126

Longboat Key, FL Homes for Rent

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  • 842 Bayport Way Unit 842, Longboat Key, FL 34228
    842 Bayport Way Unit 842, Longboat Key, FL 34228
    842 Bayport Way Unit 842, Longboat Key, FL 34228
    /28

    $5,000 per month

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

    842 Bayport Way Unit 842, Longboat Key, FL 34228

    AVAILABLE APRIL 1ST 2025. 6 MONTH STAY $5000 PER MONTH - NO TAX/ PRIME SEASONAL RATES: Jan 1st to April 30th @ $8,500 per month plus 13% sales tax. For shorter off season stay - 3 month minimum - rental rate is $5,000 plus tax. Property may also be rented annually at $5,000 per month - no tax, includes all electricity, shorter terms $75.00 for electric. ***** 1,200 ft. of private beach (with

    Shirley Cuddy REALTY SERVICES INC

    842 Bayport Way Unit 842, 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
  • 3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    /30

    $2,500 per month

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

    3810 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

    Welcome to Beach Harbor Club, a hidden gem on Longboat Key that offers the best of both worlds—spanning from the Gulf of Mexico to Sarasota Bay! This charming one-bedroom, one-bath condo is perfect for seasonal getaways or as an investment property. Located just a 1-minute walk to both the beach and bay, it’s your gateway to coastal living at its finest.Highlights of the Community:Private

    Andrey markov ANMARK REALTY LLC

    3810 Gulf of Mexico Dr Unit 104, 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
    /35

    $4,000 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 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

    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
  • 3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    /62

    $8,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228

    Luxury Seasonal or Annual Rental in Luxurious Grand Bay Community – Longboat KeyExperience unparalleled luxury and breathtaking views from this stunning 9th-floor condominium at Grand Bay. From sunrise to sunset, enjoy panoramic vistas from your private wraparound balcony or through the floor-to-ceiling sliding glass doors that frame the living room. Designed for both relaxation and

    Alyssa Cromie NEXTHOME EXCELLENCE

    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
    /20

    $15,500 per month

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

    1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228

    Special offer!Get $2000 (total) off for leases of 4+ months.Amazing Gulf front location in Longboat Key (LBK), FloridaThis two bedroom, 2 1/2 Bath condo (plus pull-out couch) is completely renovated and remodeled. All brand-new furnishings, appliances, counters, cabinets, cookware, linens, etc. This ninth-floor unit at the luxurious Promenade offers the best of everything.

    Natasha Shevchuk 1ST PREMIER INTL PROPERTIES

    1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
  • 512 Gunwale Ln, Longboat Key, FL 34228
    512 Gunwale Ln, Longboat Key, FL 34228
    512 Gunwale Ln, Longboat Key, FL 34228
    /48

    $11,000 per month

    • 3 Beds
    • 2 Baths
    • 1,861 Sq Ft
    • House for Rent

    512 Gunwale Ln, Longboat Key, FL 34228

    Location, location, location. This furnished rental offers the perfect blend of convenience and waterfront living. Enjoy direct access to the Gulf of Mexico with a private dock and boat lift, take a walk on the pristine white sand beaches or relax and unwind in the pool. Nestled in a prime location just minutes from St. Armands Circle, you'll have access to the best dining, shopping and

    Marcia Benson Berkshire Hathaway Florida Realty

    512 Gunwale Ln, Longboat Key, FL 34228
  • 5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    /22

    $9,500 per month

    • 2 Beds
    • 2 Baths
    • 1,346 Sq Ft
    • Condo for Rent

    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228

    AVAILABLE MARCH 2025 - APRIL 10 $7,000 30 day lease. Looking for a Beach front vacation in warm sunny Florida in a condo where you walk out onto the deck and directly onto the beach? Stay in this 2 bedroom , 2 bath condo in Salty Acres with 2 parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and is in excellent condition. It must be a monthly rental. $6,950 a

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
  • 511 Bayport Way Unit 511, Longboat Key, FL 34228
    511 Bayport Way Unit 511, Longboat Key, FL 34228
    511 Bayport Way Unit 511, Longboat Key, FL 34228
    /38

    $5,499 per month

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

    511 Bayport Way Unit 511, Longboat Key, FL 34228

    RARELY AVAILABLE, LONGBOAT KEY 7-12 MONTH LEASE OFFERING FURNISHED RENTAL with Unparalleled Gulf of Mexico views! Marvel at the Gulf's turquoise waters and gorgeous sunsets from anywhere in this residence. This beautifully remodeled condo welcomes you with an open floor plan, featuring an expansive living/dining/kitchen combination and a main lanai to boast. The spacious master bedroom features a

