$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
601 Longboat Club Rd Unit 902S, Longboat Key, FL 34228
89
Condos for Rent in Longboat Key, FL with 2-Bedrooms
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$4,500 Per Month
- 2 Beds
- 2 Baths
- 1,560 Sq Ft
- Condo for Rent
601 Longboat Club Rd Unit 1004S, Longboat Key, FL 34228
601 Longboat Club Rd Unit 1004S, Longboat Key, FL 34228Property Id: 2517125This beachfront retreat offers breathtaking panoramic views from its Gulf-front and east-facing balconies, encompassing Lido and Siesta Keys, Longboat Key, and the Sarasota skyline. Inside, a sunlit living room with large windows, a dining area with ocean views, and an updated kitchen with stainless steel appliances and an in-unit washer/dryer provide comfortable
(629) 207-6561
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$11,500 Per Month
- 2 Beds
- 2 Baths
- 1,531 Sq Ft
- Condo for Rent
724 Bayport Way Unit 724, Longboat Key, FL 34228
724 Bayport Way Unit 724, Longboat Key, FL 34228 -
$9,026
Total Monthly Price
- 2 Beds
- 2 Baths
- Condo for Rent
1109 Gulf of Mexico Dr Unit SI ID1386020P, Longboat Key, FL 34228
1109 Gulf of Mexico Dr Unit SI ID1386020P, Longboat Key, FL 34228The advertised rate of $9,027/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 29, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
(941) 299-7106
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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
806 Bayport Way Unit 806, Longboat Key, FL 34228 -
$10,100 Per Month
- 2 Beds
- 2 Baths
- 1,393 Sq Ft
- Condo for Rent
4805 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
4805 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228Property Id: 2484818Available December 1st, 2026! THE OCEAN IS YOUR BACKYARD! Minutes away from world-class golfing, boating, tennis, dining, and shopping. This exclusive, private, and serene Gulf Coast Condominium unit has been a traveler's dream for so many years now. The Property offers steps to the Gulf Coast's richest Beaches. We offer a fully stocked outdoor shed with beach chairs,
(941) 207-7562
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$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
817 Bayport Way Unit 817, Longboat Key, FL 34228
817 Bayport Way Unit 817, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,426 Sq Ft
- Condo for Rent
741 Bayport Way Unit 741, Longboat Key, FL 34228
741 Bayport Way Unit 741, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
833 Bayport Way Unit 833, Longboat Key, FL 34228
833 Bayport Way Unit 833, Longboat Key, FL 34228 -
$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
829 Bayport Way Unit 829 B, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,346 Sq Ft
- Condo for Rent
5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
522 Bayport Way Unit 522, Longboat Key, FL 34228
522 Bayport Way Unit 522, Longboat Key, FL 34228 -
$10,500 Per Month
- 2 Beds
- 2 Baths
- 1,513 Sq Ft
- Condo for Rent
2425 Gulf of Mexico Dr Unit 7F, Longboat Key, FL 34228
2425 Gulf of Mexico Dr Unit 7F, Longboat Key, FL 34228 -
$11,000 Per Month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
739 Bayport Way Unit 739, Longboat Key, FL 34228
739 Bayport Way Unit 739, Longboat Key, FL 34228 -
$10,000 Per Month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
832 Bayport Way Unit 832, Longboat Key, FL 34228
832 Bayport Way Unit 832, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
830 Bayport Way Unit 830, Longboat Key, FL 34228
830 Bayport Way Unit 830, Longboat Key, FL 34228 -
$13,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
609 Bayport Way Unit 609, Longboat Key, FL 34228
609 Bayport Way Unit 609, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
805 Bayport Way Unit 805, Longboat Key, FL 34228
805 Bayport Way Unit 805, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
720 Bayport Way Unit 720, Longboat Key, FL 34228
720 Bayport Way Unit 720, Longboat Key, FL 34228 -
$12,000 Per Month
- 2 Beds
- 2 Baths
- 1,560 Sq Ft
- Condo for Rent
603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228
603 Longboat Club Rd Unit 204N, Longboat Key, FL 34228 -
$10,000 Per Month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
519 Bayport Way Unit 519, Longboat Key, FL 34228
519 Bayport Way Unit 519, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
517 Bayport Way Unit 517, Longboat Key, FL 34228
517 Bayport Way Unit 517, Longboat Key, FL 34228 -
$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
615 Dream Island Place Unit 201, Longboat Key, FL 34228 -
$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
3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228AVAILABLE 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
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$12,000 Per Month
- 2 Beds
- 2 Baths
- 1,470 Sq Ft
- Seaside Serenity: Luxurious Gulf-Front Retreat on Southern Longboat Key
2425 Gulf of Mexico Dr, Longboat Key, FL 34228
2425 Gulf of Mexico Dr, Longboat Key, FL 34228Escape 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, two-bath
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$7,000 Per Month
- 2 Beds
- 2 Baths
- 1,133 Sq Ft
- Condo for Rent
3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You
