$8,500 per month
- 2 Beds
- 2 Baths
- 1,455 Sq Ft
- Condo for Rent
1195 Coquille St Unit 309, Sarasota, FL 34242
1195 Coquille St Unit 309, Sarasota, FL 34242
162
Homes for Rent in ZIP Code 34242
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$15,000 per month
- 4 Beds
- 4.5 Baths
- 4,306 Sq Ft
- House for Rent
1145 Horizon View Dr, Sarasota, FL 34242
1145 Horizon View Dr, Sarasota, FL 34242Spend Christmas in Paradise!Available December 10th through December 31st, 2025Available 3/7-3/13/26Available after 4/11/26 Experience the best of Siesta Key living with private beach access—this expansive, exceptional home offers everything needed for the perfect coastal escape. Thoughtfully designed indoor and outdoor living spaces create comfort and privacy even when hosting a full
Robert Bevington SHOWTIME REALTY
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$2,399 per month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- Townhouse for Rent
5231 Calle de Costa Rica Unit A, Sarasota, FL 34242
5231 Calle de Costa Rica Unit A, Sarasota, FL 34242ANNUAL unfurnished lease ONLY!!!! FRONT Unit of duplex. Rarely available 1 bedroom, 1 bath with huge new deck! Off street parking. New A/C! Gorgeous original wood floors!! New bonus room floor, new appliances! Washer and dryer on site, shared only with back unit. Located just half a mile to the famous Siesta Key beaches, just steps from a Kayak launch and half a mile in the other direction to the
Patrick Ritchey RE/MAX ALLIANCE GROUP
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$6,100 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 303, Sarasota, FL 34242
1250 N Portofino Dr Unit 303, Sarasota, FL 34242Available 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
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$7,450 per month
- 3 Beds
- 3 Baths
- 1,590 Sq Ft
- House for Rent
314 Avenida de Paradisio, Siesta Key, FL 34242
314 Avenida de Paradisio, Siesta Key, FL 34242Property 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
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$16,500 per month
- 4 Beds
- 5 Baths
- 4,006 Sq Ft
- House for Rent
7647 Sanderling Rd, Sarasota, FL 34242
7647 Sanderling Rd, Sarasota, FL 34242Annual single-family pool home available for lease in Sanderling Club Siesta Key! The Ness House, originally built in 1961 via John Lambie Sr.'s innovative Lambo lithic poured concrete method and renovated in 1971 with architect Tim Seibert, exemplifies Sarasota School of Architecture. It boasts an advanced rainwater collection system, natural cooling via roof outlets and north-facing walls, and
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$5,850 per month
- 2 Beds
- 2 Baths
- 1,285 Sq Ft
- Condo for Rent
5830 Midnight Pass Rd Unit 802, Sarasota, FL 34242
5830 Midnight Pass Rd Unit 802, Sarasota, FL 34242Property 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
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$3,500 per month
- 2 Beds
- 1.5 Baths
- 1,122 Sq Ft
- Townhouse for Rent
11 Sandy Cove Rd Unit 8F, Sarasota, FL 34242
11 Sandy Cove Rd Unit 8F, Sarasota, FL 34242Sandy 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
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$4,250 per month
- 2 Beds
- 2 Baths
- 1,435 Sq Ft
- Condo for Rent
4822 Ocean Blvd Unit 3D, Siesta Key, FL 34242
4822 Ocean Blvd Unit 3D, Siesta Key, FL 34242Property 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
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$10,000 per month
- 2 Beds
- 2 Baths
- 1,115 Sq Ft
- Condo for Rent
8630 Midnight Pass Rd Unit A303, Sarasota, FL 34242
8630 Midnight Pass Rd Unit A303, Sarasota, FL 34242 -
$6,000 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Condo for Rent
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242 -
$10,000 per month
- 3 Beds
- 2.5 Baths
- 2,467 Sq Ft
- Condo for Rent
1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242Waterfront 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
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$6,200 per month
- 2 Beds
- 2 Baths
- 1,357 Sq Ft
- Condo for Rent
8735 Midnight Pass Rd Unit 206b, Sarasota, FL 34242
8735 Midnight Pass Rd Unit 206b, Sarasota, FL 34242Looking 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
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$3,300 per month
- 2 Beds
- 2 Baths
- 1,440 Sq Ft
- Condo for Rent
4822 Ocean Blvd Unit 2D, Siesta Key, FL 34242
4822 Ocean Blvd Unit 2D, Siesta Key, FL 34242This 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
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$6,500 per month
- 2 Beds
- 2 Baths
- 1,264 Sq Ft
- House for Rent
143 Whispering Sands Dr, Sarasota, FL 34242
143 Whispering Sands Dr, Sarasota, FL 34242Available for season March and April 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
Maureen Plichta STRINGER MANAGEMENT INC
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$6,000 per month
- 2 Beds
- 2 Baths
- 1,650 Sq Ft
- Condo for Rent
8710 Midnight Pass Rd Unit 203B, Sarasota, FL 34242
8710 Midnight Pass Rd Unit 203B, Sarasota, FL 34242Nestled 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
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$6,950 per month
- 2 Beds
- 2 Baths
- 1,217 Sq Ft
- Condo for Rent
1249 Dockside Place Unit 110, Sarasota, FL 34242
1249 Dockside Place Unit 110, Sarasota, FL 34242LOCATION 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
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$7,000 per month
- 2 Beds
- 2 Baths
- 1,498 Sq Ft
- Condo for Rent
5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242
5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242AVAILABLE 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
