Winding Cypress Houses For Rent

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$300 - $400 per SqFt
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Furnished, Turnkey
Winding Cypress, 7103 Lily Way, Naples, Florida 34114, image 1
$4,500
  • 4 Beds
  • 3 Baths
  • 2,461 SqFt
  • $1.83/SqFt
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House for rent in Winding Cypress
7103 Lily Way, Naples, FL 34114
Beautiful turnkey furnished single-family home available now for an annual lease in the sought-after gated community of winding cypress. Built in 2015, this spacious residence features 4 bedrooms, 3 bathrooms, and a versatile upstairs loft, offering plenty of room for comfortable living and entertaining. Enjoy an open and inviting floor plan with stylish furnishings and move-in-ready convenience. Conveniently located within walking distance to the community clubhouse and amenities. Residents of winding cypress enjoy resort-style amenities including a clubhouse, fitness center, resort-style pool, on-site restaurant, pickleball, tennis, bocce courts, dog park, walking trails, and more. Ideally located just a short drive to marco island and downtown fifth avenue in naples for world-class dining, shopping, and white-sand beaches. Don’t miss this opportunity to enjoy the southwest florida lifestyle in one of naples’ premier communities.
Furnished, Turnkey
Winding Cypress, 7631 Jacaranda Ln, Naples, Florida 34114, image 1
$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
Furnished
Winding Cypress, 6767 Pennyroyal Dr, Naples, Florida 34114, image 1
$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.

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Furnished, Turnkey
Winding Cypress, 7763 Winding Cypress Dr, Naples, Florida 34114, image 1
$15,000 $1K
  • 4 Beds
  • 3 Baths
  • 3,077 SqFt
  • $4.87/SqFt
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House for rent in Winding Cypress
7763 Winding Cypress Dr, Naples, FL 34114
Seasonal rental available for 2027. Turnkey furnished, and ready for you to enjoy. This 2 story summerwood model home with breathtaking pool and spa offers a spectacular open floor plan. This home has a very large, beautiful gourmet kitchen with dining area, generous great room with baby grand piano, 3 bedrooms, 3 bathrooms on the main floor, 1 bedroom, 1 bathroom, plus a very large loft on the 2nd floor. The lanai is large and great for entertaining. The lanai screen is picture frame which allows for maximum viewing pleasure. The gorgeous custom pool with sundeck has lighted waterfall bowls and color changing lights. In addition to all of this is a 2 car extended garage with epoxy floor. The entire home is beautifully furnished with all the comforts you would want in your home. This community has wonderful resort style amenities including walking and biking trails, fitness, restaurant, party room, catering kitchen, fire pit, play area, tennis, dog park and so much more
Furnished
Winding Cypress, 7567 Winding Cypress Dr, Naples, Florida 34114, image 1
$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!

Similar Communities & Listings

Results 3 of 27
Turnkey
Marbella Isles, 13628 Mandarin Cir, Naples, Florida 34109, image 1
$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.
Turnkey
Halfmoon Point, 14541 Stern Way, Naples, Florida 34114, image 1
$8,000
  • 2 Beds
  • 2 Baths
  • 1,819 SqFt
  • $4.40/SqFt
House for rent in Halfmoon Point
14541 Stern Way, Naples, FL 34114
Available now! This stunning heated pool home features a spacious, open floor plan with all the latest upgrades. From modern light fixtures to sleek tile flooring and designer furniture, you’ll fall in love the moment you walk through the door. The home includes a guest bedroom with a queen-size bed and a second guest room set up as a private office, along with a full guest bathroom for added convenience. Step outside to the lanai, where you’ll find a dining table that seats six, overlooking a serene lake—perfect for relaxing or entertaining. The pool area is complete with four comfortable loungers, creating your own private retreat. The primary suite offers a king-size bed, a large flat-screen tv, and spacious his-and-her closets. Cable and internet are included, and the indoor dining area also accommodates six guests. Located in the highly sought-after naples reserve community, this gated oasis features 22 lakes and beautiful nature preserves. Residents enjoy access to the island club, complete with a tiki bar, café, and resort-style pools. With its waterfront lifestyle, exceptional amenities, and prime south naples location, naples reserve is an ideal place to call home. Available for the 2027 season or as an annual rental—don’t miss this opportunity to live in one of southwest florida’s most desirable communities. 90-day minimum stay required for the 2027 season.
Furnished
Azure At Hacienda Lakes, 9195 Cayman Dr, Naples, Florida 34114, image 1
$6,000
  • 2 Beds
  • 2 Baths
  • 1,575 SqFt
  • $3.81/SqFt
Villa for rent in Azure At Hacienda Lakes
9195 Cayman Dr, Naples, FL 34114
Single family home two bedroom with den. Water view from ex-large lanai great for your morning coffee.
1 - 3 of 27 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

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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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