Houses for Rent in Winter Park, FL

This charming 3-bedroom, 2-bathroom home spans 1,653 sq. ft. and is pet-friendly, featuring smart home technology for ultimate convenience. Enjoy the cozy fireplace, eat-in kitchen, and a large backyard perfect for outdoor activities. Additional highlights include a screened porch, attached garage, and modern stainless steel appliances. Ideal for those seeking comfort and modern living in a lovely setting.

This 4-bedroom, 3-bath home offers 1,856 sq. ft. of comfortable living space, featuring a contemporary kitchen with stainless steel appliances. W/D hookups add convenience, while the outdoor swimming pool enhances relaxation. Perfect for families, this pet-friendly home is ready to make your stay enjoyable in a vibrant community.

This charming 3-bedroom, 2-bath home features 1,200 sq. ft. of comfortable living space. Enjoy the convenience of in-unit laundry hookups and a swimming pool perfect for relaxation. Pet-friendly with on-site management, making it ideal for families. Conveniently pre-leasing, ensuring easy application and a smooth transition to your new home. Don’t miss out on a cozy retreat.

Enjoy a stylish lifestyle in this 2-bed, 2-bath home featuring modern finishes, a premium kitchen, and a cozy fireplace. The fenced backyard offers a perfect retreat for pets and outdoor gatherings. With Smart Home technology and a range of convenient services included, this professionally managed property is designed for easy living. Plus, neighborhood amenities like basketball and tennis courts enhance the fun. Ideal for those seeking comfort and flair.

This inviting 3-bedroom, 2.5-bathroom rental offers a perfect blend of comfort and convenience in Winter Park. With 1,525 square feet of space, it features a fenced yard ideal for kids and pets. Residents can enjoy access to a swimming pool and on-site management for added ease. Pre-leasing options make securing this home simple. A wonderful opportunity for those looking to enjoy a vibrant community while having a cozy retreat.

This delightful 2-bedroom, 2-bath townhouse features a master suite on the second floor, perfect for privacy. Enjoy cozy evenings by the fireplace or entertaining at the wet bar. The community offers a fantastic fitness center in the clubhouse, complemented by essential appliances like a dishwasher and microwave. With a total of 1,120 square feet, this home combines comfort and convenience. Additional amenities include trash collection and water services for hassle-free living.

This charming 3-bedroom, 2-bath home boasts a spacious layout with granite countertops in the kitchen and a walk-in closet in the primary bedroom. The attached 2-car garage adds convenience, while the ceramic-tiled patio overlooking the fenced backyard is perfect for relaxation. Located in a desirable area with easy access to shopping, dining, and major highways, this residence offers both comfort and practicality. Experience the best of Winter Park living!

Enjoy vibrant Florida living in this beautifully updated 3-bedroom, 2-bathroom home offering 1,282 sq. ft. of modern comfort. Fully tiled and freshly painted, it features a convenient kitchen with included appliances, a private fenced courtyard, and a spacious two-car garage. Just moments away from Winter Park Village and the community pool, this residence provides the perfect blend of relaxation and entertainment in a fantastic location.

Nestled in Kenilworth Shores, this furnished 3-bed, 2-bath home features an open floor plan with a family/dining combo and a family room overlooking a lush, tropical backyard. Relax by the black bottom pool and enjoy the fully fenced yard with a gazebo. Utilities included for stress-free living, situated conveniently between Baldwin Park and Park Avenue.

Experience luxurious living in this modern 4-bedroom, 3.5-bath townhome featuring high-end finishes and an open-concept layout. The chef's kitchen boasts quartz countertops and stainless appliances, while large windows fill the spacious primary suites with light. Versatile third-floor spaces, ample storage, and a rear-entry garage enhance convenience. Located just steps from Winter Park's vibrant attractions, this elegant residence offers a perfect blend of comfort and style.

This move-in ready one-story home boasts 4 bedrooms and 3 full baths, perfect for families. Enjoy a large screened porch and a fenced backyard on a quiet street. Modern stainless steel appliances complement the inviting interior, freshly painted and filled with natural light. With A/C replaced in 2022 and lawn care included, this 2,070 sq ft residence offers comfort and convenience in a prime Winter Park location, just minutes from Baldwin Park and local schools.

This inviting 2-bedroom, 2.5-bath townhouse in the desirable Sandlewood Creek community offers a bright open living area, a stylish kitchen with quartz countertops, and a lovely primary suite. Enjoy outdoor relaxation on the private rear patio, and take advantage of community amenities like the pool. With easy access to Winter Park's shops, dining, and entertainment options, this home is perfect for those seeking modern living in a vibrant area.

