0 houses for rent in Winding Cypress

Experience an iconic waterfront naples lifestyle at riviera retreat in the prestigious neighborhood of the moorings! This coastal cottage has undergone a recent renovation, boasting sleek finishes throughout its interior. The pool deck is thoughtfully equipped with a pool cage for added safety, e...

This waterfront home on venetian bay in park shore boasts two stories with 5 bedrooms, a den, and 6 full bathrooms. The family room, formal dining area, breakfast nook, and fully equipped kitchen provide the perfect setting for your family to enjoy a memorable vacation. Step out onto the pool dec...

The largest 1 bed 1 bath apartment in the community. Has new light grey vinyl flooring. No carpet. Ground floor & has newly renovated kitchen cabinets ... Community is secure & gated & has lots of amenities, like community pool, gym, in house association plus access to all of the hammocks amenities.

Discover this 2020 renovated corner residence, meticulously upgraded. This 5 bedrooms 3 bathrooms home showcases a seamless blend of modern and comfort. Step into a luxury within the primary suite, walk-in closet, dual-sink bath, dual showers, and flexible space ideal for a vanity or computer exp...

Can be rented weekly for $9,500 a week, 2-weeks for $15,000 or rent an entire month for $20,000. ly updated 4 bedroom, 3 bath single-family pool home located in the moorings, one of the most desirable locations in naples. This florida classic residence has been tastefully furnished and has a layo...

Now offering 2026 season. Welcome to marbella lakes, a gated community in the heart of naples-southwest florida's vacation paradise! This home spans over 2,000 square feet and offers 3 bedrooms, a den/office, 2.5 Baths, and an attached garage. Relax in the and comfortable living room or open the ...

Perfect saratoga springs location to enjoy the 2025 racing season. Belmont stakes festival. June 4th. 8Th, $15,000.00. Entire season. July 9th. September 1st, $40,000.00. Security deposit required. Walking distance to the thoroughbred and harness tracks, saratoga performing arts center, state par...

Enjoy the naples sunshine and tropical beach lifestyle at harbour house! This newly renovated home is ideally located in the elite moorings neighborhood, an easy mile walk to the nearest beach access. The open floor plan places the fully equipped kitchen with large island at the center of the hom...

Available for off-season only in the highly sought-after verona walk community! This 3-bedroom, 2-bathroom single-family home offers a serene lakeside setting with breathtaking views and southern exposure, a private hot tub, and a screened lanai-perfect for unwinding after an active day. Designed...

Experience south florida living in this ly furnished 5-bedroom, 4-bathroom single-family home, ideal for temporary relocation, corporate stays, or seasonal living. This residence features an open-concept layout with a fully equipped kitchen, living and dining areas, and comfortable accommodations...

Schedule a showing online at: -. Nestled in the serene and sought-after community of naples, florida, this 2-bedroom, 2-bathroom home offers a perfect blend of comfort, style, and functionality you step inside, you'll be greeted by a well-maintained living space that features a combina... Club house

Experience the epitome of downtown naples living in this penthouse, where sophistication meets convenience. Just steps from the vibrant 5th avenue and a short walk to the beaches, this property offers the perfect blend of luxury and location, available for both seasonal and annual rental. Spannin...

Welcome to your personal paradise at the olde marco inn located on marco island, floridaa destination where tranquility meets coastal charm. Immerse yourself in the allure of an ly renovated 2-bedroom, 2-bathroom retreat, meticulously crafted to enhance your dream vacation you enter this 6-person...

Schedule a showing online at: -. This fully furnished 2-bedroom, 2-bathroom condo offers 1,179 square feet of thoughtfully designed living space. Located in one of naples' most desirable areas, providing a hassle-free living experience. Highligh... Credit reporting to build credit for rent payments.

Available june, july, aug, sept, $4k/mo, dec 2025 $5k/mo & jan 2026 $7k/mo! Second floor 3br/2ba coach home, turnkey furnished, professionally decorated with premium furnishings, décor and a 2 car attached garage. This coach home features tile floors, granite kitchen and bath counter-tops, stainl...

This gorgeous home has ething you need! With its modern and open concept, tall ceilings, and modern lighting you can really enjoy the space however you choose. The kitchen has new appliances, great counter space, and a large island perfect for cooking and entertaining! Facing is the living area t...

Experience luxury living in this move-in ready, unfurnished, light & bright attached villa, featuring a open floorplan with 2-bedrooms plus a den, and 2 modern bathrooms. Boasting numerous upgrades throughout to include granite countertops, premiums stainless steel appliances, convection oven isl...

Available now. Book your 2026 seasonal rental today! Contemporary designed and decorated luxury rental in the amenity rich community of naples reserve! This bright and welcoming home offers 4 bedrooms plus a den, 4 bathrooms, and over 2400 square feet of living space. Comfortable living for up to...

This 2-bedroom plus a den and 2-bathroom, 2 car garage villa, built end of december 2023 in the desirable enbrook community offers the perfect blend of comfort and convenience. This cozy home is available for a long term rent. The open floor plan creates a and airy feel, ideal for relaxing or ent...

Unfurnished annual available immediately on cul de sac with bay views and boat dock just minutes from the open river and surrounded by custom homes. Modern, bright and updated kitchen features stainless steel appliances, quartz countertops and... This house is waiting to be made into your next home!

Naples living is easy in this 5th floor masterpiece. This two bedroom, two bathroom residence offers bay views and all of the best in comfort and convenience. The unit's light grey walls and wood-look floors complement the blue water and sandy beaches just moments away to create a soothing coasta...

Discover luxury living in this meticulously designed 3-story villa, ideally located in the olde naples neighborhood. This residence features three bedrooms and three full bathrooms, complemented by a private elevator just steps from your two-car garage, ensuring seamless access to all levels. Bas...

Enjoy tropical water views from this modern home, ideally located on a gulf-access canal just off naples bay. High-end finishes are... From the canal behind the house, enjoy quick access to naples bay and the gulf of mexico with no bridges! The warm waterside naples lifestyle awaits at curlew canal!

Located in the heart of park shore walking distance to waterside, venetian village, park shore beach, and sea gate school, this 4-bedroom plus den pool home features a upper level studio/dorm/bonus room with full bath. Step out through french doors onto a little awning deck to survey park shore t...

Centrally located near highways, airport, shopping, restaurants and schools. Home features an expansive backyard for entertaining friends and family. Plenty of parking, carport and automatic gate for added security per owner, home is larger than tax roll reflects. Please call listing agent for ad...