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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
507
# of Listings
2
Avg # of Bedrooms
$867
Avg. $ / Sq.Ft.
$1,539,132
Med. List Price

Browse Long Boat Key Real Estate Listings

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$3M - $5M

Over $5M

507 Properties Found. Page 28 of 34.

**This is a 2 month minimum vacation rental** Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou section of Bay Isles, this remodeled and meticulously maintained pool home boasts nearly 3,000 square feet of living space—including 2,021 square feet on the main level and an additional 942 square feet on the walk-out lower level. As you approach the property, you’ll notice the gentle slope of the lot from the street up to the main entrance, framed by lush palms, mature oaks, and banyan trees. The double-door entry opens to an inviting, open-concept great room that seamlessly connects to a spacious outdoor deck overlooking the backyard and pool area below. The updated, modern kitchen features custom cabinetry, stainless steel appliances, a built-in double oven, and a six-burner Viking gas cooktop—perfect for entertaining. Also on the main level are three bedrooms, including two guest rooms and a full guest bathroom. The expansive master suite offers a large walk-in closet and a well-appointed en-suite bathroom. The lower level, with its wall of sliding glass doors, opens directly to the screened pool deck and a 40-foot pool equipped with a new pump. This level also includes a full bathroom and laundry area. The two-car tuck-under garage offers ample storage space and a small workshop area. As a resident of Bay Isles, you’ll enjoy access to the Private Bay Isles Beach Club, located at 2111 Gulf of Mexico Drive, just across from the community. The club features a pristine stretch of beach, picnic tables, tiki huts, barbecue grills, an ice machine, and storage bins for beach gear. A key fob, included with the rental, is required for access. More information can be found on the Bay Isles website. The base rent for January through April is 11,000 and off months is 9,000
#A4665246

LONGBOAT KEY

3390 BAYOU SOUND

3 Beds

3 Baths

4,340 Sq.Ft.

$11,000

MLS#: A4665246

Welcome to your elevated coastal retreat on Longboat Key, located behind the gate of the prestigious Longboat Key Club. Available annually at $9,000/month or seasonally from November through April at $11,500/month, this fully renovated upper-floor residence offers refined living with sweeping Gulf and Bay views from two private balconies. Set within one of the island’s most exclusive beachfront communities, this spacious two-bedroom, two-bathroom condo has been thoughtfully designed and professionally furnished to deliver a seamless blend of coastal elegance and everyday comfort. Sunlight floods the open-concept living and dining areas, where floor-to-ceiling sliders invite you to step outside and enjoy panoramic water views and soft Gulf breezes. The kitchen is outfitted with sleek countertops, high-end cabinetry, and modern stainless steel appliances, fully equipped for both everyday use and entertaining. Each bedroom serves as a luxurious private suite, complete with king-size beds, plush linens, and dedicated bathrooms. The primary suite offers a spa-style bath with a walk-in glass shower and designer finishes, creating the feel of a high-end hotel in the comfort of your own home. Enjoy morning coffee or sunset cocktails from either of the two private balconies, both offering spectacular water views and the serene ambiance of beachfront living. As a resident, you’ll have access to a suite of premier amenities, including private beach access with complimentary chairs and umbrellas, a heated pool and hot tub, lighted tennis courts, a state-of-the-art fitness center, BBQ grills with outdoor dining areas, and an air-conditioned clubhouse. The community is secured with a 24-hour guarded gate and offers concierge-like service for ultimate peace of mind. Ideally located walking distance to Longboat Key Club - just minutes from the upscale shopping, fine dining, and cultural experiences of St. Armands Circle and downtown Sarasota, and with easy access to Sarasota-Bradenton International Airport, this residence offers a rare opportunity to enjoy the very best of Longboat Key living—whether for the season or year-round. Luxury, privacy, and breathtaking views await.
#A4660546

LONGBOAT KEY

1000 LONGBOAT CLUB ROAD

2 Beds

2 Baths

1,409 Sq.Ft.

