268

Homes for Rent in ZIP Code 34242

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  • 1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    /31

    $9,300 per month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242

    Deeded Walking Access Directly to the Beach!New on the rental program - Beautifully updated 2-bedroom near the pool, tennis courts and path to the beach! Please be one of our first Guests!The moment you arrive at Gulf & Bay Club Bayside, you’ll appreciate the beauty, serenity, and charm of this "Key West” style village. Located on the bay across the street from world-famous Siesta

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
  • 1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
    /26

    $9,300 per month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242

    Enjoy all the Siesta Key and Gulf and Bay Club Bayside amenities while staying in this spacious two-bedroom/two-bathroom vacation rental condo. The condo offers a relaxing lake, pool and tennis court view from the lanai. A few of your amenities include your own private garage, a washer and dryer IN THE CONDO, and a fully-equipped kitchen The community offers BBQ grills (6), two tennis courts,

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /38

    $9,350 per month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    Unlisted Address

    Make yourself at home in our spacious two bedroom, two bath second floor condo located at the beautiful Gulf and Bay Club Bayside. The Key West style cluster buildings afford you a quiet residential feel while you are just a short walk to the powdery white quartz sand of the world famous Siesta Key/Crescent Beach.New to the rental program, our condo has previously been owner occupied and

    Andy Moore GULF COAST REALTY & MANAGEMENT

    Unlisted Address
  • 1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
    1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
    1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
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    $6,900 per month

    • 1 Bed
    • 1 Bath
    • 845 Sq Ft
    • Condo for Rent

    1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242

    Spacious one bedroom/one bathroom vacation rental at the Gulf and Bay Club Bayside on the island paradise of Siesta Key just offshore of Sarasota, Florida. Private access to Crescent Beach on the Gulf of Mexico - just steps to the beach. Free high-speed Internet connection. Please note the garage for this unit is the middle garage in the building to the right.*Taxes and Fees not included.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
  • 8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
    8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
    8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
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    $8,500 per month

    • 2 Beds
    • 2 Baths
    • 1,233 Sq Ft
    • Condo for Rent

    8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242

    BOOKED FEB/APRIL 2026. AVAILABLE JANUARY 2026. UTILITIES INCLUDED. SIESTA KEY SPECTACULAR FULL BAY/INTRACOASTAL UNOBSTRUCTED VIEWS! BOOK YOUR BEACH GETAWAY NOW! Beautifully updated throughout Turnkey "top floor" Condo in this popular community of Sunrise Cove. Located on the southern end of Siesta Key, directly across the street from Turtle Beach! Upon entering the condo, you will immediately

    Chrissie Cummings JENNETTE PROPERTIES INC

    8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
  • 5516 Avenida Del Mare, Sarasota, FL 34242
    5516 Avenida Del Mare, Sarasota, FL 34242
    5516 Avenida Del Mare, Sarasota, FL 34242
    /60

    $15,000 per month

    • 3 Beds
    • 2 Baths
    • 2,259 Sq Ft
    • House for Rent

    5516 Avenida Del Mare, Sarasota, FL 34242

    This is a short term rental. Listing reflects peak season rate. Available peak season months: January 5th - February 6th 2026, April 2026. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living

    Beth Dilley ASCENDIA REAL ESTATE

    5516 Avenida Del Mare, Sarasota, FL 34242
  • 5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
    /65

    $8,700 per month

    • 2 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Condo for Rent

    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242

    Listing reflects peak season rate. Available peak season months: January 2026, April 2026. Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot,

    Beth Dilley ASCENDIA REAL ESTATE

    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
  • 9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
    9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
    9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
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    $5,000 per month

    • 3 Beds
    • 3 Baths
    • 2,558 Sq Ft
    • Condo for Rent

    9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242

    Available May 1, 2026 for an annual lease! Rarely available 3 bed, 3 bath, plus office/work-space condo in sought-after Somerset Cay! You will love the resort-style amenities and the contemporary elegance this wonderful home offers. There are three balconies, offering views of the Bay, the Intercoastal Waterway and the Gulf. Fully updated kitchen with top-of-the-line appliances and breakfast bar,

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
  • 116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
    116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
    116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
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    $7,200 per month

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

    116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242

    Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Experience the ultimate beach getaway at "Carefree Coconut," a charming second-floor corner unit located in the heart of Siesta Key's welcoming Vista Hermosa community. True to its Spanish name, "Beautiful View," this community offers a delightful escape, blending old Florida

    Beth Dilley ASCENDIA REAL ESTATE

    116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
  • 8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
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    $4,000 per month

