Houses for Rent in Winter Park, FL

This delightful 3-bedroom, 2-bathroom bungalow combines classic charm with modern comforts. Features include a beautifully updated kitchen with stainless steel appliances and granite countertops, and an inviting living area with elegant wood flooring. An enclosed sunroom offers a perfect spot to enjoy sunny days, while the manicured, fenced yard provides privacy. With a one-car garage and convenient interior laundry, this property is a perfect blend of style and functionality.

This inviting 3-bedroom, 2.5-bath home features a modern open layout with vinyl plank flooring, quartz countertops, and stainless steel appliances. Enjoy the comforts of a smart home with a programmable thermostat and central A/C. The spacious yard offers plenty of room for outdoor activities, ideal for pets. With an attached garage and ample storage, convenience meets style in this well-maintained, pet-friendly residence. Perfect for modern living in a desirable neighborhood!

This inviting 3-bedroom, 2-bathroom home boasts a smart layout with features like vaulted ceilings and granite countertops. Enjoy the open floor plan and a screened porch that leads to a large fenced yard, perfect for pets. With central air and a convenient attached garage, this pet-friendly residence in a desirable neighborhood combines comfort and modern living seamlessly. Plus, experience the ease of the Progress Smart Home technology for added convenience.

Embrace luxury in this stunning 7,000 SF residence featuring 8 bedrooms and 6 baths. The open-concept design showcases beautiful hardwood floors and a chef-inspired kitchen with quartz countertops and double ovens. Two expansive primary suites offer serene retreats. The versatile lower level includes an in-law suite, gym, and game room. Enjoy seamless indoor-outdoor living with a covered patio and pool deck, all in a peaceful cul-de-sac, close to Park Avenue and excellent schools.

Nestled on a charming cobble stone road, this beautifully renovated 3-bedroom, 2-bathroom home boasts an upscale chef's kitchen, stone and wood flooring, and a stylish electric fireplace. Enjoy separate living areas and a large custom garage. Outdoors, relax in professionally designed gardens and a saltwater pool surrounded by elegant stone flooring. Ideal for dog lovers, this location is minutes from shopping, dining, and outdoor activities, making it a perfect retreat in historic Winter Park.

Enjoy a blend of style and convenience in this pet-friendly 4-bedroom, 2-bath home featuring hardwood floors and a functional kitchen with stainless steel appliances and granite countertops. The open floorplan is perfect for gatherings, while the private backyard invites outdoor fun. Benefit from included Smart Home technology and professional property management, making life easier in this spacious 1,964 sq. ft. residence.

This charming 3-bedroom, 2-bathroom property features 1,553 sq. ft. of comfortable living space. Enjoy abundant storage with large closets and a refreshing pool for sunny days. The outdoor patio offers a perfect spot to unwind. Convenience is enhanced with laundry hookups, making this home a delightful retreat. Pet-friendly and ready for new memories!

This pet-friendly 3-bedroom, 2-bathroom home offers a convenient layout featuring a garage and luxurious vinyl plank flooring. Enjoy the benefits of a Smart Home equipped with a video doorbell and newly added stainless steel appliances. The home is professionally managed and comes with essential amenities like high-speed internet, air filter delivery, and utility services for a hassle-free leasing experience. With a total of 1,030 square feet, it's ideal for comfortable living!

Embrace a worry-free lifestyle in this pet-friendly 3-bedroom, 2-bath home featuring quality amenities. The spacious 1,405 sq ft layout boasts luxury vinyl plank flooring and a finished kitchen with granite countertops and stainless steel appliances. Enjoy the benefits of Smart Home technology and professional maintenance. A lovely backyard provides ample space for relaxation and outdoor activities. Experience the comfort and convenience of modern living in this beautifully equipped home.

This beautifully maintained 3-bedroom, 2-bath home offers an inviting open split-bedroom floor plan and a modern kitchen with breakfast bar. Enjoy the large screened patio overlooking a private, fenced backyard—ideal for relaxation and entertaining. Recent upgrades include brand-new tile flooring, a renovated primary suite with dual marble vanities, and no HOA. Conveniently located near top-rated schools and easy access to SR-417, this move-in ready home is perfect for serene living in Winter Park.

Enjoy affordable living in this updated 2-bedroom, 1-bath home featuring a large landscaped yard on a peaceful dead-end street. Relax on the spacious screened back patio, ideal for long weekends. The modern kitchen and bathroom add to the appeal, and in-unit laundry provides convenience. At 960 sq ft, this cozy residence is ready for immediate occupancy and won't last long!

