$19,975 Per Month
5801 Gulf of Mexico Dr, Longboat Key, FL 34228
Welcome to your own Gulf-front retreat on Longboat Key!This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views.Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows that bring in natural light and frame the Gulf.The
$4,995 Per Month
2020 Harbourside Dr Unit 446, Longboat Key, FL 34228
Experience luxury island living in this beautifully remodeled 2-bedroom, 2-bath residence located in the highly sought-after Fairway Bay community within Bay Isles on Longboat Key. Available for immediate occupancy, this turnkey furnished coastal retreat offers flexible lease terms from 6 to 12 months.Step inside to discover a bright and open floor plan featuring upscale contemporary
Jeffrey Swanson VIVE REALTY
$11,000 Per Month
807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress. RARELY AVAILABLE FOR 2027 SEASON. LESING NOW FOR DECEMBER 2026 AND JANUARY TRHOUGH APRIL 30TH 2027. MINIMUM
$10,000 Per Month
1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle
Jane Hunter JENNETTE PROPERTIES INC
$5,950 Per Month
2013 Harbour Links Dr, Longboat Key, FL 34228
Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered fully furnished and ready for immediate enjoyment, this home is perfectly positioned on a quiet cul-de-sac with extra guest parking, combining privacy, luxury, and
$7,000 Per Month
3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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
Andy Moore GULF COAST REALTY & MANAGEMENT
$6,500 Per Month
3240 Gulf of Mexico Dr, Longboat Key, FL 34228
Seasonal / Short-Term Rental on Longboat KeyVacation in one of the nation’s most celebrated coastal destinations, where a leading national travel magazine ranked Longboat Key among the Top 5 Best Islands in the United States. Experience the beauty firsthand while enjoying breathtaking water views from nearly every room of this stunning condominium at Portobello. This beautifully renovated and
$7,000 Per Month
3210 Bayou Sound, Longboat Key, FL 34228
Experience the best of Longboat Key living in this beautifully updated Bay Isles pool home, offered turnkey furnished FOR LEASE and available for both short-term and long-term reservations. This furnished coastal retreat features an open floor plan with vaulted ceilings, 2 bedrooms plus an office, updated bathrooms, a spacious kitchen with premium appliances, and multiple indoor-outdoor living
Richard Ivan WAGNER REALTY
$4,000 Per Month
1000 Longboat Club Rd, Longboat Key, FL 34228
Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for
$5,500 Per Month
4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
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
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
$10,500 Per Month
4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
**BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease DECEMBER 2026 and APRIL 2027** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly
Norma Mladineo COLDWELL BANKER REALTY
$3,500 Per Month
2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
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
Alex Larchenko KELLER WILLIAMS ON THE WATER S
$10,000 Per Month
6979 Longboat Dr S, Longboat Key, FL 34228
Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room
Rinat Sikdar COLDWELL BANKER REALTY
$4,000 Per Month
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease.
Janette Schafer COLDWELL BANKER REALTY
$9,000 Per Month
775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
AVAILABLE 2026 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay views. This 1600 sq. ft. two bedroom two bath condo is located directly on the sugary beach of Longboat Key with lounge chairs and umbrellas provided. Wrap around balcony with partial Gulf of Mexico and Longboat Key Club golf views. Washer/dryer in the unit, pool, fitness
Brenda Cozy COLDWELL BANKER REALTY
$6,900 Per Month
535 Forest Way, Longboat Key, FL 34228
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
Andy Moore GULF COAST REALTY & MANAGEMENT
$4,200 Per Month
840 Bayport Way Unit 840, Longboat Key, FL 34228
This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The
Shirley Cuddy REALTY SERVICES INC
$5,500 Per Month
5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
A little slice of Gulf-front heaven. Seasonal rental only, available July 15 through December 31, 2026! 60 Day Minimum Lease, not available Jan 1, 2027-March 31, 2027. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches
Scott Nold TNG PROPERTY MANAGEMENT
$6,500 Per Month
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease.
John Schafer, V COLDWELL BANKER REALTY
$11,000 Per Month
1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. Relax on the lanai and take in the beautiful gulf views at sunset. The
Margaret Young JENNETTE PROPERTIES, INC.
$5,700 Per Month
3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
VACATION RENTAL!!! AVAILABLE JAN - MARCH 2027! 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
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
$14,000 Per Month
1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
$7,000 Per Month
1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
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
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
$29,000 Per Month
591 Putting Green Ln, Longboat Key, FL 34228
LONGBOAT KEY...If you're looking for a Luxury winter vacation home, stop searching. You have just found the perfect house located on a private & peaceful cul-de-sac. This beautiful 5 bedroom, 5.1 bathrooms has everything you would want and more with all the comforts of home. All new furniture throughout in every room. Primary, 1st & 2nd bedrooms all have king size beds. Bedrooms 3 & 4 have twin
Teresa Ribaudo JENNETTE PROPERTIES INC
$12,000 Per Month
2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
ELEGANT BEACH FRONT CONDO ON LONGBOAT KEY. This exquisite 2 bedroom, 2 bathroom condo has been totally updated. The kitchen has top of the line, state of the art appliances. Induction stove top, touchless kitchen sink faucet, cooking island, breakfast bar. From the moment you enter this property you are greeted with a wide open floor plan. Incredible views of the Gulf of Mexico and Sarasota Bay.
