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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

All listings

$250,000 - $500,000

511 Properties Found. Page 31 of 35.

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.

LONGBOAT KEY

1925 GULF OF MEXICO DRIVE G8-208

3 Beds

2 Baths

1,604 Sq.Ft.

$8,000

MLS#: A4109016

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.

LONGBOAT KEY

3235 GULF OF MEXICO DRIVE A302

2 Beds

2 Baths

1,260 Sq.Ft.

$8,000

MLS#: A4208788

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

LONGBOAT KEY

2425 GULF OF MEXICO DRIVE 4E

2 Beds

2 Baths

1,470 Sq.Ft.

$8,000

MLS#: A4494373

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.

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 201

2 Beds

2 Baths

1,393 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

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

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.

LONGBOAT KEY

380 GULF OF MEXICO DRIVE 513

3 Beds

2 Baths

2,490 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.

LONGBOAT KEY

2109 GULF OF MEXICO DRIVE 1402

2 Beds

2 Baths

1,273 Sq.Ft.

$7,500

MLS#: A4194846

#TB8406700

LONGBOAT KEY

2932 GULF OF MEXICO DRIVE 2932

2 Beds

2 Baths

1,445 Sq.Ft.

$7,500

MLS#: TB8406700

Charming turnkey-furnished 2BR/2BA condo on the beautiful island of Longboat Key. Enjoy magnificent ocean views and spectacular sunsets from the private balcony. This well-appointed unit offers an ideal winter escape with comfortable living spaces and a serene coastal atmosphere. Building amenities include an in-ground heated pool, docking station, fish cleaning station, kayak/paddleboard rack, fishing dock, outdoor grill, and private beach access. Available for rent January and February 2026. This Longboat Key gem won’t last.

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B402

2 Beds

2 Baths

1,505 Sq.Ft.

$7,500

MLS#: A4674652

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!

LONGBOAT KEY

4540 GULF OF MEXICO DRIVE PH2

2 Beds

2 Baths

1,312 Sq.Ft.

$7,500

MLS#: A4506042

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.

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 605

2 Beds

2 Baths

1,393 Sq.Ft.

$7,200

MLS#: A4452938

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!!!

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B303

2 Beds

2 Baths

1,260 Sq.Ft.

$7,200

MLS#: A4418888

Price reduced

Beautiful completely remodeled 2-bedroom, 2-bathroom Tropical Oasis on Longboat Key. Relax and enjoy the Florida lifestyle at its best with stunning gulf views from this gorgeous second floor retreat. Just steps to the beautiful white sand and warm gulf waters. Upgrades include new open floor plan with spacious rooms decorated in a soothing coastal color palette. Heightened ceilings, hardwood engineered flooring, upgraded lighting and fresh paint. Enjoy cooking meals and entertaining friends and family at the large kitchen island with quartz countertops and backsplash, new solid wood, soft close cabinets and all new stainless -steel appliances. Spectacular morning views and amazing colorful sunset views await as you step into this lovely well stocked, turnkey furnished condo. Master bedroom boasts a king size bed and 40" TV with walk-in closets, en-suite master bathroom with double sinks, walk -in shower and access to the patio for heavenly gulf breezes and views. Second bedroom features a queen size bed and TV; the third flex room offers a queen bed for additional sleeping quarters for guests. Washer/dryer are located inside the unit in the laundry closet. Enjoy hours of entertainment watching wildlife including dolphins, manatees, turtles, birds and boaters from this perfect spot. Outdoor amenities include beachside private heated pool and hot tub. This lovely community showcases mature trees and well-maintained tropical lush landscaping. Other amenities include a gym, sauna, craft room, large social room with catering kitchen, bicycle and Kayak storage. This property is available from December - April.

LONGBOAT KEY

5757 GULF OF MEXICO DRIVE 204

2 Beds

2 Baths

1,561 Sq.Ft.

$7,000

MLS#: A4666130

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.

LONGBOAT KEY

737 BAYPORT WAY D

3 Beds

2 Baths

1,909 Sq.Ft.

$7,000

MLS#: A4663929

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