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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

All listings

$250,000 - $500,000

419 Properties Found. Page 27 of 28.

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.

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.

LONGBOAT KEY

546 SPANISH DRIVE S

2 Beds

2 Baths

1,540 Sq.Ft.

$5,500

MLS#: A4661351

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!

LONGBOAT KEY

3806 GULF OF MEXICO DRIVE C108

2 Beds

2 Baths

1,401 Sq.Ft.

$5,500

MLS#: A4660366

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

1,509 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.

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.

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

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 406

2 Beds

2 Baths

1,456 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

1912 HARBOURSIDE DRIVE 603

2 Beds

2 Baths

2,606 Sq.Ft.

$5,000

MLS#: A4658482

Rented January-April 2026. 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.

$5,000

MLS#: A4622485

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

2,606 Sq.Ft.

$5,000

MLS#: A4658263

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

1,390 Sq.Ft.

$5,000

MLS#: A4566128

#TB8394447

LONGBOAT KEY

640 BROADWAY STREET

2 Beds

2 Baths

1,500 Sq.Ft.

$4,995

MLS#: TB8394447

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

1,434 Sq.Ft.

$4,800

MLS#: A4571215

Looking for an extended Longboat Key getaway? This well appointed corner condo in Bayport Beach and Tennis Club has everything for carefree, comfortable island living. Located on the first level in the private 800 "cluster", the spacious, living area opens out to a screened lanai and large outdoor patio overlooking landscaped grounds. Enjoy this serene space for relaxing, entertaining, or reading a good book. There is a gas grill for al fresco meals and a patio gate out to the grounds. The primary bedroom has a king bed, ensuite bath, large walk-in closet, and an alcove with a desk overlooking the garden. A second bedroom is currently set up with a king bed but can easily be converted to two twins. There is one covered parking space and a locked storage closet under the unit, plus plenty of guest parking.
Bayport Beach and Tennis Club is a Gulf-to-Bay community, conveniently located mid-key with award-winning design and fantastic amenities. Residents and guests enjoy a heated, Jr Olympic pool, private fishing pier, kayak and paddleboard launch, tennis courts, club house with full kitchen and fitness room, plus access to 1,200 feet of private beach with beach chair set-up.
Publix, parks and other amenities are within 2-3 miles, with shopping and terrific dining dotted along the Key. Sarasota's entertainment and cultural attractions are a short drive away. Available as a long term rental or, short term with a 3 month minimum January through April, at $7500 per month and May through November at $4500.00 per month. Rentals under 6 months are plus 13% tax. Special pricing for longer stays.

LONGBOAT KEY

842 BAYPORT WAY 842

2 Beds

2 Baths

1,570 Sq.Ft.

$4,500

MLS#: A4663263

SUMMER RATE ONLY: Take a 60 second stroll across the street to the Beach from this Beautiful Renovated unit with an onsite heated pool. Enjoy Peek-a-views of the gulf beach right from the Living Room Sofa, or Private Wrap Around Balcony. There's truly Nothing else like it on the island. Located just 2 blocks from Publix with beach access across the street. Just bring your personal belongings as everything is right here awaiting your arrival - bikes, beach chairs, board games, bidet toilets, fireplace, all kitchenware & gadgets, large screen smart tv's in every room, high speed internet, printer, beach chairs and a ton more. You will surely love it here! Also currently available for the 2026 Season at the seasonal rate. Hurry Before It's Gone!

LONGBOAT KEY

2932 GULF OF MEXICO DRIVE 2932

2 Beds

2 Baths

1,500 Sq.Ft.

$4,500

MLS#: TB8406700

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