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Long Boat Key

One of the most popular communities provided by Michael Graf

Long Boat Key

About Long Boat Key

Longboat Key, Florida, is a tranquil paradise that offers the perfect blend of luxurious living and natural beauty. Nestled between the sparkling waters of the Gulf of Mexico and Sarasota Bay, residents enjoy stunning beaches, picturesque sunsets, and a laid-back, island lifestyle. The community is renowned for its upscale amenities, including gourmet dining, boutique shopping, and world-class golf courses, all while maintaining a quaint, small-town charm. With year-round warm weather, ample outdoor recreational activities, and a strong sense of community, Longboat Key is an ideal place for both relaxation and adventure, making it a highly desirable destination for those seeking a serene coastal retreat.
One of the most popular communities provided by Michael Graf
511
# of Listings
2
Avg # of Bedrooms
$856
Avg. $ / Sq.Ft.
$1,506,912
Med. List Price

Browse Long Boat Key Real Estate Listings

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511 Properties Found. Page 27 of 35.

Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home features four bedrooms, a spacious bonus room, and a dedicated office, providing plenty of space for both relaxation and productivity. The private heated pool and spa create a resort-style retreat in your own backyard, surrounded by lush, meticulously maintained landscaping. Inside, the gourmet kitchen boasts modern appliances, ample counter space, and an open layout ideal for entertaining. Sunlit living areas with high-end finishes enhance the home’s beauty and warmth. A boater’s paradise, this home includes an 11,000 lb boat lift for effortless access to Sarasota Bay and the Gulf of Mexico. Located just minutes from pristine beaches, championship golf courses, and the upscale shopping and dining of St. Armands Circle, this home offers the perfect blend of luxury and convenience. NO storm damage! Available for an annual rental. Contact us today to schedule a private showing! NO storm damage!
#A4643954

LONGBOAT KEY

531 BIRDIE LANE

4 Beds

3 Baths

3,268 Sq.Ft.

$14,000

MLS#: A4643954

GORGEOUS INSIDE! This beautifully remodeled ground floor, corner unit, features 3 bedrooms, 2 bathrooms with an open concept floor plan. This home welcomes you into an expansive Living/Dining/Kitchen and offers plenty of natural light. In addition, it boasts a generous size master bedroom with en suite bathroom and an alcove that accommodates a desk and seating area. Bayport Beach & Tennis Club is an amenity-rich community at sea's edge in the heart of Longboat Key. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, fitness center, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with full kitchen, hosts a number of social activities. Simply walk across the street to the private beach on the Gulf of Mexico for a morning of beachcombing, surf casting or memorable sunsets. Just minutes away from shopping, dining and entertainment in St.Armand' Circle and downtown Sarasota. Please contact Agent for availability
#T3488652

LONGBOAT KEY

716 BAYPORT WAY 716

3 Beds

2 Baths

2,134 Sq.Ft.

$13,500

MLS#: T3488652

New on site 1 day ago
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 and mesmerizing sunsets right from your home. As you enter this light and bright condo, you’ll be greeted by panoramic Gulf views that stretch as far as the eye can see. The large windows in both bedrooms and the living area flood the space with natural light, creating a warm and inviting atmosphere. Retreat to the spacious master suite, a true sanctuary featuring a plush King-sized bed and a generously sized closet. The ensuite bathroom is your personal spa, complete with a large walk-in shower that invites you to unwind after a day at the beach. Your guests will feel right at home in the cozy guest bedroom, featuring a pullout sofa bed(High end Tempur-Pedic with topper), an office desk, and equally stunning beach views, making it ideal for guests or remote work. The guest bath, with a convenient shower/tub combo, ensures that everyone has their own space to relax. The updated kitchen is a chef's dream, equipped with sleek stainless steel appliances and elegant granite countertops. Whether you’re whipping up a quick breakfast or preparing a gourmet dinner, this space is both functional and stylish. For those evenings when you prefer to dine out, you’re just a stone's throw away from some of the area’s hottest dining spots. Islands West offers a wealth of community amenities designed for your enjoyment. Take a dip in the large heated lap pool or unwind in the soothing spa. Stay active in the fitness room, host gatherings in the clubhouse equipped with cable TV and a catering kitchen, or fire up the outdoor grills for a perfect evening barbecue. For sports enthusiasts, tennis courts are available, and you’ll have direct access to the stunning beach with complimentary beach chairs and umbrellas. Situated at the intersection of the Publix Shopping Center, this prime location on the southern end of Longboat Key places you in the heart of convenience. Enjoy easy access to shopping, dining, and local attractions, with the famous St. Armand’s Circle and the vibrant Downtown Sarasota just a short drive away. If you are looking for a coastal retreat that combines luxurious living with breathtaking views and a vibrant community, look no further. This impeccable condo at Islands West is the perfect place to call home. Call today!!! Rental rate is negotiable.
#A4675505

