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Winding Cypress Real Estate For Rent

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Winding Cypress, 7631 Jacaranda Ln, Naples, Florida 34114, image 1
Furnished, Turnkey
$6,800 $200
  • 2 Beds
  • 2 Baths
  • 1,542 SqFt
  • $4.41/SqFt
Villa for rent in Winding Cypress
7631 Jacaranda Ln, Naples, FL 34114
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
Winding Cypress, 6767 Pennyroyal Dr, Naples, Florida 34114, image 1
Furnished
$10,500
  • 3 Beds
  • 2 Baths
  • 2,185 SqFt
  • $4.81/SqFt
House for rent in Winding Cypress
6767 Pennyroyal Dr, Naples, FL 34114
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.
Winding Cypress, 7567 Winding Cypress Dr, Naples, Florida 34114, image 1
Furnished
$11,500
  • 3 Beds
  • 2 Baths
  • 1,805 SqFt
  • $6.37/SqFt
House for rent in Winding Cypress
7567 Winding Cypress Dr, Naples, FL 34114
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!
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Results 3 of 19
Marbella Isles, 13419 Silktail Dr, Naples, Florida 34109, image 1
Unfurnished
$4,000
  • 2 Beds
  • 2 Baths
  • 1,858 SqFt
  • $2.15/SqFt
Villa for rent in Marbella Isles
13419 Silktail Dr, Naples, FL 34109
Beautifully appointed attached villa featuring 2 bedrooms plus a den and 2 bathrooms, thoughtfully designed with an open and inviting layout. The home showcases custom wood flooring, brand-new carpet in the bedrooms, crown molding throughout, and elegant wainscoting in the dining room, creating a refined yet comfortable living space. A glass front door welcomes in natural light, while the impact-rated sliding glass door opens to a private screened-in lanai, perfect for relaxing or entertaining. Recent upgrades include a brand-new a/c system with a 10-year transferable warranty and uv light, offering peace of mind and energy efficiency. Located in the heart of naples within marbella isles, an active, resort-style community that delivers the ultimate luxury lifestyle. Residents enjoy an expansive clubhouse with a resort-style pool, private cabanas, kids’ splash park, and playground. Stay active with a state-of-the-art fitness center, game room, indoor basketball court, three tennis courts, four pickleball courts, and bocce courts, all fostering a vibrant and social atmosphere. Ideally situated with two convenient entrances, marbella isles is just 10 minutes from naples’ pristine beaches, mercato, and waterside shops, 15 minutes to downtown naples, and 25 minutes to the airport—offering the perfect blend of comfort, convenience, and coastal living.
Marbella Isles, 13628 Mandarin Cir, Naples, Florida 34109, image 1
Turnkey
$7,500
  • 2 Beds
  • 2 Baths
  • 1,978 SqFt
  • $3.79/SqFt
House for rent in Marbella Isles
13628 Mandarin Cir, Naples, FL 34109
Exquisite former model home – prime naples location step into luxury with this impeccably maintained, turnkey former model home, perfectly located just 6 miles from naples' pristine beaches and minutes from the best shopping, dining, and entertainment in the area. This beautifully furnished 2-bedroom, 2-bathroom home with a den offers over-the-top comfort and style, designed for both relaxation and functionality. Enjoy outdoor living at its finest with a private pool and spa, surrounded by comfortable recliners and an outdoor kitchen with a tv – perfect for entertaining or unwinding. The enhanced landscaping, with lighting that illuminates the yard at night, creates an inviting and tranquil atmosphere. For added peace of mind, the home is equipped with hurricane shutters and an electronic storm smart screen on the lanai. Inside, you'll find high-end finishes throughout, including custom walk-in closets and his-and-her vanities in the primary suite. The garage is equally impressive with an epoxy floor and ample overhead storage. A buried 500-gallon propane tank and whole-house generator ensure you'll never be without power. Residents of this community also enjoy an array of first-class amenities, including tennis, pickleball, bocce, an indoor basketball court, a fully equipped gym, an aerobics room, and a game room. The social spaces are just as impressive, with a formal gathering room, a resort-style pool and spa, covered cabanas, a splash pad for kids, and a playground for family fun. This home is the epitome of luxury living, combining privacy, comfort, and high-end community amenities in one of naples' most desirable locations. Don’t miss out on the opportunity to experience it all! Available for 2027 season, 3 month minimum or annual. Rate shown is for an annual, rates vary for season. Available starting april 1, 2026.
Valencia Trails, 11899 Gardenia Ave, Naples, Florida 34120, image 1
Furnished
$4,900 $600
  • 2 Beds
  • 21/2 Baths
  • 2,497 SqFt
  • $1.96/SqFt
House for rent in Valencia Trails
11899 Gardenia Ave, Naples, FL 34120
Dreaming of an active adult resort community lifestyle? This immaculate home is available for lease, 7 month minimum. Adorned with luxurious finishes & lighting fixtures, this open-concept layout of two bedrooms, a den/study, two and a half baths, blends indoor and outdoor living. The den provides flexible space for a home office or extra guest room, while the modern kitchen opens seamlessly to the living area and lanai with summer kitchen. A 2 car attached garage with ability to charge 2 evs. Valencia trails redefines active adult living with its resort-style amenities and vibrant community atmosphere. The 43, 000 sq.Ft. Clubhouse offers an onsite restaurant, outdoor bar, social hall with a dance floor and stage, and multiple pools, including a resort-style pool, 70 ft. Lap pool, and resistance pool. Pamper yourself at the spa and nail salon, stay fit at the state-of-the-art fitness center, or gather around the outdoor firepits with new friends. Set amidst 160 acres of pristine preserve, the community features over 3 miles of scenic walking trails and endless recreational opportunities, including pickleball, tennis, bocce, a dog park, and more. Experience the best of florida living in this beautifully appointed home where luxury, comfort, and lifestyle come together seamlessly.
1 - 3 of 19 Results
Subdivision Amenities
Bike And Jog Path
Bocce Court
Business Center
Cabana
Clubhouse
Community Room
Dog Park
Fitness Center
Hobby Room
Internet Access
Library
Park
Pickleball
Play Area
Pool
Private Membership
Restaurant
Shuffleboard Court
Sidewalk
Spa/Hot Tub
Streetlight
Tennis Court(s)
Underground Utility
Barbecue
Bike And Jog Path
Bocce Court
Clubhouse
Frequently Asked Questions

