$4,900 per month
199 Whispering Sands Dr Unit 105, Sarasota, FL 34242
199 Whispering Sands Dr Unit 105, Sarasota, FL 34242Explore Siesta Key
$6,500 per month
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
$2,200 per month
5631 Midnight Pass Rd Unit 1001, Sarasota, FL 34242
5631 Midnight Pass Rd Unit 1001, Sarasota, FL 34242
$4,500 per month
137 Avenida Messina Unit 2, Sarasota, FL 34242
137 Avenida Messina Unit 2, Sarasota, FL 34242
$8,000 per month
567 Venice Ln, Siesta Key, FL 34242
Property Id: 2125810Live the island lifestyle in this beautifully furnished 4-bedroom, 2-bath home ideally located just minutes from both Siesta Key Beach and the vibrant Siesta Village. This spacious residence offers a perfect blend of comfort and convenience, with an open layout designed for entertaining and everyday living.Step outside to your private oasis featuring a large
$7,500 per month
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
$6,500 per month
420 Beach Rd Unit 505, Sarasota, FL 34242
Property Id: 2073016Magical views of Siesta Key's famed Crescent Beach and the Gulf of Mexico await you from this turnkey-furnished, beachfront unit. Be amazed at the direct and unobstructed west-facing views from this beautifully updated Siesta Gulf View property. This unit is directly on the beach and has private access to Siesta Key's white quartz sand and tranquil blue waters. Take in
$3,500 per month
5141 Saint Albans Ave, Sarasota, FL 34242
Available now for an annual or 6-month lease, this furnished home is located in a coveted Siesta Key neighborhood, just moments from Siesta Village and Siesta Beach. It combines rustic charm with modern comfort, featuring a spacious living and dining area, an open kitchen with a breakfast bar, and a screened porch with tropical views. The master bedroom loft includes an en-suite bathroom and
Anthony Dalesandro BRIGHT REALTY
$17,000 per month
5334 Calle Florida, Sarasota, FL 34242
Beautiful home that was rebuilt in 1997 located on Palm Island on Siesta Key. Palm Island is considered the “heart of Siesta Key”. When the home was rebuilt it was raised 10 feet above ground. This home is a short walk to Siesta Beach, which has been named the #1 Beach in the USA numerous times. It is also just minutes from the Village that has restaurants, shopping, etc. You would have access to
Pat Gillum RE/MAX ALLIANCE GROUP
$7,500 per month
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
$2,000 per month
6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242
Tenant has access to all amenities located within Midnight Cove II such as tennis courts, swimming pool and grilling/picnic area.
Michelle Lentini EXCEPTIONS REALTY
$6,000 per month
357 Tierra Mar Ln Unit 5, Sarasota, FL 34242
Siesta Key Furnished Annual Rental. You will love living in this quiet enclave of 6 homes, tucked away from all of the hustle and bustle but walkable to all of the many dining, shopping and entertainment venues the vibrant Siesta Key Village offers! This amazing Townhome lives like a private residence and offers 3 bedrooms, and 2 and one half baths. This gorgeous home is tastefully decorated and
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY
$7,900 per month
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
$12,000 per month
19 Whispering Sands Dr Unit 302, Sarasota, FL 34242
Experience the ultimate beachfront lifestyle in this stunning two-bedroom, two-bathroom condo that's been completely renovated with fresh style and modern touches. With 1,464 square feet of thoughtfully designed living space, this home offers breathtaking full views of the Gulf of Mexico and pristine beach right outside your door.Step inside to discover a bright, open layout that
Frank Golio SARASOTA REALTY CENTER LLC
$5,250 per month
510 Givens St, Sarasota, FL 34242
Come check out this beautiful, fully furnished home offering 2,749 square feet of thoughtfully designed living space. Featuring a spacious master bedroom with an en-suite bathroom, a walk-in shower, and a relaxing bathtub, plus two additional generously sized bedrooms perfect for family or guests. The oversized living room is filled with natural light from a patio door opening to a screened-in
Terrence Garner GULF INCOME PROPERTIES, LLC
$6,000 per month
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.
$3,600 per month
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.
$3,150 per month
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.
$2,800 per month
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.
