Houses for Rent in Winding Cypress, FL

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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

$11,500/mo

3 beds2 baths1,805 sq ft

7567 Winding Cypress Dr, Naples, FL 34114

Parking • Dishwasher • Car-dependent

ABOUT THIS HOME
House for Rent in Winding Cypress:
Discover Your Dream Home in Naples! Presenting the rare Winding Cypress model, the stunning Cressida villa. This beautiful home features a spacious private yard and lanai, perfect for entertaining or

$6,200/mo

2 beds2 baths1,574 sq ft

7638 Jacaranda Ln, Naples, FL 34114

Parking • Car-dependent • Patio/Balcony

ABOUT THIS HOME
House for Rent in Winding Cypress:
6 to 24-month $4,447/m+ 4-Month $7K/m+ Escape from stress in this clean, like-new ELEGANT POOL VILLA, maintained, updated & FURNISHED. Incomparably upgraded for discriminating guests. CENTRALLY LOCATE

$4,447/mo

2 beds2 baths1,555 sq ft

7662 Jacaranda Ln, Naples, FL 34114

Available 12/15 • Dogs welcome • Laundry in unit

ABOUT THIS HOME
House for Rent in Winding Cypress:
Apply for this rental with RentSpree: https://apply.link/R94a-nQ<br><br>Property Representative: RentSpree Partner<br><br>Welcome to your dream vacation home in Naples, Florida! This charming property

$10,000/mo

3 beds3 baths2,496 sq ft

7788 Winding Cypress Dr, Naples, FL 34114

Parking • A/C • Car-dependent

ABOUT THIS HOME
House for Rent in Winding Cypress:
Beautiful two bedrooms 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 ful

$6,800/mo

2 beds2 baths1,542 sq ft

7631 Jacaranda Ln, Naples, FL 34114

Parking • Car-dependent • Fitness Center

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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

ABOUT THIS HOME
House for Rent in Winding Cypress:
Luxury Rental Home in Naples Reserve – Dog-Friendly! Welcome to your seasonal escape in the heart of Naples Reserve, one of Naples' most sought-after resort-style communities! This newly furnished 3-

$7,500/mo

3 beds2.5 baths2,550 sq ft

14653 Tropical Dr, Naples, FL 34114

Dogs welcome • Laundry in unit • A/C

ABOUT THIS HOME
House for Rent in Winding Cypress:
Beautiful Villa located in desirable South Naples! Available to move-in now. Property can be shown with an appointment before move-in date, message us for more information. Conveniently located, th

$2,850/mo

2 beds2 baths1,496 sq ft

1212 Enbrook Loop, Naples, FL 34114

Laundry in unit • A/C • Dishwasher

3D WALKTHROUGH

ABOUT THIS HOME
House for Rent in Winding Cypress:
LAKE FRONT VILLA/ANNUAL RENTAL AVAILABLE NOW! MOVE IN BEFORE THE NEW YEAR!2 BEDROOMS +DEN/ 2 BATHROOMS built in 2023 villa in ENBROOK community, South Naples, FL! This convenient LAKE VIEW property of

$2,450/mo

2 beds2 baths1,496 sq ft

1040 Tranquil Brook Dr, Naples, FL 34114

Parking • Car-dependent

3D WALKTHROUGH

ABOUT THIS HOME
House for Rent in Winding Cypress:
Spacious Home for Rent on One of Verona Walk's Largest Lots!Enjoy bright, open living in this beautifully maintained single-family home. The white kitchen flows into the dining and living areas, which

$3,600/mo

3 beds2.5 baths1,983 sq ft

7304 Carducci Ct, Naples, FL 34114

Parking • Dishwasher • Car-dependent

ABOUT THIS HOME
House for Rent in Winding Cypress:
Annual Rental available! This GORGEOUS single family home is located in the AWARD Winning community of Verona Walk!. 3 large Bedrooms +Den. This home has been updated with high end features & finishes

$3,900/mo

3 beds2.5 baths1,997 sq ft

7651 Hernando Ct, Naples, FL 34114

Laundry in unit • Parking • Car-dependent

Property at 7767 Ionio Ct, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$5,000/mo

2 beds2 baths1,526 sq ft

7767 Ionio Ct, Naples, FL 34114

Property at 9287 Chiasso Cove Ct, Naples, FL, 34114, 3 beds, 4 baths, [object Object]

$14,850/mo

3 beds4 baths3,280 sq ft

9287 Chiasso Cove Ct, Naples, FL 34114

Property at 7025 Leopardi Ct, Naples, FL, 34114, 4 beds, 3.5 baths, [object Object]

$6,000/mo

4 beds3.5 baths2,502 sq ft

7025 Leopardi Ct, Naples, FL 34114

Property at 7528 Firenze Ln, Naples, FL, 34114, 2 beds, 2 baths, [object Object]

$2,975/mo

2 beds2 baths1,540 sq ft

7528 Firenze Ln, Naples, FL 34114

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

$20,000/mo

3 beds3 baths4,200 sq ft

8902 Shenendoah Cir, Naples, FL 34113

Property at 14404 Manchester Dr, Naples, FL, 34114, 3 beds, 2 baths, [object Object]

$2,850/mo

3 beds2 baths1,560 sq ft

14404 Manchester Dr, 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 8957 Shenendoah Cir, Naples, FL, 34113, 3 beds, 3 baths, [object Object]

$19,000/mo

3 beds3 baths2,677 sq ft

8957 Shenendoah Cir, Naples, FL 34113

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

$7,000/mo

4 beds2 baths2,362 sq ft

14265 Manchester Dr, Naples, FL 34114

Property at 9092 Chula Vista St Unit 11003, Naples, FL, 34113, 2 beds, 2 baths, [object Object]

$6,850/mo

2 beds2 baths1,404 sq ft

9092 Chula Vista St Unit 11003, Naples, FL 34113

Property at 7636 Sussex Ct, Naples, FL, 34113, 4 beds, 2 baths, [object Object]

$15,000/mo

4 beds2 baths2,293 sq ft

7636 Sussex Ct, Naples, FL 34113

Property at 7863 Valencia Ct, Naples, FL, 34113, 3 beds, 2 baths, [object Object]

$12,300/mo

3 beds2 baths2,340 sq ft

7863 Valencia Ct, Naples, FL 34113

Property at 7812 Valencia Ct, Naples, FL, 34113, 3 beds, 2 baths, [object Object]

$12,000/mo

3 beds2 baths1,924 sq ft

7812 Valencia Ct, Naples, FL 34113

Property at 7864 Valencia Ct, Naples, FL, 34113, 3 beds, 2 baths, [object Object]

$15,500/mo

3 beds2 baths2,190 sq ft

7864 Valencia Ct, Naples, FL 34113

The information is being provided by Southwest Florida Multiple Listing Service. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2025 Southwest Florida Multiple Listing Service. All Rights Reserved.

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