Houses for Rent in Winter Park, FL

Property Status: Active Available for move-in on 10/01. Welcome to this beautifully renovated 3-bedroom, 2-bathroom single-family home, perfectly positioned just minutes away from shopping, dining, and all the charm of Winter Park. This home combines modern luxury with everyday convenience. As you step inside, you're greeted by the elegance of Calacatta Quartz countertops, sleek waterproof flooring, and top-of-the-line appliances that set the tone for the entire space. The open layout flows seamlessly, making it perfect for both daily living and entertaining. With the late

Property Status: Active This active, single-family rental listing at 7033 Easter St, Winter Park, FL 32792. This spacious residence features a 4-bedroom, 3-bathroom split floor plan spanning 2,151 heated square feet, situated on an expansive, fenced 0.76-acre lot down a quiet, unpaved lane. The exterior highlights include a private, screen-enclosed swimming pool (with chemical and pool maintenance fully covered by the landlord), a massive backyard, and three dedicated storage sheds perfect for equipment or hobbies. Inside, the home offers open-concept living spaces, dual m

Property Status: Active Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having the Cady Way pool, pickleball courts, and beach volleyball courts all just a short walk away. The home is zoned for Brookshire Elementary School, Glenridge Mi

Adorable 3 bedroom, 2 bathroom one story home in Winter Park. Minutes from Baldwin Park and downtown Park Ave. The home has been beautifully renovated. There is a large backyard with paver patio area. Inside utility room with access to kitchen and carport area. Kitchen and family room are open to each other and boast plenty of built in storage. Designer light fixtures throughout the home.

Property Status: Active Exceptional luxury rental opportunity in the heart of Winter Park! Located along a beautiful tree lined brick street, this custom built residence offers an impressive combination of sophisticated finishes, generous living spaces and resort style outdoor living. Featuring 6 bedrooms, 4.5 baths and a 3-car garage, the thoughtfully designed two-story floor plan provides exceptional flexibility for everyday living, entertaining, working from home and hosting guests. Step inside to an open, light filled interior highlighted by beautiful wood flooring, cu

Property Status: Active EVERYTHING IS NEW! Available 9/1! Come see this beautifully renovated 3-bedroom, 2-bathroom townhome in highly sought-after Winter Park for yourself! With 1,332 sq. ft. of living space, this spacious two-story home is completely move-in ready and packed with updates including new flooring and updated fixtures, renovated kitchen with tons of storage, brand-new stainless steel GE appliances, renovated bathrooms, new roof, and a fenced backyard! Note washer and dryer and lawn service are included! Enjoy your morning coffee or unwind with a cold drink o

Property Status: Active Discover refined living in the heart of Winter Park in this beautifully appointed 4-bedroom, 2.5-bathroom single-family pool home. Immediately to the right of the entryway, a beautiful private office provides a convenient and quiet space for working from home or studying. Filled with natural light, the home features an inviting open layout, and a spacious living area centered around a cozy fireplace. The stylish kitchen showcases light gray cabinetry, sophisticated gold-tone accents, a center island, and generous space for cooking and entertaining.

Property Status: Active A Townhome for our times. Renovated and Made Ready; this luxurious 2 bedroom/2.5 bath residence includes a private attached garage and has been redesigned for today's needs. Securely located in a private gated Winter Park Community. "Eating In" takes on a Whole Foods new meaning with a gourmet modern kitchen. Upstairs, the Master Suite includes ample storage and a luxurious, light-filled bath. A large bonus area and a well-sized guest suite are perfect for a Home Office or guests and have vaulted ceilings, extra-large ceiling fans, and a renovated f

Property Status: Active 450 Canton Avenue - Winter Park, FL | $3,200/mo Charming and spacious, this beautifully located rental sits just 2 blocks from Park Avenue, offering walking-distance access to Winter Park's best restaurants, boutique shopping, and Winter Park Village - plus easy access to the Winter Park Train Station for effortless commuting. Step inside to find a thoughtfully laid-out floor plan featuring a front living room with a cozy wood-burning fireplace, a separate family room, formal dining room, and a versatile den just off the dining area - perfect for a

ONE MONTH FREE! Beautiful home located on a quaint, tree-lined brick street in desirable Winter Park. Step inside to a large family room featuring a wood-burning fireplace and an open kitchen with beautiful new granite countertops and backsplash. The home features two bedrooms with walk-in closets and a split bathroom with two vanities and two toilets. Fresh interior paint throughout gives the home a clean and refreshed feel. The kitchen has been updated with a custom backsplash and drop-down soffits, while the cabinets have been refreshed with new paint and hardware. T

A beautiful tile roof single-family house is available in Hawks Crest, the only gated community in Winter Park! UV sanitizing lights are installed in all bathrooms. A water filter system is installed in the kitchen sink. This 4-bed 3.5-bathroom plus an office and second-floor loft is ready to move in. When you enter the home, an open-concept floor plan leads you to the family room and the kitchen/nook area combined. 20-foot high ceiling family room with wide sliding doors to the back patio and high windows gives you plenty of natural sunlight. The large covered lanai woul

Welcome home to this beautifully renovated 2-bedroom, 2-bath townhome in desirable Winter Park, FL! Fresh, modern, and move-in ready, this inviting home offers the perfect combination of comfort, privacy, and convenience. Step inside to enjoy fresh paint, new flooring and carpet, updated cabinetry, and new appliances, creating a bright and contemporary feel throughout. Ceramic tile accents add character to the living spaces, while the private second-floor primary suite offers a comfortable retreat away from the main living area. Relax or entertain outdoors on your private

Property Status: Active Gorgeous 5-bedroom /6-bathroom Luxury Estate with Guest House & Pool in Winter Park This stunning two-story home offers the perfect blend of luxury and comfort right in the heart of Winter Park. At the center of the home is a beautiful open kitchen outfitted with high-end appliances, solid wood cabinets, and granite countertops . A true chef's layout that flows into the living spaces. You'll love the elevated details throughout, from the elegant crown molding to the beautiful flooring. The backyard is a private retreat, featuring an inviting in-grou