Siesta Key, FL Condos for Rent

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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 May 1, 2025! 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, Sauna, 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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  $3,900 per month

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Condo for Rent

  4660 Ocean Blvd Unit B2, Sarasota, FL 34242

  SIESTA KEY WATERFRONT UNIT AVAILABLE AS SHORT OR LONG TERM. Sea Village offers million dollar views and is situated on 5 acres overlooking the Gulf. It provides a peaceful retreat with opportunities to witness breathtaking sunsets, the full moon reflecting on the water, and serene walks to the beach and Siesta Village. Additionally, its location on the north end of the Key provides convenient

  Margaret Young JENNETTE PROPERTIES, INC.

  4660 Ocean Blvd Unit B2, Sarasota, FL 34242
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  $8,500 per month

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

  5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242

  ** BOOKED JANUARY THROUGH MARCH 2025 ***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 USA! The spacious unit

  Kayla Lamb NEXTHOME EXCELLENCE

  5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
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  $7,500 per month

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

  460 Beach Rd Unit A1, Sarasota, FL 34242

  Available OCT- DEC. 2024 and APR. 2025. 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

  Brenda Cozy COLDWELL BANKER REALTY

  460 Beach Rd Unit A1, Sarasota, FL 34242
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  $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 December 2025 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

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 301, Sarasota, FL 34242
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  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Condo for Rent

  1255 E Peppertree Dr Unit 201, Sarasota, FL 34242

  Bayside highrise Building with underground parking, elevator, turnkey furnished, secured building, washer and dryer nicely appointed Two heated pools, lighted tennis courts, fishing pier, fitness room and that Beautiful Siesta Beach. Restaurants, Shopping, Theater, Arts, Golfing, Bicycling whatever your pleasure you will find in Sarasota. Peppertree is a Gulf to Bay complex Available

  Lisa Beach WATERSIDE REALTY LLC

  1255 E Peppertree Dr Unit 201, Sarasota, FL 34242
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  $8,000 per month

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

  6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242

  ***AVAILABLE December, 2025 through April, 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

  Anthony DeLuca AUDREY RAIN RENTALS, INC

  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 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
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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 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
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  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Condo for Rent

  6480 Midnight Pass Rd Unit 506, Sarasota, FL 34242

  Discover the ultimate coastal getaway at our beautifully appointed weekly vacation rental on stunning Siesta Key. Wake up each morning to panoramic Gulf views from the comfort of your living room and both bedrooms — a daily reminder that you’ve arrived in paradise.This spacious 2-bedroom, 2-bathroom condo also features a dedicated office space, ideal for remote work or staying organized

  Robert Bevington SHOWTIME REALTY

  6480 Midnight Pass Rd Unit 506, Sarasota, FL 34242
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  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Condo for Rent

  6480 Midnight Pass Rd Unit 311, Sarasota, FL 34242

  Experience breathtaking Gulf of Mexico views from this charming 2-bedroom condo at Siesta Breakers on Siesta Key. Just a short walk away, you'll find yourself on the pristine shores of Siesta Key Beach, renowned for its powder-soft sand and crystal-clear waters. And for those who prefer a poolside retreat, it's an even shorter stroll to the refreshing pool, where you can unwind while gazing out

  Robert Bevington SHOWTIME REALTY

  6480 Midnight Pass Rd Unit 311, Sarasota, FL 34242
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  $12,000 per month

  • 3 Beds
  • 3.5 Baths
  • 3,524 Sq Ft
  • Condo for Rent

  1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242

  PENTHOUSE Water Views From Every Room!AVAILABLE April 15, 2025-December 31, 2025.4/15/2025-12/31/2025- $12,000Contact agent about nightly rate breakdown!

  Cole Collins COLDWELL BANKER REALTY

  1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242

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