170 properties for rent in Winding Cypress

This 1st FLOOR, 3 bedroom, 2 bathroom, 1 car garage condo located in Lely Landings is available to rent. With 1,657 sf of living space and close to everything Naples has to offer don't miss out!

2 Bedroom, 2 Bathroom Apartment For Rent. 946 Sqaure Feet. $1675/Month, $1000 Deposit. Balcony|Private Balcony|Dish Washer|Pool|Washer/Dryer|Central Air|Central Heat|Water Included|oven|garbage disposal|Community BBQ/picnic area|one assigned parking plus guest parking|refrigerator|Vehicle Wash Area|Skylight with electric shade controller. 5242 Treetops Drive, Unit L 203, Naples, FL 34113

2 Bedroom, 2 Bathroom Apartment For Rent. 1088 Sqaure Feet. $2182/Month, $0 Deposit. Dogs allowed|Pet friendly|Accessible|Car wash area|Clubhouse|Coffee bar|Dog park|24hr gym|Pool|24hr maintenance|Bbq/grill|Hot tub|Internet access|Package receiving|Trash valet|Cats allowed|Garage|Parking|Bike storage|CC payments|Conference room|Green community|Internet cafe|Key fob access|Online portal. 4360 Petal Dr Unit 102, Naples, FL 34112

Woodmere Lake Club does ALLOW 1 pet! This 1st Floor 2-bedroom, 2-bathroom Condo in Woodmere Lake Club is available to rent. This quiet Community offers tennis and pickleball and is close to everything Naples has to offer. Including Marco Island, beaches, shopping, dining, and 5th Avenue

2 Bedroom, 2 Bathroom Apartment For Rent. 1132 Sqaure Feet. $2430/Month, $0 Deposit. Dogs allowed|Pet friendly|Bocce court|Clubhouse|Dog park|Elevator|Fire pit|24hr gym|Game room|Parking|Playground|Pool|Pool table|Bbq/grill|Garage|Hot tub|Key fob access|Pickleball|Trash valet|Yoga|Walking trail|Cats allowed|Accessible|CC payments|Dog grooming area|E-payments|Internet access|Internet cafe|Online portal|Package receiving|Tennis court|Wine room. 120 Bedzel Circle Unit 05-110, Naples, FL 34104

Welcome to Cedar Hammock Golf & Country Club, your seasonal escape in one of Naples' most sought after golf communities. This beautifully updated two bedroom, two bath condo offers the perfect blend of comfort, style, amenities, and location that make Southwest Florida living so unforgettable. Step inside to find a bright, open layout designed for easy relaxation. The living and formal dining areas flow naturally toward the screened balcony, where panoramic southern views stretch across the championship course and lakes. Morning coffee, quiet afternoons, and sunset evenings all feel a little more special from this vantage point. The open-concept kitchen is both stylish and functional, featuring stainless steel appliances, abundant polished granite countertops, and an inviting eat in nook with bay windows, ideal for casual meals or planning the day's adventures. Both bedrooms are comfortably appointed, with the primary suite offering a king bed and its own bath with a step in shower and

2 Bedroom, 2 Bathroom Apartment For Rent. 1144 Sqaure Feet. $2399/Month, $0 Deposit. Dogs allowed|Pet friendly|Bocce court|Clubhouse|Dog park|Elevator|Fire pit|24hr gym|Game room|Parking|Playground|Pool|Pool table|Bbq/grill|Garage|Hot tub|Key fob access|Pickleball|Trash valet|Yoga|Walking trail|Cats allowed|Accessible|CC payments|Dog grooming area|E-payments|Internet access|Internet cafe|Online portal|Package receiving|Tennis court|Wine room. 120 Bedzel Circle Unit 06-301, Naples, FL 34104