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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
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242Discover 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
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$10,000 per month
- 2 Beds
- 2 Baths
- 1,265 Sq Ft
- Condo for Rent
6480 Midnight Pass Rd Unit 311, Sarasota, FL 34242
6480 Midnight Pass Rd Unit 311, Sarasota, FL 34242Your 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
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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
1137 N Moonmist Ct Unit L7, Sarasota, FL 34242This 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
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$3,000 per month
- 2 Beds
- 2 Baths
- 1,029 Sq Ft
- Condo for Rent
9397 Midnight Pass Rd Unit 405, Sarasota, FL 34242
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
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$8,400 per month
- 4 Beds
- 4 Baths
- 2,134 Sq Ft
- House for Rent
1100 Point of Rocks Rd, Sarasota, FL 34242
1100 Point of Rocks Rd, Sarasota, FL 34242This is a short term rental. Listing price reflects off season rate, high season rates will be higher. Whether you’re seeking a relaxing beach escape or an adventure-filled vacation, Sanctuary at the Point offers the perfect home base. Its prime location, luxurious amenities, and proximity to both the beach and South Siesta Key Village make it an exceptional choice for creating unforgettable
Beth Dilley ASCENDIA REAL ESTATE
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$6,000 per month
- 3 Beds
- 2.5 Baths
- 2,012 Sq Ft
- Townhouse for Rent
357 Tierra Mar Ln Unit 5, Sarasota, FL 34242
357 Tierra Mar Ln Unit 5, Sarasota, FL 34242Siesta 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
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$2,000 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Apartment for Rent
6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242
6327 Midnight Pass Rd Unit 999, Sarasota, FL 34242What 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
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$3,900 per month
- 1 Bed
- 1 Bath
- 778 Sq Ft
- Condo for Rent
9397 Midnight Pass Rd Unit P3, Sarasota, FL 34242
9397 Midnight Pass Rd Unit P3, Sarasota, FL 34242AVAILABLE 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
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$12,000 per month
- 2 Beds
- 2 Baths
- 1,464 Sq Ft
- Condo for Rent
19 Whispering Sands Dr Unit 302, Sarasota, FL 34242
19 Whispering Sands Dr Unit 302, Sarasota, FL 34242Experience 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
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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
4660 Ocean Blvd Unit N1, Sarasota, FL 34242Escape 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
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$7,500 per month
- 2 Beds
- 2 Baths
- 1,115 Sq Ft
- Condo for Rent
8635 Midnight Pass Rd Unit 206C, Sarasota, FL 34242
8635 Midnight Pass Rd Unit 206C, Sarasota, FL 34242Fantastic 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
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$3,500 per month
- 2 Beds
- 2 Baths
- 1,338 Sq Ft
- Condo for Rent
8776 Midnight Pass Rd Unit C107, Sarasota, FL 34242
8776 Midnight Pass Rd Unit C107, Sarasota, FL 34242Available 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
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$2,750 per month
- 2 Beds
- 2 Baths
- 1,338 Sq Ft
- Condo for Rent
8776 Midnight Pass Rd Unit C307, Sarasota, FL 34242
8776 Midnight Pass Rd Unit C307, Sarasota, FL 34242Available 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
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$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 -
$3,250 per month
- 2 Beds
- 2 Baths
- 1,357 Sq Ft
- Condo for Rent
8701 Midnight Pass Rd Unit 106A, Sarasota, FL 34242
8701 Midnight Pass Rd Unit 106A, Sarasota, FL 34242The 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
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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
6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242Welcome 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.
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$3,600 per month
- 3 Beds
- 2 Baths
- 1,737 Sq Ft
- Condo for Rent
1255 Dockside Place Unit 211, Sarasota, FL 34242
1255 Dockside Place Unit 211, Sarasota, FL 34242Welcome 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.
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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
1250 N Portofino Dr Unit 302, Sarasota, FL 3424255+ 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.
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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
6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242Welcome 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.
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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
5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242Welcome 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
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$5,000 per month
- 3 Beds
- 2 Baths
- 1,840 Sq Ft
- House for Rent
735 Birdsong Ln, Sarasota, FL 34242
735 Birdsong Ln, Sarasota, FL 34242Looking 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
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$6,300 per month
- 3 Beds
- 2.5 Baths
- 2,260 Sq Ft
- Condo for Rent
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
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