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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

511

# of Listings

2

Avg # of Bedrooms

$858

Avg. $ / Sq.Ft.

$1,508,088

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

511 Properties Found. Page 33 of 35.

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).

LONGBOAT KEY

4420 EXETER DRIVE 208

2 Beds

2 Baths

1,168 Sq.Ft.

$6,000

MLS#: O6342792

#A4552081

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 1006

2 Beds

2 Baths

1,409 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.

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.

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.

LONGBOAT KEY

957 SPANISH DRIVE N

2 Beds

2 Baths

1,399 Sq.Ft.

$5,500

MLS#: A4661509

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

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

AVAILABLE Dec. 2025-April 2026, 2 mos. min. This is a second floor walk up, two bedroom and den, two bathroom unit with over 1,600 square feet of interior living space. There is a private screened balcony/lanai and aa staircase entrance to the front door of the unit. The unit has partial water views from the living room, dining room, den, and the screened balcony and exterior open balcony/lanai over the tennis courts and grounds to the marina and bayou/bay. This is 'old Florida' at its best in ambiance and lifestyle. There are 2 lighted tennis courts, a community pool and hot tub, a community exterior shaded deck for eating, grilling and relaxing, as well as a kayak launch.

LONGBOAT KEY

3440 GULF OF MEXICO DRIVE 9

2 Beds

2 Baths

1,612 Sq.Ft.

$5,500

MLS#: A4668234

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

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, beautiful bay views, 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.

LONGBOAT KEY

3808 GULF OF MEXICO DRIVE E211

2 Beds

2 Baths

1,085 Sq.Ft.

$5,000

MLS#: A4672681

Iconic… Gulf Key.
This immaculate, newly renovated two-bedroom, two-bath villa is just a three-minute walk to the beach. Gulf Key invites you to slow down, breathe in the salt air, and truly unwind. It’s classic clay tile roof and stucco exterior reflect understated elegance and the essence of an OLD Florida lifestyle.

With only 10 units, Gulf Key offers peace and privacy in a stellar location, just a short walk to groceries, dining, pharmacy, library, and boutique shopping.
Amenities include:
• Private Patio
• Designated parking
• Wi-Fi
• AND THE BEACH!!!

(Available on or before January 31, 2026)
Gulf Key isn’t a high-rise – there are no elevators, pools or sprawling parking lots… it is just your own special retreat in the heart of coastal Florida. NO Smoking. NO Pets.

LONGBOAT KEY

540 NEPTUNE AVENUE 7

2 Beds

2 Baths

1,032 Sq.Ft.

$5,000

MLS#: A4671262

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

Desirable Furnished One Bedroom 1 1/2 Bathroom Condo on Longboat Key. It is on the 7th floor with a 20 ft lanai that has an outstanding view of the beach and the Gulf of America. The building is one of the closest to the beach with access within few feet of the building, is well managed, has a salt water heated pool & recreational area with gas grill. There is an exercise center, public kitchen, and meeting rooms. The condo has been recently painted, has new Samsung 84-inch TV and new Pottery Barn furnishings. There is an assigned covered parking spot-
Space #70. A new tenant will find it is very convenient to local restaurants like DryDock Restaurant, the Charthouse, St Armands Circle and medical facilities including Sarasota Memorial Hospital.
It is a 25 minute drive to Sarasota Bradenton Airport.

LONGBOAT KEY

4401 GULF OF MEXICO DRIVE 703

1 Beds

1 Baths

725 Sq.Ft.

$5,000

MLS#: A4672150

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 2025. Booked February through end of April 2026.

LONGBOAT KEY

750 BAYPORT WAY 750

2 Beds

2 Baths

1,370 Sq.Ft.

$5,000

MLS#: A4540609

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

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