Homes for Rent in ZIP Code 34242

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  $7,500 Per Month

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

  116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242

  An Ascendia Property! **Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** Welcome to your BOHO CHIC beach retreat located near the famous Crescent Beach on Siesta Key! You'll feel right at home when you stay in this 2 bedroom, 2 bathroom (sleeps 5) condo. Spend time cooking your favorite meals in the fully stocked kitchen... Cozy up

  Beth Dilley ASCENDIA REAL ESTATE

  116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242
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  /22

  $8,340 Per Month

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

  6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242

  Enjoy your beach vacation in this beautiful large 2 bedroom, 2 bathroom private villa. Located halfway between the private beach and the pool/clubhouse. This unit can sleep up to 6 comfortably. Flat screen HD TV's in the living room and in each bedroom and ceiling fans throughout. Updated with tile throughout, and fully appointed kitchen with new stainless steel appliances. Roomy master bedroom

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 11, Sarasota, FL 34242
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  $7,920 Per Month

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

  1001 Point of Rocks Rd Unit 408, Sarasota, FL 34242

  Villa 408 at Siesta Sands is the perfect place to slow down and enjoy the best of island living. Bright and comfortable, this thoughtfully designed villa offers an open layout filled with natural light and a calm coastal feel that makes relaxing effortless. The well-equipped kitchen and inviting living areas provide a comfortable setting for easy meals, conversation, and downtime. Take in the

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1001 Point of Rocks Rd Unit 408, Sarasota, FL 34242
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  $7,470 Per Month

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

  6154 Midnight Pass Rd Unit B03, Sarasota, FL 34242

  Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually owned. The minimum stay is 5 or 7 nights, depending on the owner. Every Unit at Casa Blanca is individually decorated and fully furnished including all cookware and linens including beach towels. They have individually controlled AC/Heating and color cable TVs, WIFI, telephones

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit B03, Sarasota, FL 34242
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  $10,700 Per Month

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

  6018 W Peppertree Way Unit 231B, Sarasota, FL 34242

  Paradise awaits you at Siesta Key! Experience the beauty of the #1 Beach in the USA with this gorgeous 2 bedroom 2 bath stunning beach view condo overlooking the pool. This beautiful condo is just steps from the pool and Direct Beach Access. Amenities for the complex include: 2 fitness centers, 2 heated pools, a fishing pier, 2 clubhouses, pickle-ball and tennis courts. You will enjoy hopping on

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6018 W Peppertree Way Unit 231B, 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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  $9,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • House for Rent

  327 Avenida Milano, Sarasota, FL 34242

  Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully

  Chrissie Cummings JENNETTE PROPERTIES INC

  327 Avenida Milano, Sarasota, FL 34242
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  $12,000 Per Month

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

  1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242

  Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. 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

  1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
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  $18,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft
  • House for Rent

  345 Avenida Leona, Sarasota, FL 34242

  Listing reflects peak season rate. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a bright, coastal-styled haven designed for relaxation and comfort. The spacious primary

  Beth Dilley ASCENDIA REAL ESTATE

  345 Avenida Leona, Sarasota, FL 34242
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  $7,650 Per Month

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

  6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242

  Starting at $255/night! Experience the ultimate beachfront getaway at Villa 40, a beautifully appointed 2-bedroom, 2-bathroom condo at Casa Mar, thoughtfully designed to accommodate up to six guests in comfort and style. This spacious retreat features a king bed in the primary bedroom, two twin beds in the second bedroom, and a queen air mattress for added flexibility. The fully equipped kitchen

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
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  $6,650 Per Month

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 705, Sarasota, FL 34242

  This property is a 30 night minimum.1125 - 705 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx.175 yards away from Crescent beach.Open kitchen floor plan. Newly remodeled kitchen with stainless steel appliances. Dual sink vanity in the Master bathroom. Assigned covered parking located in parking garage.Approx. 1200 Sq. Ft. (1480 including the lanai). Condo

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 705, Sarasota, FL 34242
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  $7,800 Per Month

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

  6039 E Peppertree Way Unit 222, Sarasota, FL 34242

  This property is a 30 night minimum.This 2 bedroom, 2 bath is a first floor garden condo on the bay side of Midnight Pass.The master bedroom has a King bed, a ceiling fan, a 32 inch smart TV, and windows for natural light. The master bathroom has updated granite counters and a walk-in shower with a sliding glass door and a removable shower head.The guest bedroom has a king bed, a

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6039 E Peppertree Way Unit 222, Sarasota, FL 34242
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  $6,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Condo for Rent

