Houses for Rent in Winter Park, FL

This beautifully updated 3-bedroom, 2-bathroom home offers 1,628 sq. ft. of stylish living space. Featuring luxury vinyl plank flooring and a smart home setup, it’s designed for modern comfort. Enjoy a fenced yard and a garage for convenience. With pet-friendly policies and professional management by Invitation Homes, it’s perfect for those seeking a worry-free lifestyle. Embrace the charm of this inviting single-story residence.

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!

This beautifully maintained 2-bedroom, 2-bath home features a bright sunroom and a flexible bonus room ideal for a home office or guest space. Enjoy a sleek galley kitchen with granite countertops and stainless steel appliances in approximately 1,200 sq. ft. of modern living space. The newly fenced backyard offers a private outdoor oasis, while lawn care and monthly A/C filters are included for hassle-free living. Steps from dining and shopping, this home balances comfort with convenience.

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 stunning 3-bedroom, 2-bath single-family home features a spacious 1,624 sq ft layout with an updated kitchen and hardwood floors. Enjoy the enclosed pool and backyard perfect for relaxation. An attached 2-car garage, in-unit laundry, and stainless steel appliances enhance convenience. Located in a desirable Winter Park subdivision, this vibrant property is available for $2,750/month, with utilities and pool maintenance covered by the lessee. No pets allowed.

This stylish 3-bedroom, 2-bath home features gorgeous fresh paint and easy-to-maintain floors throughout, enhancing its inviting atmosphere. Enjoy the spacious fenced backyard ideal for outdoor fun, complete with a cozy firepit. A second dining room adds versatility, while the chef-ready kitchen boasts stainless steel appliances. Convenient laundry facilities are located in a bonus room, making daily chores a breeze. Perfectly situated near shopping, restaurants, and parks!

This beautifully maintained 2-bedroom, 2.5-bath townhome offers an inviting open layout perfect for entertaining or relaxation. Enjoy cozy meals in the spacious kitchen and the luxury of two master bedrooms, each with en-suite bathrooms. A convenient half bath for guests and an in-unit washer and dryer enhance comfort. Step outside to a private fenced patio. Ideally located in Winter Park, this home provides easy access to shopping, dining, parks, and top-rated schools.

This spacious 2-bedroom, 1.5-bath townhouse features 1,300 sq ft of comfortable living space, complete with a single car garage and a fenced-in backyard. Enjoy the convenience of in-unit laundry and modern appliances including a glass top range and refrigerator with ice maker. Located just minutes from I-4 and Downtown Winter Park, this pet-friendly home combines practicality with style, making it perfect for comfortable living in a vibrant area.

This beautifully renovated 3-bed, 2-bath bungalow offers a cozy yet sophisticated living experience in a sought-after Winter Park neighborhood. Fully furnished with tasteful decor and an attractive kitchen that flows into the family room with a fireplace. Enjoy the large master retreat overlooking a serene backyard, perfect for gatherings. Includes two separate living quarters for guests or privacy, enhancing versatility. Conveniently located near parks and local amenities.

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 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 pet-friendly townhouse features a spacious layout with a large living area, perfect for relaxation and entertainment. The kitchen comes equipped with essential appliances, and two cozy bedrooms ensure comfort. Enjoy vinyl plank flooring in the bedrooms and a full-size washer and dryer in the kitchen. Nestled in a quiet cul-de-sac with a huge yard, this home is ideal for kids to play or for enjoying the serene outdoor space.

WOW! Discover this completely remodeled home featuring exceptional upgrades, including granite countertops and stainless steel appliances in the kitchen. Enjoy the convenience of an indoor laundry room with storage and a large screened patio overlooking a tranquil, fenced backyard. Nestled on a peaceful dead-end street in Winter Park, just off Howell Branch Rd, this property offers a super location for serene living and easy accessibility. Ideal for those seeking comfort and style!

