Winding Cypress Real Estate For Rent

Will consider a seasonal 3-4 month lease at a monthly higher rate. 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 décor and a fully stocked gourmet kitchen, allowing you to move right in and start enjoying your new home from day one. Featuring hardwood floors, stainless steel appliances, and two expansive master suites, the home is designed for both comfort and style. Each suite includes large closets and beautifully appointed bathrooms with premium finishes. The third bedroom features a closet and french doors, can also be used as an office/tv room/gym space. The screened-in lanai with a private pool and outdoor kitchen provides the perfect space for relaxing or entertaining. With an open-concept layout, generous living areas, and exceptional attention to detail, this home is a rare find. Long term rental only—don’t miss the opportunity to lease this meticulously maintained, move-in ready retreat. Beyond the exceptional home features, the winding cypress community offers a vibrant lifestyle. Just minutes away from naples' beautiful beaches, 5th avenue, and marco island, this location balances peaceful living with convenience. Residents can enjoy meals at the shady palm cafe by the resort style pool and spa with cabanas or take advantage of the clubhouse and fitness center, which are equipped with state-of-the-art facilities and fitness classes. For those who enjoy staying active, the community offers pickleball, tennis, and bocce courts, along with a scenic boardwalk for leisurely strolls through the lush, natural surroundings. This home truly embodies the essence of luxury living in a fantastic neighborhood.

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!

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 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, luxury vinyl in the living areas and lush carpeting in the bedrooms. Bicycles and beach chairs available too! From the moment you arrive at the stunning winding cypress gated entry you know you have arrived at the perfect naples winter destination. 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 minutes away from the easy access to all the surrounding areas beautiful beaches, restaurants and entertainment!

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!

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!