Longboat Key, FL Homes for Rent

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  $3,300 per month

  • 1 Bed
  • 1 Bath
  • 798 Sq Ft
  • Apartment for Rent

  3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228

  Stunning Bayfront and Marina views, this is a rare opportunity for a 1 bedroom, 1 bath, FURNISHED in a 55 + community on Longboat key . This is a beautifully designed and outfitted villa in the community of Twin Shores-located Mid Key(Close to both St. Armand's Circle and Anna Maria Island). Not only are you Sitting within Steps to Panoramic Views of the Bay, you have private DEEDED beach access

  Joseph Patoray FINE PROPERTIES

  3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228
• Explore Longboat Key

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  /100

  $40,000 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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  $10,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  700 Lands End Dr Unit 2, Longboat Key, FL 34228

  Experience refined coastal living in this fully furnished 4-bedroom, 4-bath residence ideally positioned within a private, gated enclave on Longboat Key, tucked beneath majestic banyan trees for exceptional privacy and tranquility. Designed to embrace Florida’s indoor-outdoor lifestyle, the home welcomes you through a stunning atrium entry, where natural light filters through lush tropical

  Jenn Spinelli THE AGENCY ORLANDO

  700 Lands End Dr Unit 2, Longboat Key, FL 34228
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  $70,000 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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  $3,500 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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  /18

  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Condo for Rent

  601 Longboat Club Rd, Longboat Key, FL 34228

  Welcome to your new home on Longboat Key! This charming property offers the perfect blend of comfort and convenience in one of Florida's most desirable locations. Enjoy the tranquil surroundings while being just a short drive from Sarasota's vibrant dining scene and essential amenities.Key property features include central heating and cooling, air conditioning, and ceiling fans to ensure

  601 Longboat Club Rd, Longboat Key, FL 34228
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  $10,000 per month

  • 3 Beds
  • 5 Baths
  • 2,908 Sq Ft
  • House for Rent

  3111 Bayou Sound, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION. BEAUTIFUL TURNKEY FURNISHED SINGLE FAMILY HOME available in the sought after community of Bay Isles is available to rent. This lovely light, bright 3 bedroom plus 3 bathroom, two half bathroom home boasts 2,908 square feet, double primary bedrooms, living room/dining room combination, loft/den space and much much more. The home has been fully painted and newly

  C. Alison Hunter JENNETTE PROPERTIES INC

  3111 Bayou Sound, Longboat Key, FL 34228
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  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,651 Sq Ft
  • Condo for Rent

  2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228

  Stunning Gulf-Front Condo with Breathtaking Views at Islands West! Experience the epitome of coastal living in this exquisite 2-bedroom, 2-bathroom condominium on the 12th floor of Islands West, where full Gulf views become a part of your daily life. This beautifully furnished unit is not just a rental; it’s a lifestyle choice that offers you the chance to wake up to the soothing sounds of waves

  Jane Hunter JENNETTE PROPERTIES INC

  2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228
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  /20

  $9,677 per month

  • 6 Beds
  • 5.5 Baths
  • 4,671 Sq Ft
  • Condo for Rent

  614 Norton St Unit ID1363943P, Longboat Key, FL 34228

  Experience coastal luxury in this exceptional residence on Longboat Key. Nestled along a canal with direct access to the Gulf, this expansive home is a dream for boating enthusiasts and those seeking a serene, upscale lifestyle. Feel at home in this spacious property.This property is currently unfurnished. A potential renter would need to provide their own furniture. The gourmet kitchen is

  614 Norton St Unit ID1363943P, Longboat Key, FL 34228
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  $3,950 per month

  • 1 Bed
  • 1.5 Baths
  • 761 Sq Ft
  • Condo for Rent

  3802 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228

  Seasonal turn-key furnished rental on Longboat Key available January 1, 2026 - minimum rental period is 3 months per condo association requirements. Located in Beach Harbor Club, mid Longboat Key on Buttonwood Harbor. I mile north of Publix, CVS and Post Office located at Bay Isles. Boat Marina and dock along the Bayfront. 100 steps from the Private Beach! 1 Bedroom, 1 1/2 Baths with a view

  3802 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228
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  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Condo for Rent

