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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
$858
Avg. $ / Sq.Ft.
$1,508,088
Med. List Price

Browse Long Boat Key Real Estate Listings

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511 Properties Found. Page 34 of 35.

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!
#A4658482

LONGBOAT KEY

1912 HARBOURSIDE DRIVE 603

2 Beds

2 Baths

1,590 Sq.Ft.

$5,000

MLS#: A4658482

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

1,590 Sq.Ft.

$5,000

MLS#: A4658263

Price reduced
Longboat Key vacation rental! You will love this wonderfully updated and tastefully furnished two-bedroom, two-bath third-floor condominium at the Beach Harbor Club. Located mid-key, this is a great resort-style community with deeded beach access just across the Gulf of Mexico, a beautiful heated community pool, access to the Bay for fishing and kayaking, and community grills and shuffleboard! This charming condominium has a modern kitchen with stainless appliances, the living area and bedrooms have luxury vinyl flooring and comfortable furnishings. Both baths have been updated. In the primary bedroom, you will find a queen bed, a walk-in closet and a Smart TV. The guest bedroom has a queen bed and a desk, for those who need a workspace. This condominium is light and bright and ready for occupancy! This condominium is also open for annual monthly rental plus utilities.
#A4672906

LONGBOAT KEY

3806 GULF OF MEXICO DRIVE C310

2 Beds

2 Baths

1,046 Sq.Ft.

$4,900

MLS#: A4672906

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

1,260 Sq.Ft.

$4,800

MLS#: A4571215

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

1-bed, 1-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, and get your daily work out in the fitness center! This turnkey unit boasts beautiful bay views, floods of natural light, a spacious walk-in closet, and a covered parking space. 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 amenities are still closed/damaged from the 2024 hurricanes.
#A4643358

LONGBOAT KEY

3810 GULF OF MEXICO DRIVE F304

1 Beds

1 Baths

811 Sq.Ft.

$4,000

MLS#: A4643358

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

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

Open now through end of January. Have your holidays on the Key with HEATED POOL, amazing sunsets, perfect tennis weather and the pristine beach just steps away. This well appointed and updated condo with an open open, split floor plan has plenty of space 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. Access the lanai from wall to wall sliders in the living area and both bedrooms. The serene views of Crane's Bayou and Florida water birds are a peaceful backdrop. There is a full sized washer and dryer in the unit and first floor storage for bikes and beach gear. The unit has one reserved outdoor parking space and plenty of guest parking. Portobello is a quiet, laid back community offering a heated pool, tennis courts, kayak launch, fishing pier, grill area, clubhouse, plus deeded beach access 250ft from your front door. Enjoy all the pleasures of Longboat Key with terrific dining, shops, fitness and Bayfront Park with tennis and pickleball, all close by. The mid-island location is convenient to both Sarasota and Bradenton. A slice of paradise found. Rentals less than 6 months are plus 13% tourist tax.
#A4627070

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B404

2 Beds

2 Baths

1,260 Sq.Ft.

$3,900

MLS#: A4627070

NOW AVAILABLE STARTING JUNE 1, 2026 - BRAND NEW RENOVATED and TURNKEY FURNISHED available for ANNUAL LEASE ($3,500/MONTH) OR SEASONAL ($4,600/MONTH). LEASE -3 MONTH MINUMUM RENTAL (OR INQUIRE ABOUT ANNUAL OPTION). ALL Utilities, Cable and Tax included. Come live the island life in this peaceful, fully detached villa nestled in the vibrant 55+ waterfront community of Spanish Main Yacht Club. Recently renovated and offered turnkey furnished, this charming 2-bedroom, 2-bath home is open, airy, and designed for effortless coastal living. Enjoy deeded beach access just across the street—perfect for morning walks or sunset strolls on the sands of Longboat Key. Boaters will love the private 40-slip marina with direct access to the Intracoastal Waterway, accommodating vessels up to 40 feet (first-come, first-serve) and equipped with water and electricity. Whether you're relaxing indoors or enjoying the community’s resort-style amenities, this is your gateway to the best of Gulf Coast living. Kayak, fish, or lounge beachside—your Florida escape starts here. Ideally located near St. Armand's Circle, you’ll have easy access to world-class dining, boutique shopping, and everything Longboat Key has to offer. No pets permitted, and at least one tenant must be 55 or older. Call for availability and lease details.
#A4661479

LONGBOAT KEY

573 SPANISH DRIVE N

2 Beds

2 Baths

1,380 Sq.Ft.

