Longboat Key, FL Homes for Rent with Water View

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  $2,600 Per Month

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  909 Spanish Dr N Unit 51, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. This beautifully updated/unfurnished two-bedroom, two-bath Spanish Main standalone villa with beach access is available for annual lease! The fully remodeled home features neutral tile plank flooring throughout, a spacious chef’s kitchen with 42-inch wood cabinets, quartz island that seats seven,

  Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

  909 Spanish Dr N Unit 51, Longboat Key, FL 34228
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  $11,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Condo for Rent

  1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  Seasonal. Not available Jan - April 2025. Amazing sunsets from this fabulous 5th floor, direct Gulf beach front, 2 BD, 2 BA condo. Meticulously maintained, this condo has everything you need for a care-free beach vacation! Master suite features king size bed, private bath with Gulf view. Guest room offers twin sleeping arrangements with private entrance to bath. For your comfort, there's flat

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  $7,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Condo for Rent

  3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  Absolutely beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Newly renovated bathrooms and kitchen with high end finishes round out this fabulous

  C. Alison Hunter JENNETTE PROPERTIES INC

  3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  $30,000 Per Month

  • 1 Bed
  • 1.5 Baths
  • 1,684 Sq Ft
  • Condo for Rent

  1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

  Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a

  Larry Starr SVN COMMERCIAL ADVISORY GROUP

  1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
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  $3,750 Per Month

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Condo for Rent

  1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228

  AVAILABLE IMMEDIATELY PENDING HOA APPROVAL! 2 MONTH MINIMUM! BOOKED FOR JAN-MARCH 2027 SEASON! 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

  Brigette Marcus NEXTHOME EXCELLENCE

  1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
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  $14,750 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,292 Sq Ft
  • House for Rent

  513 Gunwale Ln, Longboat Key, FL 34228

  Welcome to Beach & Boaters Paradise located on Longboat Key. Enjoy immediate access access to beautiful Sarasota Bay, the Gulf of Mexico and Longboat Key’s sugar white sand beaches and emerald green waters. Fish off the dock or walk to the beach! Or enjoy the large heated pool in this 4 bedroom, 3.5 bath luxury waterfront home designed to provide you and your family a lifetime of vacation

  Marcia Benson Berkshire Hathaway Florida Realty

  513 Gunwale Ln, Longboat Key, FL 34228
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  $11,769 Per Month

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Condo for Rent

  2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228

  ..."' short stories. ....on the island of longboat key You are on the beach included is swimming pool...and a world class tennis courtf...looking play with others and league Town of Longboat Key tennis three blocks away...fitness gym.. . This is direct Gulf front unit with interior hallways from the balcony ,the kitchen,the living room couch...Your on the water.. Breathtaking view of the

  Gerald Cunningham KELLER WILLIAMS ON THE WATER S

  2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
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  $4,000 Per Month

  • 1 Bed
  • 1.5 Baths
  • 1,080 Sq Ft
  • Condo for Rent

  1000 Longboat Club Rd Unit 406, 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

  Cody Smith RENT SARASOTA

  1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
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  $11,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,602 Sq Ft
  • Condo for Rent

  775 Longboat Club Rd Unit 904, Longboat Key, FL 34228

  AVAILABLE DEC. '26 THROUGH FEB.'27. Beautiful 9th floor, 1600 sq. ft. 2 bedroom 2 bath at the sort after Beaches condominium which is within the gates of the Longboat Key Club. Updated kitchen and bathrooms. Fabulous bay, and Longboat Key Club golf views. Wrap around balcony with partial Gulf view. Washer/dryer in the unit, pool, fitness center and tennis courts plus 24 hr. Concierge and garage

  Brenda Cozy COLDWELL BANKER REALTY

  775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
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  $18,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

  2027 Season Rental Rate will be $24,000. The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
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  $5,700 Per Month

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Condo for Rent

  540 Neptune Ave Unit 7, Longboat Key, FL 34228

  ****Enchanting, Iconic...Gulf Key****~Discover Relaxation and Island Charm Just Steps from the Beach~Unwind at Gulf KeyWelcome to Gulf Key, a truly iconic villa community where the spirit of “old Florida” meets modern comfort. This immaculate, newly renovated 2-bedroom, 2-bath villa is perfectly situated just a 5-minute walk from the beach, making it an ideal destination for