Experience contemporary living in this renovated 2-bedroom, 2.5-bath townhome featuring a stylish kitchen with stainless steel appliances and granite counters. Each bedroom boasts its own private balcony, while the master offers a versatile loft space. Enjoy a private fenced patio with a newly built deck for entertaining, plus the convenience of a covered carport. Just steps away from vibrant shops and restaurants, this home combines comfort and a prime location for a delightful lifestyle.

Embrace stylish living in this renovated 2-bedroom, 2.5-bath townhome featuring a modern kitchen with stainless steel appliances and granite counters. Each bedroom boasts a private balcony, and the versatile loft space above the master offers a perfect nook for work or relaxation. A private, fenced patio with a new deck ensures delightful outdoor gatherings. Ideally situated near Park Avenue's vibrant shops and dining, this home balances comfort and prime location seamlessly.

This stylish 3-bed, 2-bath home is designed for comfort and ease, featuring modern finishes and abundant natural light throughout its 1,909 sq ft. Enjoy a spacious layout with ample storage, and step outside to the inviting yard perfect for gatherings or gardening. Conveniently located in a vibrant neighborhood with access to schools, parks, and dining, this pet-friendly property offers a perfect blend of indoor and outdoor living.

This cozy 3-bedroom, 2-bathroom residence presents a blend of charm and convenience, featuring an open-concept living area filled with natural light. The kitchen boasts granite countertops and full-size appliances, while the primary suite offers ample storage. Enjoy the expansive fenced backyard, perfect for pets and entertaining, complete with a fire pit and covered sections. Located near Winter Park Village and Park Avenue, this home is ideal for anyone seeking a peaceful yet vibrant community.

This beautifully renovated 5-bedroom, 3-bathroom corner home offers over 2,200 sq ft of bright and versatile living space. Enjoy modern finishes, a brand-new air conditioning system, and ample natural light in a serene setting just three blocks from Winter Park's vibrant dining and shopping scene. Perfectly balancing comfort and convenience, this home invites residents to experience the best of Winter Park's charm and outdoor lifestyle.

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!

This charming, updated 2-bedroom home features a large landscaped yard and a fantastic screened back patio, perfect for long weekend lounging. Inside, enjoy modern amenities like an updated kitchen and bathroom, plus a convenient in-unit washer and dryer. With 960 square feet of affordable living space, this Winter Park residence is a must-see!

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.

Experience luxury living in this stunning 3-bedroom, 2.5-bath townhome, boasting 1,682 sq. ft. of stylish upgrades. With 10-foot ceilings, a modern kitchen, and elegant moldings, this residence offers comfort and sophistication. Enjoy the serene screened lanai and generous storage throughout. Located in a beautiful gated community, residents are just minutes from Interstate 4 and the vibrant Park Avenue. Ideal for those seeking a sophisticated yet relaxed Florida lifestyle.

This serene 3-bedroom, 2-bathroom townhouse offers a peaceful cul-de-sac setting, featuring high ceilings and a carpet-free design with laminate wood and tile flooring throughout. The bright primary suite includes sliding glass doors to the backyard, while the updated kitchen and separate dining area enhance the cozy atmosphere. Enjoy the convenience of a one-car garage and proximity to local amenities, making it an ideal choice for comfortable living in Winter Park.

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.

Enjoy comfortable Florida living in this delightful 3-bedroom, 2-bath home featuring over 1,600 sq. ft. of space. The modern kitchen with stainless steel appliances complements two distinct living areas perfect for entertaining. A dedicated laundry room adds convenience, while the fully fenced backyard offers a private oasis for pets and relaxation. Yard maintenance and pest control are included, making this rental a hassle-free choice in the desirable Kenilworth Shores neighborhood.

This stunning 3-bedroom, 2.5-bath townhome features a desirable water view and an upgraded screened porch, perfect for enjoying the outdoors. The open layout of the first floor includes a modern kitchen with stainless steel appliances, leading to a spacious gathering room and patio. The luxurious master suite boasts a walk-in closet and ensuite bath. Additional perks include included high-speed internet, a community pool, and a corner unit for added privacy, all in a prime location near Winter Park amenities.

