Siesta Key, FL Homes for Rent

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  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Apartment for Rent

  5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242

  Newly remodeled and furnished “Bougie beach bungalow” on Siesta Key Island. This Condo will “wow” you from the first moment you enter. Just say Alexa turn lights on and your command will be answered. This condo is on the first floor and it’s just a few minutes walk from the siesta key public beach access. The community is very welcoming to all guest and has a heated pool year-round and also many

  Stephanie Fox EXP REALTY LLC

  5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242
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  $3,400 per month

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

  4660 Ocean Blvd Unit P1, Sarasota, FL 34242

  Long term rental turnkey furnished waterfront condo in the desirable Sea Village community. Enjoy stunning views of Big Pass and the Gulf, plus easy access to the community pool. The home features travertine flooring, crown molding, hurricane-rated sliders, plantation shutters, and an open living/dining layout. The kitchen includes wood cabinetry, granite countertops, a breakfast bar, and quality

  Nelson Reyes SHOWTIME REALTY

  4660 Ocean Blvd Unit P1, 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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  /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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  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Condo for Rent

  5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242

  Available April 2026 and Beyond! The rate shown reflects the annual rental price. Seasonal rates for April 2026 may vary. Don’t miss the opportunity to secure this property, reach out for availability and details. Step into paradise at Casarina, a beautifully maintained beachfront community right on Siesta Key’s world-famous Crescent Beach. With 200 feet of private beach access, you’re just steps

  Cole Collins COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242
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  $7,500 per month

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

  5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

  Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is

  Robert Bevington SHOWTIME REALTY

  5830 Midnight Pass Rd Unit 54, 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. Available peak season months: January 2026, February 2026, April 2026. 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

  Beth Dilley ASCENDIA REAL ESTATE

  1137 N Moonmist Ct Unit L7, Sarasota, FL 34242
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  $7,900 per month

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

  4660 Ocean Blvd Unit N1, Sarasota, FL 34242

  Escape to Paradise on Siesta Key! Your dream seasonal getaway awaits at 4660 Ocean Blvd Unit N1, Sarasota, FL 34242. Immerse yourself in the tranquil beauty of the Gulf Coast, where pristine sands meet crystal-clear waters.This exquisite 2-bedroom, 2-bathroom condo is your ticket to an unforgettable retreat. Step into your sun-drenched sanctuary, tastefully furnished to embody comfort and

  Robert Bevington SHOWTIME REALTY

  4660 Ocean Blvd Unit N1, Sarasota, FL 34242
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  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,210 Sq Ft
  • House for Rent

  6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242

  Welcome to your bright and inviting Siesta Key vacation retreat! Enjoy deeded beach access to the stunning Siesta Key Beach, just steps away, where sun and surf await. Relax by Siesta Key’s largest heated pool or unwind in the lush, park-like setting with peaceful bay views. Explore the nearby vibrant Village on Siesta Key, filled with diverse dining, unique shops, and lively events. With

  Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

  6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242
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  /23

  $3,600 per month

  • 3 Beds
  • 2 Baths
  • 1,737 Sq Ft
  • Condo for Rent

  1255 Dockside Place Unit 211, Sarasota, FL 34242

  Welcome to your ideal Siesta Key retreat! This charming 2-bedroom, 2-bath condo comfortably sleeps up to 6 guests and is just a short walk from the world-famous Siesta Key Beach. Whether you’re looking to relax or stay active, this inviting property offers everything you need for an unforgettable vacation.The Space:Step inside this peaceful condo featuring a spacious main bedroom with

  Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

  1255 Dockside Place Unit 211, Sarasota, FL 34242
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  $3,150 per month

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

  1250 N Portofino Dr Unit 302, Sarasota, FL 34242

  55+ Harbor View Haven on Siesta Key w/beach access!Discover relaxation and adventure at our Siesta Harbor condo on Siesta Key. This bright 2 bedroom unit offers modern comfort and stunning harbor views from the screened porch. Enjoy deeded beach access and watch breathtaking sunsets. You'll have access to amenities like a fishing pier, boat slips, a pool, and clubhouse activities. Whether

  Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

  1250 N Portofino Dr Unit 302, 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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  $10,000 per month

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

  5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242

  Welcome to Gulf Horizon, your luxurious coastal escape at the Gulf & Bay Club in beautiful Siesta Key. Professionally managed by Gulf Coast Vacations, this stunning 2-bedroom, 2-bathroom sixth-floor gulf-view condo offers the ultimate blend of elegance, comfort, and breathtaking scenery in one of the island’s most exclusive beachfront communities.From the moment you step into the elegant

  Andy Moore GULF COAST REALTY & MANAGEMENT

  5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242
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  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Condo for Rent