This stunning 4-bedroom, 2.5-bath residence features recent updates and a stylish interior, including hardwood floors and granite countertops. The gourmet kitchen flows into a cozy family room with a wood-burning fireplace. A spacious master suite offers a luxurious bath and access to a delightful second-floor deck. Enjoy the serene front porch and lush backyard with fruit trees. Ideally situated near shops, restaurants, and top schools, this home is perfect for Florida living.

This charming 4-bedroom, 2-bath home offers 1,411 sq ft of comfortable living space, complete with a bonus room ideal for an office or play area. The eat-in kitchen comes with stainless steel appliances, perfect for family meals. Enjoy the convenience of a 2-car carport and proximity to major roads, shopping, and Full Sail University. Pet-friendly with a spacious yard, make this Winter Park residence a perfect family retreat!

This stunning 4-bedroom, 3.5-bathroom home features numerous upgrades and a spacious layout, ideal for entertaining. The gorgeous kitchen shines with solid wood cabinets, granite counters, and a gas stove, flowing into a bright family room. Enjoy hardwood floors, a bonus loft, and an exquisite primary suite that opens to a private balcony. The fenced yard and covered patio complete this beautiful family oasis, conveniently located near parks, shops, and top-rated schools.

This extraordinary residence features 8 bedrooms and 6 bathrooms across three levels, offering an exceptional blend of sophistication and livability. The chef's kitchen and expansive primary suites are just the beginning. Entertain seamlessly between the spacious family room and covered patio, while a fully-equipped in-law suite downstairs promises flexibility. Located in a prestigious neighborhood, it's the perfect retreat for modern living.

Embrace contemporary living in this stylish 3-bedroom, 2.5-bathroom townhouse in a gated community by Lake Howell. The open floor plan features tile flooring, an upgraded kitchen with granite countertops, and stainless steel appliances. The primary suite offers a walk-in closet and elegant bath. Enjoy outdoor relaxation in the private backyard patio, plus community amenities like a pool, cabana, park, and playground. Convenient access to Winter Park dining and shopping.

This beautifully maintained 3-bed, 3-bath home offers 1,747 sq. ft. of open living space, complete with a dedicated office, ideal for remote work. Enjoy a fully fenced backyard featuring a sparkling pool perfect for relaxation or entertainment. The property includes an attached garage and ample parking, with lawn care and pool service included. Nestled in a coveted neighborhood, this pet-friendly residence is close to parks and amenities, offering convenience for the whole family.

This remodeled 3-bedroom, 2.5-bath townhouse offers modern comforts with an updated kitchen and bathrooms. Enjoy the enclosed/screen patio overlooking a tranquil green view and courtyard. Additional perks include a solar boosted water heater and a pet-friendly environment, perfect for dog lovers. With 1,727 sq ft of living space, this townhome blends convenience and style, making it an ideal retreat in Winter Park.

This inviting 3-bed, 1.5-bath residence spans 1,351 sq. ft. and offers a large living room bathed in natural light, connecting to a spacious backyard with a deck. Enjoy the tranquility of the fenced yard bordered by a serene watercourse. Conveniently located near schools, parks, and restaurants, this pet-friendly home comes with a washer/dryer and boasts no HOA. With a move-in incentive of $500 for a December move, it’s a perfect opportunity for a fresh start!

Fully renovated 4-bedroom, 3-bath home offers 2,207 SF of sunlit living space just steps from Winter Park Racquet Club. The private backyard features a sparkling pool and heated spa, surrounded by lush landscaping for perfect outdoor relaxation. Enjoy modern comforts with a new roof, dual-speed AC, and included services for gardening and pool maintenance. This dreamy retreat combines luxury with low utility costs, making it an ideal choice for effortless Florida living.

This fully furnished 3-bedroom, 1.5-bath midcentury modern home boasts refinished parquet hardwood floors and an abundance of natural light. Enjoy open living areas, two Florida rooms, and a fenced backyard. Additional features include a one-car garage and a large driveway. Located just minutes from I-4, this stylish retreat offers easy access to premier shopping and dining in the vibrant Winter Park area, making it an ideal rental escape.

This adorable 3-bedroom, 1-bathroom mid-century modern bungalow boasts new tile wood floors and an updated kitchen with sleek white appliances. The refreshed bathroom features a stylish mosaic tile floor. Enjoy a spacious backyard complete with a wooden deck, perfect for outdoor gatherings. With included washer, dryer, and lawn care, this inviting home is a fantastic find in Winter Park!

This stunning 3-bedroom, 2.5-bath residence showcases elegance and comfort in 1,880 sq ft. The gourmet kitchen boasts wood cabinetry, stainless steel appliances, and granite countertops, perfect for culinary enthusiasts. French doors lead to a large, secluded patio, ideal for entertaining. The spacious master suite features an ensuite with dual vanities and a jacuzzi. Conveniently located near Park Avenue and Rollins College, this pet-friendly home is a true delight.

