Siesta Key, FL Homes for Rent with Water View

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  $5,370 Per Month

  • 2 Beds
  • 1.5 Baths
  • 840 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242

  Starting at $179/night! Step into luxury and comfort at our newly renovated 2-bedroom, 1.5-bathroom condo, perfectly designed for your next getaway. This vibrant space features a fully equipped kitchen ready for your culinary adventures and a private carport just steps from the unit for hassle-free parking. Recently updated in Summer 2023, the condo comfortably accommodates up to six guests with

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
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  $10,770 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • House for Rent

  6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242

  We welcome you to stay in our updated oceanfront condo on Siesta Key Crescent Beach - the best beach in Florida! Our spacious 2 bed/2 bath oceanfront home is 1080 square feet with an ocean view that cannot be beat! Unit #206 is part of the Casa Blanca Vacation Beach Resort, and the crystal white sand is steps away! Remodeled in 2023, fully equipped kitchen with quiet dishwasher, spacious living

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242
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  $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 (weekly) rental. Listing reflects off season rate. 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 designed interior with thoughtful updates

  Beth Dilley ASCENDIA REAL ESTATE

  5577 Contento Dr, Sarasota, FL 34242
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  $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
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  $10,230 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Condo for Rent

  6154 Midnight Pass Rd Unit 202, Sarasota, FL 34242

  Completely remodeled in 2019. Endless Gulf views from every room. TWO queen sized beds in Master, two twins in second bedroom means plenty of space for your family, and everything is new and sparkling clean! Additional Person fees may apply. Enjoy a dip in one of the largest pools on Siesta Key! This second floor apartment has direct gulf views for stunning sunsets of the only beach to be voted

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 202, Sarasota, FL 34242
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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

  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
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  $10,230 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Apartment for Rent

  6154 Midnight Pass Rd Unit 102, Sarasota, FL 34242

  Wake up to views of the beautiful gulf and beach from every room. Walk out to the best beach in the world. End your day with a breathtaking sunset dinner on the lanai. 102 is a ground floor, beach front apartment with 2 bedrooms and 2 baths. It is an open floor plan with porcelain tile throughout, comfortable seating in the living area, a full kitchen with all cookware and service items, and

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 102, Sarasota, FL 34242
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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

  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
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  $10,230 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Condo for Rent

  6154 Midnight Pass Rd Unit 301, Sarasota, FL 34242

  This beautiful condo, is right ON the beach! Siesta Key Beach, designated #1 beach in America, Unit #301 offers a superior, sweeping view of the entire 6 mile long, white sand (quartz) beach. Sliding glass doors open to the lanai and to the living room to allow for sea breezes and sounds of the surf. Each bedroom has the same dramatic view and you are just steps from the beach. Private Wireless

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 301, Sarasota, FL 34242
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  $7,850 Per Month

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Condo for Rent

  Unlisted Address

  FULLY FURNISHED AND INTERIOR DESIGNED 2 BEDROOM / 2 BATH UNIT now available in Harbor Towers on Siesta Key. This beautifully designed condo offers a total of 1,700 sq ft of indoor/outdoor living, including 1,152 sq ft of air-conditioned space and a spacious 540 sq ft private patio finished with travertine and turf. The unit features 9 ft ceilings, floor-to-ceiling windows, stylish furnishings,

  Andres Ospina Rivera LPT REALTY, LLC

  Unlisted Address
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  $5,370 Per Month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 64, Sarasota, FL 34242

  Starting at $179/night! Step into your perfect getaway at this charming ground-floor 1-bedroom unit nestled within the Casa Mar complex, just steps from the beach off Midnight Pass Road. Relax on the screened lanai overlooking a tranquil courtyard, where not one but two inviting pools beckon you to unwind. A leisurely stroll along the sidewalk leads you straight to the sandy shores. Enjoy the

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 64, Sarasota, FL 34242
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  $3,300 Per Month

  • 2 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • Condo for Rent

  4822 Ocean Blvd Unit 5F, Sarasota, FL 34242

  Annual – Unfurnished | Gulffront Living on Siesta Key Live on the water and enjoy breathtaking Gulf views from this beautiful condo in Siesta Towers. This luxury 11-story, 65-unit beachfront building sits directly on the Gulf of Mexico, offering spectacular panoramic views and an unbeatable island lifestyle. The condo features an open floor plan filled with natural light from large sliding glass

