$9,500 per month
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
$7,000 per month
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242
$4,500 per month
137 Avenida Messina Unit 2, Sarasota, FL 34242
137 Avenida Messina Unit 2, Sarasota, FL 34242
$6,300 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
$7,450 per month
314 Avenida de Paradisio, Siesta Key, FL 34242
Property Id: 2218418Walk through your private courtyard to this 3 bedroom, 3 bath home. This Split plan home has 2 bedrooms and 2 baths on one side and master bedroom and spa bath adjacent. Feature's a modern kitchen design with all stainless appliances and granite countertops and placement for easy entertaining and accessibility to living room and pool. Floors in the home have been
$6,100 per month
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
$5,850 per month
5830 Midnight Pass Rd Unit 802, Sarasota, FL 34242
Property Id: 2194753The stunning vistas of The Jamaica Royale Penthouse welcome you to your dream condo located on the 8th floor, overlooking the magnificent Siesta Key Beach. This fully remodeled and elegantly furnished 2-bedroom, 2-bathroom condo is the perfect getaway for anyone looking to enjoy the beauty of the Gulf Coast.As soon as you step into the condo, you'll be struck
$3,500 per month
11 Sandy Cove Rd Unit 8F, Sarasota, FL 34242
Sandy Cove – 2-Bedroom Vacation Rental! Available Nov 1 and beyond! Private Beach!The owner is offering unbelievable seasonal rates!Located in the sought-after Sandy Cove Community, just steps from Siesta Village with its own private beach and breathtaking Gulf sunsets. Fully turnkey furnished and ready to enjoy!
Cole Collins COLDWELL BANKER REALTY
$4,250 per month
4822 Ocean Blvd Unit 3D, Siesta Key, FL 34242
Property Id: 2175264This Siesta Key condominium in Siesta Towers offers two master suites. Welcome to this extraordinary living experience and location where every day you can enjoy the gulf views and the palm trees dotting the horizon. Swim and relax in the heated outdoor pool that sits right on the waterfront. Enjoy a drink on the cocktail pier while you watch the dolphins swim or bask
$6,500 per month
143 Whispering Sands Dr, Sarasota, FL 34242
Available for season 2026! 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
$3,300 per month
4822 Ocean Blvd Unit 2D, Siesta Key, FL 34242
This beautiful, UNFURNISHED, waterfront condo offers a luxurious and tranquil living experience on the shores of the Gulf of America and the Intercoastal waterway. With breathtaking views and a serene environment, this home is the perfect oasis for those seeking sophistication and relaxation. Located on the sought-after shores of Siesta Key, this condo truly captures the essence of coastal
$6,950 per month
1249 Dockside Place Unit 110, Sarasota, FL 34242
LOCATION< LOCATION< LOCATION! Welcome beach lovers. This 2 bedroom, 2 bath first floor condo with a one car garage on Siesta Key will fulfill all your dreams! Spend the day on the famous Siesta Key Beach (just steps away) then take a sunset boat! Play tennis/pickle ball on the private courts, lounge by the pool or fish out your back door. This condo is being offered turnkey furnished. Updated
Marisa Marino BRIGHT REALTY
$7,000 per month
5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242
AVAILABLE ASAP and SEASON 2026! Rates Vary! 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 away from the soft white sands and turquoise waters that make this destination so special.Your third-floor condo retreat comes fully furnished and ready for your
Cole Collins COLDWELL BANKER REALTY
$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
$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
What a deal!! Included is water, electric, wi-fi and cable. 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 or Seasonal Rental (4 month minimum). 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
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
$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
$15,000 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 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
$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
$7,500 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
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,
Robert Bevington SHOWTIME REALTY
Showing Results 1 - 40, Page 1 of 3
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.
Copyright © 2025 CoStar Group
