Houses for Rent in Winding Cypress, FL

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PROMOTED3D WALKTHROUGH

South Bay Plantation Apartments - 1901 Rookery Bay Dr, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
Discover our pet-friendly community offering spacious 1 to 3 bedroom apartments. Each unit features tile flooring, in unit washer and dryer and modern kitchen appliances. Enjoy amenities such as a

$2,150/mo

3 beds2 baths1,108 sq ft

South Bay Plantation Apartments

| 1901 Rookery Bay Dr, Naples, FL 34114

4 units available • Pets welcome • Fitness Center

7627 Jacaranda Ln, Naples, FL, 34114
7627 Jacaranda Ln, Naples, FL, 34114
7627 Jacaranda Ln, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
Available for season 2025. Light, bright and beautifully updated two bedroom plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king

$7,000/mo

2 beds2 baths1,554 sq ft

7627 Jacaranda Ln, Naples, FL 34114

Parking • Dishwasher • Car-dependent

7567 Winding Cypress Dr, Naples, FL, 34114
7567 Winding Cypress Dr, Naples, FL, 34114
7567 Winding Cypress Dr, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
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

$12,000/mo

3 beds2 baths1,805 sq ft

7567 Winding Cypress Dr, Naples, FL 34114

Parking • Dishwasher • Car-dependent

7763 Winding Cypress Dr, Naples, FL, 34114
7763 Winding Cypress Dr, Naples, FL, 34114
7763 Winding Cypress Dr, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
Annual Rental available for immediate occupancy. Turnkey Furnished, and ready for you to enjoy. This 2 story Summerwood model home with Breathtaking Pool and Spa offers a spectacular open floor plan.

$6,700/mo

4 beds3 baths3,077 sq ft

7763 Winding Cypress Dr, Naples, FL 34114

Parking • Dishwasher • Car-dependent

7631 Jacaranda Ln, Naples, FL, 34114
7631 Jacaranda Ln, Naples, FL, 34114
7631 Jacaranda Ln, Naples, FL, 34114

$3,500/mo

2 beds2 baths1,542 sq ft

7631 Jacaranda Ln, Naples, FL 34114

Laundry in unit • Dishwasher • Car-dependent

3D WALKTHROUGH

6856 Winding Cypress Dr, Naples, FL, 34114
6856 Winding Cypress Dr, Naples, FL, 34114
6856 Winding Cypress Dr, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
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/outs

$6,250/mo

3 beds2 baths2,100 sq ft

6856 Winding Cypress Dr, Naples, FL 34114

Parking • Car-dependent • Patio/Balcony

Property at 6767 Pennyroyal Dr, Naples, FL, 34114, 3 beds, 2 baths, [object Object]

$6,000/mo

3 beds2 baths2,185 sq ft

6767 Pennyroyal Dr, Naples, FL 34114

Property at 6779 Pennyroyal Dr, Naples, FL, 34114, 3 beds, 3 baths, [object Object]

$9,500/mo

3 beds3 baths2,272 sq ft

6779 Pennyroyal Dr, Naples, FL 34114

Property at 7631 Jacaranda Ln Unit Seasonal, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$7,000/mo

2 beds2 baths1,542 sq ft

7631 Jacaranda Ln Unit Seasonal, Naples, FL 34114

Property at 6770 Pennyroyal Dr, Naples, FL, 34114, 3 beds, 3 baths, [object Object]

$12,000/mo

3 beds3 baths2,128 sq ft

6770 Pennyroyal Dr, Naples, FL 34114

Property at 6694 Pennyroyal Dr, Naples, FL, 34114, 3 beds, 2 baths, [object Object]

$8,500/mo

3 beds2 baths2,175 sq ft

6694 Pennyroyal Dr, Naples, FL 34114

Property at 6787 Winding Cypress Dr, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$7,000/mo

2 beds2 baths1,654 sq ft

6787 Winding Cypress Dr, Naples, FL 34114

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Here are some rentals close to your search

14162 Nautica Ct, Naples, FL, 34114
14162 Nautica Ct, Naples, FL, 34114
14162 Nautica Ct, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
Beautifull Lakefront Home in Naples Reserve 3BR | Partially Furnished | Pet-Friendly Welcome to this beautifully maintained single-family home in the sought-after, resort-style community of Naples Re

$3,800/mo

3 beds2 baths1,684 sq ft

14162 Nautica Ct, Naples, FL 34114

Pets welcome • Laundry in unit • A/C

3D WALKTHROUGH

6971 Amen Corner Ct, Naples, FL, 34113
6971 Amen Corner Ct, Naples, FL, 34113
6971 Amen Corner Ct, Naples, FL, 34113
ABOUT THIS HOME
House for Rent in Winding Cypress:
Available for off season 2024 and 2025 season (Owner using Dec 26, 2024-Jan 10, 2025)! Beautifully decorated 3-bedroom home available for short-term rent with Players Club access! The Master & Guest b