  1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

  Welcome to your slice of paradise in Gulf & Bay Club Bayside, a highly sought-after community located on beautiful Siesta Key, Florida. Professionally managed by Gulf Coast Vacation rentals, this first-floor 2-bedroom, 2-bathroom lakefront condo offers the perfect blend of coastal charm and resort-style living. From the moment you step inside, you’ll be greeted by a beachy, relaxed vibe that

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
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  $2,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,953 Sq Ft
  • House for Rent

  5151 Oakmont Place, Sarasota, FL 34242

  Welcome to your dream home at 5151 Oakmont Place, nestled in the heart of the stunning Siesta Key, Sarasota, FL. This charming 3-bedroom, 2-bathroom residence offers 1,953 square feet of modern living space, designed for both comfort and style. Step inside to discover a thoughtfully laid-out floor plan that seamlessly blends contemporary design with functionality. The kitchen is a chef's delight,

  Beth Harris COMPASS FLORIDA LLC

  5151 Oakmont Place, Sarasota, FL 34242
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  $27,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • House for Rent

  6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242

  When only the best will do, Villa 26 at Aloha Kai is the perfect choice. Beautifully updated with meticulous attention to detail, this beachfront villa offers an ideal retreat where you can watch shorebirds, dolphins, and breathtaking sunsets from your private porch. The kitchen is a chef’s dream, while the bathrooms provide a spa-like experience for ultimate relaxation. Located on Siesta Key, a

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242
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  /22

  $8,370 Per Month

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

  6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242

  Early risers and night owls can live in harmony at Villa 50 at Aloha Kai, where the thoughtful layout features bedrooms upstairs and a convenient bathroom downstairs. This beautifully renovated villa boasts new flooring, an updated kitchen with stainless steel appliances, granite countertops, and modern bathrooms. Whether you're enjoying a meal in the spacious dining room or dining al fresco on

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 50, Sarasota, FL 34242
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  $2,450 Per Month

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft
  • Condo for Rent

  446 Canal Rd Unit 5, Sarasota, FL 34242

  This is a short term rental. Listing reflects peak season weekly rate. Discover Key Lime Retreat, an end-unit condo perfectly situated in the heart of Siesta Key. This delightful getaway combines comfort with modern style, ideal for families or a group of friends. Tucked away in a tropical garden setting, you'll enjoy access to a community pool, perfect for a refreshing dip. Everything you need

  Beth Dilley ASCENDIA REAL ESTATE

  446 Canal Rd Unit 5, Sarasota, FL 34242
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  $5,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Condo for Rent

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242

  Listing reflects off-season rate. Available August - December 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot to unwind. Step

  Beth Dilley ASCENDIA REAL ESTATE

  5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
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  /25

  $6,500 Per Month

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

  1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242

  Heaven on Siesta Key, in perfect condition, up to date, and simply beautiful. This spacious, first floor one bedroom with a bay/harbor water view from your lanai is immaculate, beautifully decorated and offers every comfort for your favorite vacation stay. The modern kitchen shines with new cabinets, lighting, paint, and kitchen work desk. Elegant bathroom with new walk in shower featuring

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1333 Siesta Bayside Dr Unit 1333D, Sarasota, FL 34242
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  $5,700 Per Month

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

  1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242

  Charming 2 bedroom/ 2 bath Condo just a short walk to the beach. Come enjoy our key-west style condo with a very rare 2 car garage. Two swimming pools, tennis court, pickleball, workout room and fishing dock round out the amenities on our lushly landscaped property. Nestled between palm trees, this ground floor condo does not have a unit above it. Impeccably clean and comfortable with a fully

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242
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  $4,700 Per Month

  • 3 Beds
  • 3 Baths
  • 1,867 Sq Ft
  • Condo for Rent

  4900 Ocean Blvd Unit 501, Sarasota, FL 34242

  Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! With three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the tropical

  Beth Dilley ASCENDIA REAL ESTATE

  4900 Ocean Blvd Unit 501, Sarasota, FL 34242
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  $7,470 Per Month

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

  6020 Midnight Pass Rd Unit 51, Sarasota, FL 34242

  New photos coming soon! Villa 51 at Aloha Kai is a beautifully updated retreat that offers the perfect setting for your beach getaway. Begin your day with coffee in the light and airy kitchen, then step out to enjoy it on your private front porch or back patio. The spacious living room features designer plantation shutters on the sliding doors, providing both elegance and privacy. The bedroom

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 51, Sarasota, FL 34242
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  $26,319 Per Month

