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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

492

# of Listings

2

Avg # of Bedrooms

$963

Avg. $ / Sq.Ft.

$1,726,903

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

492 Properties Found. Page 32 of 33.

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.

LONGBOAT KEY

1928 HARBOURSIDE DRIVE 1402

2 Beds

2 Baths

1,626 Sq.Ft.

$5,500

MLS#: A4627730

Merging classic elegance with modern luxury featuring high vaulted ceilings, a state-of-the-art kitchen, high-speed internet, and a cutting-edge reverse osmosis water system. Enjoy the convenience of an in-closet washer/dryer and UV air filtration for pristine air quality. Perfect for romantic getaways or peaceful solitude, with boat parking & public launch nearby. The property offers a furnished outdoor space on a quiet, gated lot. Seasonal rates apply for this unique retreat. Available! For further details inquire online.

LONGBOAT KEY

6980 POINSETTIA AVENUE

1 Beds

1 Baths

700 Sq.Ft.

$5,500

MLS#: TB8384422

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.

LONGBOAT KEY

5757 GULF OF MEXICO DRIVE 305

2 Beds

2 Baths

1,561 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 January through March 2025, and May of 2025.

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 208

3 Beds

2 Baths

1,411 Sq.Ft.

$5,500

MLS#: A4580185

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.

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 102

2 Beds

2 Baths

1,336 Sq.Ft.

$5,500

MLS#: A4544891

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.

LONGBOAT KEY

750 BAYPORT WAY 750

2 Beds

2 Baths

1,370 Sq.Ft.

$5,000

MLS#: A4540609

AVAILABLE APRIL 1ST 2025. 6 MONTH STAY $5000 PER MONTH - NO TAX/ PRIME SEASONAL RATES: Jan 1st to April 30th @ $8,500 per month plus 13% sales tax. For shorter off season stay - 3 month minimum - rental rate is $5,000 plus tax. Property may also be rented annually at $5,000 per month - no tax, includes all electricity, shorter terms $75.00 for electric. ***** 1,200 ft. of private beach (with chaises and umbrellas). Covered private parking. Pets Considered. Enjoy a wonderful relaxing vacation at the Bayport Beach & Tennis Club on Longboat Key. This finely appointed 2-bedroom 2 bath condo located in a truly tropical setting with a bounty of amenities that include 4 Har-tru Tennis Courts considered to be the best of the Key. One of the largest swimming pools (75' X 36") on the Island: maintained at a temperature between 82- and 85- degrees year-round, a fishing pier and 1,200 feet of beachfront. The clubhouse has a full kitchen facility and is large enough for meeting, private parties and social functions. The exercise room is very well equipped with machines and free weights. Classes in Water-Aerobics are held 3 times a week during the winter months at a nominal cost: private tennis lessons may be arranged.

LONGBOAT KEY

842 BAYPORT WAY 842

2 Beds

2 Baths

1,260 Sq.Ft.

$5,000

MLS#: A4641688

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.

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 804

2 Beds

2 Baths

1,409 Sq.Ft.

$5,000

MLS#: A4567693

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

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 406

2 Beds

2 Baths

1,336 Sq.Ft.

$5,000

MLS#: A4535853

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!

LONGBOAT KEY

1922 HARBOURSIDE DRIVE 1102

2 Beds

2 Baths

1,590 Sq.Ft.

$5,000

MLS#: A4658263

New on site 4 days ago

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!

LONGBOAT KEY

1912 HARBOURSIDE DRIVE 603

2 Beds

2 Baths

1,590 Sq.Ft.

$5,000

MLS#: A4658482

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.

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 502

2 Beds

2 Baths

1,290 Sq.Ft.

$5,000

MLS#: A4566128

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.

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE 603

2 Beds

2 Baths

1,260 Sq.Ft.

$4,800

MLS#: A4571215

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!

LONGBOAT KEY

4780 GULF OF MEXICO DRIVE

2 Beds

2 Baths

1,168 Sq.Ft.

$4,500

MLS#: A4622485

#TB8394447

LONGBOAT KEY

640 BROADWAY STREET

3 Beds

2 Baths

1,500 Sq.Ft.

$4,450

MLS#: TB8394447

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