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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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Over $5M

140 Properties Found. Page 9 of 10.

Rented January-April 2026. This immaculate 2-bedroom, 2-bath ground-floor villa located in the highly sought-out community of Windward Bay has peek-a-boo views of the Gulf. Turnkey furnished with one carport at your front door. The community of Windward Bay is pristine. There is private deeded beach access just across the street, two public beach access, two marinas BBQ grills, 1/2 mile of walking trails, two heated pools, lighted tennis courts, pickleball court, fitness center, locker rooms, saunas, shuffleboard, bike racks, clubhouse with kitchen, lending library, and covered parking. Guests enjoy 3 access points to the gulf with one being private deeded access!
#A4622485

LONGBOAT KEY

4780 GULF OF MEXICO DRIVE

2 Beds

2 Baths

1,168 Sq.Ft.

$5,000

MLS#: A4622485

Turnkey Townhouse on Longboat Key – Resort-Style Living! Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy. Enjoy private beach access to the stunning Gulf of Mexico, take a dip in the heated pool and spa, and soak in the relaxed coastal lifestyle. You're just minutes from the world-famous St. Armands Circle, with its fabulous shopping, dining, and entertainment options, and a quick drive to vibrant downtown Sarasota and the local theater scene. Additional charges 13% sales/resort tax to be paid by tenants if lease is three to six months. This rental has it all—location, luxury, and lifestyle. Just bring your suitcase!
#A4658263

LONGBOAT KEY

1922 HARBOURSIDE DRIVE 1102

2 Beds

2 Baths

2,606 Sq.Ft.

$5,000

MLS#: A4658263

Available 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais, walk in closets. Double queen beds in one of the ensuites. open floor plan features large eat in area with granite counters neutral tile floors, and extra storage outside unit. Laundry is located right outside of your unit. Covered Carport and guest parking available. Building amenities WIFI, renovated social room and fitness center. Resort style living with heated Olympic size pool, tennis courts, biking trails, and outside showers. Enjoy the Publix Grocery just minutes away along with many restaurants for fine dining. This building is located the furthest South end of Longboat Key so you miss a lot of traffic. Just minutes to St. Armand's Circle for shopping, restaurants and entertaining. Enjoy Lido Beach also just minutes away.
#A4566128

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 502

2 Beds

2 Baths

1,390 Sq.Ft.

$5,000

MLS#: A4566128

2025 Hurricane-Rebuild! Longboat Key Retreat: Serene 2-Bed, 2-Bath with Home Office! Discover tranquility in this fully rebuilt 2-bedroom, 2-bath Longboat Key home with a built-in home office that may be utilized as a guest bedroom. Nestled on a peaceful corner lot surrounded by lush tropical foliage. Enjoy an open-concept layout featuring a modern kitchen, brand new bathrooms, and a spacious living room. The master suite includes a wet bar, mini fridge, and windowed ensuite bath. Relax in the backyard oasis with a scenic lily pad pond and cozy fire pit. Bedrooms: King-sized master, queen in second bedroom, full Murphy bed in office. Amenities: Fully furnished, modern appliances. Location: Steps from Whitney Beach, historic fisherman’s village, and kayaking in the bay. Close to fine dining in Longboat Key, Anna Maria Island, and Sarasota. Amenities: Fully furnished, modern appliances. Location: Steps from Whitney Beach, historic fisherman’s village, and kayaking in the bay. Close to fine dining in Longboat Key, Anna Maria Island, and Sarasota. Seasonal rates vary. Book your serene escape today!
#TB8394447

LONGBOAT KEY

640 BROADWAY STREET

2 Beds

2 Baths

1,500 Sq.Ft.

$4,995

MLS#: TB8394447

VACATION RENTAL!!! AVAILABLE JAN - MARCH 2026! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your beautiful private balcony. The master bedroom features a king size bed and private bath and twin beds in the second bedroom. The deeded private beach access is right across the street! Community amenities feature heated community pool, club house, tennis court, boat dock and fishing pier...all yours to enjoy! The exclusive shops and restaurants at St Armands circle are a short drive away as well as the famous Lido Beach. Take a drive over the John Ringling bridge into downtown Sarasota and you'll find theater, art galleries as well as exquisite dining and shops. Don't wait...your home away from home is move-in ready! No pets or smoking.
#A4571215

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE 603

2 Beds

2 Baths

1,434 Sq.Ft.