    Patrick Ritchey RE/MAX ALLIANCE GROUP

    511 Bayport Way Unit 511, 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

    $3,000 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
  • 990 Bogey Ln, Longboat Key, FL 34228
    990 Bogey Ln, Longboat Key, FL 34228
    990 Bogey Ln, Longboat Key, FL 34228
    /57

    $7,500 per month

    • 3 Beds
    • 2 Baths
    • 1,962 Sq Ft
    • House for Rent

    990 Bogey Ln, Longboat Key, FL 34228

    Introducing a charming 3-bedroom, 2-bathroom single family home located in the prestigious Country Club Shores of Longboat Key, FL. This fully furnished property boasts deeded beach access, perfect for enjoying the sun and surf just steps away from your front door. The fenced backyard provides privacy and a great space for outdoor entertaining. Situated just 2.8 miles from the vibrant St. Armands

    Ray Shope ROSEBAY INTERNATIONAL REALTY, INC

    990 Bogey Ln, Longboat Key, FL 34228
  • 1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
    /32

    $5,500 per month

    • 2 Beds
    • 2.5 Baths
    • 1,626 Sq Ft
    • Townhouse for Rent

    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228

    Experience luxury and tranquility in this stunning unit at 1928 Harbourside Dr, Unit 1402, located within the Bay Isles community on Longboat Key. This residence offers a spacious layout designed for comfort and style, with access to top-tier amenities including a nearby marina, private golf course, swimming pool, and spa. Enjoy the privacy and security of this exclusive gated community, all just

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
  • 2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    /34

    $5,500 per month

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

    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228

    Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    2012 Harbourside Dr Unit 2102, 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
    /32

    $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

    Here's an opportunity to become immersed in the laid back island lifestyle. Available for a six month rental starting late June through January, this nicely updated condo is located on the Bay side of popular Portobello with deeded beach access directly across the road. There's plenty of room for everyone to spread out in this fourth floor condo with an open, split floor plan and a screened lanai

    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! 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 covered parking. The Master suite features

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
  • 448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
    448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
    448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
    /30

    $11,700 per month

    • 2 Beds
    • 2 Baths
    • 1,474 Sq Ft
    • Condo for Rent

    448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228

    LONGBOAT KEY SOUTH...This is a 3 bedroom, 2 bathroom, end unit on the main floor which makes this unit light & bright with extra windows. The interior is decorated tastefully with warm neutral colors. Beautiful views of Sarasota Bay. Fully equipped kitchen which features stainless appliances, granite countertops and wood cabinets. There is a king size bed in the main bedroom and a queen bed in

    Teresa Ribaudo JENNETTE PROPERTIES INC

    448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228
  • 4410 Exeter Dr Unit 204, Longboat Key, FL 34228
    4410 Exeter Dr Unit 204, Longboat Key, FL 34228
    4410 Exeter Dr Unit 204, Longboat Key, FL 34228
    /68

    $3,300 per month

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

    4410 Exeter Dr Unit 204, Longboat Key, FL 34228

    AVAILABLE STARTING MAY 1ST FOR UP TO A 9 MONTH LEASE. MINIMUM 1 MONTH LEASE REQUIRED. SPECTACULAR VIEWS IN THE LUXURY OF LONGBOAT HARBOUR! LUXURY LIVING IN THOS RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER COMMUNITY ON LONGBOAT KEY. This gorgeous 2nd floor condo comes turnkey furnished and located a short distance from St. Armand’s circle. When you walk in you will be blow away

    Brigette Marcus NEXTHOME EXCELLENCE

    4410 Exeter Dr Unit 204, 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

    $10,000 per month

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

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

    Available Now! Absolutely stunning waterfront turnkey furnished short term 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,

    Christian Higgins ANDRE LECLAIR PROPERTIES LLC

    2675 Gulf of Mexico Dr Unit 302, 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
    /38

    $4,500 per month

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

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228

    This immaculate 2-bedroom, 2-bath ground-floor villa located in the highly sought-out community of Windward Bay has peek-a-boo views of the Gulf. Turnkey furnished with one carport at your front door. The community of Windward Bay is pristine. There is private deeded beach access just across the street, two public beach access, two marinas BBQ grills, 1/2 mile of walking trails, two heated pools,

    Joseph Stephens ONE STEP AHEAD REALTY INC

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 657 Cedars Ct Unit 657, Longboat Key, FL 34228
    657 Cedars Ct Unit 657, Longboat Key, FL 34228
    657 Cedars Ct Unit 657, Longboat Key, FL 34228
    /43

