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Siesta Key, FL Homes for Rent with Water View

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  • /56

    $17,000 Per Month

    • 5 Beds
    • 5 Baths
    • 3,126 Sq Ft
    • House for Rent

    5624 Cape Leyte Dr, Sarasota, FL 34242

    Prime Siesta Key Waterfront Retreat – Fully Furnished & Walk to the Beach Welcome to 5624 Cape Leyte Drive, a fully furnished luxury beach retreat just a short walk to world-famous Siesta Key Beach. This turnkey property showcases refined coastal elegance with designer furnishings, Italian tile and quartz finishes throughout, and spa-inspired bathrooms featuring rainfall showers. Every detail

    Agent Photo

    Wally Sabrii

    SARASOTA INTERNATIONAL REALTY

    5624 Cape Leyte Dr, 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 THRU DECEMBER 2026. BOOKED FOR SEASON AND THEN AVAILABLE AGAIN APRIL 2027*** 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

    Agent Photo

    Anthony DeLuca

    AUDREY RAIN RENTALS, INC

    6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
  • /65

    $22,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,788 Sq Ft
    • House for Rent

    3939 Higel Ave, Sarasota, FL 34242

    Arrive. Unwind. Experience Siesta Key at its finest.Welcome to your private luxury retreat on Siesta Key, a modern sophisticated 4-bedroom, 4-bathroom home designed for elevated coastal living. Tucked away in one of the island’s most desirable locations, this residence offers the perfect blend of privacy, comfort, and effortless elegance.From the moment you step inside, you’re welcomed by

    Agent Photo

    Raffilena Hamilton

    GOOD LIFE REALTY LLC

    3939 Higel Ave, Sarasota, FL 34242
  • /63

    $15,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,524 Sq Ft
    • Condo for Rent

    1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242

    AVAILABLE 1/4/27 Experience the pinnacle of coastal living in this exceptional penthouse at Marina Del Sol with PRIVATE 52 FT BOAT SLIP. Perfectly positioned moments from the #1-rated Siesta Key Beach. This rare residence offers panoramic Gulf of Mexico sunsets on one side and serene Bay views on the other—an unmatched indoor-outdoor lifestyle framed by water in every direction.****Designed for

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    Tracy Srodes

    FINE PROPERTIES

    1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242
  • /53

    $4,000 Per Month

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

    1250 N Portofino Dr Unit 301, Sarasota, FL 34242

    Gorgeous updated 2 BR, 2 Bath condo on a Canal Available Now Through December 31st or April 1, 2027 and beyond! Sailboat water, fishing pier, private beach access directly across the street. Beautifully furnished vacation home with water view from main bedroom, Livingroom and lanai. End unit so more light and larger kitchen space. Everything you will need for your beach vacation. Amenities

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
  • /28

    $7,050 Per Month

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Condo for Rent

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242

    This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 703AA, 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
  • /30

    $4,000 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 through January 15, 2027 or April 2027! 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

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
  • /21

    $8,970 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242

    Villa 22 at Aloha Kai is where memories are made while spending time at the beach with family and friends, offering the perfect spacious setting. Its open floor plan fosters conversation and connection, encouraging moments away from screens. After a day of sunshine and sandy toes, gather in the updated kitchen, featuring a casual dining bar designed to invite everyone to join in meal preparation.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 22, Sarasota, FL 34242
  • /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
  • /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 quick,

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 202, Sarasota, FL 34242
  • /78

    $2,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 860 Sq Ft
    • Condo for Rent

    1700 Cove II Place Unit 310, Sarasota, FL 34242

    Available 2950.00 Monthly - April 20th 2026 through December 31st 2026... Not Available 2027 Jan through April 15th 2027 Stunning Water Views & Deeded Beach Access | Siesta Key plus taxes and fees. Live your Dream on Siesta Key for the Summer...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

    Robert Bevington SHOWTIME REALTY

    1700 Cove II Place Unit 310, 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 you're

    Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

    1250 N Portofino Dr Unit 302, Sarasota, FL 34242
  • /38

    $2,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    4660 Ocean Blvd Unit G1, Sarasota, FL 34242

    Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The open kitchen is perfect for those who enjoy cooking, and the living area provides ample space for relaxation and entertaining. Each bedroom is a comfortable haven with custom closets for added

