10

Osprey, FL Houses for Rent with Pool

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  • /47

    $12,000 per month

    • 3 Beds
    • 3 Baths
    • 3,681 Sq Ft
    • House for Rent

    600 Eagle Watch Ln, Osprey, FL 34229

    Beautiful completely renovated home with all the upgrades you can want. Available for annual, and shorter term leases. Pricing is for annual rent.

    Agent Photo

    Joe Murphy

    COLDWELL BANKER REALTY

    (941) 837-8093

    600 Eagle Watch Ln, Osprey, FL 34229
  • /44

    $3,950 per month

    • 3 Beds
    • 3 Baths
    • 1,781 Sq Ft
    • House for Rent

    451 N Shore Dr, Osprey, FL 34229

    Welcome to your new spacious home in the beautiful waterfront neighborhood of Sorrento Shores. As you approach this three bedroom, three bath POOL house you will notice the quiet charm that this highly sought-after neighborhood provides. The streets are lined with tropical fruit trees, palms, and plants that create a tranquil atmosphere. The open concept, split floor plan, and wonderfully updated

    Justin Ulrich ZACHOS REALTY & DESIGN GROUP

    451 N Shore Dr, Osprey, FL 34229
  • /49

    $9,000 per month

    • 3 Beds
    • 2 Baths
    • 1,977 Sq Ft
    • House for Rent

    18 N Casey Key Rd, Osprey, FL 34229

    Beautifully remodeled in 2012, this bayfront residence combines elegance, functionality and an enviable location. The living room, kitchen and family room are great places to gather, and the split floor plan provides room for all, privacy to retreat with a good book or work from home options. The classic coastal style provides a view of the bay and intracoastal waterway from the primary bedroom.

    Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

    18 N Casey Key Rd, 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

    Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 90 Day minimum stay in Peak Season at $10,500/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 retreat

    Dave Holt PMI SARASOTA

    521 Habitat Blvd, Osprey, FL 34229
  • /51

    $8,000 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
  • /100

    $3,750 per month

    • 4 Beds
    • 4 Baths
    • 3,183 Sq Ft
    • House for Rent

    650 Crane Prairie Way, Osprey, FL 34229

    Now Available – Lease Option or Lease Purchase Opportunity in Willowbend! Flexible lease terms now offered:Lease Option with option fee - OR - Lease Purchase with buyer commitment and possible rent credit. Lease Option: Lease now with the option—but not the obligation—to purchase later. You are not obligated to buy, but the seller retains the option fee if you don’t. Lease Purchase: Lease

    Cheri Castro KELLER WILLIAMS ON THE WATER

    650 Crane Prairie Way, Osprey, FL 34229
  • /17

    $3,999 per month

    • 3 Beds
    • 2 Baths
    • 2,298 Sq Ft
    • House for Rent

    510 Latitude Ln, Osprey, FL 34229

    Custom, Lee Wetherington home with a private heated pool in the sought after, maintenance free community of Willow Bend. Located close to Pineview School, Legacy Trail, Oscar Scherer Park and our world-famous beaches. This home features volume tray ceilings with lots of natural light, natural gas cooking, crown molding, built in features and indoor laundry. The large master suite features double

    Marisa Marino BRIGHT REALTY

    510 Latitude Ln, Osprey, FL 34229
  • /68

    $21,000 per month

    • 4 Beds
    • 6 Baths
    • 9,081 Sq Ft
    • House for Rent

    854 MacEwen Dr, Osprey, FL 34229

    **RENTAL OPPORTUNITY (unfurnished)** SPACIOUS, LUXURIOUS and BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE situated behind the SECURE GATES of The Oaks Country Club Community, Boasting OVER 9,000sf and located on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths + Office/Library + Home Theater + Game

    Mark Lyda GENEROUS PROPERTY

    854 MacEwen Dr, 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
  • /42

    $4,500 per month

    • 2 Beds
    • 2 Baths
    • 1,682 Sq Ft
    • House for Rent

    5305 Bartolomeo St, Sarasota, FL 34238

    Annual lease (no short term) turn-key furnished 3 bedroom two bath w/private heated pool and spa. Life-style community with all the resort amenities and activities: Clubhouse, pickleball, tennis courts, fitness gym, exercise rooms, day spa, Bahama Bar, resort pool, resistance pool, pool side spa, trails, & direct access to the Legacy Bike Trail.Primary suite is a peaceful retreat with a tray

    Leonard Giarrano RE/MAX ALLIANCE GROUP

    5305 Bartolomeo St, Sarasota, FL 34238
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