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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
507
# of Listings
2
Avg # of Bedrooms
$867
Avg. $ / Sq.Ft.
$1,539,132
Med. List Price

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507 Properties Found. Page 32 of 34.

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.

$6,500

MLS#: A4648967

AVAILABLE Jan - Mar 2026!!! : Stunning Gulf views and incredible sunsets await you from this JUST completely renovated 2 bedroom, 2 bath condo on Longboat Key. You’ll fall in love with the contemporary soft-palette, coastal style! The open layout offers a seamless blend of kitchen, dining and living space, perfect for entertaining and relaxing. The gourmet kitchen features state-of-the-art GE Profile appliances and plenty of storage. The Master retreat features new king accommodations, chic-like bath, large walk-in shower and dual vanities. Such a tranquil sanctuary with its own private balcony. See yourself waking up every morning with serene Gulf views, dolphins and water birds with morning coffee. Wow! The large and private Guest bedroom is complete with 2 queen beds, en-suite bath, walk-in closet with washer/dryer. For your added comfort, you’ll enjoy Smart TV’s, Direct TV, Wi-Fi and desk area, just in case you need to get a little work done. Residents of Westchester enjoy a wide range of amenities including heated pool, deck chairs, lounges with umbrellas, private beach access, tennis, miles of beach to walk and enjoy, covered parking and outside storage right next to your carport. This gorgeous part of Longboat Key has so much to offer, with lots of new restaurants, shopping and activities going both North, and South on the key. So close to everything!! Located just 5 miles from fashionable St. Armands Circle and only a short drive to downtown Sarasota with arts, theatre, restaurants and shopping. Available: September through Dec 14th $4,000 monthly. Available: January 4th – April 31st at $7,200 monthly plus standard fees. This is non-smoking unit. Sorry, this condo association does not allow pets.
#A4620764

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 203

2 Beds

2 Baths

1,604 Sq.Ft.

$6,500

MLS#: A4620764

Escape to paradise with a stay in this newly renovated 2-bedroom, 2-bath second floor condominium at Bayport Beach & Tennis Club on Longboat Key. Perfectly positioned for your dream beach getaway, this condo blends comfort, style and unbeatable amenities. Bright, modern, and welcoming, this condo has been thoughtfully updated with all the comforts of home, including a king-size bed in the primary bedroom. Enjoy access to Bayport's Junior Olympic-sized pool, clay court tennis, bocce ball court, and a private dock on Sarasota Bay with stunning sunrise views. Located mid-island, you have private access to our white sand beach with stunning Gulf Coast views. Chairs and umbrellas are provided--ideal for morning walks, sunbathing, or watching the sunset. The property offers a semi-private entrance, providing a more secluded and peaceful experience for your vacation. Whether you're looking to relax by the pool, play tennis, or simply enjoy the beach, Bayport Beach & Tennis Club is the perfect blend of relaxation and recreation--a true hidden gem. 30 Day minimum stay required. Available: DECEMBER 2025, JANUARY 2026, MAY 2026, SEPTEMBER 2026, OCTOBER 2026, NOVEMBER 2026, DECEMBER 2026.
#A4667152

LONGBOAT KEY

618 BAYPORT WAY BAYPORT WAY 618

2 Beds

2 Baths

1,570 Sq.Ft.

$6,050

MLS#: A4667152

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

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

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

Newly renovated and elegantly designed 2-bedroom, 2-bathroom condo in the highly desirable Longboat Harbour Condominiums, located just 600 feet from the shore and a 3-minute walk to the beach. This fully furnished ground floor unit offers a modern open layout with scenic views, access to Sarasota Bay, and resort-style community amenities including four swimming pools (one located right behind the unit), a gym, kayaking, tennis courts, pickleball, a game room with pool tables, and a community grill area perfect for family barbecues. Residents also enjoy private beach access with a pavilion, bathrooms, and showers for ultimate convenience. $6,000/month. Available for rent from December 2026 to April 2027. Minimum rental period: 2 months Perfect for seasonal living!!
#O6353609

LONGBOAT KEY

4360 CHATHAM DRIVE 108

2 Beds

2 Baths

1,316 Sq.Ft.

$6,000

MLS#: O6353609

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. AVAILABLE STARTING 11/1/2025 - ANNUAL LEASE ONLY,
#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

Must read entirely. 2025 WINTER RENTAL- Not Available 01/21/26-2/21/26. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina slips MAY be available so you can bring your boat! The home was newly renovated with space and comfort in mind. The Master has a king size bed and a great view of the canal! The screened in porch overlooks the intercoastal with all its wildlife. Try out Sarasota and stay on the beach! St. Armand’s circle is nearby with world class shopping/dining and entertainment. Cleaning fee/resort taxes not included. HOA application with background and credit check required. NO PETS. NON SMOKING UNIT. Available long term (3 months) for $5,000/monthly. Vacation rental rates: October-November: $4,500; December -April: $6,000; and May: $4,500. 2-month minimum stay during peak season (December through April).
#O6342792

LONGBOAT KEY

4420 EXETER DRIVE 208

2 Beds

2 Baths

1,376 Sq.Ft.

$6,000

MLS#: O6342792

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

AVAILABLE STARTING MAY 1, 2026. WITH 3 MONTH MINUMUM RENTAL. FULL WATERFRONT NEWLY RENOVATED (internal new photos coming soon) and TURNKEY FURNISHED VILLA for SEASONAL OR ANNUAL LEASE. Seasonal Lease December to April is $7,000 per month (OR inquire about annual/off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Panoramic Bay Views - Spanish Main Yacht Club | Longboat Key Welcome to your own slice of coastal serenity! This rarely available freestanding waterfront villa offers sweeping full-bay views and an effortless blend of comfort and elegance in the heart of Longboat Key. Beautifully updated and bathed in natural light, the spacious 2-bedroom, 2-bath floorplan lives like a single-family home—offering privacy, tranquility, and uninterrupted water vistas from morning to night. Step outside and you’re just feet from the Intracoastal Waterway. Sip your morning coffee while the sun rises over the bay, and unwind in the evening with a cocktail as boats gently glide by. Boaters will appreciate the private 40-slip marina (first come, first serve) accommodating vessels up to 40 feet. And just across Gulf of Mexico Drive, your deeded beach access opens to powder-soft sand and crystal Gulf waters—true island living at its finest. Located in the active and welcoming Spanish Main Yacht Club 55+ community. Residents enjoy beautifully maintained grounds, a heated pool, clubhouse, and an easy, maintenance-free lifestyle. Just minutes to St. Armand's Circle and Downtown Sarasota. Enjoy boutique shopping, fine dining, and cultural attractions, all within reach—then retreat back to the peace and privacy of the bayfront. Please note: Per community guidelines, pets are not permitted.
#A4661509

LONGBOAT KEY

957 SPANISH DRIVE N

2 Beds

2 Baths

1,698 Sq.Ft.

$5,500

MLS#: A4661509

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