Winding Cypress Houses for Rent

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,

Sam Wells Coldwell Banker Realty

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 decor and a fully stocked gourmet kitchen, allowing you to move right in and start enjoying your new home from day one.

Aimee O'Connor Coldwell Banker Realty

Gorgeous kitchen with an oversized island is open to the bright and airy great room as well as your very own private pool and spa! Sliding doors fold all the way back allowing for fabulous inside/outside entertaining. The chef's dream kitchen offers GAS cooking, a huge pantry and counter island seating. Your private pool and spa is heated by gas as well! Be sure to notice the unique lighting

Maureen Vita Berkshire Hathaway FL Realty

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!

Patricia Moreno Naples Homes and Rentals Inc

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

Dave Garafola Reed Property Mgt. & Sales

Unwind in this brand new, pristine vacation rental. Revel in the allure of a splendid pet-friendly home with a dazzling outdoor lanai, designed for the ultimate outdoor living experience. This residence boasts abundant natural light, a refreshing coastal contemporary interior, and an inviting open floor plan. With three bedrooms plus a versatile office you'll have ample space to accommodate your

Ashley Baird Coldwell Banker Realty