    $4,000 per month

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

    657 Cedars Ct Unit 657, Longboat Key, FL 34228

    Annual turnkey furnished renovated 1/2 close to pool, bay and beach. Enjoy morning coffee from your peaceful balcony retreat in this private townhouse located mid-island in the popular Cedars East Tennis Resort. Spacious, bright and pet-friendly, this 1-bedroom, 2-bath townhome has a large open dining and living room, with a peaceful screened balcony. 1st level: enclosed parking garage; 2nd

    Henry Rossi RENT SARASOTA

    657 Cedars Ct Unit 657, 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 JANUARY through MARCH 2026 with the option to include 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

    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

    $8,500 per month

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

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

    BEAUTIFULLY RENOVATED VACATION RENTAL: 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
  • 3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    /49

    $3,750 per month

    • 2 Beds
    • 2 Baths
    • 1,175 Sq Ft
    • Condo for Rent

    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

    Escape to this 2-bed, 2-bath penthouse paradise at Beach Harbor Club. The penthouse features more spacious living and dining areas with stunning Gulf views. The unit includes an outside patio, as well as a washer/dryer. Beach Harbor Club is a beach to bay community and has a bundle of awesome amenities. Enjoy exclusive beach access, complete with grills, showers, and beach/lounge chairs. Take a

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
  • 501 Reclinata Dr, Longboat Key, FL 34228
    501 Reclinata Dr, Longboat Key, FL 34228
    501 Reclinata Dr, Longboat Key, FL 34228
    /83

    $6,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,784 Sq Ft
    • House for Rent

    501 Reclinata Dr, Longboat Key, FL 34228

    One or more photo(s) has been virtually staged. Introducing a stunning 3 bedroom, 3.5 bath, 2-story home, perfectly nestled on the tranquil north end of Longboat Key. This fully renovated gem is a true paradise, offering a blend of luxury and comfort. Step inside and be captivated by the elegant design and meticulous attention to detail throughout. The spacious living areas are bathed in natural

    Robert Louloudes STARZ REAL ESTATE, LLC

    501 Reclinata Dr, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
    /41

    $11,800 per month

    • 2 Beds
    • 2.5 Baths
    • 1,484 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228

    AVAILABLE JANUARY & FEBRUARY 2025. 2 bedroom 2 bath with office. Enjoy fantastic gulf views from your private lanai, living room, kitchen and master bedroom. Many upgrades have already been very tastefully made to this residence. Unit fitted with electric hurricane shutters, tankless hot water heater, sound system in every room, darkening shades and solar shades in master bedroom plus

    Brenda Cozy COLDWELL BANKER REALTY

    4325 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
  • 1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    /77

    $3,650 per month

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

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228

    ANNUAL RENTAL AVAILABLE 4/1/25! LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the condo has to give with the natural light that floods through

    Brigette Marcus NEXTHOME EXCELLENCE

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
  • 700 Hideaway Bay Ln, Longboat Key, FL 34228
    700 Hideaway Bay Ln, Longboat Key, FL 34228
    700 Hideaway Bay Ln, Longboat Key, FL 34228
    /53

    $17,500 per month

    • 4 Beds
    • 4.5 Baths
    • 3,306 Sq Ft
    • House for Rent

    700 Hideaway Bay Ln, Longboat Key, FL 34228

    Enjoy the relaxed luxury living in Hideaway Bay, a lovely private community of only 18 single-family homes on Longboat Key. This 4BR/4.5 B home Nestled on a waterfront canal near the serene shores of Longboat Key, 700 Hideaway Bay offers an exquisite retreat in the heart of Florida’s Gulf Coast. This stunning property is a sanctuary of luxury and tranquility. The residence boasts elegant

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    700 Hideaway Bay Ln, Longboat Key, FL 34228
  • 6979 Longboat Dr S, Longboat Key, FL 34228
    6979 Longboat Dr S, Longboat Key, FL 34228
    6979 Longboat Dr S, Longboat Key, FL 34228
    /30

    $10,000 per month

    • 3 Beds
    • 2 Baths
    • 1,454 Sq Ft
    • House for Rent

    6979 Longboat Dr S, Longboat Key, FL 34228

    This stunning property on Longboat Key is a true garden oasis, with butterflies fluttering around the lush landscaping and a private heated pool to relax in. The spacious lanai is perfect for al fresco dining, and the fully renovated kitchen boasts top-of-the-line appliances including a Wolf stove. The bedrooms and bathrooms have also been beautifully updated, with a brand new king-size bed in

    Rinat Sikdar COLDWELL BANKER REALTY

    6979 Longboat Dr S, 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
    /49

    $5,000 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

    Daniel Goldman COMPASS FLORIDA LLC

    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • 3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    /14

    $6,000 per month

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

    3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

    PORTOBELLO - SHORT TERM RENTAL - 2 Bedrooms, 2 Baths in the #1 Beach of Florida, white quartz sand and dreamy sunsets Ample and chic apartment fully furnished to enjoy vacation time. 2 Parking spots

    Valeria Fucaraccio Benesch Brokers, LLC

    3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
  • 3235 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    3235 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    3235 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
    /22

    $3,700 per month

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

    3235 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

    PORTOBELLO - BEACH FRONT Elevate your quality life, Working from home? Retired? relax and enjoy this wonderful two bedrooms, two full baths apartment in front of the #1 beach in Florida, white quartz sands and dreamy sunsets. 2 Parking spots.