Welcome to Crown Pointe Shores, a perfectly located community offering easy access to the best of Naples. Step into this updated, naturally bright home and enjoy a comfortable, welcoming atmosphere throughout. The primary suite features a king bed, while the second and third bedrooms each offer queen beds-every room equipped with TVs. The fully equipped kitchen includes stainless-steel appliances and a pass-through counter, making meal preparation easy and enjoyable. A full-size washer and dryer and an attached garage provide the everyday conveniences. In the evenings, unwind on the screened lanai as you take in awe-inspiring sunsets over the lake. Community amenities enhance the experience even further, with a clubhouse offering a heated pool, fitness room, social room, tennis courts, and more. Excellent shopping is just moments away, and the world-class restaurants and shops of 5th Avenue South are only a short drive from your door. Beach lovers will appreciate the nearby white-sand

2 Bedroom, 2 Bathroom Apartment For Rent. 1235 Sqaure Feet. $2000/Month, $2000 Deposit. Additional Storage|Storage Space|Balcony|Private Balcony|Dish Washer|Pool|Washer/Dryer|Updated Bathroom|Updated Kitchen|Central Air|Central Heat|Water Included. 4977 Pepper Circle, Unit 205, Naples, FL 34113

1 Bedroom, 1 Bathroom Apartment For Rent. 814 Sqaure Feet. $1999/Month, $0 Deposit. Dogs allowed|Pet friendly|Bocce court|Clubhouse|Dog park|Elevator|Fire pit|24hr gym|Game room|Parking|Playground|Pool|Pool table|Bbq/grill|Garage|Hot tub|Key fob access|Pickleball|Trash valet|Yoga|Walking trail|Cats allowed|Accessible|CC payments|Dog grooming area|E-payments|Internet access|Internet cafe|Online portal|Package receiving|Tennis court|Wine room. 120 Bedzel Circle Unit 02-407, Naples, FL 34104

1 Bedroom, 1 Bathroom Apartment For Rent. 808 Sqaure Feet. $2125/Month, $0 Deposit. Dogs allowed|Pet friendly|Bocce court|Clubhouse|Dog park|Elevator|Fire pit|24hr gym|Game room|Parking|Playground|Pool|Pool table|Bbq/grill|Garage|Hot tub|Key fob access|Pickleball|Trash valet|Yoga|Walking trail|Cats allowed|Accessible|CC payments|Dog grooming area|E-payments|Internet access|Internet cafe|Online portal|Package receiving|Tennis court|Wine room. 120 Bedzel Circle Unit 02-408, Naples, FL 34104

Lago Villaggio community located inside the gates of Glen Eagle Golf & Country Club. Seasonal rental available starting January 2028. Stunning lakefront home with brand new sleek kitchen, 4 bedrooms, 2 baths, pool, spa 2-car garage. TV's(6). Two bedrooms with queen size beds, 2 bedroom with king size beds. The social membership is transferable during your stay to enjoy country club amenities which includes: Country Club Restaurants, Fitness Center, Tennis Har-tru courts with lights for evening fun, Library, game room/pingpong, billiards, community pool, bocce ball, close to Greenway Bike trails, sidewalks throughout the community and dazzling lakes, flower beds, and golf course. (Please note golf IS NOT included in this social membership). No pets

1 Bedroom, 1 Bathroom Apartment For Rent. 676 Sqaure Feet. $1850/Month, $0 Deposit. Cats allowed|Dogs allowed|Accessible|Pool|Gym|Pet friendly|Bbq/grill|Business center|Clubhouse|Community garden|Dog park|E-payments|Internet access|Online portal|Pickleball|Walking trail. 3809 Azalea Park Circle Unit 3877-205, Naples, FL 34114

3 Bedroom, 2 Bathroom Apartment For Rent. 1244 Sqaure Feet. $2472/Month, $0 Deposit. Business center|Clubhouse|Gym|Pool|Garage|Cats allowed|Dogs allowed|Accessible|Pet friendly|Basketball court|Car wash area|CC payments|Dog grooming area|E-payments|Fire pit|Online portal|Package receiving|Pickleball|Tennis court|Volleyball court. 6975 Sierra Club Circle Unit 3112, Naples, FL 34113