LONGBOAT KEY

2525 GULF OF MEXICO DRIVE 12F

2 Beds

2 Baths

1,651 Sq.Ft.

$13,500

MLS#: A4675505

Looking for a 3 month renter for January, February, and March or the month of January 2026. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floor plan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous countertops and wonderful warm beachy flooring, this home has it all. Sit outside on the upper deck with a view of the refreshing pool during breezy afternoons or the covered deck downstairs which offers shade while not sunning. Ping pong and bocce ball complete the picture for hours of fun. The dining table sits (6) with (4) breakfast bar seats nearby. Two bedrooms have (1) Queen and (1) twin each, one quest bedroom has a Queen and the master has a King bed, all with large screen televisions.
#A4468386

LONGBOAT KEY

501 CHANNEL LANE

4 Beds

3 Baths

2,349 Sq.Ft.

$13,000

MLS#: A4468386

Available for season 2026 This home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Open floor concept with formal dining. The kitchen as the heart of the home is expertly appointed with everything you will need for your home cooked meals. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step into the crystal clear deep end. Plenty of new stone pool deck on the offered lounge chairs to bask in the Florida sun. Welcome to peaceful Buttonwood Harbour, composed of 50 homes in one of Longboat Key's oldest and sought-after communities. Situated in the middle of Longboat Key, it is walking distance for most, to Publix, the Shoppes of Bay Isles, Tennis, post office, and CVS. Full of friendly neighbors and a favorite place for nature lovers. Boaters and fisherman will be happy with accessibility to the BHA boat ramp for launching and ability to dock your boat at the house during your stay, even utilize the kayak storage if you decide to rent them. No bridges from Buttonwood Harbour out to Sarasota Bay's open waters. Enjoy the day at Bayfront Park, 1.4 miles from the house. Amenities found at Bayfront Park include a 1,350 square foot indoor Recreation Center, a playground, a basketball court, shuffleboard courts, a multi-purpose open field, 3 dedicated pickleball courts, a tennis court, picnic tables, restrooms, and parking for a Town public beach access located across the street. The Bayfront Park Recreation Center is a public recreation facility run by the Town of Longboat Key. You will also find a dog park for your fur babies.
#A4655401

LONGBOAT KEY

613 BUTTONWOOD DRIVE

3 Beds

2 Baths

1,871 Sq.Ft.

$13,000

MLS#: A4655401

ELEGANTLY PRESENTED! This bright and spacious property located just steps away from a private deeded beach is perfect for those who appreciate easy access to sun and sand. This residence boasts modern features and well-thought-out design, making it an ideal retreat for relaxation and comfort. The living area is characterized by an open layout that seamlessly connects to the kitchen, promoting an inviting atmosphere for gatherings. Large windows allow natural light to flood the space, enhancing its airy feel. The living room features elegant architectural details and is well-suited for both intimate and larger gatherings. The kitchen is a standout feature of the property, equipped with quartz countertops that offer a sleek and durable workspace. The cabinetry is crafted from wood, providing ample storage and a classic touch to the contemporary design. Stainless steel appliances ensure that this kitchen is both functional and stylish, making meal preparation a pleasure. The bedroom area is designed with comfort in mind, featuring spacious layouts and tasteful fixtures. It serves as a serene escape from the day, complete with quality finishes and thoughtful touches. Each bedroom presents opportunities for personalized decor while maintaining a cohesive aesthetic throughout the property. Outdoor areas are no less impressive, offering opportunities for enjoyment of the beautiful Florida weather amidst a backdrop of lushly mature tropical landscaping that contributes to its welcoming ambiance. The resort amenities feature a private beach, junior Olympic-sized heated pool, four Har-tru tennis courts, fitness center, fishing pier, kayak storage and a clubhouse with an active social calendar. In summary, 609 Bayport Way is not just a home; it is a lifestyle choice, perfectly positioned for easy beach access and designed to meet modern living needs. Come discover the comfort and convenience this property has to offer, and envision your new life in this coastal gem. NOW AVAILABLE !
#TB8435893

