Winding Cypress Real Estate For Rent

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 fixtures and ceiling fans, as well as the plantation shutters in all the bedrooms, living room and office. Master bedroom is located away from the two guest bedrooms and office. The laundry room has full size stainless washer and dryer as well as additional cabinetry with a sink. There is also a storage closet in the laundry room. The home has an oversized 2 car garage. The beautiful club house offers a state of the art fitness center, movement studio, outdoor yoga deck, card room, library, meeting room plus so much more. Enjoy tennis, pickleball, bocce, etc. Or meet up with friends at the community pool or hot tub and enjoy a bite to eat or a refreshing drink at the shady palm poolside restaurant.

** nicely furnished 3 bedroom plus a den - bath single family home in winding cypress with resort-style living in naples, florida ** long-term tenant for october 2025 or seasonal tenant ready ** best amenities at winding cypress **welcome to winding cypress, one of naples' premier gated communities, where luxury meets nature and every day feels like a vacation. This beautifully furnished single-family home, built in 2021, offers 2 bedrooms, 2 bathrooms, plus a spacious den, and features 2, 086 square feet of thoughtfully designed living space. Property highlights: new construction (2021) – modern design, high-end finishes 3 bedrooms + den / 2 bathrooms primary bedroom has a king bed secondary bedroom has a king bed den has a sofa bed and 65" tv smart tv's for streaming -- 65" in living room gym equipment shown in photo will be removed, and a pullout couch will be installed beautifully furnished – move-in ready with tasteful décor extended lanai – perfect for entertaining or relaxing outdoors 2-car garage pets welcome – both small and large dogs and cats accepted with hoa approval first step inside to find a bright, open-concept floor plan, ideal for both everyday living and entertaining. The spacious lanai provides seamless indoor-outdoor flow and is perfect for enjoying the warm sw florida climate year-round. Community amenities – live like you’re on vacation: resort-style pool & spa with ample lounging space outdoor bar & grill for social gatherings state-of-the-art fitness center & movement studio tennis, bocce ball, and pickleball courts dog park with separate areas for small and large dogs nature boardwalk & scenic pavilion overlooking the preserve fire pit for cozy evenings with neighbors elegant clubhouse with club room, library, and catering kitchen on-site activities director organizing community events and clubs location perks: minutes to us-41 and i-75 for easy travel short drive to restaurant row, famous 5th avenue south, and vibrant marco island only 20 minutes to the beach, naples pier, and scenic waterfronts close to rookery bay and tarpon club marina – ideal for boating enthusiasts nestled next to picayune strand state forest – perfect for nature lovers this home offers the perfect blend of luxury, convenience, and community, all set in one of the most desirable locations in southwest florida. Whether you're seeking a seasonal retreat or a full-time residence, this winding cypress gem is ready to welcome you home. Important note: the owner's personal property will be removed prior to taking occupancy. Availability & rates: 12-month lease: $3, 995 a month tenant would be responsible for all utilities except for lawn maintenance first, last and security deposit collected prior to move-in seasonal rate & availability: jan-april: $8, 000 a month may-sept: $4, 000 a month oct-december: $7, 000 a month available starting: october 1, 2025

Only available during off season.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 needs. The master bedroom features a king-sized bed, while the other two bedrooms are fitted with queen-sized comfort. Featuring, a spacious kitchen equipped with a gas cooktop ensures culinary delight and endless space for memories to be made with your loved one. Nestled in the amenity-rich community of winding cypress, your vacation paradise is complete with a community center, pool, fitness center, pickle ball, tennis, bocce ball, dog park, and endless community activities. Located perfectly between the shopping, dining, and entertainment of downtown naples and the quaint beach town of marco island.

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 bed, second bedroom has a queen size bed and den has a queen size murphy bed. Spacious attached 2-car garage. Water filter system purifies all water throughout the villa. Sit back and relax with your coffee in the morning or cocktail in the evening while enjoying the sunset on the screened lanai that overlooks the heated private pool with peaceful lake views. 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, 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, dog park and bird watching overlook. If you enjoy an active lifestyle you will not be bored as there is always something going on to become involved in. 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

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

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!