  601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228

  Your winter on the Gulf begins here. This is a rare opportunity to enjoy direct Gulf front living in a fully furnished seasonal residence, available January through March 2026. Tucked behind the private gates of Longboat Key, this premium condo blends the ease of coastal condo living with the comfort of generous, well-designed interiors. Mornings begin with soft sunrise views over the golf course

  

  Irma Scherer

  COMPASS FLORIDA LLC

  (941) 401-1756

  601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228
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  /59

  $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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  /15

  $7,500 per month

  • 2 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • Condo for Rent

  3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228

  Charming turnkey-furnished 2BR/2BA condo on the beautiful island of Longboat Key. Enjoy magnificent ocean views and spectacular sunsets from the private balcony. This well-appointed unit offers an ideal winter escape with comfortable living spaces and a serene coastal atmosphere. Building amenities include an in-ground heated pool, docking station, fish cleaning station, kayak/paddleboard rack,

  Juliana Brando Perez BROKER & BAKER INTERNATIONAL REALTY

  3240 Gulf of Mexico Dr Unit B402, Longboat Key, FL 34228
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  $20,000 per month

  • 4 Beds
  • 4 Baths
  • 2,943 Sq Ft
  • Condo for Rent

  4473 Gulf of Mexico Dr, Longboat Key, FL 34228

  Experience Gulf-front living at its finest on the pristine shores of Longboat Key. This exceptional 4-bedroom, 4-bathroom coastal retreat spans nearly 3,000 sq. ft. and sits on over half an acre of direct beachfront property. Thoughtfully furnished with a mix of modern and timeless design, this two-story residence offers stunning water views from almost every room. ( Available December 1st, 3

  

  Curtis Andrews

  BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  (941) 294-4305

  4473 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $2,999 per month

  • 2 Beds
  • 2 Baths
  • Condo for Rent

  3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228

  LONGBOAT ARMS - This beautiful and professionally decorated apartment is ready to enjoy good times with zero afford. Ideal for work from home people, and those who value the benefit of have a prime space in front of the most panoramic surroundings. Live in the place where people takes vacation!

  Valeria Fucaraccio Benesch Brokers, LLC

  3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228
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  /26

  $9,800 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  640 Broadway St, Longboat Key, FL 34228

  Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024

  Christina Vescovo LPT REALTY, LLC

  640 Broadway St, Longboat Key, FL 34228
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  $14,400 per month

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  701 Broadway St, Longboat Key, FL 34228

  Completely reimagined 1920s historic bungalow, originally the Longboat Key Post Office, located just two blocks from Whitney Beach and one block from Sarasota Bay and public boat ramp access. This charming single-story residence is a meticulous rebuild with an open-concept great room featuring high ceilings, abundant natural light, and a gourmet kitchen equipped with stainless steel appliances

  Christina Vescovo LPT REALTY, LLC

  701 Broadway St, Longboat Key, FL 34228
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  /23

  $5,000 per month

  • 1 Bed
  • 1.5 Baths
  • 725 Sq Ft
  • Condo for Rent

  4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228

  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,

  David Gardner PINEBROOK IRONWOOD REALTY

  4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228
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  $4,900 per month

  • 2 Beds
  • 2 Baths
  • 1,046 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228

  Longboat Key vacation rental! You will love this wonderfully updated and tastefully furnished two-bedroom, two-bath third-floor condominium at the Beach Harbor Club. Located mid-key, this is a great resort-style community with deeded beach access just across the Gulf of Mexico, a beautiful heated community pool, access to the Bay for fishing and kayaking, and community grills and shuffleboard!

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
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  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,085 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228

  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

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3808 Gulf of Mexico Dr Unit 211, 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 ($4,600/MONTH). LEASE -3 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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  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Condo for Rent

  540 Neptune Ave Unit 7, Longboat Key, FL 34228

  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

  Pamala Casey CASEY REALTY CORPORATION

  540 Neptune Ave Unit 7, Longboat Key, FL 34228
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  $25,000 per month

  • 1 Bed
  • 1.5 Baths
  • 1,721 Sq Ft
  • Condo for Rent

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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  $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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  $25,000 per month