    • 2 Beds
    • 2 Baths
    • 1,286 Sq Ft
    • Condo for Rent

    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242

    Siesta Key living just steps from the Gulf of Mexico at beautiful, tranquil Island Reef on the quiet end of the Island. Spacious 2 bedrooms, 2 baths, laundry in residence, carport, and guest parking. Tile flooring throughout the condo. Island Reef is a serene waterfront community, one of the few true Gulf to Bay properties, that offers many desirable amenities including: beach and boat docks

    Erick Shumway RE/MAX ALLIANCE GROUP

    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
  • 8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
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    $4,000 per month

    • 2 Beds
    • 2 Baths
    • 1,286 Sq Ft
    • Condo for Rent

    8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242

    Look no further than Siesta Key's "Island Reef" for your annual vacation getaway. The stunning Gulf to Bay location features the fourth-floor unit overlooking the intercostal waterway, just a short walk to the beach. The Siesta Key village and local dining are just a stroll away. The property has a beautiful community pool, tennis courts, shuffleboard, and more. The stylish decore and nicely

    Erick Shumway RE/MAX ALLIANCE GROUP

    8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
  • 8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
    8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
    8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
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    $3,500 per month

    • 2 Beds
    • 2 Baths
    • 1,303 Sq Ft
    • Condo for Rent

    8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242

    Seasonal Property available on the top floor in Siesta Key, Look no further than "Island Reef" This Gulf to Bay location features the top floor PH unit directly overlooking the intercostal water way, just a short walk to the beach and very close to the Siesta key village and local dining. The property has a beautiful community pool, Tennis courts, shuffle board and much more. Entering the unit

    Lee Brewer RE/MAX ALLIANCE GROUP

    8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
  • 345 Avenida Leona, Sarasota, FL 34242
    345 Avenida Leona, Sarasota, FL 34242
    345 Avenida Leona, Sarasota, FL 34242
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    $18,000 per month

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • House for Rent

    345 Avenida Leona, Sarasota, FL 34242

    Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a

    Beth Dilley ASCENDIA REAL ESTATE

    345 Avenida Leona, Sarasota, FL 34242
  • 20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
    /46

    $12,000 per month

    • 2 Beds
    • 2 Baths
    • 1,282 Sq Ft
    • Condo for Rent

    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242

    Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the sounds of the surf? Look no further than this stunningly remodeled 2 bed, 2 bath condo in the Whispering Sands Community. This wonderful 55+ community offers you the convenience of village living but is very peaceful and private at the same time. Leave the hustle and bustle of

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
  • 915 Seaside Dr Unit 512, Sarasota, FL 34242
    915 Seaside Dr Unit 512, Sarasota, FL 34242
    915 Seaside Dr Unit 512, Sarasota, FL 34242
    /30

    $26,319 per month

    • 2 Beds
    • 3 Baths
    • 1,750 Sq Ft
    • Condo for Rent

    915 Seaside Dr Unit 512, Sarasota, FL 34242

    Bask in the sunshine and sit in the pristine crystal white sands on Crescent Beach, rated #1 in the country by Dr. Beach. This beachfront sanctuary offers a fitness center, heated pool, outdoor grotto style whirlpool hot tub, bicycles, kayaks and barbecue grills, the tiki bar offers food from the famous Morton’s and cabanas to shield you from the sun when you want some shade. The unit has top of

    Andy Moore GULF COAST REALTY & MANAGEMENT

    915 Seaside Dr Unit 512, Sarasota, FL 34242
  • 1140 Seaside Dr Unit 101, Sarasota, FL 34242
    1140 Seaside Dr Unit 101, Sarasota, FL 34242
    1140 Seaside Dr Unit 101, Sarasota, FL 34242
    /27

    $25,048 per month

    • 4 Beds
    • 3 Baths
    • 2,430 Sq Ft
    • House for Rent

    1140 Seaside Dr Unit 101, Sarasota, FL 34242

    Serenity at its finest! If luxury is calling, come indulge at the Beach House Residences for your ultimate beach vacation experiences. A place to escape and rediscover you. Renew your senses, inspire your mind and relax your body. Take advantage of the magnificent sunsets, tranquil waters, immense sunshine of world-renowned Crescent Beach. The most discerning traveler will appreciate the island

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1140 Seaside Dr Unit 101, Sarasota, FL 34242
  • 1257 S Portofino Dr Unit 38, Sarasota, FL 34242
    1257 S Portofino Dr Unit 38, Sarasota, FL 34242
    1257 S Portofino Dr Unit 38, Sarasota, FL 34242
    /96

    $4,500 per month

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

    1257 S Portofino Dr Unit 38, Sarasota, FL 34242

    Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice decor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the

