Winding Cypress Real Estate For Rent

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 relaxing in paradise. Inside, a dedicated front entrance and a large foyer welcome you into an open yet well-defined living area. The master bedroom has a king-size bed, the guest bedroom includes a twin bed, and there's a den with a pull-out couch and a desk, ideal for an office. The fully equipped kitchen is perfect for preparing meals and gathering with family and friends. Winding cypress is one of naples’ most desirable resort communities, set on over 800 acres of pristine preserve between marco island and downtown naples' vibrant 5th avenue. Amenities include a dog park and vegetable garden for a touch of nature, the impressive club at winding cypress with a resort-style pool and sunset cabanas, bocce ball, pickleball, and clay tennis courts for year-round fun, a yoga deck, a large fitness center, fire pits for relaxing evenings, scenic nature trails and locker rooms, and a lively sand bar and restaurant with professional activity staff to keep your days energized. Don’t miss this amazing opportunity!

Available for 2026 season! Welcome to this beautifully appointed seasonal rental located in the highly sought after winding cypress community. This spacious home offers three bedrooms plus a den, three full bathrooms, and a two and a half car garage. Fully turnkey furnished and thoughtfully designed, the home features an open concept floor plan that flows seamlessly from the interior living spaces to the outdoors. The kitchen serves as a central gathering space with a large island, natural gas range, and stainless steel appliances, making it ideal for both everyday meals and entertaining. Expansive zero corner sliding glass doors open to an exceptional outdoor living area, where a paver pool deck, screened in lanai, and complete outdoor kitchen with a built in propane grill create a private oasis for enjoying the florida lifestyle. The owner’s suite is a true retreat, offering a generous walk in closet and a spacious en-suite bathroom designed for comfort and privacy. The community clubhouse serves as the social heart of winding cypress, offering an elegant and inviting environment for gatherings, events, and relaxation, with direct access to the resort style pool and spa set among lush landscaping, palm trees, and comfortable lounging areas. The shady palm café provides a lively poolside setting where residents can enjoy meals, refreshing drinks, and casual socializing in the florida sunshine. Fitness and wellness amenities include a state of the art fitness center with modern cardio and strength equipment, along with a dedicated movement room designed for classes, stretching, and individual workouts. Outdoor recreation is abundant, featuring five clay tennis courts, four pickleball courts, and well maintained bocce courts that encourage active living and community connection, while a scenic boardwalk winds through preserved natural areas, offering a peaceful escape and a close connection to the surrounding landscape. Winding cypress is conveniently located just a short drive from a variety of destinations, offering easy access to beaches, dining, shopping, and entertainment. Perfectly positioned between downtown naples and marco island, this home offers an exceptional opportunity to enjoy a luxurious and active seasonal lifestyle within one of naples’ premier gated communities and experience the best of southwest florida living.

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 full size pullout couch that sleeps 2 and includes a full wardrobe armoire for clothing . Spacious attached 2-car garage. Relax on the spacious lanai that overlooks the private pool and peaceful lake view. Winding cypress has resort class amenities. Clubhouse has plenty of space for social gatherings so neighbors can interact with each other and build community bonds. State-of-the-art fitness center, catering kitchen, community room, and activity room. Fabulous resort-style pool, lap pool, spa, shady palm poolside restaurant, outdoor movement studio, bocce ball courts, pickle ball, tennis courts, fire pit, boardwalk with pavilion, and bird watching overlook. If you like an active lifestyle you will not be bored as there is always something to join in and enjoy. 20 minutes to marco island, 20 minutes to naples pier and magnificent area beaches, 15 minutes to fifth avenue and third street shopping & dining, 10 minutes to i-75, 5 minutes to us-41

This newly completed and spacious pet friendly home offers 3 bedrooms (king, king & 2 twins) plus a den that is equipped with a queen-size murphy bed. This home is full of entertaining options that allow you to bring the extended family along. With its open floor plan as well as zero-corner sliders that blend the interior seating with the outside kitchen and bar. As soon as you drive through the winding cypress gate access, you are instantly put into vacation mode as you pass the resort style clubhouse and community grounds. The amenities include a resort style pool, restaurant/bar, fire pit, world-class fitness center, outdoor yoga deck, pickle-ball, tennis, bocce ball, community garden, a dog park, and a nature trail boardwalk that meanders throughout the protected preserves. Conveniently located between marco island and fifth avenue south, you are only minutes away from sandy beaches and all the shopping, dining, and entertainment you could ask for!

Available for season 2026 and 2027! Beautifully furnished 3+den single family home in the highly sought-after, gated community of winding cypress in naples. This thoughtfully appointed home offers a comfortable and stylish escape, perfect for enjoying the southwest florida lifestyle during season. The residence features an open-concept layout filled with natural light, a well-equipped kitchen ideal for entertaining, and inviting living and dining spaces designed for relaxation. The home includes 3 spacious bedrooms and an office with an additional daybed. Primary suite boasts an en-suite bathroom and lake views. Two guest rooms, both with queen beds, share access to a second full bath. An expanded screened lanai with sparkling pool and outdoor kitchen complete the lifestyle package at this exceptional seasonal escape. 2 car attached garage. Winding cypress is known for its resort-style amenities, providing an exceptional lifestyle for seasonal residents. Community features include a stunning clubhouse, resort-style pool and spa, state-of-the-art fitness center, tennis and pickleball courts, bocce ball, a dog park, and miles of scenic walking and biking trails. The community is guard-gated, and hosts an active social calendar. Ideally located, winding cypress is just minutes from naples’ world-class beaches, shopping, dining, golf courses, and downtown attractions as well as easy access to marco island.

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 backyard, including a grand clubhouse, resort pool, sports courts, dog park, community garden, and more. One of the most sought after new communities in the area!