Experience the charm of this lovely 3-bedroom, 2-bath home with a bright open layout, featuring a spacious kitchen and a cozy living area filled with natural light. The private primary suite offers a perfect retreat, while the lovely backyard is ideal for enjoying morning coffee or weekend gatherings. Conveniently located near shopping, dining, parks, and top-rated schools, this home blends comfort, style, and unbeatable convenience.

This beautifully updated 3-bedroom, 3-bathroom residence combines classic charm with modern comforts. Gleaming hardwood floors flow through the light-filled layout, leading to a cozy, window-lined kitchen. The serene primary suite features high ceilings and outdoor views. Enjoy the fenced backyard and private brick patio for relaxation. Conveniently located near parks, schools, and vibrant shopping on Park Avenue, this home offers the perfect blend of tranquility and accessibility.

Enjoy contemporary living in this spacious 4-bedroom, 2-bathroom home, featuring 1,925 sq. ft. of stylish space. Highlights include a lovely eat-in kitchen, a grand primary suite with vaulted ceilings and walk-in closet, and a fenced yard perfect for pets. Located near shops, restaurants, and schools, this pet-friendly residence combines comfort and convenience for an ideal lifestyle.

This inviting 3-bedroom, 2-bathroom home features an open floor plan that welcomes natural light, ideal for relaxation and entertaining. Enjoy a gated oversized backyard, perfect for outdoor activities, and exclusive access to Lake Killarney for paddle boarding or kayaking. Located just minutes from top dining and shopping spots, this dog-friendly residence includes central air, hardwood floors, and utilities like gas, internet, and water are included in the rent.

This 3-bedroom, 2.5-bathroom home offers a practical open layout with laminate and tile flooring throughout. Enjoy a first-floor master suite with private bath and two additional bedrooms upstairs. The eat-in kitchen features glass doors leading to a fenced backyard. A one-car garage adds convenience, while community amenities include a refreshing pool, perfect for relaxing on warm days. Experience comfort and accessibility in a delightful setting!

This stunning 4-bedroom, 4-bathroom residence offers 3,654 sq ft of living space on a lush half-acre corner lot. The family room features soaring windows and a cozy fireplace, while French doors lead to a serene master suite complete with a private courtyard. Enjoy the Florida sunshine by the inviting pool and hot tub, surrounded by beautiful landscaping and privacy hedges. Ideal for entertaining, with lawn care, pest control, and pool maintenance included for a hassle-free lifestyle.

This beautifully renovated 3-bedroom, 2-bath pool home features over 1,600 sq ft of entertainment space, two living rooms, and a spacious kitchen with quartz countertops. Enjoy a cozy wood-burning fireplace, large fenced backyard, and a screened-in porch perfect for gatherings. The primary suite boasts a walk-in closet and updated bath, while the convenience of no HOA adds to its charm. Every corner reflects style and comfort in this Winter Park retreat!

Enjoy a delightful blend of comfort and style in this beautiful 2-bedroom, 2-bathroom home featuring a spacious family room with a wood-burning fireplace and a large patio for outdoor relaxation. The downstairs bedroom boasts a stylish bathroom with a freestanding tub, while the upstairs offers a loft area. With new paint, plush carpet, and modern updates, this pet-friendly residence ensures convenient living near Park Avenue and outstanding schools. Lawn care is included!

Embrace comfort in this pet-friendly 3-bedroom, 2-bathroom home featuring an open floor plan with warm tile and wood floors. Each oversized bedroom includes walk-in closets, while the modern kitchen boasts stainless steel appliances and wood cabinets. Enjoy outdoor entertaining on the screened patio overlooking a spacious backyard. Convenience meets relaxation, all just moments from shopping and dining. 1334 sq ft of inviting living space awaits!

Embrace comfort in this pet-friendly, 3-bed, 2-bath home featuring a functional layout and modern finishes. The open and airy design is filled with natural light, while ample storage in the kitchen and closets makes living easy. Enjoy outdoor gatherings or gardening in the spacious yard. Located in a vibrant neighborhood with access to schools, parks, and dining, it's a perfect blend of convenience and homey charm. Experience hassle-free living with tech-enabled maintenance services.

