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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
411
# of Listings
2
Avg # of Bedrooms
$793
Avg. $ / Sq.Ft.
$1,324,575
Med. List Price

Browse Long Boat Key Real Estate Listings

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$500,000 - $1M

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$3M - $5M

Over $5M

411 Properties Found. Page 26 of 28.

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

Available for season 2026! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by the heated pool, gather at picnic areas and cabanas with grills, or explore the water with provided kayaks. Residents also enjoy a newly renovated clubhouse with library and card & game room and state-of-the-art fitness center. In addition to that, get crafty at the wood workshop (all tools included). This ground floor condo has room to sleep six with three queen size beds. The kitchen is fully equipped with everything you need to prepare meals. There is ample seating for dining and gathering space. In addition to our renowned beaches, Sarasota and Manatee county boasts a vibrant cultural scene, with live theater, concerts, ballet, opera, galleries, museums, and even a rich history with the circus arts! Escape the winter and come enjoy Florida living on Longboat Key!
#A4660366

LONGBOAT KEY

3806 GULF OF MEXICO DRIVE C108

2 Beds

2 Baths

1,401 Sq.Ft.

$5,800

MLS#: A4660366

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

FULL WATER FRONT NEWLY RENOVATED (internal photos coming soon) and TURNKEY FURNISHED VILLA for SEASONAL LEASE -3 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

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

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

Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk in closet and dual sinks and a spacious shower. The second bedroom has a Queen bed, and there is a lovely guest bath. This wonderful end-unit condo has all you need for your perfect vacation! This boutique community offers a sparkling heated pool and private beach, grill area, club room and sauna. All rates are plus taxes and fees. Rates vary by month, call for availability. Booked February through end of April 2026.
#A4580185

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 208

3 Beds

2 Baths

1,411 Sq.Ft.

$5,500

MLS#: A4580185

Centrally located on Longboat Key, FL 2bed/2bath stand-alone villa in Spanish Main Yacht Club. Spacious lanai is suitable year-round. Queen bed in guest room and King bed in primary. Villa is FULLY REMOMDELED, with new kitchen appliances and washer/dryer. Deeded beach access is just steps across to Gulf of Mexico Drive. Community pool, Close to many restaurants, Durante Park, and Bayfront Park, offering beautiful walking trails, tennis, pickle ball and dog park. *At least one in the rental party must be 55 or older. Pets allowed but must be approved by villa owner and be under 25lbs; nonsmoking; tenant responsible for internet and Florida Power & Light usage. Owner keeps electric account, and tenant pays with the following months' rent.
#A4661351

LONGBOAT KEY

546 SPANISH DRIVE S

2 Beds

2 Baths

1,540 Sq.Ft.

$5,500

MLS#: A4661351

AVAILABLE OFF SEASON RENTAL JULY 1, 2025 THROUGH NOVEMBER 30, 2025 AT $5000 A MONTH AND SEASONAL JANUARY 2026 THROUGH APRIL 30, 2026 through MAY 30, 2026 Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor residence. Views from all windows and from the outdoor patio a great view of of the Gulf. Split bedroom plan for privacy. Master bedroom with a king size bed, walk in closet and the all tile bathroom has a convenient walk in shower. 2nd bedroom has a queen comfortable pull out sofa and built in desk area and bathroom tub and shower combination. Large open living area completely tiled with dining table and enjoy all the best of the galley kitchen for easy entertaining. The amenities will complete your time in Paradise in Florida. New clubhouse room with full kitchen. Enormous heated swimming pool and spa, fitness center, sauna, tennis courts, bike storage, pickle ball and have dinner on the beach with outdoor grill area. Restaurants are everywhere along with only minutes to Famous ST. Armand's Circle for great shopping and more of top notch Restaurants. . Walk the 9 mile Beach or ride your bike on Special Longboat Key. Includes internet, electric and cable and more. Turn key furnished. Just pack your bags. Won't last long.
#A4567693

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 804

2 Beds

2 Baths

1,509 Sq.Ft.

