Winding Cypress Houses For Rent

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$300 - $400 per SqFt
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Results 3 of 3
Winding Cypress, 7631 Jacaranda Ln, Naples, Florida 34114, image 1
Furnished, Turnkey
$7,000 $200
  • 2 Beds
  • 2 Baths
  • 1,542 SqFt
  • $4.54/SqFt
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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
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House for rent in Winding Cypress
6767 Pennyroyal Dr, Naples, FL 34114
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
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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 22
Azure At Hacienda Lakes, 9020 Mayreau Way, Naples, Florida 34114, image 1
Furnished
$5,500 $1K
  • 2 Beds
  • 2 Baths
  • 1,569 SqFt
  • $3.51/SqFt
Villa for rent in Azure At Hacienda Lakes
9020 Mayreau Way, Naples, FL 34114
Perfect for your winters in swfl! Spacious attached villa with a 2 car garage. Two bedrooms and a den, two full bathrooms, open concept kitchen with an island. Beautiful lake view out of the screened in lanai. Azure at hacienda lakes is an amenity rich community with a gorgeous pool, clubhouse, fitness room and more! Dogs are welcome with owner's approval! Available october - december at a reduced rate.
Marbella Isles, 13419 Silktail Dr, Naples, Florida 34109, image 1
Unfurnished
$3,750 $250
  • 2 Beds
  • 2 Baths
  • 1,858 SqFt
  • $2.02/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.
1 - 3 of 22 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
Comparable & Nearby Subdivisions
Schools
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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