$11,000

MLS#: A4660546

This beautifully remodeled end unit condo, boasts two bedrooms, two bathrooms and has an open concept floor plan which features an expansive Living/Dining/Kitchen combo. In addition, it has a generous sized master bedroom with en suite bathroom, an alcove that accommodates a small desk and a private lanai leading off the bedroom. Begin each day by enjoying nature's' most beautiful the serene garden views from your enclosed lanai from either the family room or the master suite. An additional outdoor deck from the front of the condo allows for outdoor lounging, sunbathing or dining while being able to experience some of the most amazing sunset views. This gulf to bay community is full of lush, mature landscaping and offers private beach access across the street. The amenities feature a junior Olympic-sized heated pool, four Har-tru tennis courts, fitness center, fishing pier, kayak storage, clubhouse with active social calendar, and more. Just minutes away from shopping, dining, and entertainment in world famous St. Armand's Circle and downtown Sarasota. NOW AVAILABLE
#T3550537

LONGBOAT KEY

739 BAYPORT WAY 739

2 Beds

2 Baths

1,876 Sq.Ft.

$11,000

MLS#: T3550537

Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. Relax on the lanai and take in the beautiful gulf views at sunset. The Large primary bedroom has a King bed and bathroom with a walk-in shower with his/her sinks and a separate seating area. A privacy door has been added from the Master bedroom to the en-suite bathroom. The unit comes with a large utility closet for ample storage and a stackable washer and dryer in the kitchen. Guest Bedroom has 2 twin beds and an adjoining bathroom. Amenities include a 24 hour manned guard gate, private beach access, Wi-Fi, lighted tennis courts, pickleball, heated pool and hot tub, two state of the art fitness centers, and BBQ gas grills by the pool. This condo comes with 2 parking spaces - one inside the building close to the elevator and the other outside. Minutes to St. Armand's Circle for first class shopping and dining. Off-season guests pay the monthly electric bill. Sorry, no pets or smoking permitted.
#A4480600

LONGBOAT KEY

1125 GULF OF MEXICO DRIVE 403

2 Beds

2 Baths

1,642 Sq.Ft.

$11,000

MLS#: A4480600

Seasonal/short term rental on Longboat Key Beautifully renovated 3 bedroom 2 1/2 bathroom villa right on the golf course in prestigious, guard gated, Bay Isles. This spacious light filled delight has vaulted ceilings with sky lights, and new high impact windows and doors. The open floor plan is perfect for family time and entertaining. The kitchen is very large and has solid cherry wood cabinetry, topped with quartz counters, breakfast bar, massive butlers pantry, breakfast bar and an eat in space and stainless steel appliances. The flooring is all solid surface, either tile or wood so no carpeting. The main bedroom has his and her closets, ensuite bathroom with dual sinks, soaker tub, water closet and walk in shower. The screened in lanai has two levels and plenty of space for entertaining, and an outdoor kitchen. Just outside the gate is the Bay Isles Beach Club with beach access on the Gulf, BBQ grills and covered outdoor dining, and volleyball court. This amazing villa is available during high season (December thru April) at $10,995 per month, or off season (rest of the year) at $5,000 + tax. Call today to sign up for your time in paradise!
#A4648139

LONGBOAT KEY

2339 HARBOUR OAKS DRIVE

3 Beds

2 Baths

2,922 Sq.Ft.

$10,995

MLS#: A4648139

No damage to unit after storms. Call for rates and availability. Available December - April. One month minimum. Tremendous view of the Gulf from this Gulfside/Beachside 2 BR/2 B condo. Direct Gulf front unit. Breathtaking view of the pristine waters of the Gulf of Mexico. Sit on the balcony to your 7th floor unit. Take in the sunsets with your loved ones and friends. Just a couple minutes and you'll be walking on the fine sandy beach. Go for a swim in the heated pool or the invigorating Gulf waters. Close to St. Armand Circle and Downtown Sarasota. Enjoy the best that Longboat Key offers.
#A4621809

LONGBOAT KEY

2425 GULF OF MEXICO DRIVE 7F

2 Beds

2 Baths

1,513 Sq.Ft.

$10,500

MLS#: A4621809

STUNNING GULF VIEWS! Enjoy the sparkling glimmer of the morning waters and picturesque sunsets from almost every room. This meticulously maintained 2 bedroom, 2 bathroom furnished condominium features an open concept floor plan with expansive Living/Dining/Kitchen area. The generous size primary bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a small alcove that accommodates a desk. Bayport Beach & Tennis Club is an amenity-rich community at sea's edge with 27 acres of lush mature tropical landscaping. This gulf to bay community offers an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and 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 to St. Armand's Circle which is well known for its world class shopping and dining. Cross over the Ringling Bridge to Downtown Sarasota where you will find additional dining, theater, opera, ballet, symphony, art galleries, the Van Wezel Performing Arts Hall, Selby Gardens and of course the Ringling Museum.
#TB8408216

LONGBOAT KEY

724 BAYPORT WAY 724

2 Beds

2 Baths

1,600 Sq.Ft.

