17

Osprey, FL Houses for Rent

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    $5,500 per month

    • 3 Beds
    • 2 Baths
    • 2,172 Sq Ft
    • House for Rent

    557 Crane Prairie Way, Osprey, FL 34229

    Welcome to this beautiful fully furnished 3-bed, 2-bath home in the gated community of Willowbend in Osprey. With 2,172 sq ft of bright, open living space, this seasonal rental offers comfort, style, and plenty of room to relax. Enjoy a spacious kitchen, a large primary suite, and a peaceful screened lanai perfect for morning coffee or evening sunsets.The community features a pool, fitness

    Agent Photo

    Craig McCoy

    PREFERRED SHORE LLC

    (941) 392-7290

    557 Crane Prairie Way, Osprey, FL 34229
  • /44

    $4,500 per month

    • 3 Beds
    • 2 Baths
    • 2,188 Sq Ft
    • House for Rent

    1308 Thornapple Dr, Osprey, FL 34229

    Welcome home to Willow Bend, a tropical maintenance-free community located in middle of everything southwest Florida has to offer! Gorgeous turnkey 3 bedroom& 2 Bath Furnished annual rental near Nokomis Beach. Peaceful Lake views on an oversized lot. The pretty lanai features travertine marble tile and a HEATED POOL. Many upgrades include quartz kitchen counters, wood plank oak flooring, and

    Agent Photo

    Rachel Tritschler

    RE/MAX ALLIANCE GROUP

    (941) 236-5116

    1308 Thornapple Dr, Osprey, FL 34229
  • /40

    $6,000 per month

    • 2 Beds
    • 3 Baths
    • 1,709 Sq Ft
    • House for Rent

    716 Sarabay Rd, Osprey, FL 34229

    Experience Waterfront Luxury at 716 Sarabay Road, Osprey, FL. Welcome to your private waterfront retreat on Little Sarasota Bay. This stunning 2-bedroom, 3-bath residence offers over 100 feet of direct bay frontage and has been meticulously renovated throughout, combining modern luxury with timeless coastal charm. The open-concept living space is bright and inviting, featuring designer finishes

    Agent Photo

    Mitchell Roberts

    PARADISE REALTY OF VENICE INC

    (941) 241-3260

    716 Sarabay Rd, Osprey, FL 34229
  • /20

    $3,345 per month

    • 3 Beds
    • 2 Baths
    • 2,250 Sq Ft
    • House for Rent

    692 Stillwater Ct, Osprey, FL 34229

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3524.90. That covers your base rent, $3345.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Pool

    692 Stillwater Ct, Osprey, FL 34229
  • /15

    $3,500 per month

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • House for Rent

    2068 Preymore St, Osprey, FL 34229

    Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in

    Kenia Nunez PREFERRED SHORE LLC

    2068 Preymore St, Osprey, FL 34229
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    $1,830 per month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • House for Rent

    455 Pennsylvania Ave, Osprey, FL 34229

    Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,

    455 Pennsylvania Ave, Osprey, FL 34229
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    $2,950 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    4429 Conchfish Ln, Osprey, FL 34229

    Steps from Pine View School, Florida's #1 public school, with 2,008 sq. ft. of living space, this home features brand-new thick waterproof laminate wood flooring in all bedrooms and closets, an ocean-inspired guest bathroom, and tile throughout the main living areas for easy maintenance. Enjoy the covered lanai overlooking a private backyard, perfect for relaxing or entertaining, and take

    JIA SONG Jia Song Realty

    4429 Conchfish Ln, Osprey, FL 34229
  • /37

    $2,900 per month

    • 4 Beds
    • 2 Baths
    • House for Rent

    4417 Conchfish Ln, Osprey, FL 34229

    This one-story home offers 1861 sqft living space, with four bedrooms, two bathrooms, and a two-car garage. Open-concept floor plan. Welcome to 4417 Conchfish Ln, a beautifully maintained 4-bedroom, 2-bathroom home located in the highly sought-after community of Osprey, FL just steps from the top-rated Pine View School. This spacious home features an open kitchen layout with a brand-new

