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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
417
# of Listings
2
Avg # of Bedrooms
$787
Avg. $ / Sq.Ft.
$1,318,741
Med. List Price

Browse Long Boat Key Real Estate Listings

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$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

417 Properties Found. Page 24 of 28.

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

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

3,400 Sq.Ft.

$8,000

MLS#: A4431350

Stunning Portobello Vacation 2/2 Condo on Longboat Key. This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style décor, new windows and sliding glass doors, new laminate flooring and carpet, new kitchen appliances, three flat screen TVs with HD boxes and HD Extreme channel lineup, king size Master bed and guest bedroom provides two double beds, in unit washer and dryer for convenience. One assigned parking space and guest parking available for second car. Wi-Fi and cable package are provided. Heated swimming pool, tennis court and boat dock located conveniently across the street on the bayside of the complex. Only 1/2 mile to Publix shopping and dining center and approximately 5 miles from fabulous St. Armand's Circle. Sorry no pets permitted (no exceptions). No smoking permitted. 13% sales and tourism taxes apply for any rental less than 6 months. Property is available Apr 2025-Dec 2025 and Apr 2026 and after.
#A4208788

LONGBOAT KEY

3235 GULF OF MEXICO DRIVE A302

2 Beds

2 Baths

1,420 Sq.Ft.

$8,000

MLS#: A4208788

Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Primary Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive white sand beach on the Gulf of Mexico.
#A4109016

LONGBOAT KEY

1925 GULF OF MEXICO DRIVE G8-208

3 Beds

2 Baths

2,110 Sq.Ft.

$8,000

MLS#: A4109016

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

2,892 Sq.Ft.

$8,000

MLS#: A4571577

Welcome to Grand Bay on Longboat Key! Your private elevator will take you directly to your unique double-door entry. Once you are inside you are greeted with panoramic water views from all angles of your exclusive wrap-around balcony. This luxury condo is turnkey furnished with tasteful updates throughout. There are two spacious bedrooms and a third that was converted into a den with a pull-out sofa. The master bedroom has a large en-suite bathroom with an oversized master closet. The guest bedroom also has its own on-suite bath and two twin beds. You will find the kitchen has been fully equipped and is perfect for entertaining. Grand Bay is located behind three gates to offer the highest level of security. There are amenities galore which include a private garage parking off the lobby, lap pool, gym, hot tub, large clubhouse, newly remodeled lobby, and private beach access. You will live close to fine dining and entertainment on St. Armand’s Circle, Ana Maria Island, and Downtown Sarasota. Enjoy boating on the beautiful waters, fantastic golf courses, and award-winning beaches all within a few miles of your new home. 30-day minimum application process. Available for short-term 3 to 6 Month Lease at $9500 per month and a 12 Month Lease is $8000 per month.
#A4650491

LONGBOAT KEY

3010 GRAND BAY BOULEVARD 445

3 Beds

2 Baths

2,843 Sq.Ft.

$8,000

MLS#: A4650491

LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen. Master bedroom has two full size beds as well as one full size bed in the 2nd bedroom. A five minute walk to shopping & pharmacy. Short drive to St. Armand's or downtown Sarasota, for restaurants , theaters and boutique shopping. SARASOTA FL.BEACHFRONT,GULF OF MEXICO,RENTAL,SEASONAL,LUXURY
#A4494373

LONGBOAT KEY

2425 GULF OF MEXICO DRIVE 4E

2 Beds

2 Baths

1,701 Sq.Ft.

$8,000

MLS#: A4494373

LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with ease. Enjoy shopping on St. Armands Circle, downtown Sarasota or on the key. South end of Longboat Key makes for easy access anywhere you want to go. Plenty of restaurants to choose from, from the key to downtown Sarasota. VACATION, LUXURY, GULF OF MEXICO, SARASOTA FL. RENTALS.
#A4194846

LONGBOAT KEY

2109 GULF OF MEXICO DRIVE 1402

2 Beds

2 Baths

1,422 Sq.Ft.

$8,000

MLS#: A4194846

SNOW BIRDS WELCOME! Fully Furnished and turnkey, immaculate 2 bedroom condo at The Islander Club with over 40 foot terrace. Renters have access to private beach and all ammenities; Clubhouse and Tennis Courts, New Pool, New Fitness Center, New Saunas. Islander Club is minutes to grocery, convenience stores, restaurants, The Longboat Key Club and a short distance to world famous St. Armands Circle!!! Available in September for 1 month. THREE MONTH MINIMUM after October through March 2026
#A4659952

LONGBOAT KEY

2295 GULF OF MEXICO 54S

2 Beds

2 Baths

1,450 Sq.Ft.

$8,000

MLS#: A4659952

Newly remodeled bungalow blocks from Whitney Beach & a block from bay. Historic home was once a post office in the 1920's. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! Sleep tight in a quiet neighborhood that allows zero public parking. Very serene, private fenced-in property - what happens here, stays here! Boat parking & convenient to public water access. Walk to Mar Vista, or join the fun in St. Armand's. Available furnished, for a 28 day minimum, sleeps 6 in king/king with 2 closets in each room & a cozy queen sofa.
#TB8384380

LONGBOAT KEY

701 BROADWAY STREET

2 Beds

2 Baths

2,331 Sq.Ft.

$7,850

MLS#: TB8384380

SEASONAL: 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, in unit washer/dryer, large walk-in closets and covered parking. The Master suite features King-sized bed, TV, & opens to a private balcony. The comfortable guest bedroom offers a Queen and 1 twin bed with ceiling fan, and guest bathroom with tub/shower. The Westchester community is located on 7-plus acres of beautifully landscaped grounds, meticulously maintained with tennis court, 2 heated pools, updated Clubhouse and 3 private Tiki-hut areas. Gulf beaches are what make Longboat Key unique and you can walk for miles on the beach from the condo. Longboat Key also has 10 miles of bicycle paths on either side of Gulf of Mexico Drive. Located just 6 miles from fashionable St. Armands Circle and only a short drive to downtown Sarasota with arts, theatre, restaurants and shopping. This is non-smoking unit. Sorry, this condo association does not allow pets. BOOKED JAN-MAR, 2026.
#A4651021

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 201

2 Beds

2 Baths

1,604 Sq.Ft.

$7,800

MLS#: A4651021

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