Teresa Ribaudo JENNETTE PROPERTIES INC
$9,587 Per Month
4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean breezes flow through the unit and the peaceful sound of
Gerald Cunningham KELLER WILLIAMS ON THE WATER S
$11,300 Per Month
2823 Gulf of Mexico Dr, Longboat Key, FL 34228
July 2026 is currently available! Call today! Welcome to BEACHFRONT PARADISE on Longboat Key! This outstanding location offers a RARE OPPORTUNITY to enjoy coastal living with BREATHTAKING VIEWS of the shoreline. Nestled along the PRISTINE SHORES of Longboat Key, this three-bedroom, three-bathroom single family home invites you to experience the ultimate beachfront lifestyle. Relax under the sun,
Michael Cella CELLA'S REAL ESTATE INC
$4,000 Per Month
3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
Steps from the Sand – Luxury Beach Condo with Pool Access!Leave the snow behind and soak up the sun! This stunningly turnkey renovated 2-bedroom, 2-bathroom condo has everything you need for a carefree beach living– including a washer and dryer for sandy swimsuits!Enjoy private access to the shimmering Gulf beaches, relax by the heated pool, or paddle your cares away in the community
nicoletta buonaccordo ALTIS REALTY
$6,000 Per Month
Unlisted Address
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
Jane Hunter JENNETTE PROPERTIES INC
$13,000 Per Month
501 Channel Ln, Longboat Key, FL 34228
Booked May-July, September, and November 2026. Looking for a 3 month rental for January-March 2027. Booked April-December 2027. Experience elevated island living in this stunning coastal retreat featuring 4 bedrooms, 3 bathrooms, a private pool, and exceptional indoor-outdoor entertaining spaces. Designed with comfort and style in mind, the bright open-concept living area features soaring
Jennifer Le Blanc PRECISE REALTY CORP
$10,000 Per Month
1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
Available for 2027 Season. Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each offering a
Jenna Genovese KELLER WILLIAMS ON THE WATER S
$12,000 Per Month
2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
SEASONAL: 90 day minimum. No damages sustained in Hurricane. Beautiful unit from floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
$35,000 Per Month
7147 La Lenaire Dr, Longboat Key, FL 34228
A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian
Chase Moore SIGHT REAL ESTATE, LLC
$11,550 Per Month
500 Schooner Ln, Longboat Key, FL 34228
Booked May-June 8th, October, and Dec 2026 through April 15th 2027, May 2027. **2-Week Minimum Stay Required** Escape to this beautifully renovated waterfront retreat on Longboat Key. This spacious 2-bedroom, 2-bath home features an open-concept design, designer coastal décor, and a gourmet kitchen with a large island, wine cooler, and premium finishes throughout. Both bedrooms offer tranquil
Jennifer Le Blanc PRECISE REALTY CORP
$5,000 Per Month
1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
Available 05/01/2026 through 12/30/2026 FOR $5000. LEASED SEASON JAN, 2026 THROUGH MARCH, 2027. 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
Marni Hayden CHROME REALTY LLC
$40,000 Per Month
1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$5,500 Per Month
957 Spanish Dr N, Longboat Key, FL 34228
AVAILABLE STARTING MAY 1, 2026. WITH 4 MONTH MINUMUM RENTAL DURING SEASON and 3 MONTHS OFF SEASON. FULL WATERFRONT NEWLY RENOVATED 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
Norma Mladineo COLDWELL BANKER REALTY
$7,800 Per Month
4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
SEASONAL: 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, in unit washer/dryer, large walk-in closets and covered parking. The Master suite
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
$3,200 Per Month
747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
GORGEOUS BAY VIEWS. Located in a quiet association of only eight units. Annual Unfurnished unit; open kitchen/living and dining area with master bedroom and tub/shower combo in en-suite bath. Canal views with private dock and boat lift (a boater and fisherman's dream). Drop a line outside your back door! Screened lanai with washer/dryer. Exterior parking immediately outside the unit with gas BBQ
Gregory Koss WAGNER REALTY
$9,500 Per Month
691 Russell St, Longboat Key, FL 34228
Experience luxury coastal living in this completely renovated annual rental on the desirable north end of Longboat Key. Situated on an oversized double lot just minutes from the pristine Gulf beaches, this exceptional pool home offers the perfect blend of style, comfort, and convenience. Thoughtfully redesigned from top to bottom, the home features a bright, open-concept floor plan with
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
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