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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
419
# of Listings
2
Avg # of Bedrooms
$786
Avg. $ / Sq.Ft.
$1,316,143
Med. List Price

Browse Long Boat Key Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

419 Properties Found. Page 26 of 28.

"SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE OF LONGBOAT KEY. BOOKED FOR FEB-APRIL 2026. AVAILABLE NOV 2025 AT $3,500, DEC 2025 AT $5,000 & JAN 2026 AT $6,500. 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 the 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. **This is a 3-month minimum rental. ** Sorry, no pets allowed.
#A4650120

LONGBOAT KEY

1945 GULF OF MEXICO DRIVE M2-402

2 Beds

2 Baths

1,019 Sq.Ft.

$6,500

MLS#: A4650120

SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST ARMANDS CIRCLE of restaurants, shops and entertainment.
#A4572396

LONGBOAT KEY

1975 GULF OF MEXICO DRIVE 208

2 Beds

2 Baths

1,392 Sq.Ft.

$6,000

MLS#: A4572396

Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for the occasional guests. The condo comfortably sleeps 6. This beachfront community features a large, heated swimming pool, fitness rooms, bicycle racks, and a clubhouse with a catering kitchen perfect for get-togethers. Conveniently located across from the Centre Shops and just a short drive north to the famous Beer Can Island or drive south to St. Armand’s Circle and downtown Sarasota. The possibilities are endless! Perfect for an extended stay.
#A4451608

LONGBOAT KEY

5393 GULF OF MEXICO DRIVE 208

2 Beds

2 Baths

1,300 Sq.Ft.

$6,000

MLS#: A4451608

Furnished beachfront vacation rental! This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is located in a smaller building, on an uncrowded segment of beach that can often be enjoyed in complete solitude. The unit was recently upgraded with a new washer/dryer, luxury vinyl flooring in the bedrooms, a plethora of fresh artwork, accents, linens, beach amenities, and more! Enjoy cable TV and high speed WiFi that is nearly as reliable as your view of the sunset! The fully equipped kitchen is truly a chef's pleasure, featuring both a wine fridge and a Keurig coffee maker. Located in the heart of the recreational wonderland that is Longboat Key, this particular spot is so incredibly tranquil and private, yet so well connected to amenities, airports, cities and towns. Available long term for $6500/month. Vacation rental rates (1 month minimum): January: $10,000 February: $12,000 March: $12,000 April: $10,000 May through October: $5,000 (per month) November: $6,000 December: $6,000 3 month minimum stay during peak season (January through April) Please note that a $150 application fee is due directly to the HOA, and your stay is pending their approval.
#A4655690

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 305

2 Beds

2 Baths

1,456 Sq.Ft.

$6,000

MLS#: A4655690

Welcome to the Sanctuary. This beach front community is located inside the private gates of The Longboat Key Club. This 1st floor walk out residence that feels like a beach house will impress you with the space and tasteful decor/furnishings. Spend your time walking the private beach with the turquoise blue waters of the Gulf of Mexico along with a game of tennis, private fitness center, Olympic sized pools/spa or ride bikes to St. Armand's circle for a great lunch or dinner. The kitchen is spacious and upgraded with lovely granite and top of the line appliances if you prefer to stay at home and cook. At the Sanctuary you will be part of 18 incredible beachfront acres. Conveniently located on south Longboat Key close to St. Armand's and downtown Sarasota. Available today Annually or possibly seasonally.
#A4663441

LONGBOAT KEY

535 SANCTUARY DRIVE A102

3 Beds

2 Baths

3,380 Sq.Ft.

$6,000

MLS#: A4663441

This beautiful 2 bedroom/2 bath split and open floor plan condo is spacious and bright. The kitchen featuring a built-in desk and granite counters has been opened to the dining/living room area with views of the pond, fountain and lush tropical landscaping. A stackable washer/dryer in closet for your convenience. Lanai enclosed with tropical views. Bayport Beach and Tennis Club is bordered by the Gulf of Mexico to the West with 1200 feet of private beach and Sarasota Bay to the East. This resort community is situated in the heart of Longboat Key. A popular residential enclave of 136 quality-constructed homes on 27 picturesque acres. Residents enjoy a heated, Jr Olympic sized pool. fishing pier, steps to a private Gulf beach, kayak launch and storage, 4 Har-Tru tennis courts, golf practice net, bocce court, social room with full kitchen, library, piano, fitness center, shelled nature walking paths, tropical gardens and a number of social activities. Shopping, Restaurants and the Arts are located within minutes including St Armand’s Circle, Downtown Sarasota & Anna Maria to name a few. Golf, Marina and Restaurants at the Longboat Key Club. A “PET” friendly community.
#T3488636

LONGBOAT KEY

706 BAYPORT WAY 706

2 Beds

2 Baths

1,832 Sq.Ft.