This stunning 4-bedroom, 3-bath home spans 2,479 sq ft in a secure gated community. The bright, open kitchen offers ample storage, while the large screened-in patio is perfect for entertaining. With a loft upstairs and a 2-car garage, there's room for everything. Lawn care is included, making this home a hassle-free haven!

Embrace the convenience of this charming studio townhome with 597 sqft of bright, open living space. Situated in Winter Park, enjoy easy access to shops, dining, and parks. The kitchen offers ample counter space, perfect for meal prep. Ideal for singles or couples, this pet-friendly townhome is nestled in a lively community, providing both comfort and accessibility.

This spacious 3-bedroom, 2.5-bath townhome features an open floor plan and high ceilings, flooded with natural light. The modern kitchen is a chef’s delight, boasting stainless steel appliances, a large island, and a walk-in pantry. The primary suite offers a luxurious upgraded closet and ensuite bath. Enjoy outdoor living on the lanai and a two-car garage for convenience. Located in the gated Hawks Crest community, residents benefit from a pool, playground, and fitness trail, all near Winter Park's vibrant amenities.

This inviting 3-bedroom, 2-bath home features a generous living space totaling 2,150 sq ft. Highlights include a spacious open kitchen with stainless steel appliances, a cozy family room, and a large utility room for extra storage. Enjoy outdoor living on the covered back patio overlooking a huge fenced yard, perfect for pets or gatherings. Conveniently located near Advent Health, restaurants, and entertainment, this property offers both comfort and accessibility.

This spacious 2-bedroom, 2-bathroom residence features an inviting layout filled with natural light. Enjoy community amenities such as a sparkling pool, fitness center, and tennis courts. Convenient in-unit laundry and pet-friendly options enhance the charm of this home. Water, sewer, and lawn care are included, providing hassle-free living in a vibrant community. Perfect for an active lifestyle or for simply relaxing in the Florida sun!

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 impressive 5-bedroom, 4-bathroom residence boasts over 3,900 sqft of elegant living space, ideal for entertaining. Featuring high vaulted ceilings, beautiful hardwood floors, and a spacious open floor plan, the home includes a separate pool home or in-law suite with its own bath and kitchenette. Enjoy the large yard, oversized pool, and a private master retreat with a spa-like bathroom. Conveniently located near Park Avenue's dining and boutique shopping, this home is a rare find!

This stunning 3-bedroom, 2-bath home, completely rebuilt in 2019, combines modern design with refined comfort. The spacious open floor plan features soaring ceilings and a chef’s kitchen with gas appliances and quartz counters. The luxurious primary suite offers a spa-like bath and walk-in closets, while the third bedroom is perfect for a home office. Situated near Park Avenue and boasting elegant finishes, this residence embodies the essence of luxury living in Winter Park.

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 well-maintained 3-bedroom, 2-bath townhouse boasts updated bathrooms and a cozy dining area alongside a kitchen with ceramic tile. An enclosed atrium creates an ideal workspace, complemented by a fully fenced private backyard perfect for outdoor enjoyment. The community features two large pools and a tennis court, while being conveniently located near shopping centers, fitness facilities, and major highways. A must-see residence for comfortable living!

This brand new Springdale II townhome offers an inviting layout with 3 bedrooms and 2.5 baths across 1,782 sq ft. Stylish finishes include white cabinetry, quartz countertops, and 18" ceramic tile. Enjoy a spacious covered lanai, gated entrance, and community pool. With high-speed internet and Whirlpool appliances included, this home balances modern comfort and convenience in a prime location just minutes from downtown Winter Park.

This beautifully designed 3-bedroom, 2-bathroom home boasts 1,371 square feet of elegance and comfort. Featuring an inviting open layout that maximizes natural light, every detail reflects quality craftsmanship. Enjoy a fully fenced backyard and the convenience of top-rated schools and local amenities nearby. Perfect for both entertaining and relaxing, this welcoming retreat presents an ideal balance of functionality and charm.

Experience the charm of this remodeled 2-bedroom, 1-bath home featuring an open living and dining area, a modern kitchen with granite counters and stainless appliances, and sleek terrazzo floors throughout. Enjoy a screened patio with storage, a generously sized master bedroom, and a fully fenced yard. Deeded access to Lake Killarny offers endless fun with water activities. Conveniently located near parks, highways, and vibrant downtown Orlando.

