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    House for rent
  • Accepts Zillow applications
    $11,000/moFees may apply

    7788 Winding Cypress Dr, Naples, FL 34114

    3beds
    2,496sqft

    Price may not include required fees and charges. Price shown reflects the lease term provided. Learn more|

    Fast & easy Zillow application.

    This property accepts Zillow applications. Click 'Apply now' to fill out the online form once and apply to as many participating properties as you want. Just $35 for 30 days.

    Single family residence
    Available Fri Jan 1 2027
    Cats, dogs OK
    Air conditioner, central air
    In unit laundry
    Attached garage parking
    Central, natural gas

    What's special

    Pool and hot tubSpacious floor areaCentral heating and cooling
    Welcome to your dream vacation home in Naples, Florida! This charming property in Winding Cypress offers a wonderful opportunity for comfortable living in a vibrant community. With less than a 5 minute drive to grocery & convenience stores, you'll have everything you need right at your fingertips. Located just a short drive from Marco Island and Downtown Naples with a large variety of shops and restaurants. Key property features include Pool and Hot Tub, WiFi, central heating and cooling, as well as air conditioning and ceiling fans. The spacious floor area provides ample room for relaxation. You can also enjoy our magnificent clubhouse with a luxury community pool, Tiki Bar, Fitness centers, and lounge area ensuring a pleasant atmosphere. Don't miss out on this opportunity to experience Naples living. This rental is available for the high season starting January 1st 2027 through April 30th 2027. As required by the HOA of Winding Cypress, a minimum rental period of 30 days is mandatory, but would prefer a 3 month rental. The rental fee is $11,000 per month, and the 11% State Tax and TDT fee are the responsibility of the renter. Additionally, there is an application process and associated fees through the management company.
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    Zillow last checked:

    Listing updated:

    Travel times

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 3
    • Full bathrooms: 3
    Heating
    • Central, Natural Gas
    Cooling
    • Air Conditioner, Central Air
    Appliances
    • Included: Dishwasher, Freezer, Microwave Oven, Oven, Refrigerator, Stove
    • Laundry: In Unit
    Features
    • Flooring: Tile
    • Furnished: Yes
    Interior area
    • Total interior livable area: 2,496 sqft

    Property

    Parking
    • Parking features: Attached, Garage
    • Has attached garage: Yes
    • Details: Contact manager
    Features
    • Has private pool: Yes
    • Pool features: Pool
    • Has spa: Yes
    • Spa features: Spa
    Details
    • Additional structures: Garage(s)
    • Parcel number: 82679019084
    • Other equipment: Generator

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence

    Community & HOA

    HOA
    • Amenities included: Hot Tub, Pool, Spa
    Location
    • Region: Naples

    Financial & listing details

    • Lease term: Sublet/Temporary

    Price history

    DateEventPrice
    7/1/2026Listed for rent$11,000+10%$4/sqft
    Source: Zillow Rentals Report a problem
    11/24/2025Listing removed$10,000$4/sqft
    Source: Zillow Rentals Report a problem
    11/3/2025Listed for rent$10,000$4/sqft
    Source: Zillow Rentals Report a problem
    9/9/2025Sold$975,000-18.4%$391/sqft
    Source: Marco Multi List #2242184 Report a problem
    8/25/2025Pending sale$1,195,000$479/sqft
    Source: Marco Multi List #2242184 Report a problem
    8/7/2025Price change$1,195,000-4.4%$479/sqft
    Source: Marco Multi List #2242184 Report a problem
    6/26/2025Price change$1,250,000-10.4%$501/sqft
    Source: Marco Multi List #2242184 Report a problem
    3/31/2025Price change$1,395,000-10%$559/sqft
    Source: Marco Multi List #2242184 Report a problem
    11/5/2024Listed for sale$1,550,000+151.7%$621/sqft
    Source: Marco Multi List #2242184 Report a problem
    4/2/2019Sold$615,855$247/sqft
    Source: Public Record Report a problem
    9/17/2018Listing removed--
    Source: DiVosta Report a problem
    9/9/2018Listed for sale--
    Source: DiVosta Report a problem

    Neighborhood: Winding Cypress

    Nearby schools

    GreatSchools rating