Longboat Key, FL Homes for Rent with Water View

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  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • Condo for Rent

  Unlisted Address

  SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST

  Jane Hunter JENNETTE PROPERTIES INC

  Unlisted Address
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  $4,800 per month

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

  3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

  VACATION RENTAL!!! AVAILABLE JAN - MARCH 2026! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
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  $5,000 per month

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

  1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228

  AVAILABLE OFF SEASON RENTAL JULY 1, 2025 THROUGH NOVEMBER 30, 2025 AT $5000 A MONTH AND SEASONAL JANUARY 2026 THROUGH APRIL 30, 2026 through MAY 30, 2026 Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
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  $5,000 per month

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

  1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228

  Available 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais,

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
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  $10,000 per month

  • 3 Beds
  • 3 Baths
  • 2,698 Sq Ft
  • Condo for Rent

  1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228

  LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle

  Jane Hunter JENNETTE PROPERTIES INC

  1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
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  $11,550 per month

  • 2 Beds
  • 2 Baths
  • 1,657 Sq Ft
  • House for Rent

  500 Schooner Ln, Longboat Key, FL 34228

  Booked January, May, October, and Dec 2026 through February 2027, There is 2 week minimum stay required. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathrooms. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a

  Jennifer LeBlanc PRECISE REALTY CORP

  500 Schooner Ln, Longboat Key, FL 34228
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  $11,950 per month

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

  2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228

  Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room.Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom,

  Andrey markov ANMARK REALTY LLC

  2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
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  $6,000 per month

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

  1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228

  Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
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  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,839 Sq Ft
  • Condo for Rent

  1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and

  C. Alison Hunter JENNETTE PROPERTIES INC

  1485 Gulf of Mexico Dr Unit 109, 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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  $5,000 per month

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

  750 Bayport Way Unit 750, Longboat Key, FL 34228

  AVAILABLE NOW DUE TO A CANCELLATION, OPEN FEBRUARY, MARCH, APRIL AND BEYOND!!!Seasonal Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat Key Community, featuring one of the most beautiful beach fronts, and Bay front locations on Longboat Key. This well-appointed and tastefully furnished, updated home welcomes you with its understated

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  750 Bayport Way Unit 750, Longboat Key, FL 34228
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  $9,587 per month

  • 3 Beds
  • 2.5 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

  THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean breezes flow through the unit and the peaceful sound of

  Gerald Cunningham KELLER WILLIAMS ON THE WATER S

  4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
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  $9,000 per month

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

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

  Available March 2026. 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

  Shaun Cumston STERLING REALTY

  4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
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  $25,000 per month

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

  455 Longboat Club Rd Unit 1, Longboat Key, FL 34228

  This EXQUISITE 3 bedroom - 3 1⁄2 bath Penthouse has everything you will ever want in a Luxury Beachfront Condo; an open floor plan with plenty of space for living, dining and entertaining and custom appointments throughout. Natural light fills the condo from the moment you enter the foyer and a large skylight is overhead. Floor to ceiling windows frame the 14’ ceiling’s perimeter creating a

  Teresa Ribaudo JENNETTE PROPERTIES INC

  455 Longboat Club Rd Unit 1, Longboat Key, FL 34228
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  $9,000 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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  $7,000 per month

  • 1 Bed
  • 2 Baths
  • 1,244 Sq Ft
  • Condo for Rent

  655 Cedars Ct, Longboat Key, FL 34228

  AVAILABLE. 2026 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay

  Brenda Cozy COLDWELL BANKER REALTY

  655 Cedars Ct, 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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  $10,000 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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  $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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  $11,000 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: 90 day minimum. No damages sustained in Hurricane. Beautiful unit 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

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
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  /22

  $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). 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

  Terri Lindsay LINDSAY LEASING LLC

  3235 Gulf of Mexico Dr Unit 302, 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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  /25

  $12,500 per month

  • 3 Beds
  • 2.5 Baths
  • 2,532 Sq Ft
  • House for Rent

  2319 Harbour Oaks Dr, Longboat Key, FL 34228

  SEASONAL: All three baths have been 100% renovated. Just gorgeous! Photos to come. Harbour Oaks is resort-style living positioned behind the guarded Harbourside gates of Bay Isles. This updated 3 bedroom, 2 1/2 bath home overlooks the Longboat Key Club golf course! With over 2,500 sq. feet of living space, pool, private Beach Club access and sought after Southern Longboat address this is the

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  2319 Harbour Oaks Dr, 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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