Homes for Rent in ZIP Code 34228

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  /48

  $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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  /12

  $7,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • House for Rent

  537 Outrigger Ln, Longboat Key, FL 34228

  Welcome boating enthusiasts to this exceptional waterfront residence located in the highly desirable Country Club Shores community on Longboat Key. Situated on a deep-water canal with direct access to the Gulf of America, this beautifully updated two-bedroom, two-bath home with a den offers the ultimate island lifestyle for boaters and beach lovers alike. The property features a brand-new

  537 Outrigger Ln, Longboat Key, FL 34228
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  /31

  $15,000 Per Month

  • 1 Bed
  • 2 Baths
  • 1,556 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228

  Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
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  /23

  $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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  /20

  $11,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Condo for Rent

  807 Bayport Way, 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

  807 Bayport Way, Longboat Key, FL 34228
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  $5,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft
  • Condo for Rent

  5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228

  Experience true beachfront living at 5611 Gulf of Mexico Drive, Unit 3103. This beautifully kept 3-bedroom, 2-bath residence is in excellent condition and offers stunning views of the Gulf of Mexico in a setting that is hard to beat.Located directly on the beach with no road to cross, this property gives you effortless access to the shoreline just steps from your door. Guests can enjoy

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  5611 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
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  /20

  $12,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,293 Sq Ft
  • Condo for Rent

  615 Dream Island Rd Unit 107, Longboat Key, FL 34228

  Welcome to one of the most sought-after condo units in the Harbour Villa Club. This magnificent unit is for rent fully furnished. Opening the front door, you will enjoy a beautiful view of the serene intracoastal waterway and stunning Florida palm trees. No need to mess with an elevator, this first floor unit opens directly to the swimming pool and is only steps away from a 40’ deeded boat slip

  Jerome Henin HENIN REALTY

  615 Dream Island Rd Unit 107, Longboat Key, FL 34228
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  /65

  $12,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • House for Rent

  Unlisted Address

  Enjoy resort-style living on prestigious Longboat Key in this completely updated and renovated 3-bedroom, 2.5-bathroom villa. Located in Harbour Circle, an enclave of 42 villas in the guard-gated, maintenance-free, community of Bay Isles, this 2,396 SF open floorplan has soaring ceilings and an abundance of natural light through the new high-impact doors and windows that uplifts and illuminates.

  Teresa Ribaudo JENNETTE PROPERTIES INC

  Unlisted Address
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  /40

  $4,800 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • House for Rent

  616 Lyons Ln, Longboat Key, FL 34228

  Come and enjoy a little piece of Paradise! This beautiful canal front home is located in the idyllic and picturesque Longboat Key. A charming mid-century style cottage nestled in one of Longboat Key's most private and serene settings. This spacious 2 bedroom + Bonus room, 2.5 bathrooms with outdoor shower residence offers 1,755 square feet of luxurious living space perfect for those seeking a

  Steve Barthelemy ROOST REALTY INC.

  616 Lyons Ln, Longboat Key, FL 34228
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  $4,000 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228

  Annual Only. Beachfront Longboat Key Luxury Living. Wake up every day to sweeping **Gulf views** from this beautifully renovated **5th-floor beachfront residence**. Designed for comfort, tranquility, and effortless coastal living, this 12-month annual rental places you steps from the sand and moments from the world-class dining and boutique shopping of **St. Armands Circle**.Property

  Donna Channey WAGNER REALTY

  1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
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  $2,800 Per Month

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

  1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  FURNISHED CONDO ON THE BEACH ! AVAILABLE MAY 1ST! SORRY JAN 1- MARCH 2027 IS NOT AVAILABLE . May - November are AVAILABLE MONTHS. This wonderful Condo 2 bed/2 bath and den is now available. Beach Place is one of the most sought out places on Longboat Key. Located mid-island, this association has a FANTASTIC beach, large heated pool, spa and his/hers fitness areas, EV charging station, tennis,

  Annabelle Newland STOCKTON REALTY ADVISORS LLC

  1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
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  /57

  $24,750 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,940 Sq Ft
  • Condo for Rent

