Newest Homes for Rent in Siesta Key, FL

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  $9,900 Per Month

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

  1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242

  Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park your car and store all the beach equipment you will need for the beach. It's only a short 10 min. walk down the private deeded beach access to the beautiful white sands of Siesta Key beach. We share

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
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  $7,200 Per Month

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

  1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242

  Relax in the spacious living area or enjoy a glass of wine on the lanai.This condo is turnkey furnished including washer /dryer and private garage. Guests are walking distance away from private beach access to Siesta Key's world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key!**Taxes and fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242
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  $9,300 Per Month

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

  1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242

  This fabulous two bedroom features the primary bedroom with a King bed and the guest with a queen bed. The spacious living area opens onto a tiled lanai surrounded with sliding windows/doors that can be opened or closed as desired. Enjoy your breakfast there in the morning sun or relax with a glass of wine as the sun sets.The condo is turnkey furnished including washer / dryer and private

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242
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  $9,300 Per Month

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

  1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242

  This spacious, private and light-colored 2-bedroom/2-bathroom end unit has a lanai that overlooks a lake with frequent bird sightings. Walk right out to an inland waterway and fishing dock. A large, heated pool is just across from the unit. Beach accessories as well as fishing gear and bicycles are available in the private garage.THIS CONDO REQUIRES A TWO WEEK MINIMUM

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242
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  $12,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft
  • Condo for Rent

  1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242

  Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
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  $6,900 Per Month

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft
  • Condo for Rent

  1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242

  This lovely well-maintained and upgraded condo in a gated community, is located on the ground floor and offers one bedroom plus an additional den furnished as a small guest bedroom. The condo is turnkey furnished including washer /dryer and private garage, an approximate 5-minute walk, via deeded, walking access across the street, to the #1 beach in the U.S.A., Siesta Key! Choose to enjoy two

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242
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  $9,300 Per Month

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

  1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242

  Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access – 5 minute walk. Tile floors throughout and completely re-decorated and furnished with many amenities for your family’s enjoyment. King bed in the master and two doubles in the guest room.*Taxes and fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
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  $9,300 Per Month

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Condo for Rent

  1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242

  Relax in this spacious two bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private, walking beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key*Taxes and fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
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  $7,000 Per Month

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft
  • Condo for Rent

  1360 Siesta Bayside Dr, Sarasota, FL 34242

  This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private beach access to Siesta Key's world- renowned white sandy beach on the

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1360 Siesta Bayside Dr, Sarasota, FL 34242
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  $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
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  $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
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  $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
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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
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  $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. 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 areas – a fun zone for the kids downstairs and a relaxing haven for adults

  Beth Dilley ASCENDIA REAL ESTATE

  5516 Avenida Del Mare, Sarasota, FL 34242
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  $5,000 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 2027-April 2027. Off season rates start at $5,000. 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

  Beth Dilley ASCENDIA REAL ESTATE

  5855 Midnight Pass Rd Unit 426, 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. 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 bright, coastal-styled haven designed for relaxation and comfort. The spacious primary

  Beth Dilley ASCENDIA REAL ESTATE

  345 Avenida Leona, Sarasota, FL 34242
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  $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
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  $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 décor. 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
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  $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 August - December 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 to unwind. Step

  Beth Dilley ASCENDIA REAL ESTATE

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
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  $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
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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
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  $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
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  $8,000 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
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  $9,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,489 Sq Ft
  • Condo for Rent

  6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242

  ***AVAILABLE MAY 2026*** one MONTH MIN***Welcome to the Beach! Prime Siesta Key location. This large, spacious 2 Bedroom/2 Bath split floor plan condo comes with a full-length balcony with views of the gulf and intracoastal waterway, as well as the beautiful sunsets. Available as a monthly rental, the interior boasts a decorative fireplace, reclining sofa, two walk-in closets, washer and dryer in

  

  Anthony DeLuca

  AUDREY RAIN RENTALS, INC

  (941) 271-7125

  6415 Midnight Pass Rd Unit 602, 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 Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 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 portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open

  Margaret Young JENNETTE PROPERTIES, INC.

  1257 S Portofino Dr Unit 36, Sarasota, FL 34242
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  $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 full wall length closet for guests. The walk-in closet is reserved for the Owners. The guest bedroom has 2 single beds that can be combined to

  Margaret Young JENNETTE PROPERTIES, INC.

  1250 N Portofino Dr Unit 107, Sarasota, FL 34242

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