Properties For Rent in Winding Cypress, FL

Stylish 2BR/2.5BA villa in Ole at Lely Resort, Naples. Over 1500 sq ft, chef's kitchen, private suites, 2-car garage, resort amenities (pool, fitness center, dining), near beaches and golf. Perfect for seasonal rentals.

Quiet 2 bed, 2 bath apartment with private garage, in-unit laundry, large lanai & outdoor kitchen. Community pool & sundecks nearby. Ideal for those seeking a quiet, convenient, and affordable large unit.

Fully renovated lakefront home in Woodstone Estates with private pool & spa. Spacious open floor plan, 3 bedrooms, 2 baths, stainless steel appliances, and electric car charger. Enjoy nearby beaches, parks, and dining.

Freshly painted apartment unit with new appliances and tile floors. Oversized 1.5 car garage available for an extra charge. Ideal for those seeking modern convenience and ample parking.

Beautiful 3-bedroom, 3-bath end unit townhouse in Meadowood. Freshly painted, upgraded flooring, quartz countertops, new appliances, and a large den. Enjoy lake & fountain views, resort-style amenities, and a convenient location near beaches, shopping, and restaurants. Perfect for families or professionals.

Luxury 3-bedroom, 2-bath condo near Hammock Bay Golf Course. Fully renovated, open-plan living, screened lanai with southern vistas, modern kitchen. Community pool, close to beaches, dining, and shopping. Ideal for golfers and those seeking a relaxing escape.

Spacious 3-bedroom + Studio home in Naples, FL. Turnkey furnished, hot tub, pet-friendly. Short & long-term leases available. Close to beaches, restaurants, and shopping.

Brand new spacious apartment unit in Golden Gate City. Features beautiful tile, Samsung appliances, wood cabinets, quartz countertops, and in-unit washer/dryer. Electric and water included.

Luxury waterfront home in Naples Bay with stunning views. Expansive patio, pool, spa, 4 bedrooms, 5 baths, office, 3-car garage. Perfect for those seeking upscale living.

Beautiful 3 bed, 2 bath townhouse in gated Pelican Marsh. Enjoy resort-style amenities including pools, tennis, pickleball, and a party house. New paint, carpet, AC, and appliances. High ceilings, large balcony, and eat-in kitchen. Water, trash, and exterior maintenance included. Perfect for those seeking a luxurious and convenient lifestyle.

Beautifully updated 2 bed, 2 bath garden unit near Smokehouse Bay. Features updated kitchen, courtyard with heated pool, and carport parking. Unfurnished, 12-month lease required.

Spacious two-story house for rent. First floor available for sublease, including kitchen and bath.

Turnkey furnished 3-bedroom, 2.5-bathroom townhouse in Naples' Stratford Place. Features an open-concept living space, screened lanai with lake views, 1-car garage, and resort-style community amenities. Perfect for families or those seeking a convenient, luxurious lifestyle.

2 bedroom, 2 bathroom townhouse for rent in Lakewood community. Features a hot tub and is located near Davis Blvd, 41, and downtown. Dead-end street provides a quiet setting.

Newer Toll Brothers home in Azure at Hacienda Lakes. 3 beds plus den, 2.5 baths, 2-car garage. Gourmet kitchen, primary suite with walk-in closets. Elegant pool & spa (completion June/July 2025). Resort-style amenities. Available January 2025.

3 bed, 3 bath house with open floor plan, 2-car garage, private pool, lake view, and resort amenities. Perfect for families seeking a luxurious lifestyle.

5 bedroom, 4 bath luxury home in Naples, Florida. Modern design, peaceful neighborhood, perfect for families or remote workers. Easy access to Bonita Beach Road, Immokalee, and I-75.

Cozy apartment near 5th Ave and Naples Beach, available for seasonal rent (Jan-Apr 2025). Small pets allowed. Includes internet, water, electricity. Common laundry.

Spacious 3-bedroom condo in Naples, FL available for a 12-month lease (furnished or unfurnished). Features an open floor plan, private lanai, and access to community amenities like a pool, tennis, and pickleball courts. Perfect for those seeking comfortable Florida living.

Beautiful 3-bedroom, 2-bathroom home in gated North Naples community. Features lake view, private lanai, hurricane windows, upgraded kitchen, wood floors, and community amenities including a resort pool and fitness center. Perfect for families seeking a luxurious lifestyle.