  Cody Smith RENT SARASOTA

  4822 Ocean Blvd Unit 5F, Sarasota, FL 34242
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  $9,500 Per Month

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft
  • Condo for Rent

  5400 Ocean Blvd Unit 10-02, Sarasota, FL 34242

  Welcome to The Terrace 10-2 on Siesta Key, a fully renovated 10th-floor beachfront condo offering some of the most breathtaking panoramic views on Florida’s Gulf Coast. Designed by the renowned architect Frank Folsom Smith, The Terrace stands as one of Siesta Key’s most architecturally significant landmarks, combining mid-century sophistication with timeless coastal beauty. The Space This

  Sean Altice ALTEZ VACATIONS, LLC

  5400 Ocean Blvd Unit 10-02, Sarasota, FL 34242
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  $12,600 Per Month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  301 Avenida Madera Unit B, Sarasota, FL 34242

  Welcome to your perfect island getaway at 301 Avenida Madera #B, ideally located in the heart of Siesta Key—this is truly THE location! Just steps from popular spots like Village Cafe and The Hub Baja Grill, and only a short walk to the world-famous Siesta Key Beach, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of comfort and coastal charm. Inside, you’ll find a bright

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit B, Sarasota, FL 34242
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  $5,070 Per Month

  • 1 Bath
  • 420 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 29, Sarasota, FL 34242

  Starting at $169/night. Discover the perfect beach getaway at our charming studio on beautiful Siesta Key, just steps from the world-famous white sands of Siesta Beach. Ideal for couples or solo travelers, this cozy and well-appointed retreat offers everything you need for a relaxing escape. Nestled in the heart of Siesta Key, you’ll be within easy walking distance of the beach, local shops, and

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 29, Sarasota, FL 34242
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  $8,070 Per Month

  • 1 Bed
  • 1 Bath
  • 757 Sq Ft
  • Apartment for Rent

  6154 Midnight Pass Rd Unit 103, Sarasota, FL 34242

  Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach from the 1st floor of this tastefully decorated one bedroom, one bath apartment with tile throughout. Enjoy morning coffee and stunning sunsets on the lanai every day! Newly updated fully equipped kitchen. The property offers one of the largest pools on Siesta Key. Come in, unpack and relax! Siesta Key Beach has

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 103, Sarasota, FL 34242
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  $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
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  $6,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • House for Rent

  4830 Higel Ave, Sarasota, FL 34242

  More pictures to come, waiting for the rest of the furniture to arrive. Florida charm at it’s best in this turnkey furnished vacation home on Siesta Key. The home is a mid-century in the style of the Sarasota School of Architecture. The home is on 1/3 of an acre on the Grand Canal with a dock and kidney-shaped heated pool. The new hardwood flooring and new impact windows make this home bright and

  toyia Youtzy JENNETTE PROPERTIES, INC.

  4830 Higel Ave, Sarasota, FL 34242
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  $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
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  $3,500 Per Month

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft
  • Condo for Rent

  1250 N Portofino Dr Unit 303, Sarasota, FL 34242

  Available for season 2026/2027! Enjoy true waterfront living on the sought-after barrier island of Siesta Key with direct deeded private beach access to the world-famous white sand beaches. Boat slips are also available for renters, making this the perfect seasonal getaway for beach and boating enthusiasts alike. This updated waterfront condo offers serene canal and Intercostal Waterway views,

  Angela Bailey MONARCH PROPERTY GROUP LLC

  1250 N Portofino Dr Unit 303, Sarasota, FL 34242
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  $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
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  $8,340 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Apartment for Rent

  6154 Midnight Pass Rd Unit 305, Sarasota, FL 34242

  Experience breathtaking, unobstructed views of the sparkling Gulf of Mexico and the pristine shores of Crescent Beach from the spacious 3rd-floor lanai of this beautifully appointed two-bedroom, two-bathroom beachfront apartment. Perfectly designed for comfort and relaxation, this well-maintained unit features a fully equipped kitchen with all the essentials needed to prepare everything from

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 305, Sarasota, FL 34242
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  $9,420 Per Month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • Condo for Rent

  6154 Midnight Pass Rd Unit 101, Sarasota, FL 34242

  Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach, from the 1st floor of this beautifully appointed two- bedroom, two-bathroom apartment with fully-equipped kitchen. Relax in the living room that overlooks the gulf. Enjoy your morning coffee sitting out on the screened in lanai just steps from the sand.This unit features Private wireless internet, Double

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 101, Sarasota, FL 34242
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  $17,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Condo for Rent

  6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242

  Beachfront Bliss at Casa Mar – Siesta Key Discover 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 whit e sands of Crescent Beach Classic Coastal Charm – Thoughtfully

  Robert Bevington SHOWTIME REALTY

  6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242
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  $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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  $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
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  $7,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,467 Sq Ft
  • Condo for Rent

  1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242

  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

  1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242

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