LONGBOAT KEY

609 BAYPORT WAY 609

2 Beds

2 Baths

1,260 Sq.Ft.

$13,000

MLS#: TB8435893

Discover a tranquil retreat at 806 Bayport Way, where coastal living meets sophisticated design. This exceptional property is ideally located near a private beach, providing residents with exclusive access to sun-soaked shores and beautiful ocean views. Upon entering, you’ll be greeted by a thoughtfully designed space that emphasizes both comfort and functionality. The kitchen features elegant cabinetry and modern appliances, providing a perfect environment for culinary enthusiasts. The open layout seamlessly connects the kitchen to the living area, which boasts natural light flowing through large sliding glass doors, leading directly to an outdoor patio. This space is perfectly suited for entertaining or simply enjoying the surrounding mature landscaping. The interior boasts high-quality finishes, including sophisticated flooring and ambient lighting, which creates a welcoming atmosphere throughout. The living room serves as a focal point for relaxation, with ample space for social gatherings or quiet evenings. This property features spacious bedrooms, each designed with comfort in mind. The primary suite offers a serene escape with large windows that frame views of lush greenery, enhancing the overall tranquility of the home. The bathroom is designed with modern fixtures, providing a spa-like experience at home. Residents will benefit from a range of resort-style amenities, including well-maintained outdoor spaces, ideal for leisure activities or quiet reflection. Ample space for recreation ensures that every resident can enjoy an active lifestyle while embracing the natural beauty that Longboat Key offers. Experience the lifestyle you deserve at 806 Bayport Way, where elegance, comfort, and nature harmoniously intertwine. Schedule your private showing today to explore this exquisite property further.
#TB8436077

LONGBOAT KEY

806 BAYPORT WAY 806

2 Beds

2 Baths

1,260 Sq.Ft.

$13,000

MLS#: TB8436077

SEASONAL: All three baths have been 100% renovated. Just gorgeous! Photos to come. Harbour Oaks is resort-style living positioned behind the guarded Harbourside gates of Bay Isles. This updated 3 bedroom, 2 1/2 bath home overlooks the Longboat Key Club golf course! With over 2,500 sq. feet of living space, pool, private Beach Club access and sought after Southern Longboat address this is the perfect Winter getaway. One visit to this 3BD+Den/2.5BA golf course detached home will have you wanting more! It has been updated in all the newest tones, is fresh, and combined with natural lighting, is so inviting. Pavered drive and lush landscaping and walkway lead you into the foyer entry. The combined living/ dining area is warm and inviting with vaulted ceilings, tile flooring and new comfortable furnishings. The kitchen is designed for entertaining or just relaxing with a marvelous view of the 2nd green. The den is a cozy retreat for TV or for catching up on work or emails in the dinette area. The private and spacious master suite offers ensuite bath and has a seating area to relax and enjoy the views! The second bedroom features queen accommodations and the third bedroom offers twins. All have their own private entrance for a relaxing stay. Additional charges for pool heater use. This marvelous turnkey residence comes complete with gated security, Wifi, inside laundry, 2 car garage, private and community pool and easy access to shopping, dining and cultural arts from St. Armands Circle to downtown Sarasota. Booked Jan 5th - April 5th, 2026.
#A4151865

LONGBOAT KEY

2319 HARBOUR OAKS DRIVE

3 Beds

2 Baths

2,532 Sq.Ft.

