Homes for Rent in ZIP Code 34242

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  /26

  $9,300 per month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242

  Enjoy all the Siesta Key and Gulf and Bay Club Bayside amenities while staying in this spacious two-bedroom/two-bathroom vacation rental condo. The condo offers a relaxing lake, pool and tennis court view from the lanai. A few of your amenities include your own private garage, a washer and dryer IN THE CONDO, and a fully-equipped kitchen The community offers BBQ grills (6), two tennis courts,

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
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  $9,350 per month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  Unlisted Address

  Make yourself at home in our spacious two bedroom, two bath second floor condo located at the beautiful Gulf and Bay Club Bayside. The Key West style cluster buildings afford you a quiet residential feel while you are just a short walk to the powdery white quartz sand of the world famous Siesta Key/Crescent Beach.New to the rental program, our condo has previously been owner occupied and

  Andy Moore GULF COAST REALTY & MANAGEMENT

  Unlisted Address
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  /27

  $6,900 per month

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

  1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242

  Spacious one bedroom/one bathroom vacation rental at the Gulf and Bay Club Bayside on the island paradise of Siesta Key just offshore of Sarasota, Florida. Private access to Crescent Beach on the Gulf of Mexico - just steps to the beach. Free high-speed Internet connection. Please note the garage for this unit is the middle garage in the building to the right.*Taxes and Fees not included.

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
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  /65

  $3,800 per month

  • 2 Beds
  • 2 Baths
  • 1,233 Sq Ft
  • Condo for Rent

  8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242

  AVAILABLE FOR SEASON 2026 $8,500/MONTH AND OFF-SEASON MONTHS 2025 AT $3,800/MONTH. UTILITIES INCLUDED. SIESTA KEY SPECTACULAR FULL BAY/INTRACOASTAL UNOBSTRUCTED VIEWS! BOOK YOUR BEACH GETAWAY NOW! Beautifully updated throughout Turnkey "top floor" Condo in this popular community of Sunrise Cove. Located on the southern end of Siesta Key, directly across the street from Turtle Beach! Upon

  Chrissie Cummings JENNETTE PROPERTIES INC

  8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
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  /60

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 2,259 Sq Ft
  • House for Rent

  5516 Avenida Del Mare, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 5th - February 6th 2026, April 2026. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kiddos

  Beth Dilley ASCENDIA REAL ESTATE

  5516 Avenida Del Mare, Sarasota, FL 34242
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  $6,500 per month

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

  1350 N Portofino Dr Unit 108, Sarasota, FL 34242

  Gorgeous Canal View Condo now available on Siesta Key as an annual rental. Rent for the remainder of 2025 through the Winter Season until December 2026 and work from home on your walk-out lanai watching the deep water boats on the Intracoastal Waterway. Incredible View of the Intracoastal Waterway, Beautiful two bedroom, two bath spacious first floor walk-out condo with lots of natural light.

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  1350 N Portofino Dr Unit 108, Sarasota, FL 34242
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  /65

  $8,700 per month

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Condo for Rent

  5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, April 2026. Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot,

  Beth Dilley ASCENDIA REAL ESTATE

  5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
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  /60

  $8,500 per month

  • 3 Beds
  • 3 Baths
  • 2,558 Sq Ft
  • Condo for Rent

  9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242

  Open for April and beyond! Rent 3 months for $8000 per month, 6 months for $7000 per month or a year for $6500! Rarely available 3 bed, 3 bath, plus office/work-space condo in sought-after Somerset Cay! You will love the resort-style amenities and the contemporary elegance this wonderful home offers. There are three balconies, offering views of the Bay, the Intercoastal Waterway and the Gulf.