$12,000/mo

3 beds2 baths1,749 sq ft

6971 Amen Corner Ct, Naples, FL 34113

Parking • Car-dependent • Swimming Pool

7450 Emilia Ln, Naples, FL, 34114
7450 Emilia Ln, Naples, FL, 34114
7450 Emilia Ln, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
ENJOY THIS TURNKEY FURNISHED VILLA WITH LAKE VIEW, PRIVATE HEATED POOL and 2 car Garage in the Gated community of Verona Walk. This Capri Villa has an open concept, light bright and airy, with vaulte

$5,000/mo

2 beds2 baths1,554 sq ft

7450 Emilia Ln, Naples, FL 34114

Dogs welcome • Parking • Dishwasher

NEW 4 HRS AGO

881 Enbrook Loop, Naples, FL, 34114
881 Enbrook Loop, Naples, FL, 34114
881 Enbrook Loop, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
2/2 + Den villa for rent. Newly constructed home, built by DR Horton Situated in a gated community, this smart home is move-in ready and offers a comfortable and convenient lifestyle. With 2 bedrooms

$2,700/mo

3 beds2 baths1,503 sq ft

881 Enbrook Loop, Naples, FL 34114

Parking • Car-dependent • Swimming Pool

7170 Marconi Ct, Naples, FL, 34114
7170 Marconi Ct, Naples, FL, 34114
7170 Marconi Ct, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
Impeccably clean 2 bedroom two bath plus den home located on a wide lot with views of the lake. Annual rental available now. Amenities include fitness center, lap pool, community swimming pool, pickle

$2,600/mo

2 beds2 baths1,540 sq ft

7170 Marconi Ct, Naples, FL 34114

Parking • Car-dependent • Swimming Pool

7767 Ionio Ct, Naples, FL, 34114
7767 Ionio Ct, Naples, FL, 34114
7767 Ionio Ct, Naples, FL, 34114
ABOUT THIS HOME
House for Rent in Winding Cypress:
Available for 2025- 26 season, Off Season at a six month minimum, OR available to lease turn key annually!! This nicely furnished Capri floor plan offers a large great room, 2 master suites, and an o

$5,000/mo

2 beds2 baths1,526 sq ft

7767 Ionio Ct, Naples, FL 34114

Parking • Car-dependent • Swimming Pool

Property at 9064 Cherry Oaks Trl, Naples, FL, 34114, 3 beds, 2 baths, [object Object]

$4,500/mo

3 beds2 baths1,876 sq ft

9064 Cherry Oaks Trl, Naples, FL 34114

Property at 14704 Stillwater Way, Naples, FL, 34114, 4 beds, 2 baths, [object Object]

$2,550/mo

4 beds2 baths2,046 sq ft

14704 Stillwater Way, Naples, FL 34114

Property at 8902 Shenendoah Cir, Naples, FL, 34113, 4 beds, 3 baths, [object Object]

$20,000/mo

4 beds3 baths4,200 sq ft

8902 Shenendoah Cir, Naples, FL 34113

Property at 7643 Novara Ct, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$2,995/mo

2 beds2 baths1,540 sq ft

7643 Novara Ct, Naples, FL 34114

Property at 7706 Sicilia Ct, Naples, FL, 34114, 4 beds, 3.5 baths, [object Object]

$6,500/mo

4 beds3.5 baths2,506 sq ft

7706 Sicilia Ct, Naples, FL 34114

Property at 15492 Rio Ponace Ct, Naples, FL, 34114, 3 beds, 3 baths, [object Object]

$5,500/mo

3 beds3 baths2,900 sq ft

15492 Rio Ponace Ct, Naples, FL 34114

Property at 7653 Rozzini Ln, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$2,700/mo

2 beds2 baths1,540 sq ft

7653 Rozzini Ln, Naples, FL 34114

Property at 7640 Rozzini Ln, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$2,650/mo

2 beds2 baths1,540 sq ft

7640 Rozzini Ln, Naples, FL 34114

Property at 9630 Campanile Cir, Naples, FL, 34114, 3 beds, 3 baths, [object Object]

$15,000/mo

3 beds3 baths2,283 sq ft

9630 Campanile Cir, Naples, FL 34114

Property at 14672 Edgewater Cir, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$4,500/mo

2 beds2 baths1,519 sq ft

14672 Edgewater Cir, Naples, FL 34114

Property at 14151 Fall Creek Ct, Naples, FL, 34114, 3 beds, 2 baths, [object Object]

$2,850/mo

3 beds2 baths1,895 sq ft

14151 Fall Creek Ct, Naples, FL 34114

Property at 14321 Manchester Dr, Naples, FL, 34114, 3 beds, 2 baths, [object Object]

$9,750/mo

3 beds2 baths2,248 sq ft

14321 Manchester Dr, Naples, FL 34114

Property at 14265 Manchester Dr, Naples, FL, 34114, 4 beds, 2 baths, [object Object]

$8,500/mo

4 beds2 baths2,362 sq ft

14265 Manchester Dr, Naples, FL 34114

Property at 14533 Edgewater Cir, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$2,800/mo

2 beds2 baths1,519 sq ft

14533 Edgewater Cir, Naples, FL 34114

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