    Kay Esposito SIGNATURE REALTY ASSOCIATES

    1257 S Portofino Dr Unit 38, Sarasota, FL 34242
  • 5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    /57

    $5,000 per month

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Condo for Rent

    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242

    Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot

    Beth Dilley ASCENDIA REAL ESTATE

    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
  • 6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
    6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
    6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
    /42

    $5,000 per month

    • 2 Beds
    • 2.5 Baths
    • 1,332 Sq Ft
    • Condo for Rent

    6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242

    Variable rent based on season

    Terry Dorrity INTEGRITY INVESTMENTS REALTY

    6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
  • 1250 N Portofino Dr Unit 102, Sarasota, FL 34242
    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
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    $6,500 per month

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

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242

    Available January to April 1, 2026! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
  • 5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    /42

    $6,000 per month

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft
    • Condo for Rent

    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242

    ** AVAILABLE APRIL 2026! ** BOOKED JANUARY THROUGH MARCH 2026 ***GORGEOUS BEACHFRONT HOME LOCATED IN THE HIGHLY SOUGHT AFTER GULF & BAY COMMUNITY! Enjoy spectacular sunsets and views of the Gulf of Mexico from this 6th floor 2 Bedroom/ 2 Bath luxury condo. Full Gulf views from living room/dining room combo and master bedroom! Gulf & Bay Club is located on Siesta Key Beach, voted #1 Beach in the

    Kayla Lamb NEXTHOME EXCELLENCE

    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
  • 460 Beach Rd Unit A1, Sarasota, FL 34242
    460 Beach Rd Unit A1, Sarasota, FL 34242
    460 Beach Rd Unit A1, Sarasota, FL 34242
    /15

    $7,500 per month

    • 2 Beds
    • 2 Baths
    • 1,363 Sq Ft
    • Condo for Rent

    460 Beach Rd Unit A1, Sarasota, FL 34242

    Available May 2026. Direct beach front condo on Siesta Key beach. This unit has it all for that Florida vacation. 2 bedroom, 2 baths, located on the 2nd floor with private lanai. Living room and dining area face the Gulf of Mexico which allows for beautiful sunsets. The condo is tastefully decorated with wood and tile floors. Cool off in the pool located next to the unit, take a walk along the

    Brenda Cozy COLDWELL BANKER REALTY

    460 Beach Rd Unit A1, Sarasota, FL 34242
  • 1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    /82

    $6,500 per month

    • 2 Beds
    • 2 Baths
    • 1,123 Sq Ft
    • Condo for Rent

    1250 N Portofino Dr Unit 301, Sarasota, FL 34242

    Immaculate End Unit in the Marlin building, Ready for you to Enjoy through January 2026 and April 2026 through year-end 2026! Stunning all the way, Great Location in the complex, close to the pool, clubhouse, spa, sauna, 2 bedroom 2 full baths, enclosed lanai overlooking the canal, steps to Deeded beach access through Crescent Arms, for your pleasure daytime or sunset time! Siesta Harbor offers a

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
  • 1257 S Portofino Dr Unit 36, Sarasota, FL 34242
    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
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    $5,000 per month

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft
    • Condo for Rent

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242

    Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a new coffee table, an electric fireplace, new shower heads, a portable electric grill, bikes, beach

    Margaret Young JENNETTE PROPERTIES, INC.

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
  • 1250 N Portofino Dr Unit 107, Sarasota, FL 34242
    1250 N Portofino Dr Unit 107, Sarasota, FL 34242
    1250 N Portofino Dr Unit 107, Sarasota, FL 34242
    /27

    $6,400 per month

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

    1250 N Portofino Dr Unit 107, Sarasota, FL 34242

    This 2 bedroom, 2 bath condo in this popular 55+ community, is conveniently located on the ground floor next to the club house and swimming pool, and features new appliances, granite counter tops and ceramic flooring. Queen size bed in the Master with a walk in closet plus a full wall length closet. The guest bedroom has 2 single beds that can be combined to make a King. Updated bathrooms

    Margaret Young JENNETTE PROPERTIES, INC.

    1250 N Portofino Dr Unit 107, Sarasota, FL 34242
  • 5519 Azure Way, Sarasota, FL 34242
    5519 Azure Way, Sarasota, FL 34242
    5519 Azure Way, Sarasota, FL 34242
    /25

    $12,000 per month

    • 4 Beds
    • 3 Baths
    • 2,460 Sq Ft
    • House for Rent

    5519 Azure Way, Sarasota, FL 34242

    Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car! A brand new beautiful granite topped Kitchen space opens to a family room all

    Catherine Foley JENNETTE PROPERTIES, INC.

    5519 Azure Way, Sarasota, FL 34242

Showing Results 241 - 268, Page 7 of 7

Florida Sarasota County Sarasota 34242

Homes for Rent in ZIP Code 34242

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