One of the most popular communities provided by {{page_data.agentName}}

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

495

# of Listings

2

Avg # of Bedrooms

$950

Avg. $ / Sq.Ft.

$1,697,901

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

495 Properties Found. Page 31 of 33.

AVAILABLE. 2025 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay views from the master lanai. Unit has a washer/dryer and 2 full baths. Feel free to bring your small dog as well. Easy access to St. Armands Circle and Bradenton Beach.

LONGBOAT KEY

655 CEDARS COURT 655

1 Beds

2 Baths

2,376 Sq.Ft.

$7,000

MLS#: A4478968

SEASONAL/VACATION RENTAL! AVAILABLE FOR 2026 SEASON! CALL TODAY! Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, large walk-in closets and covered parking. The Master suite features King-sized bed, TV, & opens to a private balcony. The comfortable guest bedroom offers twin beds with ceiling fan, and guest bathroom with tub/shower. The Westchester community is located on 7-plus acres of beautifully landscaped grounds, meticulously maintained with tennis court, 2 heated pools, updated Clubhouse and 3 private Tiki-hut areas. Gulf beaches are what make Longboat Key unique and you can walk for miles on the beach from the condo. Longboat Key also has 10 miles of bicycle paths on either side of Gulf of Mexico Drive. Located just 6 miles from fashionable St. Armands Circle and only a short drive to downtown Sarasota with arts, theatre, restaurants and shopping. This is non-smoking unit. Sorry, this condo association does not allow pets. Amenities include 2 pools, tiki hut, tennis and pickleball court, clubhouse, grilling area and kayakk storage. Non smoking residence.

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 202

2 Beds

2 Baths

1,393 Sq.Ft.

$7,000

MLS#: A4626398

Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You are just across the street from the gorgeous Gulf Beaches, with private beach access. Upon entering this condo, you will see an ocean view from the third floor. As you enter, you will find the large kitchen, which has stainless steel appliances, six barstools, a giant kitchen island, a lounge area with a sofa, and plenty of space to prepare your family’s favorite treats. You will find lovely natural lighting throughout, due to this condo having windows on all four sides. Adjacent is the dining table, with gorgeous West Elm chairs that accommodate up to six. The spacious living room has a sizeable “L” shaped couch, an entertainment center, and beautiful natural lighting through the windows. There are views from the master bedroom and the reading nook in the kitchen area, where you will love to enjoy your morning coffee with the sunshine streaming in those windows. The primary bedroom has a king-size bed, a chair, a TV, and plenty of closet space for your personal belongings. Attached is the primary bathroom, which has a large vanity with a stunning walk-in shower that has exquisite masonry work, and a detachable showerhead. The second bedroom has a queen-size bed and plenty of closet space. The second bathroom has a large vanity with a shower/tub combo. There is community Kayaks with a lift for use by renters, there are two rooftop patios in the building which are shared. The one at the front is perfect for watching the sunset every evening. This condo is a short drive to St. Armands Circle and Downtown Sarasota where there are restaurants, boutiques, shopping, theater, opera, ballet, botanical gardens etc. we are close to many great restaurants. Come see why people come to Longboat Key year after year. There is a dedicated covered parking spot and additional guest parking. House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets.

**Taxes and fees not included.

LONGBOAT KEY

3804 GULF OF MEXICO DRIVE B307

2 Beds

2 Baths

1,133 Sq.Ft.

$7,000

MLS#: A4555216

LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. Open floor plan, with vaulted ceilings, hardwood floors throughout. Private screened in pool with a view of the golf course and evening sunsets with plenty of space for entertaining. Kitchen is equipped with everything a cook would need including a separate wet bar with a built-in wine cooler. Access to the private deeded Bay Isles Beach Club. Just a short drive to the Longboat Key's Town Center for all your shopping needs.
Owner will consider short term rentals, Dec-April $12,000 a month + tax, May-Nov. $8,000 a month + tax with an application fee of $200.

LONGBOAT KEY

2369 HARBOUR OAKS DRIVE

3 Beds

2 Baths

2,892 Sq.Ft.

