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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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$500,000 - $1M

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$3M - $5M

Over $5M

511 Properties Found. Page 30 of 35.

Seasonal rental in Bayport Beach and Tennis Club which is a beautiful, established, award-winning, amenity-rich community with immediate access to a peaceful private beach that continues in both directions for miles along the Gulf of Mexico shore. The complex includes a large pool surrounded by flowering trees, four immaculately maintained clay tennis courts, fitness center, a large clubhouse, bike trails, and a private fishing pier on the bay side surrounded by mangroves. Turnkey furnished on the upper level of a quiet end unit, including two full bedrooms - one with a king bed and the other with two twin beds. You can see the Gulf from the entrance and the guest bedroom. Each bedroom has its own bathroom; the guest bath has a shower and the master bath has double sinks and a bathtub. The kitchen has granite countertops and there is a separate tiled dining area with a glass table, that seats up to six. There is also seating in the kitchen at a granite counter. The living room has comfortable, large couch with an entertainment unit. The condo has a lanai overlooking lovely tropical gardens. In unit washer/dryer. Nearby is a convenient grocery store, great restaurants, museums, galleries, marinas and shops at St. Armand’s Circle. One covered parking space is provided, with plenty of guest parking spaces.
#T3488580

LONGBOAT KEY

519 BAYPORT WAY 519

2 Beds

2 Baths

1,456 Sq.Ft.

$9,500

MLS#: T3488580

Gorgeous Inside! Furnished Rental at the exceptional Bayport Beach and Tennis Club. Single story end unit with private entrance. Very Private screened lanai and patio area. Amenities abound at this beautifully landscaped Beach and Tennis Club. Four professional quality Hart-Tru Clay Courts with ball machine, Junior Olympic (heated) swimming pool, ping pong table, bocce ball court, fitness center and fishing pier on the bay. The grounds of this community resemble the botanical gardens. Just walk across the street to the Gulf of Mexico pristine Longboat Key Beach. Please contact Agent for availability. NOW AVAILABLE AT FROM AUGUST 1ST - DECEMBER 31ST, 2024 .
#T3337994

LONGBOAT KEY

517 BAYPORT WAY 517

2 Beds

2 Baths

1,260 Sq.Ft.

$9,500

MLS#: T3337994

SEASONAL; PRICE REDUCED!!! Available FEBRUARY - MARCH 2026!!! 30 day minimum. No damages sustained in Hurricane. Beautiful unit from floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is beautifully renovated with professionally designed interior. Sip your morning coffee on the balcony with new glass railings as you plan your daily adventures. The light and bright living room features exquisite leather recliners and fabric sofas, one of which is a sleeper for an extra guest. Thoughtfully planned, you'll enjoy state of the art digital components including 85-inch TV and DVR while relaxing.Entertaining is a delight in the gourmet kitchen with stainless appliances. Escape to the tranquil master bedroom retreat with exquisite bedding overlooking azure waters with 65 inch smart TV, sitting area and ensuite master bath. For added comfort during your stay there’s a dedicated desk, stacked washer and dryer, built-in closet systems, wifi and 65' large smart tv in guest suite. Parking is conveniently located at the building's front door. Live the life you’ve always imagined with resort-style amenities that include Gulf-side heated pool, har-tru tennis court, updated social room, state of the art fitness area and kayak, paddle board & bike storage. Conveniently located to shopping, dining, St. Armand’s Circle and downtown Sarasota and the Arts. No pets or smoking permitted.
#A4215382

LONGBOAT KEY

2425 GULF OF MEXICO DRIVE 7C

2 Beds

2 Baths

1,470 Sq.Ft.

