Siesta Key, FL Homes for Rent with Water View

/57
$7,900 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Property for Rent
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

4660 Ocean Blvd Unit N1, Sarasota, FL 34242
/34
$6,000 per month
- 2 Beds
- 2 Baths
- 1,210 Sq Ft
- House for Rent
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.

6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242
/23
$3,600 per month
- 3 Beds
- 2 Baths
- 1,737 Sq Ft
- Condo for Rent
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.

1255 Dockside Place Unit 211, Sarasota, FL 34242
/20
$3,150 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
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.

1250 N Portofino Dr Unit 302, Sarasota, FL 34242
/27
$2,800 per month
- 1 Bed
- 1 Bath
- 748 Sq Ft
- House for Rent
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.

6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
/49
$10,500 per month
- 2 Beds
- 2 Baths
- 1,270 Sq Ft
- Condo for Rent
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

5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
/37
$6,500 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
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

1215 S Portofino Dr Unit 202, Sarasota, FL 34242
/76
$3,500 per month
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
- Condo for Rent
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

1700 Cove II Place Unit 310, Sarasota, FL 34242
/55
$5,000 per month
- 3 Beds
- 2.5 Baths
- 2,080 Sq Ft
- House for Rent
4946 Commonwealth Dr, Sarasota, FL 34242

Available as a monthly rental starting in May. 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,

Beth Dilley ASCENDIA REAL ESTATE

4946 Commonwealth Dr, Sarasota, FL 34242
/91
$14,000 per month
- 4 Beds
- 3 Baths
- 2,341 Sq Ft
- House for Rent
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

412 Treasure Boat Way, Sarasota, FL 34242
/40
$12,600 per month
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
- House for Rent
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

301 Avenida Madera Unit B, Sarasota, FL 34242
/26
$12,600 per month
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
- House for Rent
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

301 Avenida Madera Unit A, Sarasota, FL 34242
/36
$4,000 per month
- 1 Bed
- 2 Baths
- 780 Sq Ft
- Condo for Rent
1300 N Portofino Dr Unit 205, Sarasota, FL 34242

Available now until 4.4.26. 55+ community. 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 stroll away, you'll enjoy deeded access to Siesta Key's

Jonathan OSteen O'STEEN GROUP INC

1300 N Portofino Dr Unit 205, Sarasota, FL 34242
/84
$9,000 per month
- 3 Beds
- 2 Baths
- 1,704 Sq Ft
- House for Rent
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. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully

Chrissie Cummings JENNETTE PROPERTIES INC

327 Avenida Milano, Sarasota, FL 34242
/81
$9,000 per month
- 2 Beds
- 2 Baths
- 1,435 Sq Ft
- Condo for Rent
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

4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
/30
$3,500 per month
- 2 Beds
- 2 Baths
- 991 Sq Ft
- Condo for Rent
1215 S Portofino Dr Unit 308, Sarasota, FL 34242

BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane glass lanai,

Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

1215 S Portofino Dr Unit 308, Sarasota, FL 34242
/36
$2,300 per month
- 1 Bed
- 2 Baths
- 780 Sq Ft
- Condo for Rent
1350 N Portofino Dr Unit 207, Sarasota, FL 34242

This stunning one-bedroom, two-bathroom condo in Siesta Harbor in the Tarpon Building is the perfect combination of luxury, convenience, and breathtaking views. Located in a prime location, boating access, canal frontage, and mesmerizing Intracoastal Waterway views. Step inside and be captivated by the modern elegance of this home. The kitchen is a chef's dream, featuring stainless steel

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1350 N Portofino Dr Unit 207, Sarasota, FL 34242
/41
$5,000 per month
- 2 Beds
- 2 Baths
- 1,424 Sq Ft
- House for Rent
5577 Contento Dr, Sarasota, FL 34242

This is a short term rental. Listing reflects off season rate. Available peak season month: January 3rd - 31st, 2026. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously

Beth Dilley ASCENDIA REAL ESTATE

5577 Contento Dr, Sarasota, FL 34242
/89
$4,700 per month
- 3 Beds
- 3 Baths
- 1,867 Sq Ft
- Condo for Rent
4900 Ocean Blvd Unit 501, Sarasota, FL 34242

Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! With three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the tropical

Beth Dilley ASCENDIA REAL ESTATE

4900 Ocean Blvd Unit 501, Sarasota, FL 34242
/98
$18,000 per month
- 3 Beds
- 2 Baths
- 1,617 Sq Ft
- House for Rent
345 Avenida Leona, Sarasota, FL 34242

Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a

Beth Dilley ASCENDIA REAL ESTATE

345 Avenida Leona, Sarasota, FL 34242
/46
$12,000 per month
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
- Condo for Rent
20 Whispering Sands Dr Unit 903, Sarasota, FL 34242

Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the sounds of the surf? Look no further than this stunningly remodeled 2 bed, 2 bath condo in the Whispering Sands Community. This wonderful 55+ community offers you the convenience of village living but is very peaceful and private at the same time. Leave the hustle and bustle of

Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
/96
$4,500 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1257 S Portofino Dr Unit 38, Sarasota, FL 34242

Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice décor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the

Kay Esposito SIGNATURE REALTY ASSOCIATES

1257 S Portofino Dr Unit 38, Sarasota, FL 34242
/57
$5,000 per month
- 2 Beds
- 2 Baths
- 1,361 Sq Ft
- Condo for Rent
5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242

Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot

Beth Dilley ASCENDIA REAL ESTATE

5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
/42
$5,000 per month
- 2 Beds
- 2.5 Baths
- 1,332 Sq Ft
- Condo for Rent
6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242

Variable rent based on season

Terry Dorrity INTEGRITY INVESTMENTS REALTY

6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
/72
$6,500 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 102, Sarasota, FL 34242

Available January to April 1, 2026! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1250 N Portofino Dr Unit 102, Sarasota, FL 34242
/42
$6,000 per month
- 2 Beds
- 2 Baths
- 1,337 Sq Ft
- Condo for Rent
5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242

** AVAILABLE APRIL 2026! ** BOOKED JANUARY THROUGH MARCH 2026 ***GORGEOUS BEACHFRONT HOME LOCATED IN THE HIGHLY SOUGHT AFTER GULF & BAY COMMUNITY! Enjoy spectacular sunsets and views of the Gulf of Mexico from this 6th floor 2 Bedroom/ 2 Bath luxury condo. Full Gulf views from living room/dining room combo and master bedroom! Gulf & Bay Club is located on Siesta Key Beach, voted #1 Beach in the

Kayla Lamb NEXTHOME EXCELLENCE

5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
/82
$6,500 per month
- 2 Beds
- 2 Baths
- 1,123 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 301, Sarasota, FL 34242

Immaculate End Unit in the Marlin building, Ready for you to Enjoy through January 2026 and April 2026 through year-end 2026! Stunning all the way, Great Location in the complex, close to the pool, clubhouse, spa, sauna, 2 bedroom 2 full baths, enclosed lanai overlooking the canal, steps to Deeded beach access through Crescent Arms, for your pleasure daytime or sunset time! Siesta Harbor offers a

Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

1250 N Portofino Dr Unit 301, Sarasota, FL 34242
/49
$9,500 per month
- 2 Beds
- 2 Baths
- 1,489 Sq Ft
- Condo for Rent
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242

***AVAILABLE MAY 2026*** one MONTH MIN***Welcome to the Beach! Prime Siesta Key location. This large, spacious 2 Bedroom/2 Bath split floor plan condo comes with a full-length balcony with views of the gulf and intracoastal waterway, as well as the beautiful sunsets. Available as a monthly rental, the interior boasts a decorative fireplace, reclining sofa, two walk-in closets, washer and dryer in

Anthony DeLuca AUDREY RAIN RENTALS, INC

6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
/72
$5,000 per month
- 1 Bed
- 2 Baths
- 780 Sq Ft
- Condo for Rent
1257 S Portofino Dr Unit 36, Sarasota, FL 34242

Siesta Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open

Margaret Young JENNETTE PROPERTIES, INC.

1257 S Portofino Dr Unit 36, Sarasota, FL 34242
/27
$6,400 per month
- 2 Beds
- 2 Baths
- 929 Sq Ft
- Condo for Rent
1250 N Portofino Dr Unit 107, Sarasota, FL 34242

This 2 bedroom, 2 bath condo in this popular 55+ community, is conveniently located on the ground floor next to the club house and swimming pool, and features new appliances, granite counter tops and ceramic flooring. Queen size bed in the Master with a full wall length closet for guests. The walk-in closet is reserved for the Owners. The guest bedroom has 2 single beds that can be combined to

Margaret Young JENNETTE PROPERTIES, INC.

1250 N Portofino Dr Unit 107, Sarasota, FL 34242
/25
$12,000 per month
- 4 Beds
- 3 Baths
- 2,460 Sq Ft
- House for Rent
5519 Azure Way, Sarasota, FL 34242

Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car! A brand new beautiful granite topped Kitchen space opens to a family room all

Catherine Foley JENNETTE PROPERTIES, INC.

5519 Azure Way, Sarasota, FL 34242
/48
$10,000 per month
- 2 Beds
- 2 Baths
- 1,265 Sq Ft
- Condo for Rent
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

6480 Midnight Pass Rd Unit 311, Sarasota, FL 34242
/49
$12,000 per month
- 2 Beds
- 2 Baths
- 1,265 Sq Ft
- Condo for Rent
6480 Midnight Pass Rd Unit 506, Sarasota, FL 34242

Siesta Key's beautiful coastline offers you the chance to enjoy your dream vacation in this fantastic 2-bedroom ocean-view condominium. Situated directly on the beach and across the street from the South Village, you’ll be mere steps away from both the beautiful water and a vast array of destinations. The South Village includes a full-service grocery store and numerous restaurants, ice cream

Robert Bevington SHOWTIME REALTY

6480 Midnight Pass Rd Unit 506, Sarasota, FL 34242

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