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Winding Cypress Real Estate For Rent

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Winding Cypress, 6690 Pennyroyal Dr, Naples, Florida 34114, image 1
Turnkey
$4,950 $550
  • 3 Beds
  • 21/2 Baths
  • 2,123 SqFt
  • $2.33/SqFt
House for rent in Winding Cypress
6690 Pennyroyal Dr, Naples, FL 34114
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.
Winding Cypress, 7638 Jacaranda Ln, Naples, Florida 34114, image 1
Furnished
$7,000
  • 2 Beds
  • 2 Baths
  • 1,574 SqFt
  • $4.45/SqFt
Villa for rent in Winding Cypress
7638 Jacaranda Ln, Naples, FL 34114
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!
Winding Cypress, 6770 Pennyroyal Dr, Naples, Florida 34114, image 1
Furnished
$10,000
  • 3 Beds
  • 3 Baths
  • 2,128 SqFt
  • $4.7/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!
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Winding Cypress, 6754 Pennyroyal Dr, Naples, Florida 34114, image 1
Unfurnished
$12,000
  • 3 Beds
  • 3 Baths
  • 2,158 SqFt
  • $5.56/SqFt
House for rent in Winding Cypress
6754 Pennyroyal Dr, Naples, FL 34114
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!
Winding Cypress, 6779 Pennyroyal Dr, Naples, Florida 34114, image 1
Furnished
$13,000
  • 3 Beds
  • 3 Baths
  • 2,272 SqFt
  • $5.72/SqFt
House for rent in Winding Cypress
6779 Pennyroyal Dr, Naples, FL 34114
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!
Winding Cypress, 7567 Winding Cypress Dr, Naples, Florida 34114, image 1
Furnished
$12,000
  • 3 Beds
  • 2 Baths
  • 1,805 SqFt
  • $6.65/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 26
Marbella Isles, 13429 Coronado Dr, Naples, Florida 34109, image 1
Furnished, Turnkey
$4,800
  • 2 Beds
  • 21/2 Baths
  • 2,052 SqFt
  • $2.34/SqFt
Villa for rent in Marbella Isles
13429 Coronado Dr, Naples, FL 34109
"live life beautifully in southwest florida" welcome to this spacious york floor plan villa home, perfectly situated on a desirable corner lot with an expansive side yard and peaceful lake views in the heart of marbella isles. This 2-bedroom + den, 2.5-bath residence offers a light and bright coastal contemporary design, filled with high-end upgrades throughout. Enjoy cooking and entertaining in the model-style kitchen, featuring upgraded quartz countertops, modern cabinetry, and sleek tile flooring that flows seamlessly through the main living areas. The extended lanai is the perfect space to relax and enjoy serene water views year-round. Offered turnkey furnished, this home includes designer lighting, stylish ceiling fans, and elegant furnishings — ready for you to move right in! Marbella isles is a gated, resort-style community with low hoa fees and incredible amenities, including: a stunning resort-style pool (also serves as a lap pool) separate kids’ water play area with slides fitness center, card room, and game room, pickleball, tennis, bocce ball, and a jungle gym. All of this, just 3.5 miles from southwest florida’s white sandy beaches, 15 minutes to downtown naples, 25 minutes to rsw airport, and close to the best shopping, dining, and entertainment naples has to offer. Don’t miss your chance to own a piece of paradise in one of naples’ most sought-after communities!
Esplanade At Hacienda Lakes, 8110 Calle Canovas St, Naples, Florida 34114, image 1
Furnished, Turnkey
$5,750 $250
  • 2 Beds
  • 2 Baths
  • 1,558 SqFt
  • $3.69/SqFt
Villa for rent in Esplanade At Hacienda Lakes
8110 Calle Canovas St, Naples, FL 34114
Price reduction - available for the 2026 season! Enjoy serene lakefront living in this beautifully maintained 2-bedroom + den, 2-bath attached villa with a 2-car garage, located in the highly sought-after gated community of esplanade at hacienda lakes. Offering 1, 558 sq. Ft. Of bright, open-concept living space, this home features peaceful water views from the main living areas and screened lanai, a contemporary kitchen that seamlessly connects to the dining and living spaces, and a flexible den—perfect for a home office or additional guest room. Ideally situated just minutes from downtown naples, world-class dining, shopping, and the gulf’s stunning white-sand beaches, this villa also grants access to outstanding resort-style amenities. Enjoy a lap and leisure pool, full-service spa, state-of-the-art fitness center, tennis, pickleball, bocce, a children’s playground, and a vibrant clubhouse offering year-round social events. This is your opportunity to embrace the best of florida living in both comfort and style.
Marbella Isles, 13628 Mandarin Cir, Naples, Florida 34109, image 1
Turnkey
$7,000
  • 2 Beds
  • 2 Baths
  • 1,978 SqFt
  • $3.54/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 2026 season 3 month minimum or annual.
1 - 3 of 26 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: Irrigation Water, Lawn/Land Maintenance, Manager, Master Assn. Fee Included, Rec Facilities, Reserve, Sewer, Street Lights, Street Maintenance, Insurance, Irrigation Water, Legal/Accounting, Pest Control Exterior, Repairs, Lawn/Land Maintenance, Security, Trash Removal, Cable, Internet/Wi Fi Access, .

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

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

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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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