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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
494
# of Listings
2
Avg # of Bedrooms
$951
Avg. $ / Sq.Ft.
$1,701,329
Med. List Price

Browse Long Boat Key Real Estate Listings

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Over $5M

494 Properties Found. Page 30 of 33.

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

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.

$8,000

MLS#: A4648967

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

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

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

Luxury Seasonal or Annual Rental in Luxurious Grand Bay Community – Longboat Key Experience unparalleled luxury and breathtaking views from this stunning 9th-floor condominium at Grand Bay. From sunrise to sunset, enjoy panoramic vistas from your private wraparound balcony or through the floor-to-ceiling sliding glass doors that frame the living room. Designed for both relaxation and sophistication, this residence offers the elegance of a luxury waterfront home with the convenience of condominium living. Step off your private elevator and through double entry doors to be greeted by sprawling water views from every angle. This home features a welcoming foyer, a versatile den, a formal dining room for eight, and a spacious kitchen with ample storage and a cozy breakfast nook. It features two large bedrooms, four luxurious bathrooms—including a master suite with dual water closets and a bidet—and a private laundry room with a service entrance. Thoughtfully designed by Grand Bay’s interior designer, it exudes modern coastal elegance. Residents of Grand Bay enjoy world-class amenities, including: - Private garage parking with lobby access - Lap pool, hot tub, fitness center, and a newly remodeled clubhouse and lobby - Private beach access just steps away - Three gated entrances for added security. - Located minutes from St. Armands Circle, Anna Maria Island, and Downtown Sarasota, you’ll have access to fine dining, cultural attractions like ballets and operas, award-winning golf courses, boating on emerald waters, and some of the nation’s most beautiful beaches. Special Features: Watch fireworks light up the Sarasota and Bradenton coastlines on New Year’s Eve from the comfort of your home. All utilities, taxes, and insurance are included in the rental fee (tenant responsible for cable). Pets allowed with an additional security deposit. No residents under 10 years old. This rare opportunity to join the exclusive Grand Bay community requires a 30-day HOA application process and two references. Don’t miss your chance to make unforgettable memories in one of Florida’s most coveted locations! Contact us today to schedule your private tour.
#A4630041

LONGBOAT KEY

3040 GRAND BAY BOULEVARD 292

3 Beds

3 Baths

2,143 Sq.Ft.

$8,000

MLS#: A4630041

BEACHFRONT JULY SPECIAL! $7,999 for the month. $2,000 discount! Available from 07-01-25 to 12-31-25, call for more details. Welcome to beachfront paradise on Longboat Key! This rare opportunity offers the best of coastal living with spectacular views of the coastline! Nestled along the shores of the Gulf of America, this three-bedroom, three-bathroom home invites you to enjoy the ultimate beachfront experience. This is the perfect property for relaxing, soaking up the sun, enjoying breathtaking sunsets, and savoring your morning coffee to the sounds of waves crashing just steps away. With direct beachfront access, you'll find yourself in an effortless coastal experience. Located only minutes away from Publix for all your grocery needs. Only a 5-mile drive to the celebrated St. Armands Circle where you can enjoy exceptional dining and shopping! This deal won't last long. Taxes and fees apply. Call today to reserve!
#A4592798

LONGBOAT KEY

2823 GULF OF MEXICO DRIVE

3 Beds

3 Baths

3,166 Sq.Ft.

$7,999

MLS#: A4592798

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

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

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

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

New on site 3 days ago
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

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

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