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.
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|
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
- 4 days |
- -- |
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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
| Date | Event | Price |
|---|---|---|
| 7/1/2026 | Listed for rent | $11,000+10%$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 11/24/2025 | Listing removed | $10,000$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 11/3/2025 | Listed for rent | $10,000$4/sqft |
Source: Zillow Rentals Report a problem | ||
| 9/9/2025 | Sold | $975,000-18.4%$391/sqft |
Source: | ||
| 8/25/2025 | Pending sale | $1,195,000$479/sqft |
Source: | ||
| 8/7/2025 | Price change | $1,195,000-4.4%$479/sqft |
Source: | ||
| 6/26/2025 | Price change | $1,250,000-10.4%$501/sqft |
Source: | ||
| 3/31/2025 | Price change | $1,395,000-10%$559/sqft |
Source: | ||
| 11/5/2024 | Listed for sale | $1,550,000+151.7%$621/sqft |
Source: | ||
| 4/2/2019 | Sold | $615,855$247/sqft |
Source: Public Record Report a problem | ||
| 9/17/2018 | Listing removed | -- |
Source: DiVosta Report a problem | ||
| 9/9/2018 | Listed for sale | -- |
Source: DiVosta Report a problem | ||
Neighborhood: Winding Cypress
Nearby schools
GreatSchools rating
- 7/10Lely Elementary SchoolGrades: PK-5Distance: 3.6 mi
- 7/10Manatee Middle SchoolGrades: 6-8Distance: 0.7 mi
- 5/10Lely High SchoolGrades: 9-12Distance: 3.6 mi







