Sarasota, FL Homes for Rent in a Gated Community

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  $4,800 Per Month

  • 2 Beds
  • 2.5 Baths
  • 2,368 Sq Ft
  • House for Rent

  8784 Pebble Creek Ln, Sarasota, FL 34238

  Live your best life! This beautiful villa is available MAY 15th - OCTOBER ONLY and is in the desirable gated community of Stoneybrook Golf & Country Club. Enjoy the challenging 18-hole championship golf course completely renovated and redesigned by Kipp Schultes or play tennis/pickle ball with the active tennis community. Other amenities include the well-designed fitness center with a variety of

  Maureen Plichta STRINGER MANAGEMENT INC

  8784 Pebble Creek Ln, Sarasota, FL 34238
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  $5,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,389 Sq Ft
  • Condo for Rent

  8325 38th Street Cir E Unit 102, Sarasota, FL 34243

  Beautiful turnkey furnished condo located in Serenata. This former model unit is located on the first floor and has three bedrooms, two bathrooms, laundry room, open floor plan and split bedrooms. The primary bedroom has a king sized bed, large walk in closet and an on suite bathroom with a tub/shower combination. The guest bedrooms each have queen sized beds and walk in closets. The guest

  C. Alison Hunter JENNETTE PROPERTIES INC

  8325 38th Street Cir E Unit 102, Sarasota, FL 34243
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  $6,800 Per Month

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Condo for Rent

  1000 Benjamin Franklin Dr Unit 205, Sarasota, FL 34236

  This 2 bedroom/2 bath is spacious and has a gorgeous lanai lending itself to you enjoying the warmth of Florida in January, February, and March. You won’t see any snowflakes here! The master bedroom has a huge king sized bed and the guest bedroom has two twin beds. Open living room, dining room, and kitchen with new lighting. Entire unit has all new flooring as well. After you wrap up Christmas,

  Pamala Casey CASEY REALTY CORPORATION

  1000 Benjamin Franklin Dr Unit 205, Sarasota, FL 34236
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  $8,370 Per Month

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • House for Rent

  6020 Midnight Pass Rd Unit 40, Sarasota, FL 34242

  New photos coming soon! Villa 40 at Aloha Kai offers the perfect beach getaway. With tile floors, tranquil furnishings, and a beautifully updated bath featuring a walk-in shower, this villa invites you to kick off your shoes and stay awhile. The primary bedroom includes an en suite half bath for added privacy and comfort. Enjoy your morning coffee on the enclosed porch or the open patio before

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 40, Sarasota, FL 34242
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  $1,525 Per Month

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

  1015 Villagio Cir Unit 202, Sarasota, FL 34237

  LIGHT, BRIGHT AND SPACIOUS 1 BEDROOM 1 BATHROOM 2ND FLOOR CONDO LOCATED IN THE HIGHLY SOUGHT AFTER VILLAGIO CONDOMINIUMS COMMUNITY. This unit has everything you have been looking for. When you walk in you will love the way that the updated vinyl flooring that goes through out the entire living space, high tray ceilings in the living and dining rooms and open floor plan give this home a clean and

  Kayla Lamb NEXTHOME EXCELLENCE

  1015 Villagio Cir Unit 202, Sarasota, FL 34237
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  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,331 Sq Ft
  • Condo for Rent

  9397 Midnight Pass Rd Unit 905, Sarasota, FL 34242

  $4,800/month for annual renters! Welcome to 9397 Midnight Pass Rd #905 Sarasota, FL 34242 at The Pointe on Siesta Key, a fully renovated 1,348 SF, 2-bedroom, 2-bathroom luxury condo offering breathtaking Little Sarasota Bay and Intracoastal waterway views from the 9th floor. This stunning residence underwent a complete custom renovation in 2023, setting it apart from every other unit in the

  Emerson Robbins HARRY ROBBINS ASSOC INC

  9397 Midnight Pass Rd Unit 905, Sarasota, FL 34242
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  $8,800 Per Month

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • House for Rent

  6030 E Peppertree Way Unit 222A, Sarasota, FL 34242

  This property is a 30 night minimum. 6030 is a small garden unit, located on the Bayside of Midnight Pass Ground Floor unit. 2 bedroom, 2 bath unit . Approx. 1250 Sq. Ft. (1350 including the lanai). Bedding:Master bedroom: KingGuest Bedroom: Queen Electronics:Living room: 32 inch Flat PanelMaster Bedroom: 20 inchGuest Bedroom: 12 inch Bathrooms:Master: ShowerGuest:

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6030 E Peppertree Way Unit 222A, Sarasota, FL 34242
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  $7,700 Per Month

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

  1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242

  Beautiful Key West-style three bedroom, two bath, turnkey furnished condo with its own garage in a lush, tropical resort setting. The townhouse, second/third floor condo, is meticulously maintained and beautifully furnished - There's even a teeny "peek-a-boo" water view from the lanai. The furnishings and flooring are stylish and perfect for the beach. The updated kitchen has granite counter tops

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
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  $4,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,678 Sq Ft
  • House for Rent

  11230 Sandhill Preserve Dr, Sarasota, FL 34238

  Seasonal Availability, look no further. Experience the ultimate Florida lifestyle in this beautifully appointed home, ideally located in the highly sought-after Palmer Ranch community, just minutes from the world-renowned Siesta Key Beach, Lido Key, and the vibrant shopping, dining, and cultural attractions of downtown Sarasota.Nestled within an exclusive gated community of Sandhill

  John Dowd MEDWAY REALTY

  11230 Sandhill Preserve Dr, Sarasota, FL 34238
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  $8,370 Per Month

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

  6020 Midnight Pass Rd Unit 56, Sarasota, FL 34242

  Light, bright, and beachy—Villa 56 at Aloha Kai welcomes you with its retro charm and casual coastal elegance. The inviting interior is enhanced by an updated bath that offers a spa-like retreat, perfect for unwinding after a sun-soaked day at the beach or an afternoon exploring the shops and restaurants in town. In the evening, enjoy a peaceful sunset stroll along the shoreline, then return to

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 56, Sarasota, FL 34242
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  $6,500 Per Month

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

  1255 E Peppertree Dr Unit 305, Sarasota, FL 34242

  his property is a 30 night minimum.1255 - 305 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay.Open kitchen floor plan. Dual sink vanity in Master bathroom. Living room has a sleeper sofa available. Condo is located on third floor. Equipped with Xfinity cable service and free Wi-Fi. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft.

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1255 E Peppertree Dr Unit 305, Sarasota, FL 34242
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  $2,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Property for Rent

  5972 Brigadoon Way Unit 58, Sarasota, FL 34233

  Experience modern comfort and style in this brand-new two-bedroom, two-bath home with a versatile bonus room ideal for a den, office, hobby space, or guest retreat. The bright open-concept layout features a beautiful kitchen with stainless steel appliances, abundant cabinetry, built-in microwave, and seamless flow into the dining and living areas. A split-bedroom design provides privacy, with the

  Sandra Bergman Cove Communities

  5972 Brigadoon Way Unit 58, Sarasota, FL 34233
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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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  $5,500 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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  $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

  Available annually starting April 4, 2027. 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

  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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  $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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