$10,500

MLS#: TB8408216

**BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease APRIL 2026** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly on the beach, offering you breathtaking full views of the shimmering turquoise waters, sparkling sand, and those iconic Florida sunsets. This is the perfect opportunity to immerse yourself in the serenity of beachfront living during the best time of year. Imagine waking up each morning to the calming sound of waves and enjoying your morning coffee on the balcony as the sun rises over the Gulf. Step inside and be welcomed by the calm coastal colors and casual elegance that make this condo the ideal beach retreat. The community of Arbomar offers amenities that ensure your stay is as relaxing as possible. Take a dip in the heated community pool, stay active in the fitness room, or gather with friends in the community kitchen and lounge. Additional conveniences include climate-controlled storage lockers, a kayak rack, beach chair storage, and laundry rooms on each floor. With all-new Miami Dade certified high-impact windows, including turtle-tinted beachside windows to protect our local sea turtles, you can enjoy the view and feel secure. This spectacular Penthouse condo fresh on the market emphasizes the exclusivity and appeal of spending winter in a beachfront condo, encouraging potential renters to secure their spot for the popular January to March/April 2026 period as soon as possible!
#A4622055

LONGBOAT KEY

4485 GULF OF MEXICO DRIVE PH2

3 Beds

2 Baths

1,736 Sq.Ft.

$10,500

MLS#: A4622055

***NEW VACATION RENTAL LISTING** * Booked Dec1st-March 31st 2026. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to beach chairs along the private beach. Under-building assigned parking directly across from security coded entry lobby with elevator and mailboxes. Plenty of guest parking inside the welcome security gates. Full time maintenance crew keeps the grounds immaculate. Wake up to beach and water views from Living room, both bedrooms and terrace. The apartment has an fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room furniture, decor and linens. Utility room with Maytag washer and dryer. Sunset Beach is currently replacing all lobby and hallway flooring. 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.
#A4584050

LONGBOAT KEY

2109 GULF OF MEXICO DRIVE 1203

2 Beds

2 Baths

1,631 Sq.Ft.

$10,000

MLS#: A4584050

BAYPORT BEACH and TENNIS CLUB, a Gulf to Bay, FULLY FURNISHED 2/2 residence. Bayport is an award winning community situated in the heart of Longboat Key. A friendly, popular, residential enclave of 136 quality-constructed homes on 27 picturesque acres of impeccably maintained grounds. Tastefully decorated and well maintained with over 1600 square feet of living area; perfect for entertaining friends, relaxing with a morning coffee or your favorite beverage on a lushly landscaped private garden patio. Bordered by the Gulf of Mexico to the west with 1200 feet of private Gulf beach and Sarasota Bay to the east. Enjoy an active island lifestyle with 4 HarTru tennis courts, an enormous heated pool, a fishing pier, kayak facilities, Bocce court and nature trails. The spacious clubhouse, with fitness room and full kitchen, hosts a number of social activities. A short walk to the Gulf of Mexico for morning beachcombing or memorable sunsets. Minutes to grocery and other shops as well as the area's finest restaurants. Bayport Beach and Tennis Club is a special island property with remarkable beauty and fabulous amenities.
#TB8335223

LONGBOAT KEY

832 BAYPORT WAY 832

2 Beds

2 Baths

1,601 Sq.Ft.