$12,500

MLS#: A4151865

Price reduced
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 offering a front-row seat to breathtaking sunsets, gentle sea breezes, and the soothing sound of waves meeting the shore. Offered fully furnished, this home is designed for both style and comfort, making it the perfect seasonal escape or extended retreat. The residence features a spacious and thoughtfully designed floor plan that emphasizes relaxation and entertaining. The living and dining spaces flow effortlessly toward the water, creating a serene atmosphere for hosting guests or enjoying quiet evenings by the Gulf. The well-equipped kitchen, comfortable bedrooms, and elegant furnishings reflect a refined coastal aesthetic, allowing you to settle in with ease from the very first day. Life at The Privateer is defined by its unparalleled amenities and direct beachfront setting. Residents enjoy a heated beachfront pool and jacuzzi overlooking the Gulf, a fully equipped fitness center, tennis courts, and beautifully maintained grounds. Outdoor grilling areas, shaded dining spaces, and gathering lounges provide endless opportunities for entertaining or enjoying the company of neighbors. For days spent on the sand, beach chairs and umbrellas are thoughtfully provided, ensuring every day feels like a private resort experience. Located on the southern end of Longboat Key, The Privateer combines the peace and privacy of a gated beachfront community with convenient access to world-class dining, shopping, and cultural attractions in nearby St. Armands Circle and downtown Sarasota. Available seasonally beginning October 15, 2025, with owners open to discussing longer lease terms, this residence is the perfect opportunity to experience the best of Longboat Key living—where luxury, comfort, and the beauty of the Gulf of Mexico meet. 3D walkthrough available!!
#A4666443

LONGBOAT KEY

1000 LONGBOAT CLUB ROAD 1001

2 Beds

2 Baths

1,409 Sq.Ft.

$12,000

MLS#: A4666443

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 furnishings, new custom kitchen and bathrooms. Floor to ceiling glass with panoramic views from every room in the house. MOVE-In and enjoy the Luxury lifestyle and amenities that abound at Grand Bay. GRAND BAY is a 24-hour-manned, GATED community where residents can enjoy two heated swimming pools, hot tub spa, fitness center, tennis, private garage, large clubhouse, many on site activities, and a private beach club access to the world famous beach on the Gulf of Mexico. Close to St. Armand's Circle, Downtown Sarasota, and Ana Maria Island. OPEN FOR 2026 SEASON RESERVATION THREE MONTH or longer stay. There is a 30 day tenant application process with the Grand Bay COA. NO PETS/No Smoking. Included in the monthly rent charges to be paid by owner: monthly electric, Xfinity cable TV/Internet and weekly housekeeping. 13% sales/resort tax to be paid by tenants. Rates for December through April $12,000 month. Off Season Rates May and November $6500 monthly. Call today to schedule in person showing or virtual showing.
#A4645666

LONGBOAT KEY

3060 GRAND BAY BOULEVARD 172

3 Beds

3 Baths

2,250 Sq.Ft.

$12,000

MLS#: A4645666

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 appliances. The dining area can accomodate six, there is a wet bar with beverage chiller for convenience. The living room offers comfortable seating, a flat screen TV and amazing water views! The primary bedroom has a king bed, amazing views, a flat screen TV, and a walk-in closet. The primary bath offers dual sinks and a walk-in shower. The guest bedroom has a Queen bed and Flat screen TV. You will love this wonderful location, with shopping and dining close by, and Historic St. Armands Circle is just a short drive away. Welcome to Paradise! (All rates are plus taxes and fees, available Janaury through April 2026
#A4608766

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 408

2 Beds

2 Baths

1,411 Sq.Ft.

