Siesta Key, FL Homes for Rent in a Gated Community

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  $5,500 Per Month

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

  5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242

  SIX+ MONTH RENTAL SPECIAL - OCTOBER 2026 THROUGH MARCH 2027, or Available for the 2027 Season. This beautifully updated 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded vacation retreat with a gorgeous view of the heated pool and ICW. Ten-minute walk or free trolley ride to the famous Siesta Key Beach. Turnkey furnished with all of the amenities you

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242
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  $7,470 Per Month

  • 1 Bed
  • 1 Bath
  • 696 Sq Ft
  • House for Rent

  6020 Midnight Pass Rd Unit 11, Sarasota, FL 34242

  Feel the sun on your shoulders and sand between your toes when you choose the updated Villa 11 at Aloha Kai. With a spacious front porch and a back patio, this villa offers plenty of opportunities to make the most of your beach getaway. Just steps from the pool and private beach, it’s an ideal retreat for sun lovers. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 11, 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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  $7,500 Per Month

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

  6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242

  No roads to cross to get to the beach! Just listed- This clean, updated, cheery one bedroom/one bath condo in Casa Mar is ready for your beach stay! Covered parking, on-site community laundry rooms, and heated pool are just some of the amenities this Association has to offer. A recently added security gate adds value. This condo is ready for your stay- includes linens & beach towels. Pack your

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
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  $17,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Condo for Rent

  6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242

  Beachfront Bliss at Casa Mar – Siesta Key Discover this beautifully updated two-bedroom, two-bathroom beachfront condo in Casa Mar, offering direct access to Crescent Beach, a serene and less crowded alternative to Siesta Key’s main beach. Why You’ll Love This Condo: Prime Beachfront Location – Step right onto the powdery whit e sands of Crescent Beach Classic Coastal Charm – Thoughtfully

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242
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  $6,300 Per Month

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

  1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242

  Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.As you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area,

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
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  $5,500 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,798 Sq Ft
  • Condo for Rent

  3954 Hamilton Club Cir Unit 14, Siesta Key, FL 34242

  • UNFURNISHED • ANNUAL RENTAL ~ Rarely available in the exclusive Hamilton Club, this spacious 3-bedroom, 3.5-bath townhome offers over 4,000 square feet of space in one of Siesta Key's most desirable deep-water boating communities. A standout feature of this home is the expansive lower-level garage area, providing exceptional flexibility. In addition to the oversized two-car garage, there is a

  Tony Andrews ANDREWS & ASSOCIATES REALTY

  3954 Hamilton Club Cir Unit 14, Siesta Key, 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

  Siesta Key's beautiful coastline offers you the chance to enjoy your dream vacation in this fantastic 2-bedroom ocean-view condominium. Situated directly on the beach and across the street from the South Village, you’ll be mere steps away from both the beautiful water and a vast array of destinations. The South Village includes a full-service grocery store and numerous restaurants, ice cream

  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

  Your Gulf-View Getaway at Siesta Breakers awaits!Wake up to the sparkling blue waters of the Gulf of Mexico in this welcoming 2-bedroom condo at Siesta Breakers on Siesta Key. Just a short stroll brings you to the world-famous Siesta Key Beach, where you can sink your toes into powdery soft whit e sand and swim in crystal-clear waters.If lounging by the pool is more your style,

  Robert Bevington SHOWTIME REALTY

  6480 Midnight Pass Rd Unit 311, Sarasota, FL 34242
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  $7,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,467 Sq Ft
  • Condo for Rent

  1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242

  Waterfront Elegance at Marina Del Sol – Your Seasonal Retreat. Indulge in the ultimate Sarasota lifestyle at this stunning 3-bedroom, 2,467 sq. ft. residence in the exclusive Marina Del Sol. Thoughtfully designed and beautifully updated, this spacious condo offers the perfect balance of elegance and comfort, with three oversized porches capturing serene water views and warm coastal breezes. Step

  Olga Smith IMPERIAL PROPERTY GROUP LLC

  1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242

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