$4,500 per month
- 2 Beds
- 2 Baths
- 900 Sq Ft
- Condo for Rent
137 Avenida Messina Unit 2, Sarasota, FL 34242
137 Avenida Messina Unit 2, 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$9,200 per month
8710 Midnight Pass Rd Unit 405B, Sarasota, FL 34242
8710 Midnight Pass Rd Unit 405B, Sarasota, FL 34242$2,495 per month
9397 Midnight Pass Rd Unit 603, Sarasota, FL 34242
9397 Midnight Pass Rd Unit 603, Sarasota, FL 34242$9,500 per month
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242$8,500 per month
1195 Coquille St Unit 309, Sarasota, FL 34242
1195 Coquille St Unit 309, Sarasota, FL 34242$10,000 per month
8630 Midnight Pass Rd Unit A303, Sarasota, FL 34242
8630 Midnight Pass Rd Unit A303, Sarasota, FL 34242$6,000 per month
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242$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
$6,100 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
$10,000 per month
1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
Waterfront Elegance at Marina Del Sol – Your Seasonal Retreat. Indulge in the ultimate Sarasota lifestyle at this stunning 3-bedroom, 2,467 sq. ft. residence in the exclusive Marina Del Sol. Thoughtfully designed and beautifully updated, this spacious condo offers the perfect balance of elegance and comfort, with three oversized porches capturing serene water views and warm coastal breezes. Step
Olga Smith IMPERIAL PROPERTY GROUP LLC
$2,900 per month
6703 Midnight Pass Rd Unit 115, Sarasota, FL 34242
Property Id: 10621062 bedroom, 2 bath, newly updated condo located a few minutes from the beach and close to restaurants near the Stickney Point bridge. Pool and washer dryer available for tenants and reserved parking included.
$6,200 per month
8735 Midnight Pass Rd Unit 206b, Sarasota, FL 34242
Looking for a sunny escape from the winter chill? Welcome to your fully furnished seasonal rental in the sought-after Turtle Bay community on Siesta Key, just minutes from the award-winning sand of Siesta Key Beach. This beautifully updated second-floor 2-bedroom, 2-bath condo offers sweeping views of Sarasota Bay, high-quality finishes, and resort-style amenities, ideal for a 3-month seasonal
Justin Piccillo KW COASTAL LIVING III
$2,500 per month
6703 Midnight Pass Rd Unit 108, Sarasota, FL 34242
1 bedroom ground floor apartment with a garden / patio, pool, short walk to the beach. This one bedroom, one bath ground floor apartment with ceramic tile and an enclosed backyard/garden for lounging and barbecuing. Brand new AC, new cabinets, and granite counter tops in the kitchen along with a new ceramic top stove, microwave and dishwasher and a living room set with a queen size sofa
$6,000 per month
8710 Midnight Pass Rd Unit 203B, Sarasota, FL 34242
Nestled in a serene spot on Turtle Beach, this charming condo offers the perfect blend of coastal living and comfort. With breathtaking views it’s an ideal spot for relaxation or adventure. The condo features open-concept living with large windows that flood the space with natural light and allow you to enjoy the picturesque scenery right from the comfort of your own home. The interior is
Jennifer LeBlanc PRECISE REALTY CORP
$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
$10,000 per month
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
$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
$3,000 per month
9397 Midnight Pass Rd Unit 405, Sarasota, FL 34242
**NOW AVAILABLE EITHER AS A LONG-TERM OR SHORT-TERM RENTAL (minimum 3 months).** Here’s is your chance to live on the SOUTHERNMOST TIP OF SIESTA KEY and enjoy STUNNING SUNRISES & SUNSETS all year long. This WATERFRONT RENTAL is located at The Pointe, the CLOSEST CONDO complex to MIDNIGHT PASS! This one-of-a-kind gated community encompasses over 5+ acres of PRIME WATERFRONT real estate and is
Adam Waxler UKEEPCOMMISSION REAL ESTATE
$3,900 per month
9397 Midnight Pass Rd Unit P3, Sarasota, FL 34242
AVAILABLE FOR 2026 SEASON at $3,900/mo. (3-month minimum stay required.) Also available for ANNUAL RENTAL-$2800/mo. This rare penthouse rental at The Pointe on Siesta Key combines island luxury, incredible water views, and unmatched amenities—making it the ultimate Siesta Key retreat. This beautifully updated 1-bedroom, 1-bath penthouse condo blends comfort and style with sweeping water views
Andrea Eck CAPITAL REAL ESTATE ENTERPRISE
$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
$7,500 per month
8635 Midnight Pass Rd Unit 206C, Sarasota, FL 34242
Fantastic Beach to Bay community on south Siesta Key! Beach side cabanas, and bayside Boat/Fishing docks. Amazing waterfront views from this 2nd floor 2BR/2BA turnkey furnished condo. Grill areas and pools on both bay side and gulf side. Available anytime except for March 2026. 2025 rates are $1500/wk, 2026 Season rates are $7500/mo (one month minimum during season).
Stacey Andrews ANDREWS & ASSOCIATES REALTY
$3,500 per month
8776 Midnight Pass Rd Unit C107, Sarasota, FL 34242
Available November and December 2025 - 3500.00... - Not Available January through April 7th... 2026.. Experience the best of Siesta Key living at the Island Reef Association on Turtle Beach. This beautifully designed condo is offered fully turnkey furnished, showcasing exceptional attention to detail and high-quality finishes throughout.Island Reef delivers Beach-to-Bay luxury resort-style
Robert Bevington SHOWTIME REALTY
$2,750 per month
8776 Midnight Pass Rd Unit C307, Sarasota, FL 34242
Available June 1 2026 at this time. Experience the best of Beach to Bay Luxury Resort-Style Living in this beautifully designed 2-bedroom, 2-bathroom condo located in the sought-after Island Reef Association on Turtle Beach, Siesta Key. This spacious unit has been professionally designed and is offered fully turnkey furnished, with exceptional attention to detail and high-end finishes
Robert Bevington SHOWTIME REALTY
$3,250 per month
8701 Midnight Pass Rd Unit 106A, Sarasota, FL 34242
The owners are open and flexible, and are happy to consider all reasonable rental offers. Prime Location! Prime Living! Whether you're a local professional or a traveling professional seeking a long-term home base, this UNFURNISHED condo offers the perfect blend of comfort, convenience, and low-maintenance living. Located in the meticulously maintained Turtle Bay Community, this spacious and
Justin Piccillo KW COASTAL LIVING III
$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.
$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
$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
$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
$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
$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
$3,500 per month
8767 Midnight Pass Rd Unit 106F, Sarasota, FL 34242
Spacious two-bedroom Condo in Sarasota Florida on Siesta Key with deeded beach access! 2024 Trip Advisors named Siesta Key beaches the second-best in the United States and ninth best in the World. The Gulf side, private beach is less than a 5-minute walk within the confines of the Island Reef Condo Assoc. The Bay side is less congested than the Gulf Side and your pool, grill, shuffleboard, tennis
Vincent Muzychko EXP REALTY LLC
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