Siesta Key, FL Homes for Rent

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  $7,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,439 Sq Ft
  • House for Rent

  4852 Featherbed Ln, Sarasota, FL 34242

  SIESTA KEY, Sarasota, Single Family Pool Home....Well-positioned for convenience and natural attractions . . . and dinners are breezy on your patio! The advantages of this appealing home in the Siesta area of Siesta Key become apparent while you are still walking the perimeter. The clear blue pool and the patio are a perfect pairing of amenities, supporting a variety of social activities and

  Jane Hunter JENNETTE PROPERTIES INC

  4852 Featherbed Ln, Sarasota, FL 34242
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  $3,500 Per Month

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

  1250 N Portofino Dr Unit 303, Sarasota, FL 34242

  Available for season 2026! Welcome to Coastal Living at its finest, perfectly nestled on the sought after barrier island of Siesta Key. Updated unit offers serene water views, abundant natural light and the relaxed elegance that defines Florida living. Located in a meticulously maintained waterfront community, this spacious unit features an open and inviting layout ideal for seasonal

  Angela Bailey MONARCH PROPERTY GROUP LLC

  1250 N Portofino Dr Unit 303, Sarasota, FL 34242
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  $8,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft
  • Townhouse for Rent

  357 Tierra Mar Ln Unit 5, Sarasota, FL 34242

  Located in the heart of Siesta Key, live the island lifestyle year-round in this stunning turnkey furnished townhome, tucked away in a quiet enclave of only six residences, offering the perfect blend of privacy, comfort, and convenience. Available now for annual lease.This immaculate and spacious townhome features 3 bedrooms, 2.5 baths, and tasteful coastal furnishings throughout. Upon

  Chrissie Cummings JENNETTE PROPERTIES INC

  357 Tierra Mar Ln Unit 5, 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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  $4,500 Per Month

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

  1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242

  Enjoy our beautiful holiday retreat on Siesta Key Island, with private access to the stunning whites sands of Crescent Beach – Previously voted No. 1 beach in USA! Our 2 bed/2 bath condo located in this uniquely designed low rise ‘Key West’ style complex has ground floor access with sheltered South facing Garden – free WIFI throughout the condo. While away your lazy days on our fishing dock when

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
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  $7,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft
  • House for Rent

  6154 Midnight Pass Rd Unit A06, Sarasota, FL 34242

  Enjoy a perfect vacation in this spacious 2 bedroom, 2 bath large villa. With 2 Queen and 2 Twin beds, this is the perfect villa even for a large family up to 6. From this villa, you are just steps to Crescent Beach - world renowned whitest sand. Enjoy Wi-Fi community internet access, a 32" flat screen TV with HD/DVD in the living room, and a TV with DVD/VHS in the master bedroom. Kids will enjoy

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit A06, Sarasota, FL 34242
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  $8,340 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Apartment for Rent

  6154 Midnight Pass Rd Unit 305, Sarasota, FL 34242

  Experience breathtaking, unobstructed views of the sparkling Gulf of Mexico and the pristine shores of Crescent Beach from the spacious 3rd-floor lanai of this beautifully appointed two-bedroom, two-bathroom beachfront apartment. Perfectly designed for comfort and relaxation, this well-maintained unit features a fully equipped kitchen with all the essentials needed to prepare everything from

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 305, Sarasota, FL 34242
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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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  $7,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • House for Rent

  6154 Midnight Pass Rd Unit D06, Sarasota, FL 34242

  Casa Blanca is within sight of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. Most Villas have a screened Lanai with table and chairs for dining and relaxing. Those without a lanai

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit D06, 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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  $7,500 Per Month

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

  1137 N Moonmist Ct Unit L7, Sarasota, FL 34242

  This is a short term rental. Listing reflects peak season rate. Welcome to The Blue Luna, a serene stand-alone villa nestled in the tropical paradise of Polynesian Gardens on Siesta Key. This two-bedroom, two-bathroom home has been thoughtfully decorated with a calming, coastal blue palette that reflects the soft light of the moon on the water. The spacious living area is bathed in natural light,

  Beth Dilley ASCENDIA REAL ESTATE

  1137 N Moonmist Ct Unit L7, Sarasota, FL 34242
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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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  $9,420 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Condo for Rent

  6154 Midnight Pass Rd Unit 101, Sarasota, FL 34242

  Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach, from the 1st floor of this beautifully appointed two- bedroom, two-bathroom apartment with fully-equipped kitchen. Relax in the living room that overlooks the gulf. Enjoy your morning coffee sitting out on the screened in lanai just steps from the sand.This unit features Private wireless internet, Double

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 101, 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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  $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

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft
  • House for Rent

  1224 S View Dr, Sarasota, FL 34242

  Stunning Renovated Home for Long-Term Rent in Siesta Cove. Discover your dream coastal lifestyle in this beautifully renovated single-family home located in the exclusive neighborhood of Siesta Cove, just steps away from the acclaimed Siesta Key Beach—voted the number one beach in the United States! This elegant residence boasts 3 spacious bedrooms and 2 luxurious bathrooms, offering a high

  Beth Dilley ASCENDIA REAL ESTATE

  1224 S View Dr, 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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  $14,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • House for Rent

  211 Island Cir, Sarasota, FL 34242

  AVAILABLE for 2026... Jan., Feb and April Fantastic pool home located .4 mile from Siesta Beach access! Enjoy this completely renovated 3 bedroom / 2bath pool home in Palm Island on Siesta Key. With comfort in mind, vacation memories are waiting to be made here! All furnishings, appliances and flooring are new and decorated in coastal colors. Enjoy a morning walk to the powdery sand beach less

  Brenda Cozy COLDWELL BANKER REALTY

  211 Island Cir, Sarasota, FL 34242
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  $8,370 Per Month

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

  6154 Midnight Pass Rd Unit B04, Sarasota, FL 34242

  This newly furnished and decorated 2 bedroom villa with a brand new king mattress, and sleeper sofa, accommodates up to 6 guests. The master bedroom offers a king bed, private bath and cable TV. The guest bedroom offers 2 twin beds and cable. Villa B4 offers HD TV, DVD, movie choices, surround sound, and wireless internet services. Fully screened lanai offers seating and privacy shades for your

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit B04, 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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  $3,500 Per Month

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

  137 Avenida Messina Unit 2, Sarasota, FL 34242

  Flexible lease options available: 12-month annual lease at list price, or 2 plus months stays available for additional fees—perfect whether you're seeking a year-round island home or an extended winter escape. Discover the ultimate Siesta Key lifestyle in this beautifully renovated ground-floor retreat, perfectly positioned less than one block from the heart of Siesta Key Village and two blocks

  Laura Rode KW COASTAL LIVING III

  137 Avenida Messina Unit 2, Sarasota, FL 34242
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  $5,370 Per Month

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

  6006 Midnight Pass Rd Unit 5, Sarasota, FL 34242

  Starting at $179/night! Welcome to your vibrant beachside retreat—a beautifully renovated 1-bedroom, 1-bathroom oasis where modern comfort meets coastal charm. Thoughtfully designed with relaxation in mind, the serene bedroom features a deluxe queen bed dressed in premium linens, perfect for restful nights after sun-filled days. The fully equipped kitchen boasts modern appliances, cookware, and a

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 5, 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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  $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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