The current monthly maintenance fee at Winding Cypress is ~0.23 per unit SqFt.

The single_family_home dues at Winding Cypress cover: Insurance, Irrigation Water, Lawn/Land Maintenance, Legal/Accounting, Manager, Master Assn. Fee Included, Pest Control Exterior, Rec Facilities, Repairs, Reserve, Street Lights, Street Maintenance, Irrigation Water, Cable, Internet/Wi Fi Access, Security, Trash Removal, Lawn/Land Maintenance, Sewer, .

Winding Cypress Interior features include: French Doors, Pantry, Smoke Detectors, Tray Ceiling(s), Laundry Tub, Window Coverings, Laundry Tub, Volume Ceiling, Built-In Cabinets, French Doors, Walk-In Closet(s), Foyer, Pantry, Wired for Sound, Vaulted Ceiling(s), Bar, Coffered Ceiling(s), Pull Down Stairs, Zero/Corner Door Sliders, Foyer, Closet Cabinets, Closet Cabinets, Built-In Cabinets

Winding Cypress unit views: Landscaped Area, Preserve, Trees/Woods, Lake, Preserve, Landscaped Area, Water, Privacy Wall

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Scores
Walk Score®
Car-Dependent. Almost all errands require a car.
0

100
Transit Score®
Minimal Transit. It is possible to get on a bus.
0

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure.
29

100
Sound Score®
Very loud.
0

100
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Broker reciprocity logoLocal Realty Service Provided By: Hyperlocal Advisor. Information deemed reliable but not guaranteed. Information is provided, in part, by Greater Miami MLS & Beaches MLS. This information being provided is for consumer's personal, non-commercial use and may not be used for any other purpose other than to identify prospective properties consumers may be interested in purchasing.

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