  1511 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  Offered at $24,750 per month for 3 months in 2027! - Come be on the beach! Rarely available on the south end of Longboat Key, a 3 bedroom + den, 3 1/2 bath DIRECT Beachfront 3-month (90 days total) rental is now available for this coming 2027 winter and spring season. This large 2940 +/- sq ft beachfront retreat is situated on the south side of this building which offers stunning 180-degree beach

  Carol Aviles MICHAEL SAUNDERS & COMPANY

  1511 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /31

  $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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  $4,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft
  • Condo for Rent

  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

  3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
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  $2,500 Per Month

  • 1 Bed
  • 1 Bath
  • 689 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228

  1-bed, 1-bath seasonal or annual 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 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

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3808 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
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  /18

  $3,000 Per Month

  • 1 Bed
  • 1 Bath
  • 667 Sq Ft
  • Condo for Rent

  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

  747 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
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  /17

  $3,600 Per Month

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft
  • House for Rent

  420 Firehouse Ct Unit 10, Longboat Key, FL 34228

  Seldom available annual rental on the coveted north end of Longboat Key. This beautifully remodeled 2-bedroom, 2-bath condo boasts new appliances, cabinets, flooring, and modern fixtures throughout. Both bedrooms feature spacious walk-in closets, and a separate utility room includes washer and dryer hookups. Embrace the laid-back coastal lifestyle with quick access to beaches, restaurants,

  Gregory Koss WAGNER REALTY

  420 Firehouse Ct Unit 10, Longboat Key, FL 34228
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  /13

  $4,200 Per Month

  • 4 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • House for Rent

  600 Russell St, Longboat Key, FL 34228

  Remodeled Single-Family Home in Historic Longbeach Village Available for annual lease on the north end of Longboat Key, this beautifully updated 4-bedroom, 2-bath single-family home is located in the charming and historic Longbeach Village. The home features brand-new appliances, cabinetry, fixtures, and flooring throughout. Lawn maintenance is included in the monthly rent, and the utility room

  Gregory Koss WAGNER REALTY

  600 Russell St, Longboat Key, FL 34228
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  $35,000 Per Month

  • 5 Beds
  • 5.5 Baths
  • 3,503 Sq Ft
  • House for Rent

  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

  7147 La Lenaire Dr, Longboat Key, FL 34228
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  $55,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 3,130 Sq Ft
  • Condo for Rent

  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

  1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
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  $2,500 Per Month

  • 1 Bed
  • 1 Bath
  • 721 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228

  1-bed, 1-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

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3808 Gulf of Mexico Dr Unit E205, 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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  /40

  $3,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • House for Rent

  573 Spanish Dr N, Longboat Key, FL 34228

  NOW AVAILABLE STARTING JUNE 1, 2026 - BRAND NEW RENOVATED and TURNKEY FURNISHED available for ANNUAL LEASE ($3,500/MONTH) OR SEASONAL Jan - April ($5,500/MONTH). 6 MONTH MINUMUM RENTAL (OR INQUIRE ABOUT ANNUAL OPTION). ALL Utilities, Cable and Tax included. Come live the island life in this peaceful, fully detached villa nestled in the vibrant 55+ waterfront community of Spanish Main Yacht Club.

  Norma Mladineo COLDWELL BANKER REALTY

  573 Spanish Dr N, Longboat Key, FL 34228
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  /26

  $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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  /31

  $10,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Condo for Rent

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with

  Brad Wilson M&M PROPERTY MANAGEMENT GROUP

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /58

  $9,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Condo for Rent

  829 Bayport Way Unit 829 B, Longboat Key, FL 34228

  Introducing a remarkable opportunity to rent a piece of paradise at 829 Bayport Way in the scenic Longboat Key, Florida. This beautifully situated property offers an exceptional blend of modern living and serene outdoor charm, perfect for those seeking both comfort and a vibrant lifestyle by the coast. As you enter the community, you are greeted by meticulously landscaped grounds that set the

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  829 Bayport Way Unit 829 B, 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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  /40

  $10,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,514 Sq Ft
  • Condo for Rent

  615 Dream Island Place Unit 201, Longboat Key, FL 34228

  BRING YOUR BOAT, deeded private boat slip that accommodates up to a 60 ft boat INCLUDED! Picturesque Waterview of Sarasota Bay and easy access by boat to the Gulf. Recently renovated with high end appliances, finishes and designer furniture. The Harbor Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boat ramp, kayak launch/storage, 3 tennis/pickle ball courts,