Beautiful Capri villa in Verona Walk, Naples, FL. 5 min to Marco Island, 10 min to Naples Beaches. 2 master bedrooms, sleeps 6. Great amenities: resort pool, lap pool, cafe, etc. 4 month minimum lease.

Beautiful 1879 sq ft Townhouse in Orange Blossom community. Features 3 bedrooms, 2.5 baths, spacious master suite, 2-story floor plan, open kitchen, and family room. Community amenities include pools, spas, tennis, basketball, playgrounds, fitness center, and more!

Large furnished 2br/2ba condo, 1125 SF, overlooking pool & golf course. Annual rental, 4-month option available. King beds, new furniture. Good credit & background check required. No pets, non-smokers.

Beautiful 5-bedroom, 4-bathroom furnished bungalow with 2 kitchens, 2 living rooms, 2 patios, and a saltwater pool. Sleeps 10. Walk to Mercato & beach! Available March 30, 2025.

Fantastic downtown Naples canal-front rental home. Walk to 5th Ave, bike to the beach. 4 bedrooms + office (Murphy bed), 4 baths, heated pool, hot tub, dock. Sleeps 10. Available late January-March. Minimum 30 days.

Furnished 3 bed/2 bath house built in 2006, available for annual, off-season, or seasonal lease. Features include a 1-car garage, long driveway, storm shutters, fenced backyard, and new appliances. Tankless water heater and gas stove save on utilities.

Newly built 2 bed, 2 bath villa in gated Enbrook community. Features include a den/office, 2-car garage, screened lanai with lake views, and upgraded kitchen appliances. Community amenities include a clubhouse, fitness room, tennis, bocce, pickleball, and pool. Close to shopping and beaches.

Newly renovated 3-bedroom, 2-bathroom waterfront condo in Naples, FL. Enjoy stunning bay views, modern finishes, and resort-style amenities. Perfect for 55+ buyers seeking luxury waterfront living.

Private 1st floor 1 bed/1 bath unit with large screen porch, garage storage, 10ft ceilings, washer/dryer, walk-in closet & all utilities included! Perfect for a single person or couple seeking a peaceful retreat.

Newly built 4 bedroom, 3.5 bathroom townhouse for rent. Features central AC, 2nd floor patio, granite countertops, stainless steel appliances, 2-car garage, washer/dryer, and yard. No pets allowed. Available February 1st, 2025.

Luxury furnished 2B/2B condo in Naples Heritage Golf & Country Club. Enjoy lake & golf course views, plus resort amenities: fitness center, pool, tennis, pickleball, dining, and more. Close to downtown Naples and beaches.

Beautiful furnished 3BR/2BA home with heated pool, available for annual lease or seasonal rental. Enjoy nearby beaches, dining, and shopping. Features new floors, fully stocked kitchen, and a 2-car garage. Pet-friendly (upon approval).

Beautiful 2 bed/2 bath condo in Naples' La Mer gated community. Enjoy ocean views, beach access, resort amenities (pool, fitness center, social room), and a newly remodeled lobby. King bed in master, 2 twins in guest. Minimum 90-day rental.

Beautiful 2-year-old house with a lake view. Features new kitchen, bathrooms, tiles, and appliances. Spacious backyard.

Spacious tropical home with private pool, 2 fireplaces, chef's kitchen, and 2 guest suites. Ideal for families or friends. Water, electric, internet, and cable included.

Fully furnished 2 bed+den, 2 bath coach home in gated community. Available Jan 1-31, 2025, then annually from March 3. Features include attached garage, 9ft ceilings, private lanai, updated master bath, and resort-style amenities. Pet and child friendly.

Bright and sunny top floor 2-bedroom, 2-bath condo, 8 minutes from Naples' 5th Avenue and beaches. Fully furnished, updated baths, washer/dryer, screened patio, community pool & spa, covered carport, bikes, beach chairs, and optional golf course. All utilities included!

Updated home with direct water access, boat dock, pool, and close to beaches and dining. Perfect for short or long-term rentals. Available April 1st.

Fully furnished 3BR/2BA waterfront condo with dock access, 7-minute boat ride to the Gulf. Enjoy water views, heated pool, sauna, and more. Includes WiFi, cable, and smart TV. 12-month lease.

Top floor condo, 2 bed, 2 bath, updated kitchen, pool view, community pool & tennis court, washer/dryer, parking, elevator. Beach, restaurants nearby. 30-day minimum rental. No smoking, no pets.