  • 2 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Condo for Rent

  915 Seaside Dr Unit 512, Sarasota, FL 34242

  Bask in the sunshine and sit in the pristine crystal white sands on Crescent Beach, rated #1 in the country by Dr. Beach. This beachfront sanctuary offers a fitness center, heated pool, outdoor grotto style whirlpool hot tub, bicycles, kayaks and barbecue grills, the tiki bar offers food from the famous Morton’s and cabanas to shield you from the sun when you want some shade. The unit has top of

  Andy Moore GULF COAST REALTY & MANAGEMENT

  915 Seaside Dr Unit 512, Sarasota, FL 34242
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  /19

  $7,470 Per Month

  • 1 Bed
  • 10 Baths
  • 728 Sq Ft
  • House for Rent

  6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242

  Casa Blanca offers this charming 1 bedroom/1 bath villa in Siesta Key on the Gulf of Mexico. Spend your vacation in Villa A01, conveniently located to the pool and just a three-minute walk to Siesta Keys Crescent Beach, voted #1 beach in the US! This beautiful beach has soft; white quartz sands, a shade area and guests are provided with private access.The villa comes fully furnished and is a

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 1, Sarasota, FL 34242
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  $2,800 Per Month

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

  6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242

  Welcome to Sunrise Porch Lookout — your peaceful intercoastal retreat in the heart of Siesta Key. This bright and tropical second-floor condo is perfectly situated in the highly sought-after Provincial Gardens community, where Old Florida charm meets serene waterfront beauty. Overlooking the intercoastal waterway and lush park-like lawn, the screened-in wraparound porch is your front-row seat to

  Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

  6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
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  $7,470 Per Month

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

  6020 Midnight Pass Rd Unit 38, Sarasota, FL 34242

  Villa 38 at Aloha Kai offers a spacious living area that opens onto an enclosed porch—perfect for enjoying your morning coffee. Its unique design features beamed ceilings and eclectic furnishings, creating a charming beach bungalow atmosphere. The fully equipped kitchen has everything you need to prepare meals to enjoy on the patio, and a convenient walk-in shower adds to your comfort. Located on

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6020 Midnight Pass Rd Unit 38, Sarasota, FL 34242
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  $9,300 Per Month

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

  1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242

  Deeded Walking Access Directly to the Beach!New on the rental program - Beautifully updated 2-bedroom near the pool, tennis courts and path to the beach! Please be one of our first Guests!The moment you arrive at Gulf & Bay Club Bayside, you’ll appreciate the beauty, serenity, and charm of this "Key West” style village. Located on the bay across the street from world-famous Siesta

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
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  $5,370 Per Month

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

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242

  Starting at $179/night! Step into luxury and comfort at our newly renovated 2-bedroom, 1.5-bathroom condo, perfectly designed for your next getaway. This vibrant space features a fully equipped kitchen ready for your culinary adventures and a private carport just steps from the unit for hassle-free parking. Recently updated in Summer 2023, the condo comfortably accommodates up to six guests with

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
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  $8,970 Per Month

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

  6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242

  This is a fun tropically decorated beach villa that will put a smile on your face when you walk in!! This unit can easily occupy up to 6. We have recently remodeled the kitchen and both bathrooms. The master bedroom features a king size bed with a new pillow top mattress. The master bath is new with a roman walk in shower. There is an LCD TV, DVD player and a nice closet. The second bedroom has a

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 13, Sarasota, FL 34242
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  $2,995 Per Month

  • 2 Beds
  • 1.5 Baths
  • 981 Sq Ft
  • Townhouse for Rent

  Unlisted Address

  Welcome to this Siesta Key Florida fully furnished town house for rent, located on the barrier island of Siesta Key Florida #1 beach in USA, made famous for its pure quartz sugar sand. A truly tropical beach front community Sandy Cove in Siesta Key with private fishing pier, small private beach and beautiful ocean view, and only one block from Siesta Key Village. A rarely available 2 bedroom two

  Matthew fehniger JJF REALTY INC

  Unlisted Address
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  /27

  $5,700 Per Month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Apartment for Rent

  1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242

  Steps from beautiful Crescent Beach, this fully renovated 2 bedroom 2 full bathroom unit is located in Gulf-side High-rise on the 8th floor. Step into the extended living lanai area to experience wrap around views of the gulf. Enjoy a window bench, choice of comfy loveseats, or dine with a view of the blue waters and white sand.An updated kitchen with stainless steel appliances peeks through

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 802AA, Sarasota, FL 34242
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  /15