    Valeria Fucaraccio Benesch Brokers, LLC

    3235 Gulf of Mexico Dr Unit 304, 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
    /36

    $2,900 per month

    • 2 Beds
    • 2 Baths
    • 1,154 Sq Ft
    • Condo for Rent

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

    LONGBOAT ARMS . Working from home ? Retired?, Elevate your quality life, relax and enjoy this wonderful and quiet two bedrooms, two full baths apartment surrounding the #1 beach in Florida, white quartz sands and dreamy sunsets, 2 parking spots. 6 Months min. rental.

    Valeria Fucaraccio Benesch Brokers, LLC

    3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228
  • 5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    /51

    $5,000 per month

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

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    Available rental for July 15, 2025-October 2025 ONLY! 60 Day Minimum Lease. Fully remodeled and impeccably furnished with Gulf views on Longboat. Situated on the top floor, this 2 bedroom, and 2 bath residence presents coveted views of the beach and Gulf of Mexico! Take note, that the clear, Caribbean blue waters and white sand beaches are not upstaged by the finishes in this redesigned floor

    Scott Nold TNG PROPERTY MANAGEMENT

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • 5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228
    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228
    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228
    /39

    $14,000 per month

    • 3 Beds
    • 2 Baths
    • 1,675 Sq Ft
    • Condo for Rent

    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228

    DIRECTLY on the GULF. WITH PRIVATE BEACH .Be Prepared for style, relaxation and Longboat luxury. This stunning boutique condominium renovated in 2024 and located on Longboat Key's Gulf of Mexico Beach. Its newly designed layout emphasizes the magnificent ocean view throughout its open floor plan that is visible from the time you walk in the door, through the beautiful dining area, upscale

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228
  • 1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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    $15,000 per month

    • 3 Beds
    • 3 Baths
    • 1,710 Sq Ft
    • Condo for Rent

    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

    LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room

    C. Alison Hunter JENNETTE PROPERTIES INC

    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    /39

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228

    Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL

    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
  • 3210 Bayou Sound, Longboat Key, FL 34228
    3210 Bayou Sound, Longboat Key, FL 34228
    3210 Bayou Sound, Longboat Key, FL 34228
    /14

    $11,000 per month

    • 3 Beds
    • 3 Baths
    • 3,171 Sq Ft
    • House for Rent

    3210 Bayou Sound, Longboat Key, FL 34228

    Unique 3 bedrooms and 3 bathrooms property in Longboat Key ready for immediate occupancy, all repairs are done. Bay Isles community has a lot to offer to prospective long term renters. Set in The Bayou behind 2 security gates. House was remodeled in the last couple of years. Fully furnished with contemporary decoration and furniture. Kitchen equipped with high end stainless steel appliances and

    Gary Dontsov LONDON FOSTER REALTY

    3210 Bayou Sound, Longboat Key, FL 34228
  • 1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    /46

    $11,250 per month

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Condo for Rent

    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

    Rented for season of 2025. Direct Beachfront, Longboat Key remodeled 2/2 Condo in Beachplace. Beautiful Beachplace is a gated community located on the southern end of Longboat Key, FL. Our unit is located in building nine, 4th floor, with a green belt area just to the north, the beach to the west, tennis courts to the East and few steps to the pool/library,rec and workout room. It is one of four

    Jennifer LeBlanc PRECISE REALTY CORP

    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
  • 3808 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    /30

    $6,900 per month

    • 3 Beds
    • 3 Baths
    • 2,544 Sq Ft
    • Condo for Rent

    3808 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228

    LONGBOAT KEY...LUXURY CONDO. Three bedroom, three bathroom condo. Very spacious with 2544 Sq. Ft. open floor plan. All three bathrooms have marble countertops and beautiful fixtures. The views over the boat docks is incredible. Huge rooms with plenty of space to entertain family and friends. The kitchen boasts granite countertops, newer cabinets and all stainless steel appliances. Hurricane proof

    Teresa Ribaudo JENNETTE PROPERTIES INC

    3808 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    /37

    $14,000 per month

    • 2 Beds
    • 2 Baths
    • 1,598 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

    Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL

    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

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