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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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511 Properties Found. Page 32 of 35.

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

Price reduced
AVAILABLE January 2026 $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. $4500 a month April - October. $5,000November, $5,900December, $7,000 January, $7,000 February, $11,000 March $13,000
#A4631757

LONGBOAT KEY

5621 GULF OF MEXICO DRIVE 102

2 Beds

2 Baths

1,346 Sq.Ft.

$7,000

MLS#: A4631757

Price reduced
RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach! Start living the island lifestyle in this beautifully updated, furnished 2-bedroom, 2-bath condo at the Islander Club on South Longboat Key! This turnkey rental is ready for immediate enjoyment—just bring your suitcase. Enjoy a bright, open layout with floor-to-ceiling hurricane impact windows and a spacious 38-ft garden terrace—perfect for soaking up morning sunrises and relaxing with tropical breezes. The updated kitchen features granite countertops, plenty of storage, and flows seamlessly into the living room—ideal for relaxing or entertaining. The primary suite includes a walk-in closet, en-suite bath, and sliding doors opening to the terrace—fall asleep to the sound of waves! The guest bedroom also offers terrace access and garden views. Both bathrooms are updated with granite counters and modern glass showers. In-unit washer included. Resort-style amenities include a beachfront Jr. Olympic pool, fitness center, clubhouse, library, game room, and direct beach access. On-site management and secure entry add peace of mind. Located across the street from the Avenue of the Flowers shopping center (Publix, CVS, Post Office) and just a short drive to St. Armands Circle and Downtown Sarasota with shopping, dining, and arts.
#A4650448

LONGBOAT KEY

2295 E GULF OF MEXICO DRIVE E 55

2 Beds

2 Baths

1,235 Sq.Ft.

$7,000

MLS#: A4650448

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

1,192 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

Price reduced
Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January and February 2026! An opportunity that won’t last long. Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access. Appreciate the convenience of pulling directly into your private carport with no steps or elevators and relish the peace and privacy of having no neighbors above or below during your stay. This beautifully appointed coastal villa features two bedrooms, two bathrooms, a spacious open concept living area, and an opulent interior design that is soaked in sunlight. The brand new remodeled and fully equipped kitchen is ideal for preparing meals with fresh local ingredients from nearby farmers' markets or head out to dine at one of the delectable nearby restaurants. Windward Bay is a low-density, wildlife-rich community nestled mid-Longboat Key on 26 acres, offering resort-style amenities including two heated pools, two tennis/pickleball courts, two marinas, kayak racks, shuffleboard, a clubhouse with kitchen, library, fitness room, two saunas, and multiple fire pits and barbecue areas throughout the property. Enjoy half a mile of scenic waterfront trails and direct access to the Gulf or Bay for boating, fishing, or simply soaking up the sun. Located just minutes from Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and vibrant cultural attractions. This is a rare opportunity to create lasting memories in a home that guests return to year after year. This villa is more than a vacation rental — it’s a tradition. One couple has returned every March and April for over a decade, drawn by the comfort, beauty, and unbeatable location.
#A4668115

LONGBOAT KEY

4780 GULF OF MEXICO DR. VILLA 5

2 Beds

2 Baths

1,256 Sq.Ft.

$6,500

MLS#: A4668115

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.

$6,500

MLS#: A4648967

AVAILABLE Jan - Mar 2026!!! : 1 month minimum. 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 $6,500 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

1,393 Sq.Ft.

$6,500

MLS#: A4620764

Escape to paradise with a stay in this newly renovated 2-bedroom, 2-bath second floor condominium at Bayport Beach & Tennis Club on Longboat Key. Perfectly positioned for your dream beach getaway, this condo blends comfort, style and unbeatable amenities. Bright, modern, and welcoming, this condo has been thoughtfully updated with all the comforts of home, including a king-size bed in the primary bedroom. Enjoy access to Bayport's Junior Olympic-sized pool, clay court tennis, bocce ball court, and a private dock on Sarasota Bay with stunning sunrise views. Located mid-island, you have private access to our white sand beach with stunning Gulf Coast views. Chairs and umbrellas are provided--ideal for morning walks, sunbathing, or watching the sunset. The property offers a semi-private entrance, providing a more secluded and peaceful experience for your vacation. Whether you're looking to relax by the pool, play tennis, or simply enjoy the beach, Bayport Beach & Tennis Club is the perfect blend of relaxation and recreation--a true hidden gem. 30 Day minimum stay required. Available: DECEMBER 2025, JANUARY 2026, MAY 2026, SEPTEMBER 2026, OCTOBER 2026, NOVEMBER 2026, DECEMBER 2026.
#A4667152

LONGBOAT KEY

618 BAYPORT WAY BAYPORT WAY 618

2 Beds

2 Baths

1,260 Sq.Ft.

$6,050

MLS#: A4667152

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

1,257 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

1,336 Sq.Ft.

$6,000

MLS#: A4655690

Newly renovated and elegantly designed 2-bedroom, 2-bathroom condo in the highly desirable Longboat Harbour Condominiums, located just 600 feet from the shore and a 3-minute walk to the beach. This fully furnished ground floor unit offers a modern open layout with scenic views, access to Sarasota Bay, and resort-style community amenities including four swimming pools (one located right behind the unit), a gym, kayaking, tennis courts, pickleball, a game room with pool tables, and a community grill area perfect for family barbecues. Residents also enjoy private beach access with a pavilion, bathrooms, and showers for ultimate convenience. $6,000/month. Available for rent from December 2026 to April 2027. Minimum rental period: 2 months Perfect for seasonal living!!
#O6353609

LONGBOAT KEY

4360 CHATHAM DRIVE 108

2 Beds

2 Baths

1,316 Sq.Ft.

$6,000

MLS#: O6353609

This beautiful 2 bedroom/2 bath split and open floor plan condo is spacious and bright. The kitchen featuring a built-in desk and granite counters has been opened to the dining/living room area with views of the pond, fountain and lush tropical landscaping. A stackable washer/dryer in closet for your convenience. Lanai enclosed with tropical views. Bayport Beach and Tennis Club is bordered by the Gulf of Mexico to the West with 1200 feet of private beach and Sarasota Bay to the East. This resort community is situated in the heart of Longboat Key. A popular residential enclave of 136 quality-constructed homes on 27 picturesque acres. Residents enjoy a heated, Jr Olympic sized pool. fishing pier, steps to a private Gulf beach, kayak launch and storage, 4 Har-Tru tennis courts, golf practice net, bocce court, social room with full kitchen, library, piano, fitness center, shelled nature walking paths, tropical gardens and a number of social activities. Shopping, Restaurants and the Arts are located within minutes including St Armand’s Circle, Downtown Sarasota & Anna Maria to name a few. Golf, Marina and Restaurants at the Longboat Key Club. A “PET” friendly community. AVAILABLE STARTING 11/1/2025 - ANNUAL LEASE ONLY,
#T3488636

LONGBOAT KEY

706 BAYPORT WAY 706

2 Beds

2 Baths

1,601 Sq.Ft.

$6,000

MLS#: T3488636

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