$9,000

MLS#: A4215382

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 tone for what lies ahead. The property features a well-designed layout that maximizes space and natural light, creating a welcoming atmosphere throughout. The interior showcases an open-concept design, combining living and dining areas that enhance gatherings while providing a functional flow. High-end finishes, such as sleek tile flooring and well-placed lighting, contribute to the contemporary elegance of the home. The kitchen is a highlight, featuring up-to-date appliances and ample counter space, making it ideal for both everyday meals and entertaining guests. Large windows not only provide views of the lush surroundings but also bathe the space in sunlight, creating a warm and inviting ambiance. Step outside to discover the expansive outdoor spaces that truly elevate this property. Enjoy easy access to well-maintained walking paths and green areas, perfect for morning strolls or afternoon relaxation amidst nature. A nearby beachfront provides an oasis for sunbathing, swimming, and a variety of water activities. The stunning Gulf of Mexico and its pristine sands are just moments away, allowing residents to immerse themselves in the beauty and tranquility of coastal living. In summary, this property at 829 Bayport Way is not just a home; it’s a lifestyle. With its strategic location, architectural features, and community amenities, it offers the ideal setting for those looking to experience the best of Longboat Key. Don’t miss out on this unique opportunity to embrace sunny Florida living at its finest.
#TB8443376

LONGBOAT KEY

829 BAYPORT WAY 829

2 Beds

2 Baths

1,601 Sq.Ft.

$9,000

MLS#: TB8443376

Location! Location! Location for Winter 2026 Rental Season! Gulf-front condominium complex “Sands Point” sits on the southernmost tip of Longboat Key. This location allows you to save time in traffic. Nestled adjacent to the iconic Longboat Key Resort, this Mid-Century modern 77-unit complex boosts impeccable views, gorgeous landscaping, a full-time maintenance crew and your own covered parking space. This newly renovated condo is on the second of three floors, and is complete with two elevators for your convenience. Renters will find our newly rebuilt outdoor pool area, our private beach access with beach chairs, as well as our sunset views from under the tiki huts, as a slice of paradise! Our 1941 sq.ft. condo has all of the modern amenities one would ?nd in this upscale, modern enclave. High-end appliances for the chef, spacious living room for the family, and three private bedrooms and two full bathrooms. In addition, wash your suits and towels in the Bosch washer and dryer, enjoy a tall glass of water from the reverse osmosis water system, create a cozy atmosphere by closing the custom-made plantation shutters. In addition, the built-in cabinetry will provide you plenty of storage space! Within walking distance of well renowned St. Armands Circle for all your dining and shopping needs. No pets allowed, as per Association rules. Utilities included (Electricity, Water, Basic Cable, Wi-Fi, Garbage service. Available starting January 1, 2026, for January, February, March, and April (3 month minimum please) Monthly rate of $9,000!
#A4667355

LONGBOAT KEY

100 SANDS POINT ROAD 223

2 Beds

2 Baths

1,941 Sq.Ft.

$9,000

MLS#: A4667355

Available Dec, Jan then any month after March. Experience unparalleled Gulf-front living in this beautifully renovated 2-bedroom, 2-bathroom condo at Tiffany Plaza. Spanning 1,336 sq ft, this fully furnished residence boasts luxury vinyl flooring, a modern kitchen with marble countertops, and a spacious lanai offering breathtaking views of the turquoise waters of the Gulf of Mexico . The master suite features a king-sized bed, while the guest room offers a queen bed and a desk overlooking the Gulf. Additional amenities include in-unit laundry, high-speed Wi-Fi, and a pull-out couch for extra guests Community highlights encompass a sheltered heated pool, BBQ grill, club room with ping pong table, lending library, and beach chairs with umbrellas. Bayfront Park, just a short stroll away, offers tennis and pickleball courts, basketball, a playground, and stunning sunrise views . Rental Availability: May–November 2025: $5000/month December:$8000 January 10,000 Feb-March 12000 Full 2026 Season available at a discounted rate
#A4535853

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 406

2 Beds

2 Baths

1,336 Sq.Ft.