    Beth Dilley ASCENDIA REAL ESTATE

    4660 Ocean Blvd Unit G1, Sarasota, FL 34242
  • /21

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 54, Sarasota, FL 34242

    Starting from $179/night! Experience the charm of Villa 54, a 1-bedroom, 1-bathroom retreat at Casa Mar. Relax in the luxurious king-sized bed in the master bedroom, complemented by a cozy sleeper sofa in the spacious living area. Prepare gourmet meals in the fully equipped kitchen that seamlessly flows into an elegant dining space, perfect for entertaining or quiet meals. Outside, enjoy the

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 54, Sarasota, FL 34242
  • /11

    $7,500 Per Month

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

    6154 Midnight Pass Rd Unit 104, Sarasota, FL 34242

    Watch the magnificent sunsets over blue gulf waters from the lanai of a newly, up-dated, completely renovated, and re-decorated ground floor apartment on the white sands of Crescent Beach on Siesta Key. The 2 bedroom, 2 bathroom, apartment sleeps 4. The beds can be arranged as 1 King and 2 twin beds pushed together to form 1 Large Queen with advance notice to the office. The kitchen is granite

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 104, Sarasota, FL 34242
  • /65

    $9,500 Per Month

    • 1 Bed
    • 1.5 Baths
    • 928 Sq Ft
    • Condo for Rent

    5400 Ocean Blvd Unit 5-3, Sarasota, FL 34242

    SEASONAL RENTAL AVAILABLE AT BEACH TERRACE ON SIESTA KEY! Experience Siesta Key beachfront living at it’s best in this beautifully renovated, fifth-floor corner condo directly on world-renowned Siesta Beach, ranked #1 in the U.S. This turnkey furnished 1-bedroom, 1.5-bath retreat features floor-to-ceiling impact sliding glass doors opening to three private balconies, creating over 1,280 sq ft of

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    5400 Ocean Blvd Unit 5-3, Sarasota, FL 34242
  • /51

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft
    • Condo for Rent

    5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242

    This luxury Siesta Key beachfront unit in the exclusive Gulf and Bay Club offers full panoramic views of the Gulf of Mexico and the #1 beach in the USA, Siesta Key! This beautifully updated 2-bedroom, 2-bathroom unit features hardwood floors, granite countertops, and an abundance of cabinet space. The bathrooms are elegantly updated with tile and granite counters, making this a truly turnkey

    Robert Bevington SHOWTIME REALTY

    5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
  • /26

    $7,999 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    4660 Ocean Blvd Unit Q, Sarasota, FL 34242

    FULL GULF & SUNSET VIEWS | TURNKEY FURNISHED | WALK TO SIESTA VILLAGE & BEACHSeasonal rental available for January, February and March of 2027. Taxes are not included in the rent. Two small dogs allowed!You will be WOWED by the breathtaking full Gulf and sunset views from this TURNKEY FURNISHED Siesta Key residence! Ideally located within walking distance of the vibrant Siesta Village and

    Paul Svilokos RENTPRO MANAGEMENT LLC

    4660 Ocean Blvd Unit Q, Sarasota, FL 34242
  • /11

    $8,250 Per Month

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

    6154 Midnight Pass Rd Unit 201, Sarasota, FL 34242

    Welcome to this beautifully updated, Gulf-facing apartment located directly on the soft white sands of Crescent Beach. Designed for comfort and relaxation, this spacious unit offers sweeping views of the Gulf of Mexico and nightly sunsets that are nothing short of spectacular. Whether you're lounging in the tastefully decorated living room or enjoying a quiet moment on the private, screened-in

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6154 Midnight Pass Rd Unit 201, Sarasota, FL 34242
  • /45

    $11,000 Per Month

    • 3 Beds
    • 3 Baths
    • 3,324 Sq Ft
    • House for Rent

    681 Avenida de Mayo, Sarasota, FL 34242

    Park your Boat behind your home .... Welcome to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations. Step inside to find over-sized rooms that can be utilized for entertaining or simply

    Colette Jay HORIZON REALTY INTERNATIONAL

    681 Avenida de Mayo, 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
  • /50

    $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 in

    Robert Bevington SHOWTIME REALTY

    5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
  • /73

    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Condo for Rent

    1355 S Portofino Dr Unit 103, Sarasota, FL 34242

    Discover this exceptional 2-bedroom, 2-bathroom condo, perfectly positioned for the ultimate Florida coastal escape. Step out onto your dual balconies—one on the side and one in the back—offering breathtaking, unobstructed views of the serene Intracoastal Waterway. Watch boats glide by, spot dolphins playing, and soak in stunning the stunning views from your own private vantage points. This

    Teresa Ribaudo JENNETTE PROPERTIES INC

    1355 S Portofino Dr Unit 103, 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
  • /72

    $4,500 Per Month

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

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242

    Available April 1, 2027! 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 Fishing Pier.