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
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  $7,200 per month

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

  116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Experience the ultimate beach getaway at "Carefree Coconut," a charming second-floor corner unit located in the heart of Siesta Key's welcoming Vista Hermosa community. True to its Spanish name, "Beautiful View," this community offers a delightful escape, blending old Florida

  Beth Dilley ASCENDIA REAL ESTATE

  116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
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  /23

  $14,999 per month

  • 3 Beds
  • 3.5 Baths
  • 3,700 Sq Ft
  • Condo for Rent

  9008 Midnight Pass Rd Unit 4, Sarasota, FL 34242

  THE SEA BREEZE: Exclusive seasonal rental for the discerning taste. This beautiful 3 bedroom, 3 1/2 bath residence has magnificent views of Sarasota Bay and the Gulf of Mexico/ Premium space in this luxurious well-appointed and professionally designed tropical private residence, available in season January 1, 2024. Wall to wall windows spanning the 3700 feet of gracious living space will appeal

  Robin Turner WATERSIDE REALTY LLC

  9008 Midnight Pass Rd Unit 4, Sarasota, FL 34242
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  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • Condo for Rent

  8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242

  Look no further than Siesta Key's "Island Reef" for your annual vacation getaway. The stunning Gulf to Bay location features the fourth-floor unit overlooking the intercostal waterway, just a short walk to the beach. The Siesta Key village and local dining are just a stroll away. The property has a beautiful community pool, tennis courts, shuffleboard, and more. The stylish decore and nicely

  Erick Shumway RE/MAX ALLIANCE GROUP

  8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
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  /75

  $3,750 per month

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • Condo for Rent

  8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242

  Siesta Key living just steps from the Gulf of Mexico at beautiful, tranquil Island Reef on the quiet end of the Island. Spacious 2 bedrooms, 2 baths, laundry in residence, carport, and guest parking. Tile flooring throughout the condo. Island Reef is a serene waterfront community, one of the few true Gulf to Bay properties, that offers many desirable amenities including: beach and boat docks

  Erick Shumway RE/MAX ALLIANCE GROUP

  8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
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  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,303 Sq Ft
  • Condo for Rent

  8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242

  Seasonal Property available on the top floor in Siesta Key, Look no further than "Island Reef" This Gulf to Bay location features the top floor PH unit directly overlooking the intercostal water way, just a short walk to the beach and very close to the Siesta key village and local dining. The property has a beautiful community pool, Tennis courts, shuffle board and much more. Entering the unit

  Lee Brewer RE/MAX ALLIANCE GROUP

  8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
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  /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
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  /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
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  /30

  $26,319 per month

  • 2 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Condo for Rent

  915 Seaside Dr Unit 512, Sarasota, FL 34242

  Bask in the sunshine and sit in the pristine crystal white sands on Crescent Beach, rated #1 in the country by Dr. Beach. This beachfront sanctuary offers a fitness center, heated pool, outdoor grotto style whirlpool hot tub, bicycles, kayaks and barbecue grills, the tiki bar offers food from the famous Morton’s and cabanas to shield you from the sun when you want some shade. The unit has top of

  Andy Moore GULF COAST REALTY & MANAGEMENT

  915 Seaside Dr Unit 512, Sarasota, FL 34242
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  /27

  $25,048 per month

  • 4 Beds
  • 3 Baths
  • 2,430 Sq Ft
  • House for Rent

  1140 Seaside Dr Unit 101, Sarasota, FL 34242

  Serenity at its finest! If luxury is calling, come indulge at the Beach House Residences for your ultimate beach vacation experiences. A place to escape and rediscover you. Renew your senses, inspire your mind and relax your body. Take advantage of the magnificent sunsets, tranquil waters, immense sunshine of world-renowned Crescent Beach. The most discerning traveler will appreciate the island

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1140 Seaside Dr Unit 101, Sarasota, FL 34242
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  $3,900 per month

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

  1257 S Portofino Dr Unit 38, Sarasota, FL 34242

  DECEMBER SPECIAL *** $3,900! 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

  Kay Esposito SIGNATURE REALTY ASSOCIATES

  1257 S Portofino Dr Unit 38, Sarasota, FL 34242
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  /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
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  /99

  $5,900 per month

  • 3 Beds
  • 3.5 Baths
  • 2,490 Sq Ft
  • Condo for Rent

  1660 Summerhouse Ln Unit 301, Sarasota, FL 34242

  LOCATION, LOCATION, LOCATION!!! Stunning large luxury condo located in the sought after community of Summer Cove on Siesta Key is available for an ANNUAL LEASE. This corner unit, light and bright property has been meticulously professionally decorated and it shows. Three bedrooms, three and a half bathrooms, turnkey furnished, three open lanais that face east and west, living room/kitchen/dining