$4,800

MLS#: A4571215

Looking for an extended Longboat Key getaway? This well appointed corner condo in Bayport Beach and Tennis Club has everything for carefree, comfortable island living. Ideal as a 7-12 month rental. Located on the first level in the private 800 "cluster", the spacious, living area opens out to a screened lanai and large outdoor patio overlooking landscaped grounds. Enjoy this serene space for relaxing, entertaining, or reading a good book. There is a gas grill for al fresco meals and a patio gate out to the grounds. The primary bedroom has a king bed, ensuite bath, large walk-in closet, and an alcove with a desk overlooking the garden. A second bedroom is currently set up with a king bed but can easily be converted to two twins. There is one covered parking space and a locked storage closet under the unit, plus plenty of guest parking. Bayport Beach and Tennis Club is a Gulf-to-Bay community, conveniently located mid-key with award-winning design and fantastic amenities. Residents and guests enjoy a heated, Jr Olympic pool, private fishing pier, kayak and paddleboard launch, tennis courts, club house with full kitchen and fitness room, plus access to 1,200 feet of private beach with beach chair set-up. Publix, parks and other amenities are within 2-3 miles, with shopping and terrific dining dotted along the Key. Sarasota's entertainment and cultural attractions are a short drive away. This condo may be rented short term with a three month minimum during season (January through April), at $7800 per month. Tourist tax is applied to stays less than 6 months.
#A4663263

LONGBOAT KEY

842 BAYPORT WAY 842

2 Beds

2 Baths

1,570 Sq.Ft.

$4,500

MLS#: A4663263

SUMMER RATE ONLY: Take a 60 second stroll across the street to the Beach from this Beautiful Renovated unit with an onsite heated pool. Enjoy Peek-a-views of the gulf beach right from the Living Room Sofa, or Private Wrap Around Balcony. There's truly Nothing else like it on the island. Located just 2 blocks from Publix with beach access across the street. Just bring your personal belongings as everything is right here awaiting your arrival - bikes, beach chairs, board games, bidet toilets, fireplace, all kitchenware & gadgets, large screen smart tv's in every room, high speed internet, printer, beach chairs and a ton more. You will surely love it here! Also currently available for the 2026 Season at the seasonal rate. Hurry Before It's Gone!
#TB8406700

LONGBOAT KEY

2932 GULF OF MEXICO DRIVE 2932

2 Beds

2 Baths

1,500 Sq.Ft.

$4,500

MLS#: TB8406700

This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The beautiful upgrades to the kitchen and baths go hand in hand with the elegant decor of this property. Fully furnished and fully equipped and ready for your arrival, covered parking for one vehicle and guest parking is available as well. The clubhouse has a full kitchen facility and is large enough for meetings, private parties, and social functions, The exercise room is well equipped with machines and free weights. Classes in water Aerobics are held several times a week during the winter at a nominal cost, Available May to December at OFF Season rate of $4,200 per month plus 13% tourist tax. The property is a NO smoking/NO pet unit.
#A4641984

LONGBOAT KEY

840 BAYPORT WAY 840

2 Beds

2 Baths

1,640 Sq.Ft.

$4,200

MLS#: A4641984

New on site 1 day ago
BRAND NEW BEACH & BAY VILLA! Renovated with precision, the final finishing touches were completed March 26, 2025 for this quality engineered, down to the studs, two-bedroom and two-bath beach getaway villa. Available immediately. September & October $4,000 a month. November & December $5,000 a month. From the moment you step inside, you'll be greeted by a thoughtfully designed sunny open floor plan boasting recessed lighting and an array of sleek finishes throughout the home. Distinguishing features include the true craftmanship of custom solid core doors, chic beach themed door and cabinet knobs, custom designed laundry closet housing a Full-sized front load Samsung washer & dryer, self-close solid kitchen cabinets with a bonus spice rack cabinet, pull out shelves in the pantry and below the sink, ceramic floor tiling through-out including a curb less shower entry located in the primary suite’s “ensuite bathroom. The pièce de résistance is the Cambria Quartz (lifetime warranty) kitchen countertop chosen for the beach inspired aqua accents that showcase both a breakfast bar and a dual temperature wine/beer refrigerator for added pleasure. The second bedroom is cleverly designed to serve as both an office and a guest space, complete with a comfortable “guest chest” Murphy bed cabinet. For peace of mind while away, the villa is equipped with the latest Wi-Fi enabled keyless smart lock entry system, as well as a smart remote thermostat to monitor and manage remotely. Worry free living with a New A/C (2022), Water Heater (2024) and recent Hurricane Impact Windows/Sliding Doors, Roof, & Carport (2020). Located directly across the street, with 3 beach access points (one private deeded) is the tranquil Gulf with its crystal-clear turquoise blue waters and uncrowded sandy beaches that attract visitors from all over the world. A low-density residence and a nature lover’s delight: from captivating bird watching to the frolicking dolphins and manatees of Longboat Key. Windward Bay's unparalleled amenities include 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee (first come first served), barbecue grills throughout, fishing piers, 2 fish cleaning stations, kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits throughout the property. Conveniently accessible to Downtown Sarasota, St. Armands Circle, Anna Maria Island, Historic Cortez Fishing Village, Championship Golf Courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Welcome home to “Pet Friendly” Windward Bay, where TWO pets are allowed. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced. This wonderful condominium exemplifies “Florida Gulf to Bay Living” at its finest. Windward Bay: "A Special Place and A Gem of a Community."
#A4664273