  Pamala Casey CASEY REALTY CORPORATION

  540 Neptune Ave Unit 7, Longboat Key, FL 34228
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  $65,000 Per Month

  • 4 Beds
  • 4.5 Baths
  • 5,334 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228

  Imagine taking in this view from your private balcony pool! An exceptionally rare opportunity to lease one of the most exclusive waterfront residences ever offered on Florida’s Gulf Coast. Positioned within the iconic St. Regis Residences on Longboat Key, this extraordinary four-bedroom, four-and-a-half-bath condominium redefines annual luxury living with an unrivaled level of privacy,

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
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  $7,850 Per Month

  • 3 Beds
  • 3 Baths
  • 2,250 Sq Ft
  • Condo for Rent

  3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228

  LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major

  Patrice Ivan WAGNER REALTY

  3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
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  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Condo for Rent

  5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  Pristine Gulf Beachfront on Longboat Key Welcome to this beautifully updated 2-bedroom, 2-bathroom luxury beachside retreat located in The Shore on mid-Longboat Key. This inviting second-floor condo offers stunning Gulf views and is just steps from the powdery white sand and crystal-clear waters—an ideal setting for a relaxed island getaway. Highlights-Sweeping Gulf views from living room and

  Matt Darak DARAK GROUP INCORPORATED

  5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  $8,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Condo for Rent

  1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228

  Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Primary Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive

  Jane Hunter JENNETTE PROPERTIES INC

  1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228
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  $7,000 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,780 Sq Ft
  • Condo for Rent

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228

  Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the

  Deserea Hardy ROSSI & COMPANY INC

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
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  $6,950 Per Month

  • 2 Beds
  • 2.5 Baths
  • 2,369 Sq Ft
  • Condo for Rent

  2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228

  Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. 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

  Andrew Clark SECURE DOOR PROPERTY MANAGEMENT

  2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
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  $10,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft
  • Condo for Rent

  2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228

  *Flexible rental dates!!!* Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms.Rental dates are fully flexible to suit your needs — unlike most units that

  Michele Conn PREFERRED SHORE LLC

  2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
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  $4,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Condo for Rent

  4420 Exeter Dr Unit 208, Longboat Key, FL 34228

  Must read entirely. 2026-2027 RENTAL- Not Available until Nov 2026 or Jan 15-Mar 30. 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

  Armando Gonzalez AG REALTY SERVICES LLC

  4420 Exeter Dr Unit 208, Longboat Key, FL 34228
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  $2,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C211, Longboat Key, FL 34228

  2 bed, 2 bath 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 the community’s private beach access complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community kayaks, socialize with

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3806 Gulf of Mexico Dr Unit C211, Longboat Key, FL 34228
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  $7,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • House for Rent

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228

  Booking Now for Summer 2027! Booked for January-June 30, 2027. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access.

  Debby McCaig COLDWELL BANKER REALTY

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $11,500 Per Month

  • 3 Beds
  • 3.5 Baths
  • 3,101 Sq Ft
  • House for Rent

  2254 Harbour Court Dr, Longboat Key, FL 34228

  Nestled on the tranquil waterfront of Longboat Key, this stunning residence offers the ultimate coastal lifestyle. With direct water access and a private dock, boating and jet skiing are right at your doorstep. Two floating jet ski docks can also accommodate dinghies, making this property a boater’s dream. The home is ideally situated beside the golf course, blending serene water views with lush

  Alex Larchenko KELLER WILLIAMS ON THE WATER S

  2254 Harbour Court Dr, Longboat Key, FL 34228
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  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Condo for Rent

  3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Stunning Portobello Vacation 2/2 Condo on Longboat Key. Season rate is $8000 (Jan-Apr) and off season rate is $5500 (May-Dec). Minimum 2 month rental and full months only. This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style décor, new windows and

  Terri Lindsay LINDSAY LEASING LLC

  3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

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