  5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242

  Welcome to your perfect Siesta Key getaway! This beautifully updated 2-bedroom, 2-bath end-unit condo in the Palm Bay Club offers stunning bay views, a bright, open interior, and resort-style amenities—just steps from the Bayfront pool.At 1,270 sq. ft., this is one of the largest condos in Palm Bay. You'll love the driftwood-style cabinetry, quartz countertops, and stainless steel appliances

  Robert Bevington SHOWTIME REALTY

  5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
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  $5,000 per month

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

  6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

  Beachfront Bliss at Casa Mar – Siesta KeyDreaming of a Siesta Key getaway? Welcome to Unit 15 at Casa Mar, a charming 1BR/1BA beachfront condo that offers the perfect mix of relaxation and resort-style fun.Step outside and enjoy exclusive access to Casa Mar’s private stretch of quartz-white sand, complete with lounge chairs for sunbathing and unforgettable Gulf views. Cool off with a swim

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
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  $6,500 per month

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

  1215 S Portofino Dr Unit 202, Sarasota, FL 34242

  BEAUTIFUL WATERFRONT CONDO ON SIESTA KEY AVAILABLE NOW AND the month of January! CANAL VIEW • BEACH ACCESS • BOAT SLIPS UPON AVAILABILITY - REASONABLY PRICED. Now available In Season and as an annual Rental! Private, beautifully furnished condo with a gorgeous view of the Harbor and Sailboat Water Canal in Siesta Harbor. Enjoy water views of the canal from your enclosed balcony and just a

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  1215 S Portofino Dr Unit 202, Sarasota, FL 34242
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  $15,000 per month

  • 3 Beds
  • 3 Baths
  • 1,898 Sq Ft
  • Condo for Rent

  22 Sandy Cove Rd Unit 10-5, Sarasota, FL 34242

  RATES AND AVAILABILITY VARY. AVAILABLE SEASON 2026! Welcome to a completely renovated, light-filled penthouse in the exclusive Sandy Cove community — where coastal design meets breathtaking Gulf views in every direction. This professionally managed 3-bedroom, 3-bath residence is fully turnkey furnished and thoughtfully designed for relaxed, upscale living.Every inch of the home has been

  Cole Collins COLDWELL BANKER REALTY

  22 Sandy Cove Rd Unit 10-5, 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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  $15,000 per month

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • House for Rent

  4879 Commonwealth Dr, Sarasota, FL 34242

  FULLY FURNISHED rental available in Siesta Key, close to the beach and walking distance to Siesta Key Village. RENTAL PRICE depends on total LENGTH OF STAY. Rent a Rare Piece of Sarasota's Architectural History on Siesta Key! Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Boasting

  Daniel Petrilla PREFERRED SHORE LLC

  4879 Commonwealth Dr, Sarasota, FL 34242
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  $3,500 per month

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Condo for Rent

  1700 Cove II Place Unit 310, Sarasota, FL 34242

  Available 3500.00 Monthly - September 17th 2026 through December 31st 2026... Available January 2026 - 5,000.00 May be rented weekly. l – Stunning Water Views & Deeded Beach Access | Siesta Keyplus taxes and fees. Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and the spacious patio, along with

  Robert Bevington SHOWTIME REALTY

  1700 Cove II Place Unit 310, Sarasota, FL 34242
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  $5,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  4946 Commonwealth Dr, Sarasota, FL 34242

  Available as a monthly rental starting in May. Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the private dock,

  Beth Dilley ASCENDIA REAL ESTATE

  4946 Commonwealth Dr, Sarasota, FL 34242
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  $14,000 per month

  • 4 Beds
  • 3 Baths
  • 2,341 Sq Ft
  • House for Rent

  412 Treasure Boat Way, Sarasota, FL 34242

  Discover your dream home with this exquisite single family residence available for annual rental. This remarkable property redefines elegance and comfort, featuring stunning one-of-a-kind architecture that combines exceptional design with spacious living. Crafted for discerning tenants who appreciate the finer things in life, the home boasts four generously sized bedrooms and three luxurious

  Beth Dilley ASCENDIA REAL ESTATE

  412 Treasure Boat Way, Sarasota, FL 34242
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  $7,500 per month

  • 4 Beds
  • 3 Baths
  • 2,392 Sq Ft
  • House for Rent

  306 Island Cir, Sarasota, FL 34242

  Available now. Lovely pool home with canal water frontage located in Siesta Key's peaceful and secluded neighborhood of PalmIsland. Completely renovated with new kitchen, bathrooms, and floor coverings throughout this island retreat. Walk four blocks to the crystalsands of world famous Siesta Beach, and just a short walk to the Village. Beautiful backyard with spacious patio, heated

  Timothy Bloch QUEST PROPERTIES INC

  306 Island Cir, Sarasota, FL 34242
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  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit B, Sarasota, FL 34242

  Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit B, Sarasota, FL 34242
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  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit A, Sarasota, FL 34242

  Current Availability: 5/19/2024-5/25/2024, 5/30/2024-6/7/2024, 6/23/2024-7/26/2024, 8/24/2024-10/25/2024, 11/3/2024-11/7/2024, 11/17/2024-12/5/2024 If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is a few blocks to the beach. Beautifully updated,

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit A, Sarasota, FL 34242
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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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  $8,000 per month

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

  1200 E Peppertree Ln Unit 305, Sarasota, FL 34242

  3rd floor beautifully appointed. 2 bedroom 2 bath Unit is available Seasonal $7500; Yearly or 6 month rental $4500.000 Underground parking (1) space. Your own private washer and dryer inside unit. Tennis and pickle ball courts. Private Beach with Chairs. 2 heated pools, fitness room, clubhouses, fishing pier. Location is great.

