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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
413
# of Listings
2
Avg # of Bedrooms
$792
Avg. $ / Sq.Ft.
$1,320,352
Med. List Price

Browse Long Boat Key Real Estate Listings

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413 Properties Found. Page 25 of 28.

OPEN FOR SEASON 2026. Also available off season @$3300 per month. Rarely available tranquil 2 bed/2 bath corner unit condo with full bay views at desirable Windward Bay! This light and bright condo is the perfect place to spend your season in the sun in a quiet community directly across the street from the sparkling Gulf of Mexico waters and white sandy beaches of Longboat Key. Walk or bike along the winding estuary trails along the bay! Bring your kayak and launch from the community dock! Windward Bay is perfect for those seeking an active lifestyle. Amenities include two marinas, kayak storage, walking and bike trails, two tennis courts, fitness center, two heated pools, saunas, and direct Bay access. Centrally located to the beach access, restaurants, shops of St. Armand’s Circle and downtown Sarasota. Just a short ride over the bridge in the other direction to explore Anna Maria Island. Extremely quiet and comfortable condo. Your small dog is welcome!
#A4506042

LONGBOAT KEY

4540 GULF OF MEXICO DRIVE PH2

2 Beds

2 Baths

1,312 Sq.Ft.

$7,500

MLS#: A4506042

Absolutely beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Newly renovated bathrooms and kitchen with high end finishes round out this fabulous property. Enjoy your morning coffee while sitting on the screened lanai that looks out over the bay. Community amenities include private beach access, pool, tennis courts, clubhouse, kayak launch and BBQ area. Call today as this will not last long!!!
#A4418888

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B303

2 Beds

2 Baths

1,260 Sq.Ft.

$7,200

MLS#: A4418888

This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views. This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can’t be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered parking. As you step into this beautiful 2 bedroom 2 bath turnkey furnished condo, you will find tiled floors throughout and a split floor plan. The large family room has beautiful views of the Gulf, from the sliding glass doors that open to your screened-in balcony. Cable & Wi-Fi Included. There is a gorgeous chandelier over the quaint dining table with 4 chairs, where everyone can gather for a wonderful meal. The kitchen boasts gorgeous granite counters and white cabinetry a ceiling fan, & recessed lighting. The Master has a King-sized bed, TV, & opens to the balcony.  The en-suite Master Bath offers double sinks, a shower stall and large walk-in closet.  The adorable guest bedroom boast 2 twin beds to share, a ceiling fan, and a guest bathroom with tub/shower. Ideally located near everything the area has to offer, including world-class dining & shopping of historical St. Armand’s. There are plenty of outdoor activities as well to keep you busy, such as kayak rentals, bicycle rentals, and take a quiet stroll through Bayfront Park. Your quaint & cozy retreat awaits you! Sorry, no furry friends thank you.
#A4452938

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 605

2 Beds

2 Baths

1,393 Sq.Ft.

$7,200

MLS#: A4452938

AVAILABLE. 2026 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay views from the master lanai. Unit has a washer/dryer and 2 full baths. Feel free to bring your small dog as well. Easy access to St. Armands Circle and Bradenton Beach.
#A4478968

LONGBOAT KEY

655 CEDARS COURT 655

1 Beds

2 Baths

2,376 Sq.Ft.

$7,000

MLS#: A4478968

SEASONAL/VACATION RENTAL! AVAILABLE FOR 2026 SEASON! CALL TODAY! 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, 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 twin beds 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. Amenities include 2 pools, tiki hut, tennis and pickleball court, clubhouse, grilling area and kayakk storage. Non smoking residence.
#A4626398

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 202

2 Beds

2 Baths

1,393 Sq.Ft.

$7,000

MLS#: A4626398

Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You are just across the street from the gorgeous Gulf Beaches, with private beach access. Upon entering this condo, you will see an ocean view from the third floor. As you enter, you will find the large kitchen, which has stainless steel appliances, six barstools, a giant kitchen island, a lounge area with a sofa, and plenty of space to prepare your family’s favorite treats. You will find lovely natural lighting throughout, due to this condo having windows on all four sides. Adjacent is the dining table, with gorgeous West Elm chairs that accommodate up to six. The spacious living room has a sizeable “L” shaped couch, an entertainment center, and beautiful natural lighting through the windows. There are views from the master bedroom and the reading nook in the kitchen area, where you will love to enjoy your morning coffee with the sunshine streaming in those windows. The primary bedroom has a king-size bed, a chair, a TV, and plenty of closet space for your personal belongings. Attached is the primary bathroom, which has a large vanity with a stunning walk-in shower that has exquisite masonry work, and a detachable showerhead. The second bedroom has a queen-size bed and plenty of closet space. The second bathroom has a large vanity with a shower/tub combo. There is community Kayaks with a lift for use by renters, there are two rooftop patios in the building which are shared. The one at the front is perfect for watching the sunset every evening. This condo is a short drive to St. Armands Circle and Downtown Sarasota where there are restaurants, boutiques, shopping, theater, opera, ballet, botanical gardens etc. we are close to many great restaurants. Come see why people come to Longboat Key year after year. There is a dedicated covered parking spot and additional guest parking. House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets. **Taxes and fees not included.
#A4555216

LONGBOAT KEY

3804 GULF OF MEXICO DRIVE B307

2 Beds

2 Baths

1,133 Sq.Ft.