2 Bedroom, 2 Bathroom Apartment For Rent. 1230 Sqaure Feet. $1721/Month, $0 Deposit. Business center|Clubhouse|Gym|Pool|Garage|Cats allowed|Dogs allowed|Accessible|Pet friendly|Basketball court|Car wash area|CC payments|Dog grooming area|E-payments|Fire pit|Online portal|Package receiving|Pickleball|Tennis court|Volleyball court. 6975 Sierra Club Circle Unit 2303, Naples, FL 34113

This corner unit condo on the first floor is situated in Naples, FL, providing quick access to I-75, dining options, shopping centers, to the beaches and downtown Naples. The unit features 1 bedroom + Den, 1 bathroom, laundry facilities, along with access to a community pool, spa, and gym. Please note that this property has a strict NON-SMOKING policy, and according to HOA regulations

1 Bedroom, 1 Bathroom Apartment For Rent. 643 Sqaure Feet. $1800/Month, $0 Deposit. Cats allowed|Dogs allowed|Accessible|Pool|Gym|Pet friendly|Bbq/grill|Business center|Clubhouse|Community garden|Dog park|E-payments|Internet access|Online portal|Pickleball|Walking trail. 3809 Azalea Park Circle Unit 3877-206, Naples, FL 34114

1 Bedroom, 1 Bathroom Apartment For Rent. 643 Sqaure Feet. $1675/Month, $0 Deposit. Cats allowed|Dogs allowed|Accessible|Pool|Gym|Pet friendly|Bbq/grill|Business center|Clubhouse|Community garden|Dog park|E-payments|Internet access|Online portal|Pickleball|Walking trail. 3809 Azalea Park Circle Unit 3825-302, Naples, FL 34114

2 Bedroom, 2 Bathroom Apartment For Rent. 1088 Sqaure Feet. $2247/Month, $0 Deposit. Dogs allowed|Pet friendly|Accessible|Car wash area|Clubhouse|Coffee bar|Dog park|24hr gym|Pool|24hr maintenance|Bbq/grill|Hot tub|Internet access|Package receiving|Trash valet|Cats allowed|Garage|Parking|Bike storage|CC payments|Conference room|Green community|Internet cafe|Key fob access|Online portal. 4360 Petal Dr Unit 112, Naples, FL 34112

2 Bedroom, 2 Bathroom Apartment For Rent. 1349 Sqaure Feet. $2100/Month, $0 Deposit.. 2265 Hidden Lake Dr, Naples, FL 34112

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Annual Rental or seasonal rental. Furnished 2BR+Den Condo in the prestigious resortTreviso Bay community. Beautifully maintained and fully furnished 2-bedroom, 2-bath condo with an open den located in the prestigious community of Treviso Bay. This spacious unit features a king bed in the primary bedroom, a queen bed in the guest room, and a pull-out sofa in the den. A tiled lanai offers serene southwest views of the lake and preserve. The unit also includes a covered carport, fully equipped kitchen, in-unit laundry, and plenty of natural light throughout. Situated just minutes from Naples' beaches, shopping, dining, and downtown attractions, this property offers both comfort and convenience. An optional Social Membership is available for a one-time $850 fee, granting access to the resort-style pool and spa, Tiki restaaurant and bar, fitness center, tennis and pickleball courts, and clubhouse dining. Available immediatley for seasonal or annual lease. Season rental $7,000 per month with

3 Bedroom, 2 Bathroom Apartment For Rent. 1307 Sqaure Feet. $2520/Month, $0 Deposit. Business center|Clubhouse|Gym|Pool|Garage|Cats allowed|Dogs allowed|Accessible|Pet friendly|Basketball court|Car wash area|CC payments|Dog grooming area|E-payments|Fire pit|Online portal|Package receiving|Pickleball|Tennis court|Volleyball court. 6975 Sierra Club Circle Unit 1111, Naples, FL 34113