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
  • /18

    $2,500 Per Month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Property for Rent

    6020 Midnight Pass Rd, Sarasota, FL 34242

    DIRECT BEACH ACCESS! Beautifully located 1 bed/1 bath second-floor unit in the sought-after Aloha Kai community on Midnight Pass Rd, This fully furnished unit offers relaxing pool views and is move-in ready in this well-maintained beachside community. Available for 2 adults, no pets. Water and electricity included in rent. On-site parking available. Steps from the sand — perfect for tenants

    Koen Roelens ROELENS REALTY & PROPERTY MANA

    6020 Midnight Pass Rd, 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

    This is a short term vacation rental. 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

    Beth Dilley ASCENDIA REAL ESTATE

    4946 Commonwealth Dr, Sarasota, FL 34242
  • /27

    $12,600 Per Month

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

    301 Avenida Madera Unit A, Sarasota, FL 34242

    If you’re searching for the perfect location for your next vacation, your search ends here!This beautifully updated 2-bedroom, 2-bath home is ideally situated in the heart of Siesta Key, within Siesta Key Village and just a few blocks from the world-famous Siesta Key Beach. Designed with a bright coastal theme, the home features an inviting open layout and a fully updated kitchen with solid

    Robert Bevington SHOWTIME REALTY

    301 Avenida Madera Unit A, Sarasota, FL 34242
  • /15

    $5,070 Per Month

    • 1 Bath
    • 420 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 2, Sarasota, FL 34242

    Starting at $154/night! Escape to the perfect beachside retreat at our charming and cozy studio on beautiful Siesta Key. Just steps from the world-renowned white sands of Siesta Beach, this inviting space is ideal for couples or solo travelers looking to unwind in comfort. The studio features two plush queen-size beds, a relaxed seating area, and a flat-screen TV for your entertainment. Prepare

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 2, Sarasota, FL 34242
  • /18

    $8,970 Per Month

    • 1 Bath
    • 435 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242

    Starting at $299/night! Explore a luxurious studio-style condominium at Casa Mar, featuring one bathroom and a queen-sized murphy bed. This elegant retreat boasts a fully equipped kitchen that flows into a spacious dining area, ideal for hosting guests. Benefit from the convenience of a private carport just a few steps away from your residence. Casa Mar offers an impressive range of amenities,

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242
  • /20

    $5,070 Per Month

    • 1 Bath
    • 435 Sq Ft
    • House for Rent

    6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242

    Starting at $169/night. Discover the perfect beach getaway at our charming studio, ideally located on the beautiful Siesta Key. Just steps from the pristine white sands of Siesta Beach, this cozy, well-appointed retreat is perfect for couples or solo travelers seeking a relaxing escape. The studio features a comfortable queen-size bed, a cozy seating area, and a flat-screen TV for your

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242
  • /52

    $5,000 Per Month

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

    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

    Beachfront Bliss at Casa Mar – Siesta Key Dreaming 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-whit e sand, complete with lounge chairs for sunbathing and unforgettable Gulf views. Cool off with a swim in

    Robert Bevington SHOWTIME REALTY

    6006 Midnight Pass Rd Unit 16, 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
  • /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. 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 bright, coastal-styled haven designed for relaxation and comfort. The spacious primary

    Beth Dilley ASCENDIA REAL ESTATE

    345 Avenida Leona, Sarasota, FL 34242
  • /25

    $27,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 26, Sarasota, FL 34242

    When only the best will do, Villa 26 at Aloha Kai is the perfect choice. Beautifully updated with meticulous attention to detail, this beachfront villa offers an ideal retreat where you can watch shorebirds, dolphins, and breathtaking sunsets from your private porch. The kitchen is a chef’s dream, while the bathrooms provide a spa-like experience for ultimate relaxation. Located on Siesta Key, a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 26, 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 August - December 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 to unwind. Step

    Beth Dilley ASCENDIA REAL ESTATE

    5760 Midnight Pass Rd Unit 208, 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
  • /28

    $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
  • /9

    $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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