  • 3 Beds
  • 3 Baths
  • 3,230 Sq Ft
  • House for Rent

  690 Old Compass Rd, Longboat Key, FL 34228

  Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size

  Teresa Ribaudo JENNETTE PROPERTIES INC

  690 Old Compass Rd, Longboat Key, FL 34228
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  $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

  (941) 239-2327

  829 Bayport Way Unit 829 B, Longboat Key, FL 34228
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  $19,975 per month

  • 4 Beds
  • 4 Baths
  • 4,236 Sq Ft
  • House for Rent

  5801 Gulf of Mexico Dr, Longboat Key, FL 34228

  Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. 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

  Kevin Hase KEYRENTER SARASOTA PROPERTY MANAGEMENT

  5801 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Condo for Rent

  4360 Chatham Dr Unit 108, Longboat Key, FL 34228

  Newly renovated and elegantly designed 2-bedroom, 2-bathroom condo in the highly desirable Longboat Harbour Condominiums, located just 600 feet from the shore and a 3-minute walk to the beach. This fully furnished ground floor unit offers a modern open layout with scenic views, access to Sarasota Bay, and resort-style community amenities including four swimming pools (one located right behind the

  Jorge Perez ROI AVE LLC

  4360 Chatham Dr Unit 108, Longboat Key, FL 34228
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  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • House for Rent

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228

  BONUS FREE RENTAL DAYS! AVAILABLE 12/26/2025-1/31/2026 ONLY! Stay through New Years Eve for Free as a bonus. Fully Booked for the remainder of the 2026 season. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2025! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets

  Debby McCaig COLDWELL BANKER REALTY

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $9,000 per month

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

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

  Available January, February and March 2026 due to cancellation. Picturesque Water view of Sarasota Bay . The Harbour Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boatramp, kayak launch/storage, 3 tennis courts, covered parking and 400' of boat slips and bayfront. Features include over 1500 sq ft of livingspace in this end unit, high ceilings, Waterview

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  (941) 279-2178

  615 Dream Island Place Unit 201, Longboat Key, FL 34228
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  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Condo for Rent

  3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228

  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

  Brenda Cozy COLDWELL BANKER REALTY

  3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228
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  $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

  (941) 207-4034

  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

  (941) 390-2885

  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

  (941) 214-7905

  609 Bayport Way Unit 609, Longboat Key, FL 34228
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  $6,050 per month

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

  618 Bayport Way Unit 618, Longboat Key, FL 34228

  Escape to paradise with a stay in this newly renovated 2-bedroom, 2-bath second floor condominium at Bayport Beach & Tennis Club on Longboat Key. Perfectly positioned for your dream beach getaway, this condo blends comfort, style and unbeatable amenities. Bright, modern, and welcoming, this condo has been thoughtfully updated with all the comforts of home, including a king-size bed in the primary

  Alzira Meierling KELLER WILLIAMS ON THE WATER S

  618 Bayport Way Unit 618, Longboat Key, FL 34228
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  $10,000 per month

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

  2823 Gulf of Mexico Dr, Longboat Key, FL 34228

  Available beginning June 1st, 2026. 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 home invites you to experience the ultimate beachfront lifestyle. Relax under the sun, unwind to the sound of

  Michael Cella CELLA'S REAL ESTATE INC

  2823 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /16

  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,941 Sq Ft
  • Condo for Rent

  100 Sands Point Rd Unit 223, Longboat Key, FL 34228

  Location! Location! Location for Winter 2026 Rental Season!Gulf-front condominium complex “Sands Point” sits on the southernmost tip of Longboat Key. This location allows you to save time in traffic. Nestled adjacent to the iconic Longboat Key Resort, this Mid-Century modern 77-unit complex boosts impeccable views, gorgeous landscaping, a full-time maintenance crew and your own covered

  Diane Smith KELLER WILLIAMS ON THE WATER S

  100 Sands Point Rd Unit 223, 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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  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft
  • Condo for Rent

  1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228

  Available for 2026 and 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

  Jenna Genovese KELLER WILLIAMS ON THE WATER S

  1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
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  $11,000 per month

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

  3390 Bayou Sound, Longboat Key, FL 34228

  **This is a 2 month minimum vacation rental**Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou section of Bay Isles, this

  Jennifer LeBlanc PRECISE REALTY CORP

  3390 Bayou Sound, Longboat Key, FL 34228

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