Homes for Rent near Out-Of-Door Academy

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  $7,500 per month

  • 3 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • House for Rent

  1716 Oak St, Sarasota, FL 34236

  Available for 3 months or longer. Located in the much sought-after Laurel Park neighborhood near upscale Main Street. This unique 3BR/2 bath impeccably furnished 1927 Historic home along with a separate 2 car garage. The renovations completed in 2020 were done with care and precision, from floor to ceiling. The new owners have carefully curated the high-end furnishing, artwork and accessories in

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1716 Oak St, Sarasota, FL 34236
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  $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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  $10,000 per month

  • 3 Beds
  • 2 Baths
  • 1,415 Sq Ft
  • House for Rent

  2641 Martin St, Sarasota, FL 34237

  Welcome to Deja Blue, a designer pool home just minutes from downtown Sarasota & area beaches & walkable to Legacy Trail. This house offers designer comfort w/ room to spread out. Features include a huge heated swimming pool, fully fenced back yard, chef's kitchen with breakfast bar, separate dining area, dedicated work station w/ 2 desks, 5 flat screen tvs inside & out w/ fast wifi &

  Adam Kabinoff UPTOP REAL ESTATE SERVICES, LLC

  2641 Martin St, Sarasota, FL 34237
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  $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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  $3,400 per month

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft
  • House for Rent

  2043 Roselawn St, Sarasota, FL 34231

  Fantastic Villa with a private pool close to the North bridge to Siesta Key available for monthly rentals! The villa is fully equipped with 3 bedrooms (master has a king bed, 2nd BR with a queen, and 3rd has 2 twins). Comfortably accommodates 6 people. There is a grill in the lanai space with seating for 6 as well. 2 lounge chairs are provided by the pool. Beach chairs and towels are available

  Philip Pisano, III MICHAEL SAUNDERS & COMPANY

  2043 Roselawn St, Sarasota, FL 34231
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  $5,000 per month

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

  769 John Ringling Blvd Unit 36, Sarasota, FL 34236

  Turnkey Seasonal Rental in Sarasota Harbor East, fabulous bay views from every window, 2 bedrooms, two baths, updated and tile floors throughout. Lovely four season Lanai overlooking Sarasota Bay, watch the Dolphin and Manatee while you sip your morning coffee. The community offers a lovely heated pool, clubhouse, grills, kayak storage and boat slips on a first come, first served basis. Walk to

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  769 John Ringling Blvd Unit 36, Sarasota, FL 34236
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  $2,900 per month

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Condo for Rent

  3745 Almeria Ave Unit 7S, Sarasota, FL 34239

  ***AVAILABLE DECEMBER 15TH, 2023*****3 MONTH MINIMUM**** This beautifully updated first floor condo is tucked away in a hidden serene tropical paradise just minutes away from Siesta Key and Downtown! You will enjoy living in this bright 2 bed/2 bath corner unit with beautiful new furnishings from top to bottom! Primary bedroom has a king, and the guest has two twins. Kitchen is updated and fully

  Alex Roth ROSEBAY INTERNATIONAL REALTY, INC

  3745 Almeria Ave Unit 7S, Sarasota, FL 34239
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  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Condo for Rent

  750 N Tamiami Trail Unit 916, Sarasota, FL 34236

  LOCATION, LOCATION, LOCATION!!! Look no further as this downtown Sarasota condo located at the Renaissance has it all. The comfortably furnished and colorfully decorated condo has 2 bedrooms, 2 bathrooms, living room/dining room/kitchen combination, split floor plan and a lovely lanai to take in all of the downtown sights. The kitchen has lots of counter and cabinet space for preparing and

  C. Alison Hunter JENNETTE PROPERTIES INC

  750 N Tamiami Trail Unit 916, Sarasota, FL 34236
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  $9,000 per month

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft
  • House for Rent

  3924 Helene St, Sarasota, FL 34233

  This beautiful newly renovated pool home features 3 bedrooms, 2 bathrooms. The home sleeps 6 and is in the neighborhood of Forest Lakes South, Sarasota. Modern updates include new flooring throughout, updated bathrooms & kitchen with new quartz countertops, new exterior facade & new doors. One small dog is allowed.This home provides peaceful pool and pond views from almost every room in

  Jana L. Nizny M&M PROPERTY MANAGEMENT GROUP

  3924 Helene St, Sarasota, FL 34233
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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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  $15,000 per month