    JIA SONG Jia Song Realty

    4417 Conchfish Ln, Osprey, FL 34229
  • /25

    $2,600 per month

    • 4 Beds
    • 2.5 Baths
    • 2,064 Sq Ft
    • House for Rent

    554 Pine Ranch East Rd, Osprey, FL 34229

    ANNUAL/ GENTLY FURNISHED 4 BED/2.5 BATH. The home is gently furnished which will work perfectly for the family who has some furniture already.Available November1st - 9 month minimum - come stay here while your build your home.Master has a king bed with ensuite bathroom.- walk in shower, garden tub. Guest room has twin beds, 2nd guest room has a built in office and a Murphy bed. 4th

    Annabelle Newland STOCKTON REALTY ADVISORS LLC

    554 Pine Ranch East Rd, Osprey, FL 34229
  • /37

    $3,550 per month

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

    603 Pine Ranch East Rd, Osprey, FL 34229

    *AVAILABLE NOVEMBER 15, 2025 — PREVIEW BY APPOINTMENT ONLY*Currently occupied — showings available by appointment only.This beautifully updated 3-bedroom, 2-bathroom home, features a desirable split floor plan and a spacious 2-car garage. Offered unfurnished, with pool and yard maintenance included in the rent.HIGHLIGHTS:Open-concept layout designed for comfort, entertaining,

    Marina Yanovskiy ALL SEASONS REALTY LLC

    603 Pine Ranch East Rd, Osprey, FL 34229
  • /36

    $2,500 per month

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft
    • House for Rent

    305 Bay Vista Ave, Osprey, FL 34229

    Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment!As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows.But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh

    Jennifer . STOCKTON REALTY ADVISORS LLC

    305 Bay Vista Ave, Osprey, FL 34229
  • /15

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,738 Sq Ft
    • House for Rent

    1363 New Forest Ln, Osprey, FL 34229

    Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice

    Pamela Strom RE/MAX PALM

    1363 New Forest Ln, Osprey, FL 34229
  • /44

    $6,500 per month

    • 3 Beds
    • 3 Baths
    • 2,266 Sq Ft
    • House for Rent

    521 Habitat Blvd, Osprey, FL 34229

    REDUCED FOR THE SEASON! Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 60 Day minimum stay in Peak Season at $8,900/mo plus fees; Minimum 60 Day stay in Off Season at $6,500/mo plus fees. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

    Dave Holt PMI SOUTHWEST FLORIDA

    521 Habitat Blvd, Osprey, FL 34229
  • /9

    $2,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,173 Sq Ft
    • House for Rent

    234 Patterson Ave, Osprey, FL 34229

    Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire

    Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    234 Patterson Ave, Osprey, FL 34229
  • /51

    $7,500 per month

    • 3 Beds
    • 3.5 Baths
    • 4,519 Sq Ft
    • House for Rent

    852 MacEwen Dr, Osprey, FL 34229

    **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

    Mark Lyda GENEROUS PROPERTY

    852 MacEwen Dr, Osprey, FL 34229
  • /32

    $5,750 per month

    • 3 Beds
    • 2 Baths
    • 2,271 Sq Ft
    • House for Rent

    293 Turquoise Ln, Osprey, FL 34229

    **RARE RENTAL OPPORTUNITY (UNFURNISHED)** This STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the SECURE GATES of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank,

    Mark Lyda GENEROUS PROPERTY

    293 Turquoise Ln, Osprey, FL 34229
  • /51

    $12,000 per month

    • 4 Beds
    • 3 Baths
    • 2,546 Sq Ft
    • House for Rent

    9477 Cedar Ridge Ln, Sarasota, FL 34238

    RENTED FEBRUARY 2026, NOT AVAILABLE OFF-SEASON: Spacious single-family home at Stoneybrook Golf & Country Club situated in the center of the cul-de-sac offers stunning views from the amazing, seamlessly screened pool cage, creating a virtual oasis with overflow spa, underwater lighting, outdoor kitchen, and ample covered seating and dining area. Double entry doors greet you as you enter the

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE

    9477 Cedar Ridge Ln, Sarasota, FL 34238
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