Houses for Rent in Winter Park, FL

Experience comfort in this delightful 3-bedroom, 2-bath home featuring a cozy fireplace and ample living space. The open kitchen is fully equipped for culinary adventures, while a large screened-in patio and expansive yard provide perfect outdoor enjoyment. Additional highlights include a two-car garage and a convenient washer and dryer. This pet-friendly property promises a warm and inviting atmosphere in the heart of Winter Park.

This charming 3-bedroom, 2.5-bath home features smart home technology for seamless control and convenience. With 1,397 sq ft, enjoy an airy layout that includes vaulted ceilings and vinyl plank flooring. The outdoor area boasts a fenced yard and a patio, perfect for relaxation. Nestled near retail amenities, this pet-friendly residence combines modern comfort with a welcoming atmosphere.

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 4-bedroom, 2-bathroom rental offers a relaxing patio and balcony perfect for enjoying the fresh air. With a spacious 1,534 sq. ft. layout, convenience is key with in-unit W/D hookups and access to a refreshing swimming pool. This pet-friendly home is an excellent choice for those seeking comfort and leisure in a welcoming community. Enjoy the ease of application and leasing through FirstKey Homes, ensuring a smooth transition into your new abode.

This inviting 3-bedroom, 2-bathroom rental offers modern comforts in a vibrant setting. The well-appointed kitchen features stainless steel appliances, ready for culinary adventures. Enjoy the convenience of on-site management and laundry hookups, plus a refreshing swimming pool to unwind. Perfect for families and pet lovers alike, this home blends warmth and functionality for an ideal living experience.

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.

Experience comfort in this spacious 3-bedroom, 2.5-bath townhome-style condo with modern finishes. The kitchen features elegant granite countertops, while durable tile and luxury vinyl plank flooring add a stylish touch. Relax on your fenced patio with peaceful conservation views. This stunning 1,151 sq ft retreat is available now, complemented by in-unit laundry and central air for convenient living. Renters insurance required.

This inviting 3-bedroom, 2-bathroom home in Winter Park boasts a spacious main living area and dining room. Enjoy an updated kitchen with stainless steel appliances, a wonderful primary suite, and a large fenced backyard—perfect for pets or gatherings. A convenient 1-car garage adds to the home's appeal. Located near Park Avenue's shops, delicious restaurants, and local attractions like Mead Gardens, this residence offers a perfect blend of comfort and convenience.

Experience upscale living in this beautifully upgraded 3-bedroom, 3.5-bath townhouse featuring modern finishes and energy-saving features. With 2,342 sq ft of stylish space, enjoy a gourmet kitchen with high-end appliances, a spacious master retreat, and elegant design elements throughout. A private backyard with patio offers outdoor relaxation, all just a stroll away from the vibrant culture, shopping, and dining of Winter Park.

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.

Step into luxury with this stunning 3-bedroom, 2.5-bathroom modern farmhouse on a spacious corner lot. The open-concept design features soaring 14' ceilings and abundant natural light. A gourmet kitchen awaits with quartz countertops and high-end Zline appliances. The primary suite is a tranquil retreat with a spa-like bathroom. Enjoy beautifully landscaped grounds and convenience just blocks from shopping and dining at Winter Park Village. This meticulously maintained home is perfect for relaxed living.

This pet-friendly 2-bedroom, 1.5-bathroom bungalow offers a cozy atmosphere with beautiful parquet wood flooring, a separate dining room, and a sunroom leading to a large screened porch. The spacious kitchen features ample cabinets and counter space. Enjoy the tranquility of a fenced backyard filled with mature trees. Conveniently located near shopping and dining, this home combines comfort with accessibility, making it an ideal retreat in the heart of the city.

This charming 3-bedroom, 2.5-bath end unit townhome features an inviting open floor plan with hardwood floors and a gourmet eat-in kitchen showcasing granite countertops and stainless appliances. Enjoy your private enclosed patio, perfect for entertaining, and a serene balcony off the master suite. An oversized two-car garage adds convenience, while the location offers easy access to downtown Winter Park's shops and restaurants, making this a perfect blend of comfort and accessibility.

This stunning 4-bedroom, 2.5-bathroom residence features a delightful mix of modern updates and classic charm, boasting 2,406 sq ft of comfortable living space. Enjoy hardwood floors, gourmet kitchen with granite countertops, and a cozy family room with a wood-burning fireplace. The expansive front porch invites relaxation, while the upstairs deck offers scenic views. Situated on a picturesque brick-paved street, this home is minutes from Winter Park’s vibrant dining and shopping scene.

This cozy 2-bedroom, 1-bath home offers a prime location just minutes from dining and shopping. Featuring a sunroom with Mexican tile, a fenced backyard, and a garage, it combines convenience and charm. With walking access to YMCA and parks, this pet-friendly residence is perfect for outdoor enthusiasts. Enjoy your own slice of Winter Park living!