$5,000

MLS#: A4567693

Seasonal Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat Key Community, featuring one of the most beautiful beach fronts, and Bay front locations on Longboat Key. This well-appointed and tastefully furnished, updated home welcomes you with its understated elegance. Everything inside is new, from the flooring to the kitchen and baths, the decor is neutral with pops of color, giving the home a coastal urban vibe. The primary bedroom offers a king bed, walk-in closet with built-ins, and a desk. The primary bath has dual sinks and shower. The guest bedroom boasts queen sleeping accommodations and a TV. new luxury vinyl flooring throughout and gorgeous kitchen with stainless appliances, stone counters and lovely wood cabinetry. Outside your door you will find a bonus deck with chaises for sunbathing. This popular, Tim Siebert designed Gulf-to Bay community features 27 lushly landscaped acres, 4 Har-Tru Tennis Courts, a Jr. Olympic pool, kayak launch, bocce ball and fitness room in the clubhouse, and a gorgeous beach, located just across Gulf of Mexico Drive. St. Armands Circle is a short drive away, just over the Ringling Causeway you will find the vibrant downtown Sarasota arts and culture, as well as the many unique shopping and dining venues. Leases less than 7 months subject to additional taxes and fees. Open for 30 day stays June through December and 90 day stays January through April 2026.
#A4540609

LONGBOAT KEY

750 BAYPORT WAY 750

2 Beds

2 Baths

1,570 Sq.Ft.

$5,000

MLS#: A4540609

Welcome home! Enjoy the serenity of this 3 bed, 3 bath, 2 car garage residence, located in Harbour Oaks within the gated community of Bay Isles in the heart of Longboat Key. This tastefully appointed home with open concept floor plan features vaulted ceilings and skylights which create an abundance of natural light throughout the home. The amazing gourmet kitchen offers custom cabinets with soft-close drawers, quartz counters, an appliance package inclusive of refrigerator, induction range, dishwasher and microwave. The Great Room offers beautiful built-in cabinetry and a fireplace. The large primary bedroom, boasts an ensuite spa style bathroom with walk-in shower and dual vanities, and a walk-in closet. Two secondary bedrooms both with ensuite baths are spacious and comfortable. At the end of the day, relax on the screened in patio, overlooking the lush expanse of the manicured greens and relish in the ambiance of breathtaking sunsets or alternatively step out of your front door to enjoy a refreshing dip in the community pool. All residents have access and privileges to the private Bay Isles Beach Club with miles of sugar sand beaches and calm waters of the Gulf of Mexico. All the conveniences of shopping dining and entertainment is just a short drive over the bridge. AVAILABLE AS A SHORT OR LONG TERM LEASE. SEASONAL RENTAL RATES DIFFER FROM ADVERTISED RATE - PLEASE INQUIRE.
#TB8412756

LONGBOAT KEY

2377 HARBOUR OAKS DRIVE

3 Beds

3 Baths

2,952 Sq.Ft.

$5,000

MLS#: TB8412756

Experience unparalleled Gulf-front living in this beautifully renovated 2-bedroom, 2-bathroom condo at Tiffany Plaza. Spanning 1,336 sq ft, this fully furnished residence boasts luxury vinyl flooring, a modern kitchen with marble countertops, and a spacious lanai offering breathtaking views of the turquoise waters of the Gulf of Mexico . The master suite features a king-sized bed, while the guest room offers a queen bed and a desk overlooking the Gulf. Additional amenities include in-unit laundry, high-speed Wi-Fi, and a pull-out couch for extra guests Community highlights encompass a sheltered heated pool, BBQ grill, club room with ping pong table, lending library, and beach chairs with umbrellas. Bayfront Park, just a short stroll away, offers tennis and pickleball courts, basketball, a playground, and stunning sunrise views . Rental Availability: May–November 2025: $5000/month December:$8000 January 10,000 Feb-March 12000 Full 2026 Season available at a discounted rate
#A4535853

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 406

2 Beds

2 Baths

1,456 Sq.Ft.

$5,000

MLS#: A4535853

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