Andy Moore GULF COAST REALTY & MANAGEMENT
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$3,500 Per Month
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
- Condo for Rent
4330 Falmouth Dr, Longboat Key, FL 34228
4330 Falmouth Dr, Longboat Key, FL 34228Longboat Key Beach and Bay Access.2 Bedroom 2 Bathroom First Floor condo in a gated community with tons of amenities.✅ Deepwater channel with docks and slips available up to 34' (on waitlist)✅ Amazing water views & breezes✅ Private deeded beach access (private building on beach with showers + bathrooms, benches and tables!)✅ 4 Pools, clubhouse, gym, sauna,
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$5,500 Per Month
- 2 Beds
- 2 Baths
- 1,411 Sq Ft
- Condo for Rent
4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$5,200 Per Month
- 2 Beds
- 2 Baths
- 1,370 Sq Ft
- Amazing 2BR Condo in Longboat Key
807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress.Step inside to find a well-appointed kitchen featuring:- Electric range and stove top-
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$4,000 Per Month
- 2 Beds
- 2 Baths
- 1,106 Sq Ft
- Condo for Rent
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease.
Janette Schafer COLDWELL BANKER REALTY
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$5,950 Per Month
- 2 Beds
- 2 Baths
- 2,369 Sq Ft
- Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views Remodele...
2013 Harbour Links Dr, Longboat Key, FL 34228
2013 Harbour Links Dr, Longboat Key, FL 34228Step 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 fully furnished and ready for immediate enjoyment, this home is perfectly positioned on a quiet cul-de-sac with extra guest parking, combining privacy, luxury, and
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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
775 Longboat Club Rd Unit 405, Longboat Key, FL 34228AVAILABLE 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
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$5,500 Per Month
- 2 Beds
- 2 Baths
- 1,561 Sq Ft
- Condo for Rent
5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228Available starting July 15, 2026! 60 Day Minimum Lease. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches are perfectly complemented by the beautifully redesigned interior and thoughtfully updated floor plan. The
Scott Nold TNG PROPERTY MANAGEMENT
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$6,500 Per Month
- 2 Beds
- 2 Baths
- 1,106 Sq Ft
- Condo for Rent
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease.
John Schafer, V COLDWELL BANKER REALTY
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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
1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228Rented 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.
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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
3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228VACATION 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
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$14,000 Per Month
- 2 Beds
- 2 Baths
- 1,598 Sq Ft
- Condo for Rent
1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$7,000 Per Month
- 2 Beds
- 2 Baths
- 1,192 Sq Ft
- Condo for Rent
1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
1930 Harbourside Dr Unit 134, Longboat Key, FL 34228GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought-after Bay Isles community. The spacious Kitchen had been updated along with the both baths, with Quartz counter-tops and new cabinetry, the Primary suite offers a King bed, views of the bay and the Primary bath has dual sinks, new vanity, new
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
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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
2425 Gulf of Mexico Dr Unit 11F, Longboat Key, FL 34228ELEGANT 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
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$2,995 Per Month
- 2 Beds
- 2 Baths
- 1,106 Sq Ft
- Condo for Rent
3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228
3330 Gulf of Mexico Dr Unit 202-D, Longboat Key, FL 34228BAYSIDE CONDO WITH FULL BAY VIEWS – AVAILABLE FOR ANNUAL RENTAL Experience the best of Longboat Key living in this beautifully furnished 2-bedroom, 2-bath second-floor condo (with elevator access) located in the desirable Longboat Arms community. This turnkey residence offers stunning, unobstructed bay views and a well-designed open floor plan. The kitchen flows seamlessly into the dining and
Heidi Thompson STRINGER MANAGEMENT INC
Showing Results 1 - 40, Page 1 of 3
Rental Home Trends in Longboat Key, FL
There are currently 89 condos available for rent in Longboat Key, FL. The median rent is $7,000 per month, with 1-bedroom condos renting at $5,500, 2-bedroom condos at $6,400 and 3-bedroom condos at $9,000.
Rental Home Trends
Number of 2 Bedroom Condos for Rent
89
Median 2 Bedroom Condo Rent
$6,400
Median 2 Bedroom Townhouse Rent
$13,000
Condos for Rent by Price in Longboat Key
Rentals in Longboat Key
Condos for Rent by Bedrooms in Longboat Key
More About Living in Longboat Key
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