$3,500

MLS#: A4661479

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

Available for immediate occupancy and incredible deal on leases through the end of 2025! GULF BEACH and BAY ACCESS! This single story end unit is the perfect place to escape the cold winter months and experience Island living on Longboat Key. This 2 bedroom, 2 bathroom condo has a spacious living and dining room combo, which opens to a bright and airy Florida room, perfect for relaxing or entertaining. The Florida room is fully enclosed, and windows and sliding glass door have screens to welcome in those lovely Gulf breezes. The kitchen is well appointed and fully furnished with everything you may need to cook and enjoy meals at home and there is also a utility room with a washer and dryer for your convenience. The primary bedroom is comfortably furnished with a queen bed and en-suite bathroom. The second bedroom is currently empty and the owner will happily furnish it to meet your needs - either as a second bedroom or a den. Sutton Place offers private Gulf beach access complete with a pavilion, picnic tables, restrooms and showers. Additional amenities in the community include 2 heated pools, one of which sits on the Sarasota Bay, barbecue areas for al-fresco dining, bicycle storage, kayak storage and launch and fishing dock. Boat docks are also available for lease at a low rental fee based upon availability. The community is only 1/2 mile from Bayfront Park of Longboat Key, where you can utilize the park's 3 pickleball courts, tennis courts, basketball court, shuffleboard courts and more! Located just a short drive from St. Armand's Circle with wonderful shopping and dining venues or head North to visit the beaches of Bradenton, Coquina, Holmes and Anna Maria Island. This turnkey furnished condo is available for a 4 month minimum rental period or 3 month minimum through the end of 2025. Rental rates vary based on the season and are as follows: January-April: $4,300/mo. May-September: $2,800/mo. October-December: $2,000/mo. Annual rental: $3,000/mo.
#A4660890

LONGBOAT KEY

534 SUTTON PLACE

2 Beds

2 Baths

1,278 Sq.Ft.

$3,000

MLS#: A4660890

LONGBOAT KEY...Lovely 2 bedroom 2 bath condo directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile. Split floor plan, master suite with a king size bed and the guest room has bunk beds with one single bed and one full size bed. 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.
#A4666147

LONGBOAT KEY

3806 GULF OF MEXICO DRIVE C212

2 Beds

2 Baths

1,062 Sq.Ft.

$3,000

MLS#: A4666147

LONGBOAT KEY "SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE. AVAILABLE DEC 2025 & JAN 2026 AT $3,000/MONTH. UTILITIES INCLUDED. 2 MONTH MINIMUM REQUIRED PER HOA.BOOKED FOR FEB-APRIL 2026. Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the unit, you are met with a light, bright and open feeling with natural light coming in through the large sliding glass doors which open up onto the fully screened in and covered balcony. Beautifully furnished and decorated, living a fully equipped kitchen offering ample cabinet and storage space, washer/dryer, dining room, and living room Both the master and guest bathrooms have newly installed walk-in showers. Seaplace is one of the largest, most highly sought after complexes on Longboat Key. This resort style community offers 2 heated pools, hot tub, kiddie pool, beachfront patio, 4 grills, 3 har-tru tennis courts, game room, work out room, library, sauna, 24-hour security, and monthly events. Plus, the private beach access is just steps away from the beautiful crystal quartz sandy beaches and turquoise Gulf of Mexico waters. Conveniently located just a short drive from boutique shopping, dining and cultural attractions of St. Armand's Circle and Downtown Sarasota with the infamous Ringling Art Museum, Maria Selby Botanical Gardens, and Marina Jacks for boat tours and sunset dinner cruises. Or take a short ride over the bridge in the opposite direction to explore the beautiful Anna Maria Island. Longboat Key Club Golf Course is approx. 2 miles away. Sorry, no pets allowed.
#A4650120

LONGBOAT KEY

1945 GULF OF MEXICO DRIVE M2-402

2 Beds

2 Baths

928 Sq.Ft.

$3,000

MLS#: A4650120

Price reduced
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.

$2,500

MLS#: A4630493

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