$7,000

MLS#: A4555216

2-bed, 2-bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community kayaks, socialize with neighbors in the expansive clubhouse, or get your daily work out in the fitness center! This turnkey unit offers floods of natural light, updated finishes, and a covered parking spot. Ideally located in the middle of the key, with easy access to Publix, the chic St Armands Circle, Downtown Sarasota, and the charming Anna Maria Island. Your dream getaway awaits! ***Some of the amenities are still damaged/closed from the 2024 hurricanes***
#A4648967

LONGBOAT KEY

3802 GULF OF MEXICO DRIVE A207

2 Beds

2 Baths

1,133 Sq.Ft.

$7,000

MLS#: A4648967

GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought-after Bay Isles community. The spacious Kitchen had been updated along with the both baths, with Quartz counter-tops and new cabinetry, the Primary suite offers a King bed, views of the bay and the Primary bath has dual sinks, new vanity, new lighting, new shower and an updated large closet. The Guest bedroom has two twin beds that can be made into a King bed, and the guest bath has a new vanity, new mirror and lighting. Enjoy your morning coffee or a sunset cocktail on the Lanai overlooking the Bay and intercoastal waterway. This location has its own pool, and a larger community pool and spa with the clubhouse just a few steps away, you can take advantage of the newer fitness room and reserve a court for tennis or pickle ball. Pack up the car and spend the day at the BAY ISLES PRIVATE BEACH CLUB, located at 2111 Gulf of Mexico Drive.
#A4641782

LONGBOAT KEY

1930 HARBOURSIDE DRIVE 134

2 Beds

2 Baths

1,312 Sq.Ft.

$7,000

MLS#: A4641782

Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere. Step into island living with the second floor as your main living space, thoughtfully designed for comfort and connection. Relax on the queen-size pull-out sofa, or step out onto the screened-in lanai where you can sip your morning coffee while soaking in the serene, lush surroundings. The dining area comfortably seats up to seven, making it the perfect setting for family meals and lively conversations. Just adjacent, the kitchen offers four barstools, ample counter space, and all the essentials for preparing your favorite family dishes and beach-day snacks. Upstairs, the third level features both bedrooms. The primary bedroom is a true retreat, featuring a king-size bed, breathtaking views of the tropical landscape, and an attached, spa-inspired bathroom with dual vanities and a spacious walk-in shower. The second bedroom includes a queen-size bed with a twin trundle, a TV, and generous closet space—ideal for guests or kids to unwind in comfort. What truly sets this home apart is the incredible Cedars East community. Located on the bay side of Longboat Key, Cedars East offers a lifestyle like no other—with a heated junior Olympic-size pool, tennis courts, boardwalks through mangrove-lined nature trails, bike paths, and a bayside fishing pier. You’ll love the lush, well-manicured grounds, and how close you are to the gulf beaches, boutique shopping, and local dining that Longboat Key is famous for. Whether you're planning to spend your days exploring the beach, relaxing poolside, or simply enjoying the peace and beauty of the natural surroundings, this charming Cedars East getaway is the perfect island retreat. House Rule: No smoking. No burning candles inside of lodging. No parties. Furry friends welcome, max 2, and require a $200 per pet non-refundable pet fee to be paid directly to the management company.
#A4655086

LONGBOAT KEY

535 FOREST WAY

2 Beds

2 Baths

1,440 Sq.Ft.

$6,900

MLS#: A4655086

AVAILABLE FOR 2026 SEASON! MINIMUM 3 MONTH LEASE PLEASE. LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the condo has to give with the natural light that floods through the large sliding glass doors. From the beautifully updated kitchen, you can see the dining room, living room, screened patio and the Gulf of Mexico! The kitchen also offers stone countertops, stainless steel appliances and plenty of cabinet and counter space. The condo sleeps four (1 king bed & 2 twin beds) and has walk-in showers in both updated bathrooms. All top-of-the-line upgrades throughout the condo including impact doors and windows, Washer/Dryer and all utilities provided with two TVs in the unit. The back patio is fully screened in and features beautiful views of the ocean! The private beach access is just off the clubhouse which is steps away. Seaplace is one of the largest, most highly sought after complexes on Longboat Key. This resort style community offers 2 heated pools, hot tub, kiddie pool, beachfront patio, 4 grills, 3 har-tru tennis courts, game room, work out room, library, sauna, 24-hour security, and monthly events for anyone to enjoy. Longboat Key Club golf course is approx. 2 miles away. Also enjoy strolling around St. Armand's Circle which offers top-rated dining and shopping. ** Rent includes electricity, water, cable, internet, sewage, pest control, extra storage and all the amazing community amenities! *No pets allowed *Application Fee: $100 per applicant *HOA Application Fee: $100 per applicant *250 cleaning fee *$50 booking fee *Security Deposit: $750 for short term *13% seasonal rent tax applies to 6 month and under rentals
#A4618406

