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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
507
# of Listings
2
Avg # of Bedrooms
$867
Avg. $ / Sq.Ft.
$1,539,132
Med. List Price

Browse Long Boat Key Real Estate Listings

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507 Properties Found. Page 31 of 34.

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

Available Dec 20- April .Steps to the Sand – 3BR/3BA Beachfront Condo with Heated Pool & Spa | Longboat Key Enjoy the best of beachfront living at 5611 Gulf of Mexico Drive, Unit 105 — a beautifully appointed three-bedroom, three-bath condo located in a boutique community directly on the beach. You’re just steps away from the soft sand and turquoise waters of the Gulf of Mexico. This spacious residence offers an open and inviting layout, tastefully decorated with a relaxed coastal style. The modern kitchen is fully equipped with stainless steel appliances, quartz countertops, and all the essentials for dining at home. Each of the three bedrooms features comfortable bedding and its own bathroom, making this the perfect setup for families or couples traveling together. When you’re not enjoying the beach, take a dip in the heated beachfront pool and spa. Located mid-island on Longboat Key, this property offers easy access to St. Armands Circle, Anna Maria Island, and Downtown Sarasota—all filled with local shops, dining, and entertainment. Highlights: 3 bedrooms, 3 full baths (sleeps up to 6) unit in a beachfront building — steps to the sand Heated Gulf-front pool and spa Fully equipped kitchen with modern appliances Washer & dryer in unit Convenient mid-island location close to restaurants and shops Experience the tranquility of Longboat Key — where every day begins just a few steps from the Gulf
#A4668139

LONGBOAT KEY

5611 GULF OF MEXICO DRIVE 5

3 Beds

3 Baths

1,672 Sq.Ft.

$7,750

MLS#: A4668139

Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next Florida escape. As you step inside, you're greeted by a light, bright, and cozy atmosphere, with large windows that frame the sparkling blue waters of the Gulf. The kitchen is a chef’s delight, featuring granite countertops, stainless steel appliances, and a breakfast bar with barstool seating—ideal for enjoying a quick bite or gathering with family and loved ones. The main living space is designed for comfort and relaxation, with two plush sofas, a flat-screen TV, and an adjacent dining table that seats four comfortably—all with sweeping ocean views. Step through the sliding doors to one of the condo’s two private balconies, where you can sip your morning coffee or unwind with a glass of wine as the ocean breeze rolls in. The primary bedroom is a peaceful retreat, complete with a king-size bed, a sitting area with chairs, a TV, and its own balcony overlooking the pool and Gulf. The attached bathroom boasts an updated vanity and a gorgeous walk-in shower with modern finishes. The second bedroom features a queen-size bed, TV, ample closet space for personal belongings, and its own private balcony with more stunning ocean views. The second bathroom includes an updated vanity and a shower/tub combo, perfect for relaxing after a day in the sun. ?? Community Amenities at Privateer: Beachfront heated pool & spa Direct private beach access Tennis courts Fitness center & sauna Social room & library Grilling area & firepit Gated entry with secured building access Assigned covered parking Lush tropical landscaping throughout Located just minutes from St. Armands Circle, golf courses, fine dining, and cultural attractions in Sarasota, this condo offers the perfect blend of relaxation and adventure. Whether you're seeking tranquil beach days or exploring the vibrant coastal lifestyle of Longboat Key, this condo at Privateer is your perfect home away from home. There is a communal washer and dryer facility that is on the same floor as the unit.  It is agreed that once the application for your vacation has been approved by the board, a check in the amount of $500.00 will be sent to Privateer North Condo Assn. The check will be held if any damage to common properties. Is done during the check in/check out once your stay is complete (in and out) the deposit will be refunded.  House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets.t
#A4658787

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 702

2 Beds

2 Baths

1,290 Sq.Ft.

