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Homes for Rent in Osprey, FL with 3-Bedrooms

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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

    $4,250 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
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    $1,599 - $3,025 per month

    Alton Osprey

    1 - 3 Beds

    4000 Destination Dr, Osprey, FL 34229

    Now open for immediate move-ins, discover stunning one-, two-, and three-bedroom apartment homes in Osprey, FL. With high-end finishes outfitting each residence, offering the perfect blend of comfort and sophistication, coming home will feel like a daily retreat. Our best-in-class amenity spaces allow you the opportunity to live beyond your expectations - from our sleek business center that works

    4000 Destination Dr, Osprey, FL 34229
  • /83

    $3,300 per month

    • 3 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • Condo for Rent

    232 Hidden Bay Dr Unit 504, Osprey, FL 34229

    Annual unfurnished condominium available in Hidden Bay! Discover luxurious waterfront living in this stunning 2,000-square-foot, three-bedroom, three-bath condominium with breathtaking views of the Intracoastal Waterway. Enjoy spectacular sunsets from the expansive screened balcony, ideal for dining and relaxation. The home also comes with a private two-car garage. At the beautiful, gated

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    232 Hidden Bay Dr Unit 504, Osprey, FL 34229
  • /20

    $3,099 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 $3278.90. That covers your base rent, $3099.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Pool

    692 Stillwater Ct, Osprey, FL 34229
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    $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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    $2,995 per month

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Condo for Rent

    127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229

    Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage

    127 Explorer Dr Unit 127 Explorer Dr, 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
  • /43

    $2,400 per month

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft
    • House for Rent

    163 Pennsylvania Ave, Osprey, FL 34229

    Welcome to 163 Pennsylvania Avenue, nestled in the quaint community of Osprey, FL. This charming 3-bedroom, 2-bathroom home, built in 2018, offers a smart blend of style and energy efficiency. Spanning 1,346 square feet, the open floor plan showcases a modern grey color palette, creating an inviting ambiance throughout. Step into the kitchen, where sleek stainless steel appliances and light wood

    Beth Harris COMPASS FLORIDA LLC

    163 Pennsylvania Ave, Osprey, FL 34229
  • /45

    $2,250 per month

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • Condo for Rent

    4256 Expedition Way Unit 107, Osprey, FL 34229

    Welcome to Bay Street in Osprey! This 3-bedroom, 2-bath condominium offers the comfort of single-level living on the second floor of a two-story building. Enjoy an open layout filled with natural light and peaceful lake and fountain views from nearly every room. The kitchen is equipped with newer stainless steel appliances, plus a washer and dryer. Additional features include ceiling fans

    Geri Scheckner BRIGHT REALTY

    4256 Expedition Way Unit 107, Osprey, FL 34229
  • /38

    $6,000 per month

    • 3 Beds
    • 3 Baths
    • 2,055 Sq Ft
    • Condo for Rent

    409 N Point Rd Unit 802, Osprey, FL 34229

    **TURNKEY FURNISHED, PENTHOUSE Condo Unit has been FULLY RENOVATED** This 8TH FLOOR, Light and Bright, 3-BEDROOM plus 3 FULL BATH dwelling with screened balcony is available beginning in September, 2025. The 2055sf floorplan is tastefully furnished and offers superb views of the Intracoastal Waterway and Gulf. This unit was fully renovated in 2023 with updated oak hardwood flooring, new kitchen

    Mark Lyda GENEROUS PROPERTY

    409 N Point Rd Unit 802, Osprey, FL 34229
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    $4,200 per month

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft
    • Condo for Rent

    280 Hidden Bay Dr Unit 202, Osprey, FL 34229

    READY FOR IMMEDIATE OCCUPANCY! Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota Bay Step into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space for your

    Mike Aveni KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    280 Hidden Bay Dr Unit 202, 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
  • /39

    $4,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,166 Sq Ft
    • Condo for Rent

    Unlisted Address

    NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

    Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

    Unlisted Address
  • /39

    $7,000 per month

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft
    • Condo for Rent

    Unlisted Address

    NOW AVAILABLE FOR SEASONAL RENTAL – READY FOR IMMEDIATE OCCUPANCY AND FULLY FURNISHED!Modern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier

    Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

    Unlisted Address
  • /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
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    $6,000 per month

    • 3 Beds
    • 2 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

    CLOSE TO NOKOMIS BEACH! AVAILABLE JAN/FEB/MAR/APR 2026 $6,000/MONTH. Beautiful waterfront 5th Floor condo located in Blackburn Harbor Residences with breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was converted from a den) and

    Chrissie Cummings JENNETTE PROPERTIES INC

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
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    $6,950 per month

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft
    • Townhouse for Rent

    101 Woodland Place, Osprey, FL 34229

    Price Reduction and Now AVAILABLE FOR LEASE for FEBRUARY through APRIL 2026 at PINE RUN Condominiums in OSPREY, Florida! One month availability. 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is a WATERFRONT Community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of

    Patrice Ivan WAGNER REALTY

    101 Woodland Place, Osprey, FL 34229
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    $5,900 per month

    • 3 Beds
    • 3 Baths
    • 2,545 Sq Ft
    • Condo for Rent

    3603 N Point Rd Unit 602, Osprey, FL 34229

    **FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite

    Mark Lyda GENEROUS PROPERTY

    3603 N Point Rd Unit 602, Osprey, FL 34229
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    $7,000 per month

    • 3 Beds
    • 2 Baths
    • 2,058 Sq Ft
    • Condo for Rent

    14041 Bellagio Way Unit 316, Osprey, FL 34229

    *BOOKED DEC THROUGH JUNE 2026.* MINS TO CASEY KEY & NOKOMIS BEACH! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd floor end unit. Upon

    Chrissie Cummings JENNETTE PROPERTIES INC

    14041 Bellagio Way Unit 316, Osprey, FL 34229
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    $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
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    $4,500 per month

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Condo for Rent

    152 Navigation Cir Unit 107, Osprey, FL 34229

    BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with

    Henry Rossi RENT SARASOTA

    152 Navigation Cir Unit 107, Osprey, FL 34229
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