$2,200 per month
5631 Midnight Pass Rd Unit 1001, Sarasota, FL 34242
5631 Midnight Pass Rd Unit 1001, Sarasota, FL 34242
$15,000 per month
199 Whispering Sands Dr Unit 105, Sarasota, FL 34242
199 Whispering Sands Dr Unit 105, Sarasota, FL 34242
$6,500 per month
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
$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
Siesta Dreams at Casa Mar – 1BR/1BA Beachfront Condo with Resort AmenitiesWelcome to Siesta Dreams at Casa Mar, your perfect beach getaway on world-famous Siesta Key! This fully equipped 1-bedroom, 1-bath condo offers everything you need for a relaxing, sun-soaked vacation.Enjoy exclusive access to the resort’s private stretch of Siesta Key Beach, where lounge chairs await on the cool,
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 IN SEASON! 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 quick, short
Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC
$20,000 per month
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
$3,995 per month
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
$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
$5,500 per month
5518 Shadow Lawn Dr, Sarasota, FL 34242
2 Bedroom, 2 Bath home on Siesta Key with deep water canal access. Bring your boat & kayaks! Concrete seawall with dock. Home has been completely remediated with new drywall and cabinets. Close to Siesta Key Beach and Village. Located in the quiet neighborhood of Siesta Isles. Large home with open floor plan, screened in porch with large yard. Available immediately, annual lease, no smoking. New
Kelly Anderson RE/MAX ALLIANCE GROUP
$16,450 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
Weekly Rental – Stunning Water Views & Deeded Beach Access | Siesta KeyAlso Available Monthly from July 10th monthly 3500.00 plus 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 deeded access to the powdery white sands of world-famous Siesta Key
Robert Bevington SHOWTIME REALTY
$5,000 per month
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
$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
$13,500 per month
577 Venice Ln, Sarasota, FL 34242
Experience luxury living in this 2021 custom pool home located in one of Siesta Key’s most desirable neighborhoods. Featuring four spacious bedrooms, 3.5 baths, and a dedicated office, this modern West Indies-inspired home offers an open floor plan with soaring ceilings, abundant natural light, and coastal design. The gourmet kitchen boasts quartz countertops, stainless appliances, a walk-in
Robert Ruiz WILLIAM RAVEIS REAL ESTATE
$5,895 per month
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
$6,000 per month
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
$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
$4,000 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
$8,500 per month
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
$3,000 per month
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242
**Beachfront Bliss in Siesta Key? Modern 2 Bed, 2 Bath Condo** Discover this Gulf Front community retreat minutes walk to the heart of Siesta Key Village and #1 sand beach, with this stunning updated open floor plan 2-bedroom, 2-bathroom 2nd level resort living. Move in ready! Nestled along the pristine shores, this unit offers a wonderful blend of modern comfort and coastal charm. Step inside
Adam Sabari LPT REALTY, LLC
$3,550 per month
1269 Dockside Place Unit 115, Sarasota, FL 34242
A BOATER'S PARADISE! THE BEST OF THE BEACH AND THE BAY!! Great canal front first floor condo with large deck! Best of both worlds - across the street from Siesta Beach and a gated bayside community open to the intracoastal. Large kitchen with granite countertops, open to living/dining room. Bonus Florida room with plantation shuttered sliders that recess for an open air concept. Two bedroom, each
Susan Brooks COLDWELL BANKER SUNSTAR REALTY
$7,500 per month
6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