$7,500

MLS#: A4658787

Available now through the end of the year, off season only. Welcome to coastal elegance at Tangerine Bay Club, where sweeping bay views set the stage for an exceptional lifestyle. This furnished residence captures the charm of a single-family home with its private courtyard entrance while offering all the benefits of resort-style community living. This comfortable three-bedroom retreat features a bright, open-concept layout, a private two-car garage, and a spacious bayfront terrace. impact-rated windows and sliding doors flood the home with natural light and offer panoramic breathtaking Sarasota Bay views throughout. The heart of the home flows seamlessly from the living and dining areas to an inviting eat-in kitchen. The kitchen is both stylish and functional and equipped with all you'll need for your stay, featuring a mix of white and neutral-toned cabinetry, a farmhouse sink, large island for casual dining, a walk-in pantry, and a cozy office/desk nook. The primary suite is a peaceful sanctuary with private terrace access, a king size bed, a walk-in closet, and an en-suite bath with walk-in shower. Two additional bedrooms are located on the opposite side of the home, offering privacy and flexibility for family or guests. As a resident of Tangerine Bay Club, and a guest of this homeowner you will have membership to the exclusive Bay Isles Beach Club, providing access to pristine Gulf beaches. Perfectly located on the southern end of Longboat Key, Tangerine Bay Club is just a short walk from the Longboat Key Club, Drydock Waterfront Grill, and Chart House. And minutes away from St Armand's Circle, Lido Beach and Downtown Sarasota. Mediterranean-style architecture and lush landscaping plans will surround you in a serene, tropical setting. Gardens are being worked on now to make this place as beautiful as ever. Community amenities include gated entry, a resort-style pool on its own private island with a 25-meter heated pool and spa, tennis and pickleball courts, half-mile walking trail, fitness center, kayak launch, a day dock (first-come basis), and a vibrant social calendar. Just bring your suitcase and settle in for a long or short stay and relax on the terrace watching the dolphins jump. With a 3 month+ reservation a discount will be considered.
#A4650808

LONGBOAT KEY

380 GULF OF MEXICO DRIVE 513

3 Beds

2 Baths

3,338 Sq.Ft.

$7,500

MLS#: A4650808

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.

$7,500

MLS#: A4194846

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

1,735 Sq.Ft.

$7,500

MLS#: A4650448

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

BAYPORT TENNIS AND RAQUET CLUB has all the amenities including direct GULF Access. This tastefully furnished, one floor, three bedroom, two bathroom condo in the Bayport Beach and Tennis Club offers spacious living areas; Wonderful views of the Gulf of Mexico; and beautiful outdoor space. Large patios with tropical Gulf of Mexico views - perfect for morning coffee and sunset cocktails. Two charming lanais for additional outdoor relaxation, two intimate patios providing multiple spaces to enjoy Florida's year-round sunshine and convenient beach access. Tastefully designed Interior spacious, open layout ideal for casual living. Modern kitchen and bathrooms Washer and dryer, High-speed WIFI Three comfortable bedrooms Ample closet space, including a large walk-in in the master bedroom One covered parking space. Smooth tile floors for wheel chair access and handicap grab rails and modified toilet in one bathroom both custom showers also accommodate handicap visitors. Easy access to beach, pool and tennis courts. The master bedroom features a king bed, spacious views of the Gulf of Mexico, private access to the patio, a full bathroom, a large walk-in closet, and a big-screen TV. The second and third bedrooms each feature a queen bed and shared access to a full bathroom. The second bedroom also features a private patio with garden views. The condo comes with one assigned parking space under cover, along with ample guest parking available. Smoking is prohibited within the condo premises, ensuring a smoke-free environment for all guests. About Bayport Beach and Tennis Club: The Bayport Beach and Tennis Club provides a serene oasis with meticulously maintained lush grounds showcasing native trees and shrubs. Residents have access to numerous amenities such as Har-Tru clay tennis courts, a Junior Olympic sized swimming pool, a fitness center, clubhouse, bike and walking trails, a private fishing pier/kayak launch on Sarasota Bay. Inviting sandy beaches on the Gulf of Mexico complete with chairs and umbrellas. With a wide array of resident activities like happy hours, movie nights, book club, tennis events, knitting circles, and water aerobics, Bayport offers a vibrant community living experience enhanced by the stunning views of both the bay and the Gulf of Mexico.
#A4663929

LONGBOAT KEY

737 BAYPORT WAY D

3 Beds

2 Baths

2,504 Sq.Ft.

$7,000

MLS#: A4663929

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

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

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

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