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Winding Cypress Real Estate For Rent

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Results 4 of 4
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, 6770 Pennyroyal Dr, Naples, Florida 34114, image 1
Furnished
$10,000
  • 3 Beds
  • 3 Baths
  • 2,128 SqFt
  • $4.70/SqFt
House for rent in Winding Cypress
6770 Pennyroyal Dr, Naples, FL 34114
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!
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.
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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!
Similar Communities & Listings
Results 3 of 25
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.
Esplanade At Hacienda Lakes, 8217 Lucello Ter W #, Naples, Florida 34114, image 1
Unfurnished
$2,750 $100
  • 2 Beds
  • 2 Baths
  • 1,552 SqFt
  • $1.77/SqFt
Villa for rent in Esplanade At Hacienda Lakes
8217 Lucello Ter W #, Naples, FL 34114
Charming 2-bed + den, 2-bath villa for rent in esplanade at hacienda lakes this western-facing villa is ready for you! The open floorplan makes everyday living easy, with a kitchen featuring quartz counters, under-cabinet lighting, a breakfast bar, and pantry. Relax or entertain in your screened lanai and spacious backyard, perfect for outdoor living. The home also includes a 2-car garage, laundry with storage, and window treatments. Recent updates: guest bath shower doors (2023), fresh paint (june 2024), and vinyl flooring in bedrooms & closets (sept. 2024). Located at the end of the street for extra privacy and just minutes from downtown 5th ave., marco island, and the beaches. Enjoy all the community has to offer—tennis, bocce, pickleball, a resort-style pool & spa, clubhouse, and gym. Move in and start enjoying comfort, convenience, and fun!
Marbella Isles, 13493 Monticello Blvd, Naples, Florida 34109, image 1
Unfurnished
$4,000
  • 2 Beds
  • 2 Baths
  • 1,868 SqFt
  • $2.14/SqFt
Villa for rent in Marbella Isles
13493 Monticello Blvd, Naples, FL 34109
"live life beautifully in southwest florida" discover the beauty of southwest florida living in this stunning attached villa located in the highly sought-after marbella isles community. This 2-bedroom plus den, 2-bath home is filled with thoughtful upgrades and luxury touches that make it truly one of a kind. From the moment you enter, you’ll notice the attention to detail — engineered hardwood floors, upgraded cabinetry, and solid hardwood doors set a tone of quality and sophistication. The home features over $90, 000 in builder and post-build upgrades, including: built-in radio and intercom system throughout the home, crown moldings, instant hot water dispenser at the kitchen sink custom front entry screens for comfort and airflow, upgraded attic and garage door insulation, built-in pull-down stairs for easy attic access, epoxy-finished garage floor and widened driveway for additional parking, & a brinks 2’ x 3’ floor safe, bolted securely in the guest closet peace of mind comes standard with hurricane-impact windows and sliders, electric lanai shutter, custom interior electric shades, and a recent wind mitigation report confirming compliance with today’s hurricane standards. A new hvac system (installed july 2025) ensures year-round comfort, while plantation shutters and a custom gutter system complete the list of thoughtful details. Just a short stroll from your front door is the marbella isles clubhouse, where resort-style amenities await: sparkling resort pool and kiddie pool with slides, fitness center, game room, and card room. Half-court basketball, volleyball, pickleball, bocce, and tennis plus a full-time social director organizing community events year-round. Located in the heart of naples, marbella isles offers 24-hour guard-gated security and low hoa fees, all within minutes of white-sand beaches (10 min), downtown naples (15 min), and southwest florida international airport (25 min). Live beautifully. Live conveniently. Live the marbella isles lifestyle.
1 - 3 of 25 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 ~0.22 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®

No data.

N/A

Bike Score®

Somewhat Bikeable. Minimal bike infrastructure.

29

100

Sound Score®

No data.

N/A

Naples
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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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