$9,000

MLS#: A4535853

Beautifully appointed seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes turnkey furnished and equipped with flat screen TV's, cable and WiFi. This residence features a large outdoor patio with garden views and plenty of seating. Bayport sits on 27 lushly landscaped acres and has 1200 feet of private beach. Complimentary beach chairs and umbrellas are provided for guests. Enjoy an active lifestyle at Bayport. Community features include a junior sized heated Olympic swimming pool, 4 har-tru tennis courts for the Tennis enthusiasts, a fitness center, fishing pier, kayak storage, nature trails and a clubhouse perfect for gathering. 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. NOW AVAILABLE: JUNE - DECEMBER 2024
#T3497009

LONGBOAT KEY

830 BAYPORT WAY 830

2 Beds

2 Baths

1,456 Sq.Ft.

$9,000

MLS#: T3497009

AVAILABLE 2026 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay views. This 1600 sq. ft. two bedroom two bath condo is located directly on the sugary beach of Longboat Key with lounge chairs and umbrellas provided. Wrap around balcony with partial Gulf of Mexico and Longboat Key Club golf views. Washer/dryer in the unit, pool, fitness center and tennis courts plus. 24 hr. Concierge and garage parking. Recently painted, new flooring in bedrooms and kitchen. Short distance to St. Armands circle with upscale shopping and restaurants or drive to downtown and enjoy symphony, opera, ballet, live theater and a variety of restaurants to suit most palates.
#A4486249

LONGBOAT KEY

775 LONGBOAT CLUB ROAD 405

2 Beds

2 Baths

1,602 Sq.Ft.

$9,000

MLS#: A4486249

Picturesque Water view of Sarasota Bay . The Harbour Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boat ramp, kayak launch/storage, 3 tennis courts, covered parking and 400' of boat slips and bayfront. Features include over 1500 sq ft of living space in this end unit, high ceilings, Waterview available in all rooms, open floor plan, large enclosed balcony off living/dining room plus separate balconies off each bedroom, washer/dryer and extra-large bathrooms. Wifi, Cable TV and utilities included. Condo is Furnished. Easy access to Bay or Gulf through close by channel. Slip is offered for rent separately. Seasonal rental for select times of the year. 10 day notice required along with application for owner approval. Guest approval required.
#A4668491

LONGBOAT KEY

615 DREAM ISLAND PLACE 201

2 Beds

2 Baths

1,514 Sq.Ft.

$9,000

MLS#: A4668491

WELCOMING and tastefully decorated, this fully furnished 2 bedroom, 2 bathroom unit offers a relaxing atmosphere. The open concept floor plan with split bedrooms is spacious and inviting and this unit features two interior patios with serene canopy garden views. This amenity-rich community at sea’s edge is situated in the middle of Longboat Key and features 27 picturesque acres of well maintained gardens. Bayport is bordered by the Gulf of Mexico to the west with 1200 feet of private Gulf beach with deeded access, and Sarasota Bay to the east. Enjoy an active island lifestyle with 4 HarTru tennis courts (best on the Key), a Jr Olympic sized pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The clubhouse, with fitness center and full kitchen, hosts a number of social activities. A 2-minute walk to the Gulf of Mexico for morning beachcombing, surf casting or memorable sunsets. NOW AVAILABLE: May through November 2024 at "Off Season Rates" Please contact Agent for availability.
#T3492099

LONGBOAT KEY

833 BAYPORT WAY 833

2 Beds

2 Baths

1,456 Sq.Ft.

$9,000

MLS#: T3492099

Available December and January .Call for rates and availability .Looking for a vacation in warm sunny Florida in a condo where you walk directly out onto the deck directly onto the beach? Stay in this 3 bedroom (2 king beds/1 queen), 2 bath condo in Salty Acres with 2 covered parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and recently remodeled. It must be a monthly rental. $6,950 a month April - October. $6,000November, $5,900December, $8,000 January, $9,000 February, $11,000 March $12,000
#A4593076

LONGBOAT KEY

5621 GULF OF MEXICO DRIVE 103

3 Beds

2 Baths

1,731 Sq.Ft.