$12,000

MLS#: A4608766

Price reduced
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. Tastefully decorated with flowing neutral tones. This corner unit offers views from every room with Floor-To-Ceiling windows and remote control window treatments. There are many amenities in this beautifully maintained building. They include Climate Controlled Bicycle Room and Kayak Storage, Gulf Front Heated Pool, Har-Tru Tennis Courts, Fitness Room, Social Room and Conference Room all for your use. Walking distance to Publix Market and minutes to St Armand's Circle and Downtown Sarasota for boutique shopping, Fine and Casual Dining and our renowned Theater District. Don't hesitate to make this your next vacation spot. This property is available beginning 12/04/2025. Building requires a 3 months minimum rental. LUXURY VACATION RENTAL, LONGBOAT KEY, GULF OF MEXICO, SARASOTA VACATION RENTAL.
#A4663629

LONGBOAT KEY

2425 GULF OF MEXICO DRIVE 11F

2 Beds

2 Baths

1,513 Sq.Ft.

$12,000

MLS#: A4663629

Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath condominium boasts a stylishly designed interior that is sure to impress. Experience tranquility in the master bedroom, which offers exquisite bedding and a sitting area with a stunning view of the azure waters. The ensuite master bath provides the perfect sanctuary for relaxation. The gourmet kitchen with stainless steel appliances is perfect for entertaining and the light and bright living room features exquisite seating and state-of-the-art digital components, including a 75-inch TV and DVR. Stay connected with dedicated desk space, a washer and dryer, and Wi-Fi. Large-screen smart TVs are also available for your added enjoyment. Take advantage of resort-style amenities including a gulf-side heated pool, har-tru tennis court, updated social room, state-of-the-art fitness area, and storage for kayaks, paddleboards, and bikes. Conveniently located to shopping, dining, St. Armand’s Circle, downtown Sarasota, and the Arts, this vacation rental has everything you need for a truly unforgettable stay. Don't miss out on this opportunity to live the life you've always imagined! Minimum 4 months stay!
#A4561428

LONGBOAT KEY

2425 GULF OF MEXICO DRIVE 14B

2 Beds

2 Baths

1,470 Sq.Ft.

$11,950

MLS#: A4561428

..."' short stories. ....on the island of longboat key You are on the beach included is swimming pool...and a world class tennis courtf...looking play with others and league Town of Longboat Key tennis three blocks away...fitness gym.. . This is direct Gulf front unit with interior hallways from the balcony ,the kitchen,the living room couch...Your on the water.. Breathtaking view of the turquoise blue waters of the Gulf of Mexico. Enjoy morning coffee from your balcony on the 7th floor. Gorgeous sunsets every evening. Start your day with a leisurely walk on the beautiful sand beach. Go for a swim in the warm Gulf waters. Take a refreshing dip in the pool. Ride a bike to nearby St. Armand Circle and experience world class shopping and restaurants. Charter a boat and go deep sea fishing. Imagine yourself basking in the warm Florida sun listening to the sounds of the sea without a care in the world.
#A4547447

LONGBOAT KEY

2425 GULF OF MEXICO DRIVE 7B

2 Beds

2 Baths

1,470 Sq.Ft.

$11,769

MLS#: A4547447

Booked May 1st- June 16th, July13th-July 27th, Nov 14th-rest of 2025. Booked January, May, October, and Dec 2026 through February 2027, Must be a one month minimum stay during seasonal months and 2 week minimum stay out of season. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathrooms. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for the gourmet chef in you all. Outdoor living could be your everyday enjoyment while sipping wine by your private heated pool and on cool nights curl up at the fire pit. Sit back and relax with many seating areas and full outdoor dining table in this cozy beach themed oasis in Country Club Shores. Quiet sought out neighborhood on south end of Longboat Key with beach access between LBK Club and Beach Place. It is fully equipped with everything you will need to feel at home while enjoying the sights and comforts that Longboat Key has to offer. Just minutes to St Armand’s Circle or Lido Beach for shopping, fine dining or laying at the public beach with all your favorite people. Longboat is known for their waterfront golf, fine dining and luxury resorts. In fact, its 12 miles of white sand beaches have helped to make this a luxury Gulf Coast resort community. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events are Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack's, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, and the Van Wezel.
#A4561269

LONGBOAT KEY

500 SCHOONER LANE

2 Beds

2 Baths

1,657 Sq.Ft.

$11,550

MLS#: A4561269

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