$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
109
Longboat Key, FL Homes for Rent with Water View
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$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 -
$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 -
$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 -
$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 -
$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 -
$13,500 Per Month
- 3 Beds
- 2 Baths
- 2,134 Sq Ft
- Condo for Rent
716 Bayport Way Unit 716, Longboat Key, FL 34228
716 Bayport Way Unit 716, 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 -
$7,000 Per Month
- 3 Beds
- 2 Baths
- 1,909 Sq Ft
- Condo for Rent
737 Bayport Way Unit D, Longboat Key, FL 34228
737 Bayport Way Unit D, 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 -
$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 -
$3,200 Per Month
- 1 Bed
- 1 Bath
- 836 Sq Ft
- Condo for Rent
600 Sutton Place Unit 201, Longboat Key, FL 34228
600 Sutton Place Unit 201, 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 -
$25,500 Per Month
- 3 Beds
- 3.5 Baths
- 2,940 Sq Ft
- Condo for Rent
1511 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
1511 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228Offered at $25,500 per month for 3 months in 2027! - Come be on the beach! Rarely available on the south end of Longboat Key, a 3 bedroom + den, 3 1/2 bath DIRECT Beachfront 3-month (90 days total) rental is now available for this coming 2027 winter and spring season. This large 2940 +/- sq ft beachfront retreat is situated on the south side of this building which offers stunning 180-degree beach
Carol Aviles MICHAEL SAUNDERS & COMPANY
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$4,800 Per Month
- 2 Beds
- 2.5 Baths
- 1,755 Sq Ft
- House for Rent
616 Lyons Ln, Longboat Key, FL 34228
616 Lyons Ln, Longboat Key, FL 34228Come and enjoy a little piece of Paradise! This beautiful canal front home is located in the idyllic and picturesque Longboat Key. A charming mid-century style cottage nestled in one of Longboat Key's most private and serene settings. This spacious 2 bedroom + Bonus room, 2.5 bathrooms with outdoor shower residence offers 1,755 square feet of luxurious living space perfect for those seeking a
Steve Barthelemy ROOST REALTY INC.
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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
1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228LONGBOAT 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
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$7,500 Per Month
- 3 Beds
- 2 Baths
- 2,091 Sq Ft
- House for Rent
3210 Bayou Sound, Longboat Key, FL 34228
3210 Bayou Sound, Longboat Key, FL 34228Experience the best of Longboat Key living in this beautifully updated Bay Isles pool home, offered turnkey furnished FOR LEASE and available for both short-term and long-term reservations. This furnished coastal retreat features an open floor plan with vaulted ceilings, 2 bedrooms plus an office, updated bathrooms, a spacious kitchen with premium appliances, and multiple indoor-outdoor living
Richard Ivan WAGNER REALTY
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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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$14,000 Per Month
- 4 Beds
- 3.5 Baths
- 3,268 Sq Ft
- House for Rent
531 Birdie Ln, Longboat Key, FL 34228
531 Birdie Ln, Longboat Key, FL 34228Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home
Karie Gorgone WAGNER REALTY
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$78,000 Per Month
- 4 Beds
- 4.5 Baths
- 5,334 Sq Ft
- Condo for Rent
1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228There are moments in life that stop you mid-thought. Moments so immersive that words struggle to keep up with what you’re feeling. This penthouse is one of those moments. Offered to the public for the first time, this four-bedroom residence sits high above the Gulf of Mexico, where light, water, and horizon become part of everyday life. A private elevator opens directly into the home, setting the
Inbal August DOUGLAS ELLIMAN
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$10,500 Per Month
- 3 Beds
- 2 Baths
- 1,576 Sq Ft
- Condo for Rent
4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228**BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease DECEMBER 2026 and APRIL 2027** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly
Norma Mladineo COLDWELL BANKER REALTY
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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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$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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$29,000 Per Month
- 5 Beds
- 5.5 Baths
- 4,858 Sq Ft
- House for Rent
591 Putting Green Ln, Longboat Key, FL 34228
591 Putting Green Ln, Longboat Key, FL 34228LONGBOAT 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
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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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$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
4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228THIS 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
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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
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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
2823 Gulf of Mexico Dr, Longboat Key, FL 34228Summer 2026 is approaching! We still have the month of August available but it won't last long! 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 single family home invites you to experience the
Michael Cella CELLA'S REAL ESTATE INC
Showing Results 1 - 40, Page 1 of 3
Rental Home Trends in Longboat Key, FL
There are currently 109 homes available for rent in Longboat Key, FL. The median rent is $7,200 per month, with single-family homes renting at $10,000, townhouses at $8,500 and condos at $7,000.
Rental Home Trends
Number of Homes for Rent
109
Median Rent
$7,200
Median Single Family Home Rent
$10,000
Median Townhouse Rent
$8,500
Median Condo Rent
$7,000
Rentals in Longboat Key
Homes for Rent by Bedrooms in Longboat Key
Rentals by Price in Longboat Key
More About Living in Longboat Key
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