2 Bedroom, 2 Bathroom Apartment For Rent. 1236 Sqaure Feet. $2021/Month, $0 Deposit. Dogs allowed|Pet friendly|Accessible|Clubhouse|Courtyard|Dog park|Fire pit|24hr gym|Parking|Playground|Pool|Bbq/grill|Garage|Package receiving|Pickleball|Cats allowed|Smoke-free community|Internet access|Trash valet|Coffee bar|Key fob access|Verified listing|24hr maintenance|Internet cafe|E-payments|Pool table|Online portal|New construction|CC payments. 11496 Sumter Grove Circle Unit 8211, Naples, FL 34113

2 Bedroom, 2 Bathroom Apartment For Rent. 1100 Sqaure Feet. $2257/Month, $0 Deposit. Dogs allowed|Pet friendly|Bocce court|Conference room|Car wash area|Clubhouse|Concierge|Courtyard|Dog park|Elevator|Fire pit|Parking|Bbq/grill|Garage|Internet access|Pickleball|Yoga|Cats allowed|Pool|Gym|Bike storage|Business center|CC payments|Dog grooming area|Game room|Hot tub|Online portal|Package receiving. 7425 Inspira Circle Unit 2-401, Naples, FL 34113

For Rent. Fully Remodeled Condo in Woodmere Racquet Club (Naples, FL). Looking for a clean, updated place in a prime Naples location? This beautifully fully remodeled 2 bed / 2 bath condo in Woodmere Racquet Club checks all the boxes. Property features 2 Bedrooms / 2 Bathrooms. 1,100 sq ft of living space, fully renovated interior. Modern finishes throughout, bright, open layout with peaceful preserve view. Move-in ready! Centrally located in Naples. Just minutes to downtown, shopping, dining, and the beach. Community amenities include a community pool, tennis courts, and walking/bike paths in a quiet, well-maintained community

2 Bedroom, 2 Bathroom Apartment For Rent. 1150 Sqaure Feet. $2200/Month, $0 Deposit.. 163 Palm Drive, Naples, FL 34112

2 Bedroom, 2 Bathroom Apartment For Rent. 1209 Sqaure Feet. $2292/Month, $0 Deposit. Dogs allowed|Pet friendly|Accessible|Car wash area|Clubhouse|Coffee bar|Dog park|24hr gym|Pool|24hr maintenance|Bbq/grill|Hot tub|Internet access|Package receiving|Trash valet|Cats allowed|Garage|Parking|Bike storage|CC payments|Conference room|Green community|Internet cafe|Key fob access|Online portal. 4360 Petal Dr Unit 211, Naples, FL 34112

1 Bedroom, 1 Bathroom Apartment For Rent. 643 Sqaure Feet. $1875/Month, $0 Deposit. Cats allowed|Dogs allowed|Accessible|Pool|Gym|Pet friendly|Bbq/grill|Business center|Clubhouse|Community garden|Dog park|E-payments|Internet access|Online portal|Pickleball|Walking trail. 3809 Azalea Park Circle Unit 3861-106, Naples, FL 34114

2 Bedroom, 2 Bathroom Apartment For Rent. 1132 Sqaure Feet. $2595/Month, $0 Deposit. Dogs allowed|Pet friendly|Bocce court|Clubhouse|Dog park|Elevator|Fire pit|24hr gym|Game room|Parking|Playground|Pool|Pool table|Bbq/grill|Garage|Hot tub|Key fob access|Pickleball|Trash valet|Yoga|Walking trail|Cats allowed|Accessible|CC payments|Dog grooming area|E-payments|Internet access|Internet cafe|Online portal|Package receiving|Tennis court|Wine room. 120 Bedzel Circle Unit 01-303, Naples, FL 34104