LONGBOAT KEY

1945 GULF OF MEXICO DRIVE M2-414

2 Beds

2 Baths

928 Sq.Ft.

$6,500

MLS#: A4618406

"SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE OF LONGBOAT KEY. BOOKED FOR FEB-APRIL 2026. AVAILABLE NOV 2025 AT $3,500, DEC 2025 AT $5,000 & JAN 2026 AT $6,500. Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the unit, you are met with a light, bright and open feeling with the natural light coming in through the large sliding glass doors which open up onto the fully screened in and covered balcony. Beautifully furnished and decorated, living a fully equipped kitchen offering ample cabinet and storage space, washer/dryer, dining room, and living room Both the master and guest bathrooms have newly installed walk-in showers. Seaplace is one of the largest, most highly sought after complexes on Longboat Key. This resort style community offers 2 heated pools, hot tub, kiddie pool, beachfront patio, 4 grills, 3 har-tru tennis courts, game room, work out room, library, sauna, 24-hour security, and monthly events. Plus, the private beach access is just steps away from the beautiful crystal quartz sandy beaches and turquoise Gulf of Mexico waters. Conveniently located just a short drive from boutique shopping, dining and cultural attractions of St. Armand's Circle and Downtown Sarasota with the infamous Ringling Art Museum, Maria Selby Botanical Gardens, and Marina Jacks for boat tours and sunset dinner cruises. Or take a short ride over the bridge in the opposite direction to explore the beautiful Anna Maria Island. Longboat Key Club Golf Course is approx. 2 miles away. **This is a 3-month minimum rental. ** Sorry, no pets allowed.
#A4650120

LONGBOAT KEY

1945 GULF OF MEXICO DRIVE M2-402

2 Beds

2 Baths

1,019 Sq.Ft.

$6,500

MLS#: A4650120

SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST ARMANDS CIRCLE of restaurants, shops and entertainment.
#A4572396

LONGBOAT KEY

1975 GULF OF MEXICO DRIVE 208

2 Beds

2 Baths

1,392 Sq.Ft.

$6,000

MLS#: A4572396

Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for the occasional guests. The condo comfortably sleeps 6. This beachfront community features a large, heated swimming pool, fitness rooms, bicycle racks, and a clubhouse with a catering kitchen perfect for get-togethers. Conveniently located across from the Centre Shops and just a short drive north to the famous Beer Can Island or drive south to St. Armand’s Circle and downtown Sarasota. The possibilities are endless! Perfect for an extended stay.
#A4451608

LONGBOAT KEY

5393 GULF OF MEXICO DRIVE 208

2 Beds

2 Baths

1,300 Sq.Ft.

$6,000

MLS#: A4451608

Furnished beachfront vacation rental! This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is located in a smaller building, on an uncrowded segment of beach that can often be enjoyed in complete solitude. The unit was recently upgraded with a new washer/dryer, luxury vinyl flooring in the bedrooms, a plethora of fresh artwork, accents, linens, beach amenities, and more! Enjoy cable TV and high speed WiFi that is nearly as reliable as your view of the sunset! The fully equipped kitchen is truly a chef's pleasure, featuring both a wine fridge and a Keurig coffee maker. Located in the heart of the recreational wonderland that is Longboat Key, this particular spot is so incredibly tranquil and private, yet so well connected to amenities, airports, cities and towns. Available long term for $6500/month. Vacation rental rates (1 month minimum): January: $10,000 February: $12,000 March: $12,000 April: $10,000 May through October: $5,000 (per month) November: $6,000 December: $6,000 3 month minimum stay during peak season (January through April) Please note that a $150 application fee is due directly to the HOA, and your stay is pending their approval.
#A4655690

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 305

2 Beds

2 Baths

1,456 Sq.Ft.

$6,000

MLS#: A4655690

Welcome to the Sanctuary. This beach front community is located inside the private gates of The Longboat Key Club. This 1st floor walk out residence that feels like a beach house will impress you with the space and tasteful decor/furnishings. Spend your time walking the private beach with the turquoise blue waters of the Gulf of Mexico along with a game of tennis, private fitness center, Olympic sized pools/spa or ride bikes to St. Armand's circle for a great lunch or dinner. The kitchen is spacious and upgraded with lovely granite and top of the line appliances if you prefer to stay at home and cook. At the Sanctuary you will be part of 18 incredible beachfront acres. Conveniently located on south Longboat Key close to St. Armand's and downtown Sarasota. Available today Annually or possibly seasonally.
#A4663441

LONGBOAT KEY

535 SANCTUARY DRIVE A102

3 Beds

2 Baths

3,380 Sq.Ft.

$6,000

MLS#: A4663441

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