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Winding Cypress Homes for Rent

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  • /49

    $12,000 per month

    • 3 Beds
    • 3 Baths
    • 2,158 Sq Ft
    • House for Rent

    6754 Pennyroyal Dr, Naples, FL 34114

    AVAILABLE FOR 2026 SEASON!! Step into paradise! ONE SMALL DOG ALLOWED! Built in 2021, this newly decorated and spacious pool home offers 3 bedrooms (King, King & 2 Twins) plus a den and 3 FULL bathrooms. Features include a wonderful open floor plan with zero-corner sliders that bring the outside in! Fabulous screened-in area with heated pool, natural gas, stainless appliances, quartz counters,

    Sam Wells Coldwell Banker Realty

    6754 Pennyroyal Dr, Naples, FL 34114
  • /39

    $4,950 per month

    • 3 Beds
    • 2.5 Baths
    • 2,123 Sq Ft
    • House for Rent

    6690 Pennyroyal Dr, Naples, FL 34114

    Stunning and spacious, this 2 car garage, 3-bedroom, 2.5-bathroom home built in 2020 offers luxury living with high-end upgrades throughout and located in the sought after amenity rich community of Winding Cypress. This turnkey property comes beautifully furnished with high-end decor and a fully stocked gourmet kitchen, allowing you to move right in and start enjoying your new home from day one.

    Aimee O'Connor Coldwell Banker Realty

    6690 Pennyroyal Dr, Naples, FL 34114
  • /35

    $5,500 per month

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft
    • House for Rent

    6856 Winding Cypress Dr, Naples, FL 34114

    Gorgeous kitchen with an oversized island is open to the bright and airy great room as well as your very own private pool and spa! Sliding doors fold all the way back allowing for fabulous inside/outside entertaining. The chef's dream kitchen offers GAS cooking, a huge pantry and counter island seating. Your private pool and spa is heated by gas as well! Be sure to notice the unique lighting

    Maureen Vita Berkshire Hathaway FL Realty

    6856 Winding Cypress Dr, Naples, FL 34114
  • /50

    $9,500 per month

    • 3 Beds
    • 3 Baths
    • 2,272 Sq Ft
    • House for Rent

    6779 Pennyroyal Dr, Naples, FL 34114

    A stunning new pool and outdoor lanai, complement this exquisitely designed home, which offers tranquil views of the lake. This property features three bedrooms plus a den and three bathrooms, making it ideal for vacationing. The interior boasts a bright and airy coastal contemporary style with an open floor plan.This is a perfect vacation rental!

    Patricia Moreno Naples Homes and Rentals Inc

    6779 Pennyroyal Dr, Naples, FL 34114
  • /29

    $12,000 per month

    • 3 Beds
    • 2 Baths
    • 1,805 Sq Ft
    • House for Rent

    7567 Winding Cypress Dr, Naples, FL 34114

    From the moment you arrive at the stunning entry, Winding Cypress invites you into this wonderful community. This natural gas, resort-style community, remaining almost 2/3 preserve, welcomes you with a streetscape of superb views and new homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of world-class amenities right in your own

    Dave Garafola Reed Property Mgt. & Sales

    7567 Winding Cypress Dr, Naples, FL 34114
  • /35

    $8,500 per month

    • 3 Beds
    • 2 Baths
    • 2,175 Sq Ft
    • House for Rent

    6694 Pennyroyal Dr, Naples, FL 34114

    Unwind in this brand new, pristine vacation rental. Revel in the allure of a splendid pet-friendly home with a dazzling outdoor lanai, designed for the ultimate outdoor living experience. This residence boasts abundant natural light, a refreshing coastal contemporary interior, and an inviting open floor plan. With three bedrooms plus a versatile office you'll have ample space to accommodate your

    Ashley Baird Coldwell Banker Realty

    6694 Pennyroyal Dr, Naples, FL 34114
  • /43

    $7,000 per month

    • 2 Beds
    • 2 Baths
    • 1,542 Sq Ft
    • Condo for Rent

    7631 Jacaranda Ln, Naples, FL 34114

    Beautiful two bedroom plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king bed, second bedroom has a queen bed and den has a full size pullout couch that sleeps 2 and includes a full wardrobe armor for clothing . Spacious attached 2-car garage. Relax on the spacious lanai that overlooks the private pool with peaceful lake

    Amber Jasper Grice Realty Inc

    7631 Jacaranda Ln, Naples, FL 34114

Why Live in Winding Cypress

Winding Cypress in Naples is a gated community featuring around 800 homes and villas, predominantly in Coastal Contemporary and Mediterranean Revival styles. Residents enjoy professionally landscaped properties with trimmed lawns and flower-filled gardens. The neighborhood boasts a crime score significantly lower than the national average, providing a safer living environment. Amenities include a clubhouse, pool, dog park, community garden, and courts for tennis, bocce, and pickleball. The community is adjacent to Picayune Strand Forest, offering a boardwalk and picnic area. Golf enthusiasts will find several courses within 4 miles, such as Eagle Creek Golf and Country Club. Boating facilities are available at Tarpon Club Marina and Naples Cruise Club, less than 10 miles away. The Shady Palm Café, located in the clubhouse, is a popular spot for residents, serving food and drinks and hosting neighborhood events. Shopping options are conveniently located 2 miles away at Tamiami Crossing and Shops at Eagle Creek, featuring stores like Walmart, Aldi, and Publix. Highway 41 provides access to Naples, 10 miles away, and Marco Island, 11 miles to the south, with public transit available via Collier Area Transit. The nearest healthcare facility is Physicians Regional on Collier Boulevard, 3 miles away. Schools in the Collier County School District, including Lely Elementary, Manatee Middle, and Lely High, have high ratings. Florida SouthWestern State College - Collier Campus is also nearby, just 4 miles from the community.
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