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Condos for Rent in Longboat Key, FL with 2-Bedrooms

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  • 4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
    4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
    4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
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    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,314 Sq Ft
    • Condo for Rent

    4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228

    VACATION ALL YEAR ROUND! AVAILABLE FOR AN ANNUAL LEASE! Beautifully updated Gulf-front condo with stunning water views and refined coastal finishes. The chef’s kitchen offers high-end appliances, a center island with beverage chiller, and elegant details throughout. The living area opens to a large lanai with unobstructed Gulf views. The primary suite features a king bed, large flat-screen TV,

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    /66

    $12,000 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
  • 1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    /24

    $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 05/01/2026 through 12/30/2026 FOR $5000. LEASED SEASON JAN, 2026 THROUGH MARCH, 2027. 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

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
    /69

    $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
  • 4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
    /42

    $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
  • 1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
    /46

    $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
  • 3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
    /39

    $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 2027! 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
  • 1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    /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
  • 4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    /34

    $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
  • 4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
    /39

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228

    Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    /55

    $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
  • 1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 1005, 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 available now through 2027!! You will love 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

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
  • 2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    /63

    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,463 Sq Ft
    • Condo for Rent

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228

    Booked Dec 1st 2026-March 31st 2027. **Beachfront Bliss with Stunning Gulf Views** Experience coastal living at its finest in this beautifully updated beachfront condo. The bright, open living area flows seamlessly onto a spacious private balcony where you can enjoy panoramic Gulf views, sea breezes, and unforgettable sunsets. The renovated kitchen features sleek countertops, stainless steel

    Jennifer Le Blanc PRECISE REALTY CORP

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /46

    $11,500 Per Month

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

    Unlisted Address

    Experience the best of Longboat Key living in this beautifully updated, turnkey furnished 2-bedroom, 2-bath residence located behind the gates of the sought after Longboat Key Club. This light-filled condominium features brand-new countertops, new appliances, and an open, inviting floor plan designed for effortless coastal living. Enjoy partial Gulf views and beautiful bay vistas from two private

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    Unlisted Address
  • 1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
    /35

    $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
  • 3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
    /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
  • 4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
    /47

    $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
  • 1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    /72

    $11,000 Per Month

    • 2 Beds
    • 2.5 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 and a half 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

    C. Alison Hunter JENNETTE PROPERTIES INC

    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    /32

    $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
  • 6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    /50

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,367 Sq Ft
    • Condo for Rent

    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228

    Available September 1, 2026 through January 31, 2027 with a one-month minimum rental. Experience the best of Longboat Key in this beautifully renovated and newly furnished 2-bedroom, 2-bathroom condo. Simply pack your flip-flops and beachwear and settle into the relaxed island lifestyle. Residents enjoy an impressive array of resort-style amenities, including two heated swimming pools, tennis and

    Kelly Baldwin COLDWELL BANKER REALTY

    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    /31

    $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 AND SEASONAL. RENTAL MAY 1, 2026 THROUGH November 30, 2026 AT $5000 A MONTH AND SEASONAL JANUARY 1, 2027 THROUGH APRIL 30, 2027 for $7500. 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

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
  • 5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    /28

    $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
  • 750 Bayport Way Unit 750, Longboat Key, FL 34228
    750 Bayport Way Unit 750, Longboat Key, FL 34228
    750 Bayport Way Unit 750, Longboat Key, FL 34228
    /45

    $8,500 Per Month

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

    750 Bayport Way Unit 750, Longboat Key, FL 34228

    OPEN FOR 2027 SEASON! 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 elegance. Everything inside is new, from the flooring to the kitchen

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    750 Bayport Way Unit 750, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /67

    $13,500 Per Month

    • 2 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    **Prime Location – Luxurious Waterfront Living at Promenade, Longboat Key**This absolutely gorgeous condo is located in the prestigious Promenade on Longboat Key, offering breathtaking water views from every room. The residence features 2 bedrooms plus a den and 2 bathrooms. The spacious master suite includes a king-size bed and an elegant en-suite bathroom with a separate bathtub, walk-in

    Elsie Salazar BERKSHIRE HATHAWAY HOMESERVICE

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /34

    $2,500 Per Month

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

    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    2-bed, 2-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 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

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
  • 2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    /30

    $8,721 Per Month

    • 2 Beds
    • 2 Baths
    • 1,461 Sq Ft
    • Condo for Rent

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228

    short stories AVAILABLE NOW... Stunning 2 bedroom 2 bath Longboat Key Gulf front condo with direct sweeping view of the Gulf of Mexico. Every evening enjoy breathtaking sunsets on your private balcony. Start your day with a leisurely stroll on the soft sand beach or take a refreshing dip in the pool. This condo is beautifully furnished and professionally decorated. King size bed in both bedrooms.

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
    /12

    $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
  • 3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    /25

    $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
  • 450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
    /32

    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,301 Sq Ft
    • Condo for Rent

    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228

    Annual furnished rental: Discover the ultimate island lifestyle in this comfortably furnished 2-bedroom, 2 bath, unit located in the highly sought-after community of Bay Harbour on the southern end of Longboat Key. Just minutes from St. Armands Circle, downtown Sarasota, restaurants, shopping, county tennis and pickleball courts, walking trails, parks and of course – Longboat Key public beach

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
  • 615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    /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
  • 2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
    /25

    $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
  • 1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    /32

    $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
  • 3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    /66

    $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
  • 1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    /77

    $3,750 Per Month

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

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228

    AVAILABLE IMMEDIATELY PENDING HOA APPROVAL! 2 MONTH MINIMUM! BOOKED FOR JAN-MARCH 2027 SEASON! LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the

    Brigette Marcus NEXTHOME EXCELLENCE

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    /30

    $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
  • 775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    /36

    $11,000 Per Month

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

    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228

    AVAILABLE DEC. '26 THROUGH FEB.'27. Beautiful 9th floor, 1600 sq. ft. 2 bedroom 2 bath at the sort after Beaches condominium which is within the gates of the Longboat Key Club. Updated kitchen and bathrooms. Fabulous bay, and Longboat Key Club golf views. Wrap around balcony with partial Gulf view. Washer/dryer in the unit, pool, fitness center and tennis courts plus 24 hr. Concierge and garage

    Brenda Cozy COLDWELL BANKER REALTY

    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    /33

    $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
  • 540 Neptune Ave Unit 7, Longboat Key, FL 34228
    540 Neptune Ave Unit 7, Longboat Key, FL 34228
    540 Neptune Ave Unit 7, Longboat Key, FL 34228
    /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
  • 5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /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
  • 2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    /72

    $6,950 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,369 Sq Ft
    • Condo for Rent

    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228

    Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered

    Andrew Clark SECURE DOOR PROPERTY MANAGEMENT

    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228

Showing Results 41 - 80, Page 2 of 3

Florida Sarasota County

2-Bedroom Condos for Rent in Longboat Key, FL

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