$7,000

MLS#: A4571577

GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought-after Bay Isles community. The spacious Kitchen had been updated along with the both baths, with Quartz counter-tops and new cabinetry, the Primary suite offers a King bed, views of the bay and the Primary bath has dual sinks, new vanity, new lighting, new shower and an updated large closet. The Guest bedroom has two twin beds that can be made into a King bed, and the guest bath has a new vanity, new mirror and lighting. Enjoy your morning coffee or a sunset cocktail on the Lanai overlooking the Bay and intercoastal waterway. This location has its own pool, and a larger community pool and spa with the clubhouse just a few steps away, you can take advantage of the newer fitness room and reserve a court for tennis or pickle ball. Pack up the car and spend the day at the BAY ISLES PRIVATE BEACH CLUB, located at 2111 Gulf of Mexico Drive.

LONGBOAT KEY

1930 HARBOURSIDE DRIVE 134

2 Beds

2 Baths

1,312 Sq.Ft.

$7,000

MLS#: A4641782

Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.

Step into island living with the second floor as your main living space, thoughtfully designed for comfort and connection. Relax on the queen-size pull-out sofa, or step out onto the screened-in lanai where you can sip your morning coffee while soaking in the serene, lush surroundings. The dining area comfortably seats up to seven, making it the perfect setting for family meals and lively conversations. Just adjacent, the kitchen offers four barstools, ample counter space, and all the essentials for preparing your favorite family dishes and beach-day snacks.

Upstairs, the third level features both bedrooms. The primary bedroom is a true retreat, featuring a king-size bed, breathtaking views of the tropical landscape, and an attached, spa-inspired bathroom with dual vanities and a spacious walk-in shower. The second bedroom includes a queen-size bed with a twin trundle, a TV, and generous closet space—ideal for guests or kids to unwind in comfort.

What truly sets this home apart is the incredible Cedars East community. Located on the bay side of Longboat Key, Cedars East offers a lifestyle like no other—with a heated junior Olympic-size pool, tennis courts, boardwalks through mangrove-lined nature trails, bike paths, and a bayside fishing pier. You’ll love the lush, well-manicured grounds, and how close you are to the gulf beaches, boutique shopping, and local dining that Longboat Key is famous for.

Whether you're planning to spend your days exploring the beach, relaxing poolside, or simply enjoying the peace and beauty of the natural surroundings, this charming Cedars East getaway is the perfect island retreat.

House Rule: No smoking. No burning candles inside of lodging. No parties.

Furry friends welcome, max 2, and require a $200 per pet non-refundable pet fee to be paid directly to the management company.

LONGBOAT KEY

535 FOREST WAY

2 Beds

2 Baths

1,440 Sq.Ft.

$6,900

MLS#: A4655086

AVAILABLE FOR 2026 SEASON! MINIMUM 3 MONTH LEASE PLEASE. LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the condo has to give with the natural light that floods through the large sliding glass doors. From the beautifully updated kitchen, you can see the dining room, living room, screened patio and the Gulf of Mexico! The kitchen also offers stone countertops, stainless steel appliances and plenty of cabinet and counter space. The condo sleeps four (1 king bed & 2 twin beds) and has walk-in showers in both updated bathrooms. All top-of-the-line upgrades throughout the condo including impact doors and windows, Washer/Dryer and all utilities provided with two TVs in the unit. The back patio is fully screened in and features beautiful views of the ocean! The private beach access is just off the clubhouse which is steps away. Seaplace is one of the largest, most highly sought after complexes on Longboat Key. This resort style community offers 2 heated pools, hot tub, kiddie pool, beachfront patio, 4 grills, 3 har-tru tennis courts, game room, work out room, library, sauna, 24-hour security, and monthly events for anyone to enjoy. Longboat Key Club golf course is approx. 2 miles away. Also enjoy strolling around St. Armand's Circle which offers top-rated dining and shopping. ** Rent includes electricity, water, cable, internet, sewage, pest control, extra storage and all the amazing community amenities! *No pets allowed *Application Fee: $100 per applicant *HOA Application Fee: $100 per applicant *250 cleaning fee *$50 booking fee *Security Deposit: $750 for short term *13% seasonal rent tax applies to 6 month and under rentals

