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3-Bedroom Homes for Rent in Siesta Key, FL

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  • /50

    $6,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,260 Sq Ft
    • Condo for Rent

    5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242

    RARE OPPORTUNITY to RENT THE PENTHOUSE. 3 BEDS/2.5 BATHS full size washer/dryer and a roof top deck with panoramic views available September 2025 stay for a year, 2 or 3+ owner wants this beautiful turnkey home with a BOAT DOCK (no lift yet)RENTED LONG TERM. Owner open to lift discussion. You will enjoy Penthouse end unit in Boca Siesta is located in the heart of Siesta Key the #1 Beach in the

    Agent Photo

    Marianne LeBar

    ROSEBAY INTERNATIONAL REALTY, INC

    (941) 294-2866

    5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
  • /45

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft
    • House for Rent

    735 Birdsong Ln, Sarasota, FL 34242

    Looking for the ultimate Siesta Key getaway? This stunning 3-bedroom, 2-bath home offers everything you need for a dream vacation, just 1 mile from the famous Siesta Key Beach and a quick bike ride to the lively Siesta Key Village! Available Nov 1-Dec 21, 2025, and May 1-Nov 21, 2026. 30 day minimum stay, NOT available annually. Fully turnkey furnished, this home is ready to welcome you the

    Scott Nold TNG PROPERTY MANAGEMENT

    735 Birdsong Ln, Sarasota, FL 34242
  • /38

    $20,000 per month

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

    22 Sandy Cove Rd Unit 105W, Sarasota, FL 34242

    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 updated with all-new finishes, furnishings, and a

    Cole Collins COLDWELL BANKER REALTY

    22 Sandy Cove Rd Unit 105W, Sarasota, FL 34242
  • /39

    $3,995 per month

    • 3 Beds
    • 2 Baths
    • 2,134 Sq Ft
    • House for Rent

    733 Tropical Cir, Sarasota, FL 34242

    Siesta Key Custom Pool Home, Vaulted Ceilings and Skylights- Architectural Gem.Welcome to 733 Tropical Circle — a custom-designed retreat tucked away in the heart of Siesta Key. This 3-bedroom, 2-bathroom home offers a unique blend of natural warmth, architectural character, and relaxed coastal charm.Step inside to soaring ceilings with skylights and stunning wood accents that fill

    Alyssa Cromie NEXTHOME EXCELLENCE

    733 Tropical Cir, Sarasota, FL 34242
  • /36

    $14,000 per month

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

    211 Island Cir, Sarasota, FL 34242

    AVAILABLE 2026 Season and July-Nov. 2025. 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
  • /55

    $5,000 per month

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

    4946 Commonwealth Dr, Sarasota, FL 34242

    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, watching for playful manatees and jumping fish,

    Beth Dilley ASCENDIA REAL ESTATE

    4946 Commonwealth Dr, Sarasota, FL 34242
  • /21

    $5,895 per month

    • 3 Beds
    • 2 Baths
    • 2,098 Sq Ft
    • House for Rent

    935 Contento St, Sarasota, FL 34242

    NEW PRICE! Rare waterfront Siesta Key pool home available for annual rental! This beautifully-renovated 3/2/2 pool home in Siesta Isles is available for immediate occupancy. This impressive property offers 100 feet of waterfront along Siesta Key's Grand Canal. The gourmet kitchen features quartz counters, stainless steel appliances, built-in microwave/wall-oven combo, island cooktop with hood

    Jennifer Herman MOUNT VERNON PROPERTY MGMT INC

    935 Contento St, Sarasota, FL 34242
  • /74

    $6,000 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
  • /51

    $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
  • /40

    $8,500 per month

    • 3 Beds
    • 4 Baths
    • 2,168 Sq Ft
    • House for Rent

    1256 Riegels Landing Dr, Sarasota, FL 34242

    This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full

    Christopher Davenport STARLINK REALTY INC

    1256 Riegels Landing Dr, Sarasota, FL 34242
  • /84

    $16,000 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, this home has so much to offer. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with

    Chrissie Cummings JENNETTE PROPERTIES INC

    327 Avenida Milano, Sarasota, FL 34242
  • /56

    $5,250 per month

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

    726 Birdsong Ln, Sarasota, FL 34242

    AVAILABLE October, November 2025! Currently booked through September 2025. Also booked December - March 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

    Scott Nold TNG PROPERTY MANAGEMENT

    726 Birdsong Ln, Sarasota, FL 34242
  • /17

    $15,000 per month

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft
    • House for Rent

    339 Avenida de Paradisio, Sarasota, FL 34242

    scape to luxury in our serene Sarasota home! ????Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort.??? Just a 3-Min Drive to Siesta Beach??? 10 Minutes to Crescent Beach????? 13-Min Walk to a Local BeachDiscover the best of Sarasota with us!