  C. Alison Hunter JENNETTE PROPERTIES INC

  1660 Summerhouse Ln Unit 301, Sarasota, FL 34242
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  /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
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  /60

  $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

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1250 N Portofino Dr Unit 102, Sarasota, FL 34242
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  /43

  $3,900 per month

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Condo for Rent

  4660 Ocean Blvd Unit B2, Sarasota, FL 34242

  SIESTA KEY WATERFRONT UNIT AVAILABLE AS FURNISHED LONG TERM. Sea Village offers million dollar views and is situated on 5 acres overlooking the Gulf. It provides a peaceful retreat with opportunities to witness breathtaking sunsets, the full moon reflecting on the water, and serene walks to the beach and Siesta Village. Additionally, its location on the north end of the Key provides convenient

  Margaret Young JENNETTE PROPERTIES, INC.

  4660 Ocean Blvd Unit B2, Sarasota, FL 34242
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  /14

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 3,395 Sq Ft
  • House for Rent

  95 Sandy Hook Rd S, Sarasota, FL 34242

  6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" Available NOW!!!!!!! IN SANDY HOOK, DIRECTLY ON THE GULF AT BIG PASS. ENJOY YOUR OWN private Beach!!!TROPICAL PARADISE. SIESTA KEY'S "OUTDOOR ACADEMY"!!! ONLY 1/2 MILE AWAY! One-of-a-kind enclave of Sandy Hook at USA's No 1 BEACH. A private road takes you to Elevated living area with entry

  Joseph Russo COURTYARD MODERN

  95 Sandy Hook Rd S, Sarasota, FL 34242
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  $8,500 per month

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

  5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242

  ** BOOKED JANUARY THROUGH MARCH 2025 ***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 USA! The spacious unit

  Kayla Lamb NEXTHOME EXCELLENCE

  5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
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  /15

  $7,500 per month

  • 2 Beds
  • 2 Baths
  • 1,363 Sq Ft
  • Condo for Rent

  460 Beach Rd Unit A1, Sarasota, FL 34242

  Available OCT- DEC. 2024 and APR. 2025. Direct beach front condo on Siesta Key beach. This unit has it all for that Florida vacation. 2 bedroom, 2 baths, located on the 2nd floor with private lanai. Living room and dining area face the Gulf of Mexico which allows for beautiful sunsets. The condo is tastefully decorated with wood and tile floors. Cool off in the pool located next to the unit, take

  Brenda Cozy COLDWELL BANKER REALTY

  460 Beach Rd Unit A1, Sarasota, FL 34242
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  $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
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  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Condo for Rent

  1255 E Peppertree Dr Unit 201, Sarasota, FL 34242

  Bayside highrise Building with underground parking, elevator, turnkey furnished, secured building, washer and dryer nicely appointed Two heated pools, lighted tennis courts, fishing pier, fitness room and that Beautiful Siesta Beach. Restaurants, Shopping, Theater, Arts, Golfing, Bicycling whatever your pleasure you will find in Sarasota. Peppertree is a Gulf to Bay complex Available

  Lisa Beach WATERSIDE REALTY LLC

  1255 E Peppertree Dr Unit 201, Sarasota, FL 34242
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  $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
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  $5,000 per month

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft
  • Condo for Rent

  1257 S Portofino Dr Unit 36, Sarasota, FL 34242

  Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 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 new coffee table, an electric fireplace, new shower heads, a portable electric grill, bikes, beach

  Margaret Young JENNETTE PROPERTIES, INC.

  1257 S Portofino Dr Unit 36, Sarasota, FL 34242
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  /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 walk in closet plus a full wall length closet. The guest bedroom has 2 single beds that can be combined to make a King. Updated bathrooms

  Margaret Young JENNETTE PROPERTIES, INC.

  1250 N Portofino Dr Unit 107, Sarasota, FL 34242
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  /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

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