  • 4 Beds
  • 4 Baths
  • 3,356 Sq Ft
  • House for Rent

  460 Pheasant Dr, Sarasota, FL 34236

  If you are looking for luxurious living while indulging in the most breathtaking green scenery, then this stunning 4-bedroom, 4-bathroom waterfront home in Sarasota is the perfect place for you. With its 147 feet of waterfront, vaulted ceilings, and panoramic views of the water, this home is the perfect place to relax and enjoy the Florida sunshine. The kitchen has been updated with fusion

  Hamid Mohajir RENT SARASOTA

  460 Pheasant Dr, Sarasota, FL 34236
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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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  $2,100 per month

  • 2 Beds
  • 2 Baths
  • 1,211 Sq Ft
  • Condo for Rent

  1620 Boathouse Cir Unit GR103, Sarasota, FL 34231

  ***AVAILABLE NOVEMBER 1, 2025*** Pelican Cove is a 75-acre gated, vibrant, waterfront community nestled among manicured tropical foliage truly offering something for everyone. Abundant amenities include an 86-slip boat harbor with sailboat water, excellent rates, and a launch dock for kayaks and canoes, 6 heated swimming pools, hot tub, 3 clubhouses, 4 lighted tennis courts, shuffleboard,

  Anthony DeLuca AUDREY RAIN RENTALS, INC

  1620 Boathouse Cir Unit GR103, Sarasota, FL 34231
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  $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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  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft
  • House for Rent

  2650 Davis Blvd, Sarasota, FL 34237

  Welcome to Casa Pura Vida! This bohemian styled designer pool home is the perfect vacation rental for groups of up to 8 to relax and enjoy the "pure life". The house features 3 bedrooms, 2 bathrooms, central living & dining rooms w/ views of the sparkling blue heated pool & covered outdoor kitchen area, a private fenced backyard w/ tropical landscaping, a chefs kitchen w/ breakfast bar & separate

  Adam Kabinoff UPTOP REAL ESTATE SERVICES, LLC

  2650 Davis Blvd, Sarasota, FL 34237
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  /25

  $2,000 per month

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

  500 S Washington Dr Unit 24B, Sarasota, FL 34236

  Walk to anything you need on St. Armand's Circle from the Kingston Arms Condo's. Spend time in paradise in this 1 bed, 1 full bath 2nd story unit. There is an elevator. The condo features a King-sized bed with views of the pool. Linens are provided along with a fully equipped kitchen, internet service and all utilities. This is 1 block from morning coffee, ice cream or a 5 Star meal. Dining and

  Jane Hunter JENNETTE PROPERTIES INC

  500 S Washington Dr Unit 24B, Sarasota, FL 34236
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  $2,995 per month

  • 2 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • House for Rent

  7328 Curtiss Ave, Sarasota, FL 34231

  Not available for an annual lease. Not available for season 2025. Escape the winter and enjoy the Florida weather pool side at this 2-bedroom, 2-bath, single family home. This fresh, clean, tastefully decorated, well maintained pool home in Gulf Gate is available for a long or short stay and allows a small dog! The primary bedroom has a king size bed, double closets, 45" wall mounted TV, and en

  Maureen Plichta STRINGER MANAGEMENT INC

  7328 Curtiss Ave, Sarasota, FL 34231
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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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  $2,300 per month

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

  1647 Brookhouse Ct Unit BR146, Sarasota, FL 34231

  ***Available NOW THROUGH NOVEMBER 2025***. Phenomenal 1 bedroom 1 bathroom heavily renovated first-class touches. Easy to show! Pelican Cove is a 75-acre, gated, vibrant, waterfront community nestled among manicured tropical foliage truly offering something for everyone. Abundant amenities include the 86-slip boat harbor with excellent rates & a launch dock for kayaks and canoes, 6 heated

  Anthony DeLuca AUDREY RAIN RENTALS, INC

  1647 Brookhouse Ct Unit BR146, Sarasota, FL 34231
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  $2,400 per month

  • 2 Beds
  • 2 Baths
  • 1,211 Sq Ft
  • Condo for Rent

  1508 Pelican Cove Rd Unit GR233, Sarasota, FL 34231

  *** Available JUNE 2025*** All I can say is this unit has been heavily renovated. It's in a great location as well. 2 bedroom, 2 bath, 2nd floor unit. Pelican Cove is a 75-acre gated, vibrant, waterfront community nestled among manicured tropical foliage truly offering something for everyone. Abundant amenities include an 86-slip boat harbor with sailboat water, excellent rates, and a launch dock

  Anthony DeLuca AUDREY RAIN RENTALS, INC

  1508 Pelican Cove Rd Unit GR233, Sarasota, FL 34231

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