9

Osprey, FL Houses for Rent with Pool

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  • /40

    $7,500 per month

    • 5 Beds
    • 4.5 Baths
    • 3,981 Sq Ft
    • House for Rent

    1216 Flying Bridge Ln, Osprey, FL 34229

    DO YOU WANT COMFORT AND LUXURY WHILE YOU LOOK AROUND WATERFRONT ? JUMP ON THIS LUXURY TURNKEY RENTAL. A ROOM FOR EVERY HUMAN OR FURRY FRIEND. HEATED POOL. PREMIUM CHEFS KITCHEN, PREMIUM FLOORPLAN, AND PREMIUM NEIGHBORHOOD. FLY THROUGH AVAILABLE. CALL FOR MORE INFO. MINIMUM 3 MONTH RENTAL MAY- OCT 2025 , ONLY.

    Agent Photo

    Meredith Van Vaals

    COLDWELL BANKER REALTY

    (941) 207-3297

    1216 Flying Bridge Ln, Osprey, FL 34229
  • /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) 541-8348

    600 Eagle Watch Ln, Osprey, FL 34229
  • /35

    $4,000 per month

    • 3 Beds
    • 2 Baths
    • 2,261 Sq Ft
    • House for Rent

    1279 Thornapple Dr, Osprey, FL 34229

    ANNUAL UNFURNISHED SINGLE FAMILY POOL HOME AVAILABLE IN WILLOWBEND! Gorgeous Lee Wetherington built 3 Bedroom, 2 Bath home located in the maintenance-free neighborhood of Willowbend in Osprey. The home features a gourmet kitchen with gas cooktop and double oven, 12-foot ceilings, plantation shutters, a solar heated pool, and spacious lanai with lake view. Willowbend amenities include lawn

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1279 Thornapple Dr, Osprey, FL 34229
  • /51

    $9,500 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
  • /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

    $4,200 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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