LONGBOAT KEY

4760 GULF OF MEXICO DR. VILLA 7

2 Beds

2 Baths

931 Sq.Ft.

$4,000

MLS#: A4664273

Steps from the Sand – Luxury Beach Condo with Pool Access! Leave the snow behind and soak up the sun! This stunningly turnkey renovated 2-bedroom, 2-bathroom condo has everything you need for a carefree beach living– including a washer and dryer for sandy swimsuits! Enjoy private access to the shimmering Gulf beaches, relax by the heated pool, or paddle your cares away in the community kayaks. Socialize in the spacious clubhouse, or get energized in the fitness center. Perfectly located in the heart of the island, you’re just minutes from Publix, the charming boutiques and cafes of St. Armand's Circle, the vibrant culture of Downtown Sarasota, and the laid-back vibes of Anna Maria Island. Note: Some amenities are still recovering from the 2024 hurricanes, but the sun, surf, and island magic are waiting for you! Rent your dream beach getaway today – paradise is calling!
#S5119903

LONGBOAT KEY

3806 GULF OF MEXICO DRIVE C305

2 Beds

2 Baths

1,031 Sq.Ft.

$4,000

MLS#: S5119903

A perfect island getaway. This well appointed and updated Longboat Key condo is available as a six or seven month rental from late June through January. Located Bay side, you'll enjoy a sparkling pool, tennis, kayak launch, fishing pier, grill area and clubhouse, plus deeded beach access is 250ft from your front door. There's plenty of room to spread out with an open, split floor plan and a huge screened lanai that spans the entire unit. The primary bedroom has TWO KING SIZED beds, a huge walk-in closet and ensuite bath. The second bedroom has a king bed and generous closet space. Access the lanai from wall to wall sliders in the living area or either bedroom. The serene views of Crane's Bayou and Florida water birds provide a peaceful backdrop for entertaining, relaxing with a good book or working from your laptop. There is a full sized washer and dryer in the unit and first floor storage for bikes and beach gear. Enjoy all the pleasures of Longboat Key with terrific dining, shops, fitness and Bayfront Park with tennis and pickleball, all close by. This can be a terrific opportunity for exploring the area before buying, IMG families looking for a beachside getaway, a remote work situation or those just looking for a peaceful stretch of island time. The community is centrally located on the island for easy access to Sarasota and Bradenton. IMG Academy is 15 miles and SRQ Airport is 12 miles. A shorter rental can be considered at an adjusted price and a minimum three month stay.
#A4627070

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B404

2 Beds

2 Baths

1,434 Sq.Ft.

$3,975

MLS#: A4627070

2-bed, 2-bath 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. First floor units have their own private patios. 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***Seasonal rental price is $6,800 per month.***
#A4662043

LONGBOAT KEY

3802 GULF OF MEXICO DRIVE A107

2 Beds

2 Baths

1,085 Sq.Ft.

$3,900

MLS#: A4662043

Available 6/1/25 **** Sarasota Bay view. 1 Bedroom x 1 1/2 Bathroom Condo. Living Room looks out over the pool that sits on Sarasota Bay. Fully furnished. 90 day minimum rental period. Prefer 6 mo.- 1 year rental. Sutton Place has many amenities including two heated pools, bicycle storage, outdoor grills, Gulf beach access with beach house, 1 assigned parking spot and several shared guest spaces. Boat docks are also available for lease at a low rental fee based upon availability. Available 6/1/2025 Rental fee based on Season. Oct - Dec = $3,500/mo. Jan - April-=$4,500/mo. May - Sept =$3,000/mo. Annual Rental= $3,500/mo.
#A4602885

LONGBOAT KEY

600 SUTTON PLACE 201

1 Beds

1 Baths

836 Sq.Ft.

$3,200

MLS#: A4602885

LONGBOAT KEY...Lovely 2 bedroom 2 bath penthouse located on the top floor in Building B directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile and marble. Split floor plan, master suite with a king size bed and the guest room can be used as an office, den or bedroom with its king size murphy bed and a private en-suite bath. Spacious, open, light and bright. Very well maintained GULF TO BAY complex with lush landscaping, large heated pool, clubhouse, marina, fishing pier, kayak and bike storage, fitness center, all for your enjoyment and covered parking. OWNER PREFERS AN ANNUAL RENTAL AT $3000 A MONTH. A SEASONAL WILL ALSO BE CONSIDERED AT $5000 A MONTH + TAX & FEES. PLEASE NOTE, UTILITIES ARE NOT INCLUDED IN AN ANNUAL RENTAL. SARASOTA, VACATION RENTALS, LUXURY, GULF OF MEXICO, LONGBOAT KEY VACATION, LONGBOAT KEY ANNUAL RENTAL.
#A4663366

LONGBOAT KEY

3804 GULF OF MEXICO DRIVE B-402

2 Beds

2 Baths

1,290 Sq.Ft.

$3,000

MLS#: A4663366

2-bed, 2-bath seasonal or annual 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, tons of closet space, 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*** Rent price is $3,000 for annual and $4,500 for seasonal.
#A4630493

LONGBOAT KEY

3806 GULF OF MEXICO DRIVE C202

2 Beds

2 Baths

1,062 Sq.Ft.

$3,000

MLS#: A4630493

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