$6,000

MLS#: T3488636

Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Seasonal, furnished, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. This ground floor unit is centrally located and minutes away from urban activities with in-unit washer and dryer. The master bedroom features a queen bed, walk-in closet and ensuite bathroom; second bedroom features twin beds. The spacious living and dining area opens to a private outside patio. If you enjoy an active lifestyle, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will entice you to utilize the available kayaks, boating and fishing pier, as well as private access to the sandy beaches of the Gulf of Mexico. In addition to the over-sized heated pool, Beach Harbor Club has a new fitness center and a library/media room. Elevator accessible and assigned parking complement the amenity package. Enjoy Florida living at its best!
#A4464764

LONGBOAT KEY

3806 GULF OF MEXICO DRIVE C111

2 Beds

2 Baths

1,027 Sq.Ft.

$6,000

MLS#: A4464764

Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of the gulf. Gorgeous custom kitchen. Granite counters, beautiful muted gray plank flooring. Turnkey furnished with newer linens and a brand new hurricane door off kitchen and dining to master bedroom balcony. Just bring your toothbrush and clothes. Desired location and direct front penthouse sitting right on the Gulf of Mexico w Private beach and chairs and umbrellas for quit time on your beach. The two balconies bring the water to you so you can enjoy a breathtaking sunsets and the unobstructed views everyday. The enormous heated pool and spa, and tennis courts, clubhouse and fitness center. Onsite management from 9 to 4 Monday through Friday. Go over Longboat Key Bridge and take a turn at first stoplight into LONGBOAT KEY RESORT GOLF AND TENNIS CLUB, TELL GATE GAURD AND SAY SHOWING PRIVATEER NORTH AND GO DIRECT TO BUILDING. This complex PRIVATEER NORTH is located furthest South to St. Armand's S0 YOU ARE NOT IN A LOT OF TRAFFIC and minutes to St. Armand's and the mainland.
#A4552081

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 1006

2 Beds

2 Baths

1,509 Sq.Ft.

$6,000

MLS#: A4552081

STUNNING BAY VIEWS! Enjoy picturesque sunrises from your private deck in this tastefully decorated 2 bedroom, 2 bathroom furnished condominium. This home has an open concept floor plan which features an expansive Living/Dining/Kitchen area. The generous size master bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a small alcove that accommodates a desk. Bayport Beach & Tennis Club is an amenity-rich community at sea's edge with 27 acres of lush mature tropical landscaping. This gulf to bay community offers an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to the private beach on the Gulf of Mexico for a morning of beachcombing, surf casting or memorable sunsets. Just minutes to St. Armand's Circle which is well known for its world class shopping and dining. Cross over the Ringling Bridge to Downtown Sarasota where you will find additional dining, theater, opera, ballet, symphony, art galleries, the Van Wezel Performing Arts Hall, Selby Gardens and of course the Ringling Museum. Please call for availability. OFF SEASON RENTAL ONLY - AVAILABLE : MAY - OCTOBER 2024. Please call Agent for availability.
#T3520822

LONGBOAT KEY

817 BAYPORT WAY 817

2 Beds

2 Baths

1,601 Sq.Ft.

$6,000

MLS#: T3520822

Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Welcome to Seaside Dream! Beautifully furnished and decorated, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. If you enjoy resort-style living, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will entice you to utilize the available kayaks and kayak lift, boating, and fishing pier, and head out to enjoy the beach with private access to the sandy beaches of the Gulf of Mexico. In addition to the oversized heated pool, Beach Harbor Club has a new fitness center and a library/media room. Elevator accessible and assigned parking complement the amenity package. This second-floor unit is centrally located and minutes away from urban activities. The master bedroom features a queen bed, a TV, a walk-in closet, and an unsuited bathroom. The second bedroom features twin beds, a TV, and plenty of space for your personal belongings. The fully equipped kitchen is the perfect place to prepare all your favorite meals and treats. The spacious living and dining areas are ideal for relaxing and enjoying the beach breeze. When you are ready to explore, head out to the nearby white sandy beaches of Lido Key or Siesta Key -the choice is yours. The world-famous St. Armand’s Circle is located just a couple miles away and offers endless boutique shopping and dining experiences, or you can enjoy an array of artistic events in Downtown Sarasota, such as the Sarasota Opera, the Sarasota Orchestra, ballet, theatre, the infamous Ringling Art Museum, Maria Selby Botanical Gardens, and Marina Jacks for boat tours. If you love outdoor adventures, come get lost amid the labyrinth of mangrove tunnels and explore their unique ecosystem aboard a rented kayak or stand-up paddleboard in South Lido Beach Park, or hike the Northern Nature Trail. This area seamlessly combines the energy and vibe of Downtown Sarasota cosmopolitan life with a seaside paradise that you do not want to miss. One visit to this St. Armand’s retreat and you will not want to leave. Come, enjoy Florida living at its best! House Rule: No smoking. No burning candles inside of lodging. No parties. No pets, no exceptions, per HOA. **30 day processing for application with the HOA. **Taxes and fees not included.
#A4518730

LONGBOAT KEY

3806 GULF OF MEXICO DR DRIVE C210

2 Beds

2 Baths

1,046 Sq.Ft.

