Newest Homes for Rent in Longboat Key, FL

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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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  $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 the 2027 Season! Completely 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 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including

  Debby McCaig COLDWELL BANKER REALTY

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $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

  (941) 279-2178

  615 Dream Island Place Unit 201, Longboat Key, FL 34228
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  $7,100 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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  $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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  $10,000 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 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

  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****Availble for all of 2027** 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

  Jennifer LeBlanc PRECISE REALTY CORP

  3390 Bayou Sound, Longboat Key, FL 34228
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  $3,000 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

  ROSEBAY INTERNATIONAL REALTY, INC

  (941) 946-6594

  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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  $5,000 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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  $10,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,882 Sq Ft
  • House for Rent

  825 Tarawitt Dr, Longboat Key, FL 34228

  Welcome to your new Beach House Sanctuary!! Completely renovated Island home located 4 houses off Tarawitt point on a large 90x125ft lot! Coveted lifestyle and location on a deep water canal in the heart of Longboat Key! This waterfront home has 125ft of seawall docking for a boat up to 30 ft. plus a jet ski lift and room for other water toys. Catch bait and start fishing in less than 30 minutes!

  Ian Greenberg BRISTA REALTY LLC

  825 Tarawitt Dr, 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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  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 1,278 Sq Ft
  • Condo for Rent

  534 Sutton Place, Longboat Key, FL 34228

  Available for annual lease starting 5/1/2026! GULF BEACH and BAY ACCESS! This single story end unit is the perfect place to escape the cold winter months and experience Island living on Longboat Key. This 2 bedroom, 2 bathroom condo has a spacious living and dining room combo, which opens to a bright and airy Florida room, perfect for relaxing or entertaining. The Florida room is fully enclosed,

  Tanner Frey KELLER WILLIAMS ON THE WATER S

  534 Sutton Place, Longboat Key, FL 34228
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  $8,000 per month

  • 3 Beds
  • 3 Baths
  • 2,487 Sq Ft
  • House for Rent

  2377 Harbour Oaks Dr, Longboat Key, FL 34228

  AVAILABLE - APRIL 2026 - ANNUAL RENTAL - Welcome home! Enjoy the serenity of this 3 bed, 3 bath, 2 car garage residence, located in Harbour Oaks within the gated community of Bay Isles in the heart of Longboat Key. This tastefully appointed home with open concept floor plan features vaulted ceilings and skylights which create an abundance of natural light throughout the home. The amazing gourmet

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 336-7031

  2377 Harbour Oaks Dr, Longboat Key, FL 34228
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  $11,000 per month

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

  1000 Longboat Club Rd, Longboat Key, FL 34228

  Welcome to your elevated coastal retreat on Longboat Key, located behind the gate of the prestigious Longboat Key Club. Available annually at $9,000/month or seasonally from November through April at $11,500/month, this fully renovated upper-floor residence offers refined living with sweeping Gulf and Bay views from two private balconies. Set within one of the island’s most exclusive beachfront

  Jenna Genovese KELLER WILLIAMS ON THE WATER S

  1000 Longboat Club Rd, Longboat Key, FL 34228
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  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,401 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228

  Available for season 2026! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by

  Maureen Plichta STRINGER MANAGEMENT INC

  3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
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  $10,000 per month

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft
  • House for Rent

  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

  6979 Longboat Dr S, Longboat Key, FL 34228
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  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • Condo for Rent

  724 Bayport Way Unit 724, Longboat Key, FL 34228

  STUNNING GULF VIEWS! Enjoy the sparkling glimmer of the morning waters and picturesque sunsets from almost every room. This meticulously maintained 2 bedroom, 2 bathroom furnished condominium features an open concept floor plan with expansive Living/Dining/Kitchen area. The generous size primary bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 415-6156

  724 Bayport Way Unit 724, Longboat Key, FL 34228
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  $7,500 per month

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228

  Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
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  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Townhouse for Rent

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228

  Turnkey Townhouse on Longboat Key – Resort-Style Living! Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy. Enjoy private beach access to the stunning Gulf of Mexico, take a dip

  Victoria Campbell LPT REALTY LLC

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228
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  $17,500 per month

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft
  • House for Rent

  613 Buttonwood Dr, Longboat Key, FL 34228

  Available for season 2026 This home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Open floor concept with formal dining. The kitchen as the heart of the home is expertly appointed with everything you will need for your home cooked meals. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step into

  Jennifer LeBlanc PRECISE REALTY CORP

  613 Buttonwood Dr, Longboat Key, FL 34228
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  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Condo for Rent

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228

  Turnkey Townhouse on Longboat Key – Resort-Style Living!Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy.Enjoy private beach access to the stunning Gulf of Mexico, take

  Victoria Campbell LPT REALTY LLC

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
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  $15,000 per month

  • 2 Beds
  • 2.5 Baths
  • 2,135 Sq Ft
  • Condo for Rent

  1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

  Gorgeous gulf front vacation rental! Be the first to lease this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the open floor plan with a

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
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  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  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

  Daniel Goldman COMPASS FLORIDA LLC

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  $10,000 total monthly price

  • 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

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
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  $6,900 per month

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  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

  535 Forest Way, Longboat Key, FL 34228
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  $25,000 per month

  • 1 Bed
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228

  Welcome Serenity Oasis, your paradise at The Residences at the St.Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat. The expansive living room is

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
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  $7,800 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Condo for Rent

  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

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  $7,000 per month

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

  2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228

  RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach! Start living the island lifestyle in this beautifully updated, furnished 2-bedroom, 2-bath condo at the Islander Club on South Longboat Key! This turnkey rental is ready for immediate enjoyment—just bring your suitcase. Enjoy a bright, open layout with floor-to-ceiling hurricane

  Michele Conn PREFERRED SHORE LLC

  2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
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  $6,500 per month

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

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228

  LONGBOAT KEY "SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE. 2 MONTH MINIMUM REQUIRED. SEASON 2027 JAN-APRIL $6,500/MONTH. BOOKED FOR FEB-APRIL 2026. 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

  Chrissie Cummings JENNETTE PROPERTIES INC

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
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  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,133 Sq Ft
  • Condo for Rent

  3802 Gulf of Mexico Dr Unit 207, 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

  3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
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  $3,000 total monthly price

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

  4340 Falmouth Dr Unit 201, Longboat Key, FL 34228

  2 Bd/2 Bath on Sarasota Bay Across from Gulf of Mexico - Unit available May 1, 2026 - December 12, 2026. Prefer 6+ Month RentalsBeautiful corner unit condo with an abundance of win.dows located between Sarasota Bay and across the street from the deeded Gulf of Mexico beach. The gated community complex has every amenity imaginable - four pools, tennis/pickleball court, shuffleboard, kayak

  4340 Falmouth Dr Unit 201, 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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