This delightful 3-bedroom, 2-bathroom home features a fully tiled interior and includes all essential appliances, such as a washer and dryer. Enjoy the privacy of a fenced courtyard and patio, perfect for outdoor relaxation. The convenience of a two-car garage with remote adds to its appeal. Located close to shopping, theaters, and malls, this residence combines comfort with a vibrant local lifestyle.

This beautiful 4-bedroom, 3.5-bath home features an open-concept layout with natural light, hardwood floors, and crown molding. The gourmet kitchen is equipped with stainless steel appliances and quartz countertops. A luxurious master suite with a spa-like bath and spacious loft add to its charm. Enjoy peaceful moments on the covered patio overlooking the fenced backyard and conservation area. Located in a gated community near upscale shopping and dining.

This modern 3-bedroom, 2.5-bathroom townhouse spans 1,755 sqft in the gated Hawks Crest community. It features an open floor plan, a chic kitchen with granite counters and stainless steel appliances, plus a serene backyard patio. The upstairs primary suite boasts dual sinks and a walk-in closet. Enjoy community amenities like a pool, playground, and park. Conveniently located near Lake Howell, shopping, and dining, this pet-friendly residence is perfect for a vibrant lifestyle.

This lovely 3-bedroom, 2-bathroom home features tile flooring throughout, eliminating carpet worries. The kitchen boasts stainless steel appliances and granite countertops. The spacious master bedroom includes a walk-in closet, while both bathrooms feature granite countertops. Enjoy the outdoors on the screened patio and relax in the fenced backyard. Conveniently located near dining, shopping, and entertainment options, this pet-friendly residence is ready for new tenants!

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 charming 3-bedroom, 2-bathroom townhome in a sought-after A-rated school district features a spacious corner lot and a welcoming porched back patio. Enjoy easy living with an included washer and dryer, modern appliances, and a well-maintained community pool for relaxation and recreation. Perfect for families seeking comfort and convenience in a vibrant community, this home offers a delightful blend of space and amenities. Experience the best of family living!

This stunning 7,000 SF home features 8 bedrooms and 6 baths across three levels, perfect for family living. Enjoy a chef-inspired kitchen with quartz countertops, cozy living spaces with a gas fireplace, and dual primary suites. An impressive lower level boasts an in-law suite, gym, and game room. The outdoor area includes a covered patio and pool deck, ideal for entertaining. Located in a quiet cul-de-sac near Park Avenue, this residence is a perfect blend of luxury and comfort.

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 stunning 3-bedroom, 2.5-bath townhome boasts 1,907 sq ft of modern elegance in Grayson Square. Featuring an open-concept living space, a stylish kitchen with stainless steel appliances, and a spacious owner’s suite with a walk-in closet, this home is perfect for entertaining. Enjoy the covered rear lanai, community resort-style pool, and complimentary high-speed internet. Conveniently located near shopping, dining, and major highways, experience the best of Winter Park living.

Move-in ready 3-bedroom, 2-bathroom home featuring 1,760 sq. ft. of stylish space on a .23-acre corner lot. Highlights include a newer septic tank, a durable 2016 roof, and fresh upgrades throughout. Nestled in a highly sought-after school district, it offers an excellent choice for families seeking comfort and convenience. Don’t miss the chance to make this beautifully upgraded residence your own!

Experience upscale living in this stunning 4-bedroom, 4-bathroom townhouse, featuring modern amenities and elegant hardwood floors. Boasting a spacious 2,602 sq ft, the updated kitchen and bathrooms offer convenience and style. Enjoy the comfort of central air and heating, along with in-unit laundry and ample storage. This pet-friendly residence provides a remarkable blend of luxury and practicality, perfect for those seeking vibrant Winter Park living.

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.

Enjoy this beautifully designed 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 counters and stainless steel appliances, and a spacious primary suite with dual sinks and a walk-in closet. Outdoor highlights include a patio and a quiet backyard area, while community perks offer a pool, cabana, park, and playground. Conveniently located near shopping and dining, this pet-friendly home is perfect for modern living.

This charming 2-bedroom, 1-bath home features hand-scraped wood floors and a modern kitchen with granite counters and sleek appliances. The open layout connects the kitchen, living, and dining areas, perfect for entertaining. Enjoy the expansive covered patio overlooking the backyard, ideal for relaxation. Additional highlights include a spacious primary bedroom with a walk-in closet and a detached garage. Lawn care is included, ensuring a beautiful outdoor space year-round.