  $8,970 Per Month

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

  6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242

  Welcome to the newly renovated A04 Villa! Private entrance leads to the screened in lanai and open air space which includes the kitchen, dining area and comfortable seating to enjoy the large flat screen tv. The villa sleeps up to 6. 2 queen beds in the primary bedroom and 2 twin beds in the guest bedroom. Both bedrooms are also equipped with flat screen TVs. This large villa features 2

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit A04, Sarasota, FL 34242
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  /19

  $7,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,264 Sq Ft
  • House for Rent

  143 Whispering Sands Dr, Sarasota, FL 34242

  Available for season 2027! This 2 bedroom 2 bath villa with easy ground floor entry features tile flooring in the main living areas and plush new carpeting in the bedrooms. The stylish galley kitchen has been fully updated with custom white cabinetry, granite countertops and backsplash, recessed lighting, and brand-new GE appliances, perfect for preparing meals after a day at the beach.Enjoy

  Maureen Plichta STRINGER MANAGEMENT INC

  143 Whispering Sands Dr, Sarasota, FL 34242
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  /25

  $8,500 Per Month

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

  1125 W Peppertree Dr Unit 707, Sarasota, FL 34242

  2 BR - 2 BA - 4 Person Max - Gulf side - Mid-Rise - Approx.150 yards from beach This property is a 30 night minimum.This 2-bedroom, 2 bath located on the gulf side is approx. 150 yards from the beach. This unit is on the 7th floor, accessible via elevator or stairs. Plenty of room for dining at the 6-service dining table. Couches, a ceiling fan, and TV in the living room for

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 707, Sarasota, FL 34242
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  $10,770 Per Month

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

  6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242

  We welcome you to stay in our updated oceanfront condo on Siesta Key Crescent Beach - the best beach in Florida! Our spacious 2 bed/2 bath oceanfront home is 1080 square feet with an ocean view that cannot be beat! Unit #206 is part of the Casa Blanca Vacation Beach Resort, and the crystal white sand is steps away! Remodeled in 2023, fully equipped kitchen with quiet dishwasher, spacious living

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242
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  $7,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Condo for Rent

  19 Whispering Sands Dr Unit 106, Sarasota, FL 34242

  Still available for season January - April 2026l! Two bedroom 2 bath ground floor with view of the Gulf. Step outside and your on the sand! Escape the winter and be on the beach. Located in the heart of Siesta Key’s most desirable area, this property offers exceptional appeal with being just steps from the world-famous powdery white sand beach. Siesta Key Village is within easy walking distance,

  Maureen Plichta STRINGER MANAGEMENT INC

  19 Whispering Sands Dr Unit 106, Sarasota, FL 34242
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  $5,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • House for Rent

  5577 Contento Dr, Sarasota, FL 34242

  This is a short term rental. Listing reflects off season rate. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates throughout,

  Beth Dilley ASCENDIA REAL ESTATE

  5577 Contento Dr, Sarasota, FL 34242
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  /25

  $3,350 Per Month

  • 3 Beds
  • 4 Baths
  • 1,446 Sq Ft
  • Townhouse for Rent

  6840 Midnight Pass Rd Unit 6840, Sarasota, FL 34242

  Welcome the charming rarely available rental townhouse at Midnight Sea, a coastal paradise that promises the ultimate beachside experience. This stunning 2-bedroom plus non confirming BR on the lower level property is the epitome of convenience and coastal luxury, offering a relaxed beach lifestyle just moments away from the warm, white sands of Siesta Beach. Prime location - 200 yards to the #1

  Alina LeMay JOHN HARDING REALTY

  6840 Midnight Pass Rd Unit 6840, Sarasota, FL 34242
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  $3,550 Per Month

  • 2 Beds
  • 2 Baths
  • 1,233 Sq Ft
  • Condo for Rent

  8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242

  BOOKED FEB/APRIL 2026. AVAILABLE JANUARY 2026. UTILITIES INCLUDED. SIESTA KEY SPECTACULAR FULL BAY/INTRACOASTAL UNOBSTRUCTED VIEWS! BOOK YOUR BEACH GETAWAY NOW! Beautifully updated throughout Turnkey "top floor" Condo in this popular community of Sunrise Cove. Located on the southern end of Siesta Key, directly across the street from Turtle Beach! Upon entering the condo, you will immediately

  Chrissie Cummings JENNETTE PROPERTIES INC

  8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
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  /30

  $7,000 Per Month

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft
  • Condo for Rent

  1360 Siesta Bayside Dr, Sarasota, FL 34242

  This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The 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

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1360 Siesta Bayside Dr, Sarasota, FL 34242

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