr, Longboat Key, FL 34228
    /69

    $7,000 per month

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

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228

    Booking Now for the 2027 Season! Completely Booked for the remainder of the 2026 season. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including

    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

    $8,495 per month

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

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

    available February and March 2026. And January-March 2027 due to cancellation. BRING YOUR BOAT, deeded private boat slip that accommodates up to a 60 ft boat INCLUDED! Picturesque Waterview of Sarasota Bay and easy access by boat to the Gulf. Recently renovated with high end appliances, finishes and designer furniture. The Harbor Villa Club Complex consists of 38 condos in a 3-story plus pool,

    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

    $7,100 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

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, South Bradenton, Bayou Oaks and Indian Beach-Sapphire Shores.
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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