$5,835

MLS#: A4518730

Experience luxury and tranquility in this stunning unit at 1928 Harbourside Dr, Unit 1402, located within the Bay Isles community on Longboat Key. This residence offers a spacious layout designed for comfort and style, with access to top-tier amenities including a nearby marina, private golf course, swimming pool, and spa. Enjoy the privacy and security of this exclusive gated community, all just minutes away from the vibrant cultural scenes of St. Armands Circle and downtown Sarasota. This property is perfect for those seeking an elegant escape with convenient access to fine dining, shopping, and entertainment. Embrace the unparalleled lifestyle of Longboat Key in this exceptional rental opportunity.
#A4627730

LONGBOAT KEY

1928 HARBOURSIDE DRIVE 1402

2 Beds

2 Baths

2,532 Sq.Ft.

$5,500

MLS#: A4627730

FULL WATER FRONT NEWLY RENOVATED (internal photos coming soon) and TURNKEY FURNISHED VILLA for SEASONAL OR ANNUAL LEASE. 5 MONTH MINUMUM RENTAL. AVAILABLE STARTING DECEMBER 1, 2025. Seasonal Lease January-April is $7,000 per month (OR inquire about annual or off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Full Bay Views in Spanish Main Yacht Club – Experience the best of island living in this open and airy freestanding villa. This spacious 2-bedroom, 2-bath home is thoughtfully updated and filled with natural light, offering a serene escape on Longboat Key. Wake up to breathtaking full Bay views and unwind in the evenings with a cocktail while watching boats drift by—direct access to the Intracoastal Waterway is just steps from your door. This rare waterfront opportunity includes beach access just across Gulf of Mexico Drive and use of the private 40-slip marina (first-come, first-serve), perfect for boaters with vessels up to 40 feet. Nestled within a beautifully maintained community, Spanish Main offers an active coastal lifestyle surrounded by natural beauty, peace, and privacy AND available to all (no longer a 55+ community). Located just minutes from St. Armand's Circle and downtown Sarasota, you’re close to fine dining, boutique shopping, and award-winning beaches. Per community rules, no pets are permitted. Contact us today for availability and rental terms.
#A4661509

LONGBOAT KEY

957 SPANISH DRIVE N

2 Beds

2 Baths

1,698 Sq.Ft.

$5,500

MLS#: A4661509

Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural hubs of St. Armands Circle and downtown Sarasota, this property is ideal for those seeking a refined retreat with convenience to fine dining, shopping, and the arts. Don’t miss the opportunity to experience Longboat Key living at its finest.
#A4627728

LONGBOAT KEY

2012 HARBOURSIDE DRIVE 2102

2 Beds

2 Baths

2,570 Sq.Ft.

$5,500

MLS#: A4627728

Gorgeous Gulf front, turnkey furnished rental in Tiffany Plaza. Walk out to the beach from this lovely updated and exquisitely furnished 2 bed/2 bath condo. Coastal inspired décor, king bed in the primary bedroom, full bed and day bed with trundle in the second bedroom. Smart TV's and Wi Fi make this the perfect winter retreat! Tiffany Plaza offers a sparkling heated pool, club room with sauna, and you have a covered parking spot with plenty of guest parking. This Steller location is a short drive to fine dining and shopping venues, or take the free Trolley to St. Armand's Circle, downtown Sarasota, Lido and Siesta Key. December 2025 and January 2026 $8000 per month, February is $10,000 and March and April are $12,000. May through November are $5500 per month. Please note that seasonal and off-season rates are plus taxes and fees. (Booked for MARCH & APRIL 2026)
#A4544891

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 102

2 Beds

2 Baths

1,336 Sq.Ft.

$5,500

MLS#: A4544891

Available rental for July 15, 2025-October 2025 ONLY! 60 Day Minimum Lease. Fully remodeled and impeccably furnished with Gulf views on Longboat. Situated on the top floor, this 2 bedroom, and 2 bath residence presents coveted views of the beach and Gulf of Mexico! Take note, that the clear, Caribbean blue waters and white sand beaches are not upstaged by the finishes in this redesigned floor plan. The gathering room opens to an extended kitchen to create continuity in the main living area, perfect for entertaining. Custom imported cabinetry, with frosted glass, pantry storage and complementary hued uppers and lowers, solid surface counters and waterfall edge peninsular seating for four. Premium Kitchen-Aide appliances include a French Door refrigerator, a dishwasher, a double oven, and a cooktop. A skylight brings together natural light with LED illumination, drop and recessed lighting. Imported marble floors meet up with, porcelain tile and neutral Berber carpet throughout. Both bathrooms have been modernized with Corinthian Fossil showers, frameless glass doors, floating vanities, and Quartz countertops. The primary ensuite features a walk-in closet and a sitting area. Multiple sets of sliding glass doors access the covered, open-air balcony to enjoy our million dollar sunsets! Unwind seaside on over 500-feet of shoreline or stroll the lushly landscaped grounds, paver pathways, or enjoy the private swimming pool & spa. All lease terms shorter than 6 months are subject to 13% tourism tax.
#A4609333

LONGBOAT KEY

5757 GULF OF MEXICO DRIVE 305

2 Beds

2 Baths

1,711 Sq.Ft.

$5,500

MLS#: A4609333

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