LONGBOAT KEY

1945 GULF OF MEXICO DRIVE M2-414

2 Beds

2 Baths

928 Sq.Ft.

$6,500

MLS#: A4618406

"SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE OF LONGBOAT KEY. BOOKED FOR FEB-APRIL 2026. AVAILABLE NOV 2025 AT $3,500, DEC 2025 AT $5,000 & JAN 2026 AT $6,500. Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the unit, you are met with a light, bright and open feeling with the natural light coming in through the large sliding glass doors which open up onto the fully screened in and covered balcony. Beautifully furnished and decorated, living a fully equipped kitchen offering ample cabinet and storage space, washer/dryer, dining room, and living room Both the master and guest bathrooms have newly installed walk-in showers. Seaplace is one of the largest, most highly sought after complexes on Longboat Key. This resort style community offers 2 heated pools, hot tub, kiddie pool, beachfront patio, 4 grills, 3 har-tru tennis courts, game room, work out room, library, sauna, 24-hour security, and monthly events. Plus, the private beach access is just steps away from the beautiful crystal quartz sandy beaches and turquoise Gulf of Mexico waters. Conveniently located just a short drive from boutique shopping, dining and cultural attractions of St. Armand's Circle and Downtown Sarasota with the infamous Ringling Art Museum, Maria Selby Botanical Gardens, and Marina Jacks for boat tours and sunset dinner cruises. Or take a short ride over the bridge in the opposite direction to explore the beautiful Anna Maria Island. Longboat Key Club Golf Course is approx. 2 miles away. **This is a 3-month minimum rental. ** Sorry, no pets allowed.

LONGBOAT KEY

1945 GULF OF MEXICO DRIVE M2-402

2 Beds

2 Baths

1,019 Sq.Ft.

$6,500

MLS#: A4650120

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.

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 305

2 Beds

2 Baths

1,456 Sq.Ft.

$6,000

MLS#: A4655690

#A4451608

LONGBOAT KEY

5393 GULF OF MEXICO DRIVE 208

2 Beds

2 Baths

1,300 Sq.Ft.

$6,000

MLS#: A4451608

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.

LONGBOAT KEY

706 BAYPORT WAY 706

2 Beds

2 Baths

1,832 Sq.Ft.

$6,000

MLS#: T3488636

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.

LONGBOAT KEY

1975 GULF OF MEXICO DRIVE 208

2 Beds

2 Baths

1,392 Sq.Ft.

$6,000

MLS#: A4572396

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.

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!

LONGBOAT KEY

3806 GULF OF MEXICO DRIVE C111

2 Beds

2 Baths

1,027 Sq.Ft.

$6,000

MLS#: A4464764

#A4552081

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 1006

2 Beds

2 Baths

1,509 Sq.Ft.

$6,000

MLS#: A4552081

1 ... 29 30 31 32 33

Buyers resources

7 Reasons to Work with a Realtor

7 Principles For Home Buying Success

Getting a Mortgage To Buy a Home

Home Hazards Awareness

Key Items For Home Inspection

Questions When Buying a Condo

Questions When Choosing a Realtor

Sellers resources

8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

Buyers resources

BUYERS RESOURCES

Sellers resources

SELLERS RESOURCES

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

First Name

Last Name

Email

Phone

MLS Property Number

Your message

Reason for contacting?

Buying a home

Selling a home

Other

I agree to receive email communication and understand I can unsubscribe at any time.

Virtual Assistant

Would you like to receive some additional information on this specific property or similar properties?

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Accessibility Menu

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Email address (Must be valid)

Already have an account ? Login here

Continue your home search

Email address

First name First Name

Last name Last Name

Phone number (Optional)

Password

I agree to receive communications and understand I can unsubscribe at any time.

Already have an account ? Login here