This stunning 4-bedroom, 2.5-bathroom home features recent updates throughout, including fresh paint, hardwood floors, and granite countertops. Enjoy a cozy family room with a wood-burning fireplace and French doors leading to a beautifully landscaped yard. The master suite boasts a luxurious bathroom with a soaker tub and a spacious second-floor deck. With a charming front porch and convenient laundry room, this home blends modern amenities with a serene outdoor living experience.

Experience comfort and style in this beautifully renovated 4-bedroom, 2-bathroom home featuring elegant woodgrain tile flooring and a spacious kitchen with granite countertops and stainless steel appliances. The inviting living area flows seamlessly for entertaining, while the large, fully fenced backyard offers lush green space and paved areas perfect for outdoor dining and relaxation. Washer and dryer included, making this home both functional and exquisite.

This stunning 4-bedroom, 3.5-bath home offers a seamless open floor plan adorned with elegant finishes and Viking appliances. Enjoy your private paradise featuring an outdoor summer kitchen, fireplace, and K9 turf for pets. The luxurious master suite, versatile upstairs flex space, and a pristine pool complete this exquisite residence. Located in desirable Winter Park, experience fine dining and boutique shopping just moments away in this extraordinary rental home!

This charming 3-bedroom, 3.5-bath townhome spans 1,413 sq ft and features a bright, open kitchen with breakfast bar and fireplace in the living area. Enjoy a private balcony in the primary suite, plus a screened porch for outdoor relaxation. Sandlewood Creek community amenities include a refreshing pool and playground, perfect for family fun. Conveniently located near Park Avenue, I-4, and Downtown Orlando, this pet-friendly home is ready for immediate move-in!

This captivating 4-bedroom, 2-bath home on a corner lot blends contemporary updates with charming Winter Park vibes. Featuring stainless steel appliances, custom tilework, and updated flooring, it creates an inviting atmosphere. Enjoy the expansive deck perfect for relaxation or entertaining. With dual driveways for plenty of parking and easy access to local shopping, dining, and cultural hotspots, this residence embraces comfort and convenience in a vibrant community.

Enjoy this delightful 3-bedroom, 2-bathroom pool home, featuring a cozy living room, family room, and dining area spread over 1,526 sq ft. Located on a lovely corner lot, this pet-friendly residence includes pool service and offers added perks such as a concierge service and credit-boosting benefits. With a 2-car garage and modern amenities, this property provides comfort and convenience, making it an ideal place to call home.

This charming 3-bedroom, 2-bathroom residence features an open floor plan bathed in natural light, perfect for comfortable living and entertaining. The modern kitchen boasts ample cabinet space, and the primary suite offers a private bath and walk-in closet. Enjoy a private backyard ideal for gatherings and barbecues. This pet-friendly property includes a 2-car garage, washer/dryer hookups, and central A/C, providing both comfort and convenience in a desirable location.

This charming 4-bedroom, 2-bath home features a bright open layout with vaulted ceilings and a cozy Great Room, ideal for entertaining. The kitchen, equipped with essential appliances, flows into a casual dining space, while sliding doors lead to a fenced backyard. Retreat to the first-floor primary suite with a walk-in closet, and enjoy the versatility of an upstairs loft. Conveniently located near shops and dining, this pet-friendly residence is perfect for family 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!

Rent a fully furnished bedroom in a clean and comfortable 4-bed, 2-bath home for $700/month plus $175 for all-inclusive utilities and services. Enjoy a drama-free environment with amenities like internet, cable, maid service, and lawn care. A shared bathroom adds convenience, and off-street parking is available. Ideal for those seeking a friendly atmosphere close to everything. Move-in requires a valid ID and proof of employment.