  Lisa Beach WATERSIDE REALTY LLC

  1200 E Peppertree Ln Unit 305, Sarasota, FL 34242
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  $8,900 per month

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

  1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242

  Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. With breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat. The kitchen is equipped with stainless-steel appliances, and the adjacent dining table offers a great

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
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  $4,000 per month

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft
  • Condo for Rent

  1300 N Portofino Dr Unit 205, Sarasota, FL 34242

  Available now until 4.4.26. 55+ community. Welcome to your dream coastal escape in beautiful Siesta Harbor on Siesta Key! This turnkey furnished; spacious one-bedroom, two-bath condo is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere. Just a short stroll away, you'll enjoy deeded access to Siesta Key's

  Jonathan OSteen O'STEEN GROUP INC

  1300 N Portofino Dr Unit 205, 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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  $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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  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • Condo for Rent

  4822 Ocean Blvd Unit 2F, Sarasota, FL 34242

  Gulf Views!!Siesta Key! This captivating 2-bedroom, 2-bathroom condominium is found in Siesta Towers in Siesta Key and is close to restaurants and outdoor recreation. The complex is an easy pedestrian distance to Siesta Key Village, and convenient to Siesta Key Beach. The interior welcomes you with stylish fixtures blending seamlessly with bounteous window light and neutral decor. The large

  Jane Hunter JENNETTE PROPERTIES INC

  4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
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  $5,525 per month

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • House for Rent

  726 Birdsong Ln, Sarasota, FL 34242

  AVAILABLE after April 15, 2026! WOW! Enjoy a little slice of heaven on the World Famous Siesta Key! This beautifully renovated turnkey 3 bedroom 2 bath, heated pool home, is just a short distance to the #1 rated beaches and the quaint shops and restaurants in the downtown village. Whether it’s our million-dollar sunsets, endless watersports activities, Sunday’s famous Drum Circle, or to just

  Scott Nold TNG PROPERTY MANAGEMENT

  726 Birdsong Ln, Sarasota, FL 34242
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  $9,500 per month

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

  1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242

  Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
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  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Condo for Rent

  1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242

  Welcome to this stunning 2-bedroom, 2-bathroom lakefront condo located on the second floor in Gulf and Bay Bayside, Siesta Key. This two-story retreat features two primary bedrooms, each with a luxurious king-size bed, spacious walk-in closets, and beautifully appointed bathrooms with walk-in showers. In the second floor primary bedroom there is additional sleeping accommodations with a full-size

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
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  $3,000 per month

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

  5400 Ocean Blvd Unit 1-5, Sarasota, FL 34242

  AVAILABLE for 2026 SEASON or ANNUALLY. Turnkey furnished unit in the exclusive Terrace building on Siesta Key beach steps away from Siesta Key Village. Enjoy a swim from the elevated pool and catch a sunset while relaxing with a drink. This first floor condo offers a very large balcony with partial beach views as well as Siesta Village and is on the same floor to access the pool area. Washer and

  Brenda Cozy COLDWELL BANKER REALTY

  5400 Ocean Blvd Unit 1-5, Sarasota, FL 34242
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  $3,500 per month

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

  1215 S Portofino Dr Unit 308, Sarasota, FL 34242

  BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane glass lanai,

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  1215 S Portofino Dr Unit 308, Sarasota, FL 34242
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  $2,300 per month

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft
  • Condo for Rent

  1350 N Portofino Dr Unit 207, Sarasota, FL 34242

  This stunning one-bedroom, two-bathroom condo in Siesta Harbor in the Tarpon Building is the perfect combination of luxury, convenience, and breathtaking views. Located in a prime location, boating access, canal frontage, and mesmerizing Intracoastal Waterway views. Step inside and be captivated by the modern elegance of this home. The kitchen is a chef's dream, featuring stainless steel

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1350 N Portofino Dr Unit 207, Sarasota, FL 34242
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  $11,000 per month

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

  1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242

  Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.Guest reservations include beach tags, giving you private beach

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
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  $8,500 per month

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • House for Rent

  5216 Calle de Costa Rica, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely

  Beth Dilley ASCENDIA REAL ESTATE

  5216 Calle de Costa Rica, Sarasota, FL 34242

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