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  615 Dream Island Place Unit 201, Longboat Key, FL 34228
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  /30

  $7,750 Per Month

  • 3 Beds
  • 3 Baths
  • 1,672 Sq Ft
  • Condo for Rent

  5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

  Available Dec 20- April .Steps to the Sand – 3BR/3BA Beachfront Condo with Heated Pool & Spa | Longboat KeyEnjoy the best of beachfront living at 5611 Gulf of Mexico Drive, Unit 105 — a beautifully appointed three-bedroom, three-bath condo located in a boutique community directly on the beach. You’re just steps away from the soft sand and turquoise waters of the Gulf of Mexico.This

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
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  $13,000 Per Month

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

  806 Bayport Way Unit 806, Longboat Key, FL 34228

  Discover a tranquil retreat at 806 Bayport Way, where coastal living meets sophisticated design. This exceptional property is ideally located near a private beach, providing residents with exclusive access to sun-soaked shores and beautiful ocean views.Upon entering, you’ll be greeted by a thoughtfully designed space that emphasizes both comfort and functionality. The kitchen features

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  806 Bayport Way Unit 806, Longboat Key, FL 34228
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  $13,000 Per Month

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

  609 Bayport Way Unit 609, Longboat Key, FL 34228

  ELEGANTLY PRESENTED! This bright and spacious property located just steps away from a private deeded beach is perfect for those who appreciate easy access to sun and sand. This residence boasts modern features and well-thought-out design, making it an ideal retreat for relaxation and comfort.The living area is characterized by an open layout that seamlessly connects to the kitchen,

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  609 Bayport Way Unit 609, Longboat Key, FL 34228
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  $12,500 Per Month

  • 3 Beds
  • 3 Baths
  • 1,744 Sq Ft
  • House for Rent

  2823 Gulf of Mexico Dr, Longboat Key, FL 34228

  The month of November 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.

  Michael Cella CELLA'S REAL ESTATE INC

  2823 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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  $11,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • House for Rent

  3390 Bayou Sound, Longboat Key, FL 34228

  **Two-Month Minimum Rental** Escape to paradise at this beautifully updated Bay Isles retreat on Longboat Key. Nestled among lush tropical landscaping and majestic oak trees, this private island getaway offers the perfect blend of luxury, comfort, and relaxation. Located within the exclusive gated community of Bay Isles, guests enjoy easy access to Longboat Key's world-renowned beaches, marinas,

  Jennifer Le Blanc PRECISE REALTY CORP

  3390 Bayou Sound, Longboat Key, FL 34228
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  /13

  $2,500 Per Month

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

  3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228

  LONGBOAT KEY...Lovely 2 bedroom 2 bath condo directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile. Split floor plan, master suite with a king size bed and the guest room has bunk beds with one single bed and one full size bed. Spacious, open, light and bright. Very well maintained GULF TO BAY complex with lush

  Teresa Ribaudo JENNETTE PROPERTIES INC

  3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
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  $7,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • Condo for Rent

  737 Bayport Way Unit D, Longboat Key, FL 34228

  BAYPORT TENNIS AND RAQUET CLUB has all the amenities including direct GULF Access. This tastefully furnished, one floor, three bedroom, two bathroom condo in the Bayport Beach and Tennis Club offers spacious living areas; Wonderful views of the Gulf of Mexico; and beautiful outdoor space. Large patios with tropical Gulf of Mexico views - perfect for morning coffee and sunset cocktails. Two

  

  Marianne LeBar

  CENTURY 21 ROSEBAY

  737 Bayport Way Unit D, Longboat Key, FL 34228
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  $29,000 Per Month

  • 5 Beds
  • 5.5 Baths
  • 4,858 Sq Ft
  • House for Rent

  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

  591 Putting Green Ln, Longboat Key, FL 34228
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  /28

  $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 RENTAL- Not Available until Nov 2026. 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

  Armando Gonzalez AG REALTY SERVICES LLC

  4420 Exeter Dr Unit 208, Longboat Key, FL 34228
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  $12,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,513 Sq Ft
  • Condo for Rent

  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

  2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228
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  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,399 Sq Ft
  • House for Rent

  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

  957 Spanish Dr N, Longboat Key, FL 34228

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