2-Bedroom Homes for Rent in Longboat Key, FL

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  $5,000 per month

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

  4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228

  Experience unparalleled Gulf-front living in this beautifully renovated 2-bedroom, 2-bathroom condo at Tiffany Plaza. Spanning 1,336 sq ft, this fully furnished residence boasts luxury vinyl flooring, a modern kitchen with marble countertops, and a spacious lanai offering breathtaking views of the turquoise waters of the Gulf of Mexico .The master suite features a king-sized bed, while the guest

  Shaun Cumston STERLING REALTY

  4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
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  $5,835 per month

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

  3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228

  Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Welcome to Seaside Dream! Beautifully furnished and decorated, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. If you enjoy resort-style living, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will

  Andy Moore GULF COAST REALTY & MANAGEMENT

  3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
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  $7,500 per month

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Condo for Rent

  4540 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

  OPEN FOR SEASON 2026. Also available off season @$3300 per month. Rarely available tranquil 2 bed/2 bath corner unit condo with full bay views at desirable Windward Bay! This light and bright condo is the perfect place to spend your season in the sun in a quiet community directly across the street from the sparkling Gulf of Mexico waters and white sandy beaches of Longboat Key. Walk or bike along

  Bridget Gennett JENNETTE PROPERTIES INC

  4540 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
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  $8,000 per month

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

  2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228

  LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen.

  Teresa Ribaudo JENNETTE PROPERTIES INC

  2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
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  $9,000 per month

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

  775 Longboat Club Rd Unit 405, Longboat Key, FL 34228

  AVAILABLE 2026 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay views. This 1600 sq. ft. two bedroom two bath condo is located directly on the sugary beach of Longboat Key with lounge chairs and umbrellas provided. Wrap around balcony with partial Gulf of Mexico and Longboat Key Club golf views. Washer/dryer in the unit, pool, fitness

  Brenda Cozy COLDWELL BANKER REALTY

  775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
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  $11,000 per month

  • 2 Beds
  • 2 Baths
  • 1,642 Sq Ft
  • Condo for Rent

  1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

  Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. Relax on the lanai and take in the beautiful gulf views at sunset. The

  Margaret Young JENNETTE PROPERTIES, INC.

  1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
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  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,027 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228

  Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Seasonal, furnished, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. This ground floor unit is centrally located and minutes away from urban activities with in-unit washer and dryer. The master bedroom features a queen bed, walk-in closet and ensuite

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  3806 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
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  $7,200 per month

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

  4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

  This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views. This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can’t be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
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  $6,000 per month

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

  5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

  Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  5393 Gulf of Mexico Dr Unit 208, 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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  $11,900 per month

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

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

  SEASONAL; NOW AVAILABLE Jan - Mar 2026!!! Call now, won't last! From floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is beautifully

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
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  $8,000 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. 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 sliding glass doors, new laminate flooring and carpet, new kitchen appliances, three flat screen TVs with HD boxes

  Terri Lindsay LINDSAY LEASING LLC

  3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,273 Sq Ft
  • Condo for Rent

  2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228

  LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with

  Teresa Ribaudo JENNETTE PROPERTIES INC

  2109 Gulf of Mexico Dr Unit 1402, 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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