This beautifully maintained 3-bedroom, 3-bathroom home spans 1,747 sq. ft. and features a bright, open layout with a welcoming living area and functional kitchen. Each bedroom offers its own bath for added privacy. The fully fenced backyard includes a sparkling private pool, perfect for year-round enjoyment. An attached 2½-car garage and ample driveway parking enhance convenience. Located in a prime neighborhood close to parks and amenities, this pet-friendly home includes lawncare and pool service in the rent.

This lovely 3-bedroom, 2-bath house features hardwood floors and a newly renovated master bathroom with a walk-in shower. Enjoy a spacious master suite, good-sized additional bedrooms, and a convenient laundry room with washer and dryer included. The private patio offers a perfect outdoor retreat, and the single-car garage adds practicality. Located minutes from local attractions, this pet-friendly home combines comfort and convenience in the heart of Winter Park.

This delightful 4-bedroom, 1.5-bath home offers a bright, open layout with tile and hardwood-style flooring throughout, ensuring no carpet anywhere. The well-equipped kitchen features modern appliances and ample storage. Enjoy the convenience of an in-unit laundry closet. Outside, a large fenced backyard awaits for relaxation or entertaining. Positioned on a quiet street, it’s just minutes from downtown Winter Park and all local amenities, making it an ideal place for families.

This delightful 2-bedroom, 2.5-bath townhouse features an open living and dining area with laminate wood floors and a cozy nook. Enjoy a private patio perfect for grilling, plus an in-unit washer and dryer. The upstairs boasts two spacious bedrooms, each with en-suite baths and new vanities. Located steps from the community pool and surrounded by top schools, shopping, and dining, this home offers comfort and convenience in a peaceful neighborhood.

This stylish 2-bedroom, 2.5-bath townhouse features an oversized owner's suite with a walk-in closet and indulgent jetted tub. A culinary enthusiast's dream kitchen boasts granite countertops, stainless appliances, and a gas range. Enjoy the spacious layout with high ceilings and the bonus room/den. Step outside to a screened patio overlooking a beautifully landscaped new turf backyard. Conveniently located near shopping, dining, and top local attractions for a vibrant lifestyle.

Embrace Florida living in this stunning 4-bedroom, 3-bath house featuring 2,400 sq ft of inviting space. An open floor plan flows seamlessly to a resort-style backyard with a sparkling pool, perfect for entertaining. The modern kitchen boasts stainless steel appliances and granite countertops, while the large master suite includes walk-in closets. Located in a sought-after Winter Park neighborhood, this residence is close to top schools, parks, shopping, and dining.

This beautifully renovated 3-bedroom, 2-bathroom home offers a functional layout designed for modern living. Enjoy a stylish kitchen featuring stainless steel appliances and granite countertops. The master bedroom provides easy access to a spacious fenced backyard, perfect for outdoor gatherings. A large deck extends your living space, making it ideal for entertaining. With a new water heater and updated A/C, this move-in-ready property awaits its new owner!

This charming 3-bedroom, 2-bathroom single-story home features a smart split-bedroom layout, perfect for privacy and comfort. Enjoy the spacious open-concept living and dining areas leading to a private backyard, ideal for relaxing or entertaining under the Florida sun. Conveniently located near parks, shopping, and schools, this rental offers a perfect blend of comfort and accessibility. Plus, weekly pool maintenance is included to enhance your outdoor enjoyment!

This beautifully remodeled home features 6 bedrooms and 3 bathrooms, providing ample space for family or guests. Enjoy a large, treed backyard perfect for outdoor activities. Conveniently located near Winter Park Village and a variety of local attractions, this property combines comfort with a prime location for beach outings and city explorations. Pet-friendly for added convenience!

This stylish 4-bedroom, 3-bath residence boasts bright, open living spaces and a large kitchen with wood cabinetry and wine fridge. French doors open to a courtyard and private pool, creating an ideal entertaining space. The primary suite features direct pool access and a modern ensuite bath. Additional highlights include a detached 2-car garage, fresh interior/exterior paint, and a spacious corner lot in a prime location near Phelps Park and Park Avenue dining.

A beautifully renovated single-family home offering 2,267 sq ft of elegant living space. Featuring an open layout, bamboo flooring, and a kitchen with quartz countertops and stainless steel appliances. The oversized master suite includes a sitting area, walk-in closet, and luxurious en-suite. A private, fully fenced backyard provides ample outdoor space. Conveniently located near Park Avenue, this home perfectly blends upscale living with modern amenities in Winter Park.