This delightful 3-bedroom, 2.5-bath home spans 1,880 sq. ft., offering a spacious layout perfect for comfortable living. Features include central air for year-round comfort and a garage for added convenience. Enjoy a lovely outdoor space ideal for relaxation or gatherings. Located within a vibrant community, this residence provides a welcoming atmosphere and great potential for those seeking a cozy home.

This stunning 3-bedroom, 2.5-bath end-unit townhouse features an open-concept design filled with natural light. Enjoy a modern kitchen with stainless steel appliances and quartz countertops, along with an impressive owner’s suite complete with a walk-in closet and luxurious ensuite. The gated Grayson Square community offers a pool, cabana, high-speed internet, and cable. With a convenient two-car garage, this home is ideally located just minutes from downtown Winter Park and local shopping.

This charming 3-bed, 2.5-bath townhouse features a convenient one-car garage in a secure gated community. Enjoy the comfort of in-unit laundry and a stylish kitchen with a dishwasher. The bright living spaces are enhanced by cozy carpets, making this home perfect for relaxation and entertaining. Ideal for those seeking modern living while enjoying community security and amenities.

This beautiful 3-bedroom, 2-bath home features elegant wood-like tile flooring and stylish fixtures throughout. The inviting kitchen offers stainless steel appliances, an island breakfast bar, and ample cabinetry. A generous master bedroom boasts a walk-in closet and private bath. Enjoy a large laundry room, two-car carport, and a vast backyard perfect for relaxation. Located close to major intersections and A-rated schools, this home is ready for a seamless move-in experience with lawncare included!

This newly remodeled 3-bedroom, 1-bathroom home features a stylish kitchen with stainless steel appliances and updated cabinets. A bonus room perfect for an office and additional storage enhance functionality. Nestled in the heart of Winter Park, residents enjoy walking to nearby restaurants and shopping with easy access to I-4. Ideal for pet lovers, this charming residence combines comfort and convenience in a vibrant neighborhood.

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!

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 inviting 4-bedroom, 3.5-bathroom residence spans 2,589 sq ft and offers a serene lifestyle near modern conveniences. Enjoy spacious bedrooms, well-appointed baths, and year-round comfort with central air and heating. The property features a refreshing swimming pool and a courtyard, perfect for relaxation. Located just minutes from shopping and AdventHealth Orlando, this home combines comfort and convenience for a delightful living experience.

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!

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.

Experience luxurious comfort in this stunning four-bedroom, three-and-a-half-bath home offering 3,302 sq. ft. of refined living space. The open layout connects a gourmet kitchen with granite counters to a cozy family room, leading to a screened patio and private pool. Enjoy a relaxing primary suite with an expansive en suite bath and custom closet. Beautiful Brazilian cherry wood floors, crown molding, and high ceilings enhance the elegant ambiance. Monthly rent includes grounds care and pool maintenance for a hassle-free lifestyle.

Experience comfort in this stylish 3-bedroom, 2.5-bath townhouse spanning 1,628 sq ft. Nestled in a gated community, this residence features a convenient laundry area and a one-car garage. Enjoy serene outdoor living on the screened-in lanai and explore beautiful walking paths nearby. The high ceilings and central air add to the home's inviting atmosphere, making it perfect for both relaxation and entertaining in the vibrant Winter Park area.

This stunning 3-bedroom, 2.5-bath townhome features an open-concept design, high ceilings, and stylish finishes throughout. The gourmet kitchen boasts waterfall quartz countertops and stainless steel appliances. A private walled courtyard is perfect for outdoor entertaining, while the spacious primary suite includes a luxurious bath and walk-in closet. Built for modern living with smart-home technology, this immaculately maintained residence offers convenience near vibrant local attractions.

This fully remodeled 4-bedroom, 3-bath home boasts a chic open layout featuring high vaulted ceilings and designer porcelain tile throughout. A gourmet kitchen with Viking appliances and a lavish master suite with dual walk-in closets enhance luxurious living. The backyard is a true sanctuary, perfect for entertaining with a summer kitchen, wood-burning fire pit, and a cozy aluminum cabana. Enjoy the vibrant charm of Winter Park with restaurants, shops, and parks just moments away.

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!

Embrace vibrant Winter Park living in this beautifully updated 5-bedroom, 3-bathroom corner home, offering over 2,200 square feet of stylish space. Features include a bright open floor plan, modern finishes, and a brand-new A/C system. Located just three blocks from Park Avenue, enjoy easy access to dining, shopping, and cultural attractions while basking in the abundance of natural light and extra outdoor space this property provides.

Located just a mile from Park Avenue, this charming 4-bedroom, 2-bath home features a welcoming neighborhood with top-rated schools, perfect for families. Enjoy nearby shops and restaurants, embodying the Winter Park lifestyle. Key amenities include central air and in-unit laundry, providing comfort and convenience for everyday living in this active community.