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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
411
# of Listings
2
Avg # of Bedrooms
$793
Avg. $ / Sq.Ft.
$1,328,516
Med. List Price

Browse Long Boat Key Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

411 Properties Found. Page 23 of 28.

Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room includes bunk beds for family fun. Accommodating up to 9 guests, the property is just a short stroll to pristine Whitney Beach and nearby fishing docks, with top local restaurants and cafes — like Mar Vista, Shore, Whitney’s, and more — only minutes away. A local owner ensures attentive service to make your stay unforgettable. $10,000 off season/$14,000 season
#A4660175

LONGBOAT KEY

6979 LONGBOAT DRIVE S

3 Beds

2 Baths

1,869 Sq.Ft.

$10,000

MLS#: A4660175

GORGEOUS LONG 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 beautifully appointed. This residence offers a wonderful retreat as a annual. 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 the private beach on the Gulf of Mexico for a morning of beachcombing, surf casting or memorable sunsets. Please contact Agent for availability. NOW AVAILABLE STARTING 8/1/2024
#T3488628

LONGBOAT KEY

522 BAYPORT WAY 522

2 Beds

2 Baths

1,426 Sq.Ft.

$10,000

MLS#: T3488628

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.

$9,721

MLS#: A4597848

THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean breezes flow through the unit and the peaceful sound of the ocean is calming and soothing. Pristine turquoise water and beautiful beach. Take a refreshing dip in the pool. Enjoy magnificent color filled sunsets every evening. Take a leisurely stroll on the beach. Sun filled rooms, amazing views. Dine alfresco on the balcony and enjoy breathtaking views of the Gulf of Mexico. Located close to stylish downtown Sarasota and St. Armand Circle you will enjoy a vast array of culture, entertainment and distinctive boutique shopping. It is a remarkable destination for your getaway paradise vacation.
#A4537061

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 507

3 Beds

2 Baths

1,336 Sq.Ft.

$9,587

MLS#: A4537061

Delightfully appealing seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes fully furnished and equipped with flat screen TV's, cable and WiFi. This residence features a spacious screened lanai with garden views in addition to an outdoor sun deck with loungers for basking in the sun. Bayport sits on 27 lushly landscaped acres and has 1200 feet of pristine private beach for your exclusive use. Complimentary beach chairs and umbrellas are provided for guests. Enjoy an active lifestyle at Bayport as the Community includes 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: September - December 2023. Please contact Agent for availability.
#T3415401

LONGBOAT KEY

744 BAYPORT WAY 744

2 Beds

2 Baths

1,600 Sq.Ft.

$9,500

MLS#: T3415401

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

1,600 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

1,414 Sq.Ft.

$9,500

MLS#: T3337994

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 month April - October. $6,000November, $5,900December, $8,000 January, $10,000 February, $11,000 March $13,000
#A4631757

LONGBOAT KEY

5621 GULF OF MEXICO DRIVE 102

2 Beds

2 Baths

1,350 Sq.Ft.

$9,500

MLS#: A4631757

RARELY AVAILABLE! Welcome to L'AMBIANCE! Discover an extraordinary opportunity to rent this luxurious 2-bedroom, 2.5-bathroom condo on the island Longboat Key. Inside the Longboat Key club, this rarely available residence offers 2 car parking spaces (under building garage) private elevator, breathtaking, unobstructed views of the sparkling Gulf of America, complemented by sweeping vistas of lush golf courses, and the serene beauty of the rest of Sarasota.This exclusive community redefines luxury with exceptional, personable service and top-tier front desk and building staff, ensuring peace of mind and a lifestyle of ease. This is coastal living at its finest—a rare gem that won’t be available for long. With this prime location and unparalleled scenery, this is coastal living at its finest—don’t miss your chance to call this exclusive retreat your new home.
#A4649461

LONGBOAT KEY

435 L AMBIANCE DRIVE H402

2 Beds

2 Baths

3,436 Sq.Ft.

$9,000

MLS#: A4649461

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.

$9,000

MLS#: A4660546

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

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

1,600 Sq.Ft.

$9,000

MLS#: T3497009

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

1,600 Sq.Ft.

$9,000

MLS#: T3492099

Exceptional Rental Opportunity in Queens Harbour Introducing a remarkable opportunity to rent a stunning 4-bedroom corner lot residence in the highly sought-after Queens Harbour community, located behind the gates of the Longboat Key Club. This property features a brand new roof and offers the perfect setting for those looking to embrace the Florida lifestyle. The home is filled with abundant natural light, particularly in the expansive great room, which boasts two stories of glass. The chef’s kitchen is a standout feature, complete with a spacious center island, a Viking cooktop, an integrated Subzero refrigerator, and ample counter space—ideal for both meal preparation and entertaining. The first-floor primary suite provides a generous walk-in closet, dual vanities, and direct access to a private terrace, creating a serene retreat. The outdoor space includes a screened lanai and a heated pool, all surrounded by lush landscaping that ensures privacy. As a resident of the Bay Isles community, you'll enjoy exclusive access to the private Bay Isles Beach Club, complete with shower facilities, lockers, and picnic areas. The association also covers exterior painting and lawn maintenance, allowing for a low-maintenance lifestyle. Centrally located, this residence is just minutes from grocery stores, fine dining, and St. Armands Circle, with easy access to downtown Sarasota. This well-constructed home awaits your personal touch to transform it into your ideal living space. Brand new roof installed in 2024! Schedule a viewing today to explore the possibilities and start living your best Florida life!
#A4650297

LONGBOAT KEY

3605 FAIR OAKS PLACE

4 Beds

3 Baths

4,448 Sq.Ft.

$9,000

MLS#: A4650297

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 state-of-the-art GE Profile appliances and plenty of storage. The Master retreat features new king accommodations, chic-like bath, large walk-in shower and dual vanities. Such a tranquil sanctuary with its own private balcony. See yourself waking up every morning with serene Gulf views, dolphins and water birds with morning coffee. Wow! The large and private Guest bedroom is complete with 2 queen beds, en-suite bath, walk-in closet with washer/dryer. For your added comfort, you’ll enjoy Smart TV’s, Direct TV, Wi-Fi and desk area, just in case you need to get a little work done. Residents of Westchester enjoy a wide range of amenities including heated pool, deck chairs, lounges with umbrellas, private beach access, tennis, miles of beach to walk and enjoy, covered parking and outside storage right next to your carport. This gorgeous part of Longboat Key has so much to offer, with lots of new restaurants, shopping and activities going both North, and South on the key. So close to everything!! Located just 5 miles from fashionable St. Armands Circle and only a short drive to downtown Sarasota with arts, theatre, restaurants and shopping. Available: September through Dec 14th $4,000 monthly. Available: January 4th – April 31st at $8,500 monthly plus standard fees. This is non-smoking unit. Sorry, this condo association does not allow pets.
#A4620764

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 203

2 Beds

2 Baths

1,604 Sq.Ft.

$8,500

MLS#: A4620764

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