$9,000

MLS#: A4593076

Price reduced
short stories AVAILABLE NOW... Stunning 2 bedroom 2 bath Longboat Key Gulf front condo with direct sweeping view of the Gulf of Mexico. Every evening enjoy breathtaking sunsets on your private balcony. Start your day with a leisurely stroll on the soft sand beach or take a refreshing dip in the pool. This condo is beautifully furnished and professionally decorated. King size bed in both bedrooms. Open concept. Just a short drive to the shops and restaurants of St. Armand Circle. Enjoy great live theater, ballet, opera and symphony as well as a variety of restaurants and shopping in downtown Sarasota.
#A4597848

LONGBOAT KEY

2105 GULF OF MEXICO DRIVE 3404

2 Beds

2 Baths

1,461 Sq.Ft.

$8,721

MLS#: A4597848

Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the sparkling blue waters of the Gulf of Mexico from rear balcony with access from master bedroom and living room. Master bedroom includes king size bed, a jetted tub, walk in shower, & dual sinks. Guest bedroom with two twin beds & a King Bed in the 3rd bedroom. Kitchen includes stainless steel appliances & granite countertops. Side balcony access is from dining room and kitchen with a golf course view! Enjoy the amenities of this luxury condo resort, which includes a fitness center, a tennis court, private beach access, heated pool/spa, a gazebo with complimentary grills, 24 concierge/security, and within a golf course community. Rent includes water, sewer, basic cable, and internet. Electric will be a shared expense. Call now for more details!
#A4431350

LONGBOAT KEY

455 LONGBOAT CLUB ROAD 401

3 Beds

3 Baths

2,780 Sq.Ft.

$8,000

MLS#: A4431350

AVAILABLE - APRIL 2026 - ANNUAL RENTAL - Welcome home! Enjoy the serenity of this 3 bed, 3 bath, 2 car garage residence, located in Harbour Oaks within the gated community of Bay Isles in the heart of Longboat Key. This tastefully appointed home with open concept floor plan features vaulted ceilings and skylights which create an abundance of natural light throughout the home. The amazing gourmet kitchen offers custom cabinets with soft-close drawers, quartz counters, an appliance package inclusive of refrigerator, induction range, dishwasher and microwave. The Great Room offers beautiful built-in cabinetry and a fireplace. The large primary bedroom, boasts an ensuite spa style bathroom with walk-in shower and dual vanities, and a walk-in closet. Two secondary bedrooms both with ensuite baths are spacious and comfortable. At the end of the day, relax on the screened in patio, overlooking the lush expanse of the manicured greens and relish in the ambiance of breathtaking sunsets or alternatively step out of your front door to enjoy a refreshing dip in the community pool. All residents have access and privileges to the private Bay Isles Beach Club with miles of sugar sand beaches and calm waters of the Gulf of Mexico. All the conveniences of shopping dining and entertainment is just a short drive over the bridge.
#TB8412756

LONGBOAT KEY

2377 HARBOUR OAKS DRIVE

3 Beds

3 Baths

2,487 Sq.Ft.

$8,000

MLS#: TB8412756

LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. Open floor plan, with vaulted ceilings, hardwood floors throughout. Private screened in pool with a view of the golf course and evening sunsets with plenty of space for entertaining. Kitchen is equipped with everything a cook would need including a separate wet bar with a built-in wine cooler. Access to the private deeded Bay Isles Beach Club. Just a short drive to the Longboat Key's Town Center for all your shopping needs. Dec-April $12,000 a month + tax & fees May-Nov. $8,000 a month + tax & fees. GULF OF MEXICO, LONGBOAT KEY VACATION RENTALS, SARASOTA VACATION RENTALS.
#A4571577

LONGBOAT KEY

2369 HARBOUR OAKS DRIVE

3 Beds

2 Baths

2,424 Sq.Ft.

$8,000

MLS#: A4571577

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