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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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At a glance

Property Highlights

3 BedroomsBedrooms
3 Full BathroomsBathrooms
Sleeps 6Guest Capacity
PoolPool
Internet AccessInternet
YesPet Friendly
YesWasher / Dryer
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
Sep 01, 2026 - Sep 30, 2026
Minimum Stay: 29 Days
$207 n/a $6,000
Sep 01, 2026 - Sep 30, 2026
Minimum Stay: 29 Days
$207 n/a $6,000
Oct 01, 2026 - Oct 31, 2026
Minimum Stay: 30 Days
$200 n/a $6,000
Oct 01, 2026 - Oct 31, 2026
Minimum Stay: 30 Days
$200 n/a $6,000
Nov 01, 2026 - Nov 30, 2026
Minimum Stay: 29 Days
$207 n/a $6,000
Nov 01, 2026 - Nov 30, 2026
Minimum Stay: 29 Days
$207 n/a $6,000
Dec 01, 2026 - Dec 31, 2026
Minimum Stay: 30 Days
$333 n/a $10,000
Dec 01, 2026 - Dec 31, 2026
Minimum Stay: 30 Days
$333 n/a $10,000
Jan 01, 2027 - Jan 31, 2027
Minimum Stay: 30 Days
$333 n/a $10,000
Feb 01, 2027 - Feb 28, 2027
Minimum Stay: 27 Days
$370 n/a $10,000
Mar 01, 2027 - Mar 31, 2027
Minimum Stay: 30 Days
$333 n/a $10,000
Apr 01, 2027 - Apr 30, 2027
Minimum Stay: 29 Days
$345 n/a $10,000
May 01, 2027 - May 31, 2027
Minimum Stay: 30 Days
$200 n/a $6,000
Jun 01, 2027 - Jun 30, 2027
Minimum Stay: 29 Days
$207 n/a $6,000
Jul 01, 2027 - Jul 31, 2027
Minimum Stay: 30 Days
$200 n/a $6,000
Aug 01, 2027 - Aug 31, 2027
Minimum Stay: 30 Days
$200 n/a $6,000
Sep 01, 2027 - Sep 30, 2027
Minimum Stay: 29 Days
$207 n/a $6,000
Oct 01, 2027 - Oct 31, 2027
Minimum Stay: 30 Days
$200 n/a $6,000
Nov 01, 2027 - Nov 30, 2027
Minimum Stay: 29 Days
$207 n/a $6,000
Dec 01, 2027 - Dec 31, 2027
Minimum Stay: 30 Days
$333 n/a $10,000
About this rental

Property Description

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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