No roads to cross to get to the beach! Just listed- clean and cheery one bedroom/one bath condo in Casa Mar is ready for your beach stay! Covered parking, on-site community laundry rooms, and heated pool are just some of the amenities this Association has to offer. A recently added security gate adds value. This condo is ready for your stay- includes linens & beach towels. Pack your suit and
Robert Bevington SHOWTIME REALTY
$4,995 per month
5770 Midnight Pass Rd Unit 405, Sarasota, FL 34242
Immaculate well maintained 2 beds 2 bath condo situated in the desirable Gulf & Bay Club on Siesta Key. This 4th floor unit is meticulously maintained and tastefully decorated. Amenities include three pools, saunas, fitness center, tennis, basketball, racquetball, & 24hr security. A must see! Wake up to views of the Gulf and enjoy living your Siesta Key dream. Available for annual rent at $4,500
Pamala Casey CASEY REALTY CORPORATION
$2,500 per month
111 Pass Key Rd Unit 111, Sarasota, FL 34242
Welcome to your perfect beach getaway with this 1 Bedroom 1 Bath Condo in Sandy Cove II, located in beautiful Sarasota, FL. This cozy condo offers a serene escape with a partial ocean view, private beach access, and a fishing pier for those who love to cast a line. Enjoy the convenience of in-unit laundry and make use of the outdoor BBQ for al fresco dining. The clubhouse is perfect for social
Ray Shope ROSEBAY INTERNATIONAL REALTY, INC
$17,000 per month
6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242
Beachfront Bliss at Casa Mar – Siesta KeyDiscover this beautifully updated two-bedroom, two-bathroom beachfront condo in Casa Mar, offering direct access to Crescent Beach, a serene and less crowded alternative to Siesta Key’s main beach.Why You’ll Love This Condo:Prime Beachfront Location – Step right onto the powdery white sands of Crescent BeachClassic Coastal Charm – Thoughtfully designed
Robert Bevington SHOWTIME REALTY
$3,950 per month
4708 Ocean Blvd Unit E2, Sarasota, FL 34242
ENJOY INCREDIBLE SUNSETS AND BREATHTAKING VIEWS OF BIG PASS AND DOWNTOWN FROM TWO LARGE BALCONIES, ONE ENCLOSED AND ONE OPEN-AIR! UNIT INCLUDES DESIGNER KITCHEN WITH GRANITE COUNTERS, UPDATED BATHROOM, MARBLE FLOORING, NEW GE PROFILE APPLIANCES, REFRIGERATOR, RANGE, MICROWAVE, AND DISHWASHER. LARGE 2 CAR GARAGE WITH STORAGE CABINETS. CLOSE PROXIMITY TO RESTAURANTS AND SHOPS OF SIESTA VILLAGE.
Curt Cogan COGAN REALTY LLC
$16,000 per month
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
$9,000 per month
4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
Gulf Views!!Siesta Key! This captivating 2-bedroom, 2-bathroom condominium is found in Siesta Towers in Siesta Key and is close to restaurants and outdoor recreation. The complex is an easy pedestrian distance to Siesta Key Village, and convenient to Siesta Key Beach. The interior welcomes you with stylish fixtures blending seamlessly with bounteous window light and neutral decor. The large
Jane Hunter JENNETTE PROPERTIES INC
$5,250 per month
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
$9,500 per month
1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with
Andy Moore GULF COAST REALTY & MANAGEMENT
$6,500 per month
5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
Available August l - October 31 -2025 - 6500.00 per month plus taxes and fees. this Luxury Siesta Key Beach Front Unit in The Exclusive Gulf and Bay Club... - Enjoy Full Gulf of Mexico Views for the entire month in Paradise of Siesta Key Enjoy panoramic views of the #1 beach in the USA, Siesta Key! This beautiful 2 Bedroom, 2 Bathroom unit is fully updated with hardwood floors, granite
Robert Bevington SHOWTIME REALTY
$8,000 per month
1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
Welcome to this stunning 2-bedroom, 2-bathroom lakefront condo located on the second floor in Gulf and Bay Bayside, Siesta Key. This two-story retreat features two primary bedrooms, each with a luxurious king-size bed, spacious walk-in closets, and beautifully appointed bathrooms with walk-in showers. In the second floor primary bedroom there is additional sleeping accommodations with a full-size
Andy Moore GULF COAST REALTY & MANAGEMENT
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