    Valerie McInerney LPT REALTY, LLC

    339 Avenida de Paradisio, Sarasota, FL 34242
  • /40

    $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
  • /80

    $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
  • /48

    $13,200 per month

    • 3 Beds
    • 2.5 Baths
    • 2,041 Sq Ft
    • Condo for Rent

    306 Beach Rd Unit 306, Sarasota, FL 34242

    Take some time to get away from it all.. we have the perfect place for you and your family to stay! This Spanish style tri-level home is in one of the greatest locations on Siesta Key Beach, Florida. Walk up the windowed staircase to the second floor where you’ll enjoy cooking and hanging out with the family! Enjoy your morning coffee or dinner on the balcony. Time for some fun in the sun! Walk,

    Beth Dilley ASCENDIA REAL ESTATE

    306 Beach Rd Unit 306, Sarasota, FL 34242
  • /58

    $8,000 per month

    • 3 Beds
    • 2 Baths
    • 2,002 Sq Ft
    • House for Rent

    5640 Cape Leyte Dr, Sarasota, FL 34242

    It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the

    Beth Dilley ASCENDIA REAL ESTATE

    5640 Cape Leyte Dr, Sarasota, FL 34242
  • /59

    $10,500 per month

    • 3 Beds
    • 3 Baths
    • 1,999 Sq Ft
    • House for Rent

    5024 Higel Ave, Sarasota, FL 34242

    Spectacular is an understatement when describing this updated Siesta Key CANAL FRONT POOL HOME. Once you step inside you'll notice an open-airy floor plan, beautifully decorated to reflect a modern beach-style home! Enjoy the master bedroom with BEAUTIFUL VIEWS of the canal and your very own access to the refreshing POOL and SPACIOUS PATIO! The additional two bedrooms are roomy and private with

    Beth Dilley ASCENDIA REAL ESTATE

    5024 Higel Ave, Sarasota, FL 34242
  • /38

    $8,900 per month

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

    1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242

    Welcome to this stunning second-level condo nestled within the prestigious Gulf and Bay Club Bayside in the serene enclave of Siesta Key. Boasting breathtaking views of the shimmering lake, this meticulously designed residence offers the epitome of luxurious coastal living.As you step inside, you are greeted by an inviting ambiance that seamlessly blends modern elegance with coastal

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
  • /58

    $8,000 per month

    • 3 Beds
    • 3 Baths
    • 1,835 Sq Ft
    • Condo for Rent

    1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242

    Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
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    $5,000 per month

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

    1391 Siesta Bayside Dr Unit 1391B, 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

    1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242
  • /18

    $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
  • /89

    $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

    Beth Dilley ASCENDIA REAL ESTATE

    4900 Ocean Blvd Unit 501, Sarasota, FL 34242
  • /54

    $9,500 per month

    • 3 Beds
    • 2 Baths
    • 1,835 Sq Ft
    • Condo for Rent

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242

    Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
  • /27

    $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
  • /36

    $9,300 per month

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

    1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242

    Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access – 5 minute walk. Tile floors throughout and completely re-decorated and furnished with many amenities for your family’s enjoyment. King bed in the master and two doubles in the guest room.*Taxes and fees not included.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
  • /60

    $15,000 per month

    • 3 Beds
    • 2 Baths
    • 2,259 Sq Ft
    • House for Rent

    5516 Avenida Del Mare, Sarasota, FL 34242

    Listing reflects peak season rate. Available peak season months: January 5th - February 6th 2026, April 2026. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kiddos

    Beth Dilley ASCENDIA REAL ESTATE

    5516 Avenida Del Mare, Sarasota, FL 34242
  • /98

    $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. Available peak season months: January 2026, February 2026, March 2026, April 2026. 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

    Beth Dilley ASCENDIA REAL ESTATE

    345 Avenida Leona, Sarasota, FL 34242
  • /99

    $5,900 per month

    • 3 Beds
    • 3.5 Baths
    • 2,490 Sq Ft
    • Condo for Rent

    1660 Summerhouse Ln Unit 301, Sarasota, FL 34242

    LOCATION, LOCATION, LOCATION!!! Stunning large luxury condo located in the sought after community of Summer Cove on Siesta Key is available for an ANNUAL LEASE. This corner unit, light and bright property has been meticulously professionally decorated and it shows. Three bedrooms, three and a half bathrooms, turnkey furnished, three open lanais that face east and west, living room/kitchen/dining

    C. Alison Hunter JENNETTE PROPERTIES INC

    1660 Summerhouse Ln Unit 301, Sarasota, FL 34242
  • /43

    $3,900 per month

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

    4660 Ocean Blvd Unit B2, Sarasota, FL 34242

    SIESTA KEY WATERFRONT UNIT AVAILABLE AS FURNISHED LONG TERM. Sea Village offers million dollar views and is situated on 5 acres overlooking the Gulf. It provides a peaceful retreat with opportunities to witness breathtaking sunsets, the full moon reflecting on the water, and serene walks to the beach and Siesta Village. Additionally, its location on the north end of the Key provides convenient

    Margaret Young JENNETTE PROPERTIES, INC.

    4660 Ocean Blvd Unit B2, Sarasota, FL 34242
  • /14

    $30,000 per month

    • 3 Beds
    • 3 Baths
    • 3,395 Sq Ft
    • House for Rent

    95 Sandy Hook Rd S, Sarasota, FL 34242

    6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" Available NOW!!!!!!! IN SANDY HOOK, DIRECTLY ON THE GULF AT BIG PASS. ENJOY YOUR OWN private Beach!!!TROPICAL PARADISE. SIESTA KEY'S "OUTDOOR ACADEMY"!!! ONLY 1/2 MILE AWAY! One-of-a-kind enclave of Sandy Hook at USA's No 1 BEACH. A private road takes you to Elevated living area with entry

    Joseph Russo COURTYARD MODERN

    95 Sandy Hook Rd S, Sarasota, FL 34242
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