$10,000 per month
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
$5,000 per month
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
$8,500 per month
1221 Siesta Bayside Dr Unit 1221A, Sarasota, FL 34242
Beautifully turnkey furnished 2-bedroom, 2-bathroom, ground-floor condo available for monthly rent in a gated, resort-style community on Siesta Key. Just a short 5-minute walk to private access at world-famous Siesta Key Beach, known for its fine quartz sand and turquoise waters. This tropical retreat features a spacious open-concept layout, a fully equipped kitchen, in-unit laundry, private
Sinan Turkomer BROKER & BAKER INTERNATIONAL REALTY
$10,500 per month
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
$5,000 per month
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
$6,500 per month
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
$20,000 per month
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
$14,000 per month
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
$4,900 per month
5518 Shadow Lawn Dr, Sarasota, FL 34242
2 Bedroom, 2 Bath home on Siesta Key with deep water canal access and minutes to famous Siesta Key Beach and Village, public tennis and pickle ball courts and Out of Door Academy School. Walk to the beach, great restaurants and shopping. Bring your boat & kayaks! Concrete seawall with dock. Home has been completely remediated with new drywall and cabinets. All new stainless steel appliances and
Kelly Anderson RE/MAX ALLIANCE GROUP
$15,000 per month
4879 Commonwealth Dr, Sarasota, FL 34242
Lease 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. Originally crafted in 1957 by Frank Coleman and Tollen Twitchell, two influential figures in the Original Sarasota School of Architecture, this home seamlessly
Daniel Petrilla PREFERRED SHORE LLC
$3,500 per month
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
$5,000 per month
4946 Commonwealth Dr, Sarasota, FL 34242
Short Term Rental-Not available January-April of 2026Discover 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
Beth Dilley ASCENDIA REAL ESTATE
$14,000 per month
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
$4,500 per month
6006 Midnight Pass Rd Unit 21, Sarasota, FL 34242
Discover your beachside retreat on world-famous Siesta Key! This beautifully updated 1-bedroom, 1-bath ground-floor condo in the sought-after Casa Mar community offers the ultimate in coastal convenience—just a short stroll to private deeded beach access and the whi te sands of Siesta Beach.Step inside to a smoke-free, pet-free unit featuring wood plank flooring, modern leather furnishings, and
Robert Bevington SHOWTIME REALTY
$7,500 per month
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 swimming
Timothy Bloch QUEST PROPERTIES INC
$12,600 per month
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
$12,600 per month
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, this home
Robert Bevington SHOWTIME REALTY
$7,000 per month
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
$8,000 per month
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
$8,900 per month
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
$2,000 per month
1300 N Portofino Dr Unit 205, Sarasota, FL 34242
Available now through Dec 2025 for $2,000 per month. Available Jan-Mar 2026 for $6,000 per month. 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
Jonathan OSteen O'STEEN GROUP INC
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Siesta Key, located on a barrier island off the coast of Sarasota, Florida, is renowned for its pristine Siesta Beach, which boasts white quartz sand and was ranked the No. 2 beach in the United States by TripAdvisor in 2023. The island spans 8 miles, with most homes and activities concentrated on the north end, particularly around the downtown area and the quaint village district. This area features a variety of unique shops, restaurants, and nightclubs, enhancing the island's vibrant local flavor. Residents enjoy great walkability and a convenient trolley service that traverses the island. Housing options on Siesta Key include modern styles, Spanish Mediterraneans, ranch-style homes, cozy cottages, coastal-style homes, and several condominium complexes with amenities like pools and tennis courts. Dining highlights include the Toasted Mango Café, Miguel’s, and Captain Curt’s Crab & Oyster Bar, located roughly 3 miles south along the Midnight Pass corridor. The island also offers attractions such as Crescent Beach and Turtle Beach, with facilities for tennis, volleyball, and fishing. Education is served by the highly rated Out-of-Door Academy on the island and top-rated Sarasota County Schools, including Southside Elementary, Brookside Middle, and Riverview High. Siesta Key is accessible via the Siesta Key North Bridge and the Stickney Point Bascule Bridge, with the Sarasota Bradenton International Airport just 10 miles away.
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