Sarasota, FL Homes for Rent in a Gated Community

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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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  $5,900 Per Month

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

  5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242

  Available for the 2027 Season or Two Week Rental. This beautifully updated sunrise-facing 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded oasis with a gorgeous view of the heated pool and ICW. Rental is turnkey furnished, decorated for immediate enjoyment with all of the amenities you will need for a relaxing vacation. The stunningly renovated

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  5855 Midnight Pass Rd Unit 333, Sarasota, FL 34242
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  $11,430 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  1001 Point of Rocks Rd Unit 608, Sarasota, FL 34242

  Villa 608 at Siesta Sands is a bright and relaxing coastal hideaway, perfect for enjoying the easy pace of island life. Designed with comfort in mind, this inviting villa features an open, airy layout and a soft beach-inspired style that creates a calm and welcoming atmosphere. The well-equipped kitchen and comfortable living spaces make it easy to unwind, whether you’re enjoying quiet mornings

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1001 Point of Rocks Rd Unit 608, 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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  $2,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • House for Rent

  2401 Riverbluff Pkwy Unit V240, Sarasota, FL 34231

  Sarasota furnished annual rental!! Welcome to this spacious one level Villa located in the serene 55 plus community of Strathmore Riverside Villas along the picturesque canal of Phillipi Creek right off Swift Road. This Villa is centrally located in South Sarasota close to the beaches and all of Sarasota. This charming retreat offers a perfect blend of comfort and tranquility, making it an ideal

  Jana L. Nizny M&M PROPERTY MANAGEMENT GROUP

  2401 Riverbluff Pkwy Unit V240, Sarasota, FL 34231
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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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  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft
  • Condo for Rent

  9330 Clubside Cir Unit 3209, Sarasota, FL 34238

  RENTED JAN.FEB. 2027: Well-furnished vacation condo at Stoneybrook G&CC with golf transfer available for a fee (check with clubhouse for fee schedule.) King bed in master bedroom, queen bed in guest bedroom, nicely furnished living area, well-equipped kitchen with all you will need for a few months in the Florida Sunshine. The lanai is tiled and screened and offers a great golf course view. There

  Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

  9330 Clubside Cir Unit 3209, Sarasota, FL 34238
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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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  /27

  $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

  • 2 Beds
  • 2 Baths
  • 1,333 Sq Ft
  • Condo for Rent

  4639 Chapel Hill Dr Unit 2912, Sarasota, FL 34238

  RENTED JAN., FEB., MARCH & APRIL 2027: AVAILABLE JUNE THROUGH DECEMBER 2026: Exceptionally well cared for ground floor condo with vinyl flooring throughout, recently updated kitchen with granite counters and tile floors with breakfast bar that is open to the dining and living area, King bed in master bedroom and walk-in closets plus adjoining bathroom with two sinks and walk-in shower, 2nd

  Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

  4639 Chapel Hill Dr Unit 2912, Sarasota, FL 34238

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