This stylish 4-bedroom, 2-bath home features an open-concept design adorned with curated artwork, lush gardens, and a spacious wood deck with an outdoor kitchen, perfect for entertaining. Enjoy stunning lake views and proximity to Orlando's attractions and cultural sights. Ideal for families or professionals seeking a refined long-term stay—embrace an active lifestyle with nearby walking trails, tennis courts, and golf clubs.

Experience unparalleled craftsmanship in this exquisite 3-bedroom, 2-bathroom home, boasting over 2,000 sq. ft. of elegant living space. Highlights include a state-of-the-art kitchen with stainless appliances, a cozy family room with a fireplace, and a serene screened sunroom. The luxurious master suite features a spa-like bath, while the beautifully landscaped outdoor space and deck are ideal for entertaining. Enjoy the convenience of in-unit laundry and a double garage.

Embrace a stylish lifestyle in this pet-friendly 2-bedroom, 2.5-bathroom townhome featuring 960 sq ft of living space. Enjoy a spacious main area with open living and dining, a chic kitchen with quartz countertops, and a lovely primary suite with custom finishes. A rear patio offers outdoor relaxation, while the community pool adds a touch of fun. Located near Park Avenue's shops, dining, and recreational amenities, this home is perfect for those seeking convenience in Winter Park.

This elegant 3-bedroom, 2.5-bath home offers a perfect blend of comfort and style across 1,848 sq ft. Enjoy natural light in spacious living areas with laminate wood and ceramic flooring. Entertain in the sunny backyard or relax in cozy spaces. Conveniently located near schools, shopping, and dining, this home is ready for a new owner to embrace the Florida lifestyle. Washer and dryer included for added convenience!

A stunning 4-bedroom, 3-bath lakefront residence boasts 2,476 sq ft of sophisticated living in Winter Park. Featuring engineered wood flooring, soaring ceilings, and an open-concept design, this home is filled with natural light. The gourmet kitchen with stainless appliances and a generous island is perfect for entertaining. Enjoy a private courtyard with a hot tub, plus a detached bonus room ideal for a home office or fitness studio. Walk to dining, shopping, and cultural attractions nearby.

This stunning 4-bedroom, 3-bathroom home boasts 2,300 sqft of bright, inviting space perfect for family living and entertaining. Enjoy a modern kitchen with stainless steel appliances, and two luxurious primary suites with walk-in closets. A fenced backyard offers a private retreat, while ample parking and a convenient laundry room add to the comforts. Located on desirable Palmer Avenue, residents are steps away from Winter Park's energetic downtown, parks, and lakes.

This spacious 3-bedroom, 2.5-bath townhouse features 1,907 sq. ft. of comfortable living in a gated community. Enjoy the convenience of in-unit laundry, plus 1 GB Fiber Internet and TV included. Relax by the pool and cabana, all while being just minutes away from Orlando's finest dining, shopping, and attractions. With a holiday special of 1 month free for applications before December 31st, this opportunity is too good to miss!

This stunning custom residence spans 5,164 sq ft and showcases 5 bedrooms and 6 bathrooms, redefining luxury living with state-of-the-art technology and artful design. Highlights include a floating staircase, expansive outdoor living space with a resort-style pool, and a tranquil primary suite. Located in the desirable Virginia Heights neighborhood, this home offers deeded lake access and is a short stroll from Winter Park’s dining and shopping, embodying elegance and modern sophistication.

This stunning 3-bedroom, 2.5-bath townhome radiates coastal charm and modern efficiency in an open-concept design. Highlights include a gourmet kitchen with quartz countertops, a spacious primary suite with a designer bath, and a private courtyard for outdoor entertaining. With features like smart home technology and a WiFi-enabled garage, this immaculate residence ensures comfort and convenience just minutes from dining and shopping in vibrant Winter Park.

This charming 3-bedroom, 2-bath residence features fresh renovations and sits on an oversized, fully fenced lot, perfect for outdoor fun. Enjoy central AC, washer/dryer hookups, and proximity to A+ schools and Park Avenue's vibrant shopping and dining. An excellent choice for comfort and convenience, this pet-friendly home is ready for its next residents!

This spacious 2-bedroom, 2-bathroom ground-floor townhouse features freshly painted interiors, modern appliances, and sleek tile flooring throughout. Enjoy granite countertops in the kitchen and relax by the community pool. Conveniently located near Full Sail University, UCF, and various shopping and dining options just minutes away. A perfect blend of comfort and accessibility awaits!

Experience the vibrancy of Winter Park in this charming 3-bedroom residence featuring a bonus room perfect for a home office. Enjoy peace of mind with a fenced backyard, a cozy fireplace, and the benefits of solar panels. Conveniently located near fine dining, entertainment, and top-rated schools, this home is within minutes of rolling’s College and UCF. With 1,598 sq ft of living space, your new chapter in this inviting community awaits!