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Explore the Winding Cypress 3 Bedroom Vacation House with Internet Access, Pool and More, in Naples, FL

Home Rental in Naples Florida

Explore the tranquil setting of our Winding Cypress House in Naples, FL. This 3-bedroom vacation rental offers a pool, grill facility, washer/dryer, and internet access, providing a comfortable and convenient homestay experience.

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William Raveis Florida Rentals
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Rates from
$200 / night
Additional fees may apply
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Rental overview

Why You'll Love This Rental

Winding Cypress is a 3-bedroom, 3-bath home in Naples, Florida that sleeps 6, with an additional den/study featuring a murphy double bed. The home is pet friendly (some pets allowed) and set within the Winding Cypress community. Standout features include an open floor plan with zero-corner sliders that connect indoor living space to an outdoor kitchen and bar area, plus a screened-in patio and a privacy-wall view.

Inside, the bedroom setup includes a king in the primary suite, a queen in the second bedroom, and two twins in the third. The home includes internet access, a washer/dryer, and a grill. Community amenities referenced for Winding Cypress include a resort-style pool, tennis, pickleball, bocce ball, a fitness center, an outdoor yoga deck, a dog park, a community garden, and a nature trail boardwalk through protected preserves. Stays are monthly with a 30-day minimum, and the association requires a $75 online application with a 30-day approval period.

Good fit for
Pet-friendly stays Monthly stays
3BR plus den Three bedrooms plus a den/study with a murphy double bed.
Pet friendly Pets are allowed; pet deposit and pet fee apply.
Indoor-outdoor layout Zero-corner sliders connect interior seating to an outdoor kitchen and bar.
Screened patio Screened-in patio space is included.
Community amenities Access to community pool, tennis, pickleball, fitness center, and nature trail boardwalk.
At a glance

Property Highlights

3 BedroomsBedrooms
3 Full BathroomsBathrooms
Sleeps 6Guest Capacity
PoolPool
Internet AccessInternet
YesPet Friendly
YesWasher / Dryer
Location & nearby Explore the Area

The home is in the gated Winding Cypress community in Naples, Florida. Community grounds and a clubhouse are referenced, along with amenities such as a resort-style pool, sports courts, a dog park, and a nature trail boardwalk through protected preserves. The provided beach distance is 11 miles.

Plan your stay

Rates & Availability (USD)

Rates from
$200 per night
27-day minimum stay
Check current rates & availability

Live booking details are maintained by William Raveis Florida Rentals.

Check Availability

Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

Available Booked
Season Nightly Weekly Monthly
PMS Rate
Nov 14, 2026 - Nov 30, 2026
Minimum Stay: 29 Days
$207 n/a $6,000
PMS Rate
Dec 01, 2026 - Jan 31, 2027
Minimum Stay: 30 Days
$333 n/a $10,000
PMS Rate
Feb 01, 2027 - Feb 28, 2027
Minimum Stay: 27 Days
$370 n/a $10,000
PMS Rate
Mar 01, 2027 - Mar 31, 2027
Minimum Stay: 30 Days
$333 n/a $10,000
PMS Rate
Apr 01, 2027 - Apr 30, 2027
Minimum Stay: 29 Days
$345 n/a $10,000
PMS Rate
May 01, 2027 - May 31, 2027
Minimum Stay: 30 Days
$200 n/a $6,000
PMS Rate
Jun 01, 2027 - Jun 30, 2027
Minimum Stay: 29 Days
$207 n/a $6,000
PMS Rate
Jul 01, 2027 - Aug 31, 2027
Minimum Stay: 30 Days
$200 n/a $6,000
PMS Rate
Sep 01, 2027 - Sep 30, 2027
Minimum Stay: 29 Days
$207 n/a $6,000
PMS Rate
Oct 01, 2027 - Oct 31, 2027
Minimum Stay: 30 Days
$200 n/a $6,000
PMS Rate
Nov 01, 2027 - Nov 30, 2027
Minimum Stay: 29 Days
$207 n/a $6,000
About this rental

About This Rental

Winding Cypress is a Naples home with 3 bedrooms and 3 full bathrooms, accommodating up to 6 guests, plus a den/study with a murphy double bed. The interior is arranged around an open floor plan, and the zero-corner sliders are designed to blend the main living area with the outdoor kitchen and bar for indoor-outdoor use. A screened-in patio adds an additional space to relax, and the listed view is a privacy wall.

Sleeping arrangements include a king bed in the primary bedroom, a queen bed in the second bedroom, and two twin beds in the third. The home also includes internet access, a washer/dryer, and a grill. TVs are provided (six total).

This rental is located within the Winding Cypress community, where amenities mentioned include a resort-style pool, tennis, pickleball, bocce ball, a fitness center, an outdoor yoga deck, a dog park, a community garden, and a nature trail boardwalk that runs through protected preserves.

Booking notes: the minimum stay is 30 days. The association requires a $75 online application, and the approval period is listed as 30 days. Pets are allowed with a $2,000 pet deposit plus a $500 pet fee.

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! Association requires $75 online application.

For additional information please contact Lesley Garlock at 239.289.1351, lesley.garlock@raveis.com or Nathan Dyer at 417.350.7803, nathan.dyer@raveis.com.
Things to enjoy

Activities and Special Interests

This property provides access to the following activities and special interests:

Family Vacations
Pet Friendly
What's included

Property Amenities

Featured Amenities

Grill
Washer/Dryer
Pool
Internet Access

Other Property Amenities

Monthly-Season: $10,000 Dec - April
Monthly-Off Season: $6,000 May - Nov
Minimum Nights: 30 Days
Bldg. Complex Name: Winding Cypress
Approval Period: 30 days
Application Fee Req.: $75 (online application)
Pets: Allowed
Pet Deposit: $2,000 + $500 pet Fee
View: Privacy Wall
Beach Distance: 11 miles
Tennis: Community
Bedroom/Bathroom: 3BR+Den/3BA
Bed Size 1st/Master: King
Bed Size 2nd Rm: Queen
Bed Size 3rd Rm: 2 Twin
Den/Study: Study with a murphy double bed
Patio: Screened In
Exercise Facility: Community
Square Footage, Est.: 2128
TVs/VCR/DVD: 6 TV
Rear Exposure: West
Sec Dep - Pet: $2,000
Helpful details

Frequently Asked Questions

Winding Cypress is located in Naples, Florida.

Winding Cypress accommodates up to 6 guests.

3 Bedrooms and 3 Full Bathrooms.

Yes. The property lists Pool.

Yes. Winding Cypress is listed as pet friendly. Review the manager's policies for any pet restrictions or fees.

The property lists a 27-night minimum stay.
Local management

Professionally Managed By

William Raveis Florida Rentals
In business since 2003
View Manager Profile

Questions about this rental?

Connect directly with William Raveis Florida Rentals for current rates, availability, and local assistance.

Contact Reservations and Guest Services at William Raveis - South Bay Team
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Property reference
#177509 · Winding Cypress
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