$10,000

MLS#: TB8335223

Experience the ultimate in coastal luxury with this exceptional residence on Longboat Key. Nestled along a canal with direct access to the Gulf, this expansive home is a dream for boating enthusiasts and those seeking a serene, upscale lifestyle. Key Features: -Prime Location: Situated on a canal with private dock and direct Gulf access—perfect for boating, fishing, or simply enjoying the coastal beauty. -Four-Car Garage: Ample space for vehicles, watercraft, and extra storage. -Gourmet Kitchen: A chef's dream, equipped with six gas burners, built-in griddle and grill, high-end appliances, and generous counter space for entertaining. -Custom Hand-Painted Interiors: Each room features stunning, one-of-a-kind murals created by local St. Petersburg artist Hahn, adding character and creativity to every space. -Elevator Access & Private Owner's Retreat: Effortlessly navigate the multi-level layout with a private elevator. The top level is reserved for the ultimate owner's retreat—featuring a lounge area, a modified kitchenette, and stunning his-and-hers walk-in closets for maximum comfort and privacy. Indoor-Outdoor Living: Balconies line the rear of the home, providing stunning views of the canal and pool—perfect for both entertaining and relaxation. This is an exceptional opportunity to live in one of Longboat Key's most sought-after residences. Enjoy unparalleled style, spacious living, and the convenience of water access, all within a tranquil, upscale environment.
#A4669779

LONGBOAT KEY

614 NORTON STREET

6 Beds

5 Baths

7,941 Sq.Ft.

$10,000

MLS#: A4669779

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 breathtaking views of the Gulf Coast Ocean!  Experience a 2 Bedroom, 3 Bath Combo home with all the open floor plan that you and your family could need.  The beautifully designed, modern kitchen, is equipped with all the appliances you will need to make your trip a success, including barstool seating for four, all new stainless steel appliance's, and induction burner top oven. The Master Bedroom is equipped with a luxurious King Sized Bed, Flat Screen TV, and sliding glass doors that open directly to a private lanai overlooking the ocean.  The Master Bathroom is also equipped with a His/Her Sink, giving you the space you need to get ready to enjoy your day.   The second bedroom is equipped with two, very comfortable, full sized beds, giving everyone a comfortable space to have plenty of room for rest and relaxation.  Your guests enjoy their own bathroom as well, fully equipped with all the amenities and their own private shower. There is an all enclosed, private sitting room and office space that overlooks the beautiful courtyard of the Players Club.  The sofa pulls out into a full sized mattress, giving you room for everyone! The Players Club Complex is a luxury living community in Longboat Key.  They give you as a renter access to all the amenities of the community, up to and including:  Private Beach Access included with Beach Chairs and Umbrellas, private pool and spa area, putting greens, tennis courts. fitness center, clubhouse, library, and others!   Application must be filled out prior to arrival to register with the community itself.  If interested in long term, please inquire directly with the property management company for pricing.   No Smoking, No Pets All Amenities included at No Extra Charge!
#A4671205

LONGBOAT KEY

1445 GULF OF MEXICO DRIVE 305

2 Beds

2 Baths

1,957 Sq.Ft.

$10,000

MLS#: A4671205

GORGEOUS SHORT TERM RENTAL!!!! Bayport Beach & Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to private beach on the Gulf of Mexico for morning beachcombing, surf casting or memorable sunsets.
#T3527649

LONGBOAT KEY

838 BAYPORT WAY 838

2 Beds

2 Baths

1,601 Sq.Ft.

$10,000

MLS#: T3527649

ABSOLUTELY GORGEOUS INSIDE! Bayport Beach & Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to private beach on the Gulf of Mexico for morning beachcombing, surf casting or memorable sunsets. NOW AVAILABLE: July through December 2024 Please contact Agent for availability.
#T3492089

LONGBOAT KEY

741 BAYPORT WAY 741

2 Beds

2 Baths

1,426 Sq.Ft.

$10,000

MLS#: T3492089

Bright and Spacious! This lovely 2 bedroom, 2 bathroom furnished condominium is nestled comfortably in a lush tropical setting with a spacious eat-in kitchen that is open to the living area. Elegantly furnished in a natural color pallet. The master suite is tastefully decorated, with a built in vanity, double sinks and his and her closets. It also features a small alcove with a desk with access to a private screened in patio with gulf view. Additionally there is a large private deck for sunbathing, relaxing or enjoying an outdoor BBQ! Bayport Beach and Tennis Club is directly across from the sandy beach of the Gulf of Mexico with 1200 feet of private beach. Amenities include (4) Har-tru tennis courts, one of the largest swimming pools on the island and a clubhouse with kitchen facilities for private parties and social functions, fitness center, a fishing pier on the bay, a kayak launch and nature paths all on 27 lushly landscaped acres. NOW AVAILABLE JULY - DECEMBER 2024
#T3464450

LONGBOAT KEY

720 BAYPORT WAY 720

2 Beds

2 Baths

1,400 Sq.Ft.

$10,000

MLS#: T3464450

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