Nestled in the desirable Orwin Manor neighborhood, this 2-bedroom, 1-bathroom home features 1,027 sq ft of living space blending original character and modern upgrades. Enjoy a cozy living room, bright dinette, and spacious bedrooms with ample storage. Recent enhancements include a new galvanized metal roof, stainless appliances, and low-maintenance laminate flooring. The large fenced backyard provides a brick patio and space for outdoor activities. Conveniently located near restaurants, shopping, and parks.

This lovely 2-bedroom, 2.5-bath home offers a light-filled kitchen with newer appliances and an inviting eat-in area. Enjoy spacious living and dining areas featuring a corner fireplace and oversized sliders to the back patio. The classic stairway leads to two en-suite bedrooms, with the convenience of an upstairs laundry closet. Fresh paint and newer laminate flooring enhance the vibrant feel. A short stroll takes you to the pool, perfect for relaxation and enjoyment!

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.

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 charming 3-bedroom, 2-bath residence boasts 2,102 sq. ft. of comfortable living space with a cozy wood-burning fireplace and terrazzo floors. Enjoy separate living and dining areas, plus a large den that opens to a patio overlooking the expansive yard. Conveniently located near top schools and attractions, with deeded access to Lake Berry. The home also features an indoor laundry room and a detached garage with workshop space. Perfect for making lasting memories!

This impressive 2-bedroom, 2.5-bath condo features stylish upgrades and is tiled throughout for easy maintenance. Enjoy an open living and dining area, an eat-in kitchen with granite countertops, and a convenient laundry closet. A private patio adds to the charm, making this unit an ideal retreat. With ample space at 1,031 sq. ft., it perfectly combines comfort and modern living in a desirable community.

Available for immediate move-in, this cute 3-bedroom, 2-bath home offers 1,176 sq ft of cozy living space. Conveniently located near shopping and dining, it's perfect for those seeking a balance of comfort and accessibility. Enjoy a pet-friendly environment and professionally managed services, making this home an inviting place to settle down.

This inviting 3-bedroom, 2-bath single-family home features a large dining and living area that flows into a well-appointed kitchen with ample cabinetry and appliances. The primary bedroom offers private bath access, while the additional bedrooms are generously sized. Enjoy the convenience of a one-car garage and a spacious backyard, perfect for pets and outdoor living. Pet-friendly with specific breed and weight restrictions. Ideal for family living!

This rare mid-century lakefront home offers over 4,100 sq. ft. of living space with 4 bedrooms and 3.5 bathrooms, including a private guest suite. Enjoy breathtaking views of Lake Maitland from the screened porch and sunlit living spaces with rich wood accents and stone fireplaces. The property features a private boat dock, a 3-car garage, and an office, making it perfect for peaceful, upscale living in Winter Park. Relax in style and embrace waterfront tranquility!

Enjoy carefree living in this fantastic 3-bed, 2-bath home featuring a saltwater pool and lawn care included. The bright, open layout is enhanced by wood-look ceramic tile and French doors leading to a spacious screened porch. A cozy kitchen with a breakfast nook and ample cabinet space makes cooking a delight. With a large fenced yard surrounded by a beautiful paver patio, this property is perfect for relaxation and entertaining.

This charming single-family home offers 4 bedrooms and 2 bathrooms, including an in-law suite, all set on a generous 0.27-acre lot. Featuring recent renovations with a new roof and modern appliances, this property is fully fenced for added privacy. Ample parking space is available for boats or RVs, making it ideal for outdoor enthusiasts. Enjoy the vibrant Florida lifestyle with friends, family, and pets in your expansive backyard, all without the restrictions of an HOA.

Experience vibrant living in this stylish 3-bed, 2-bath condo featuring an open floor plan, dark wood floors, and stainless steel appliances. Enjoy two balconies and a two-car garage. Located just minutes from Rollins College and Park Avenue's shopping and dining, it’s perfect for students and faculty alike. A bright, modern space that offers ample storage and a welcoming atmosphere. Don't miss out on this fantastic opportunity!

This spacious 3-bedroom, 2.5-bath townhome-style condo features elegant granite countertops and a serene fenced patio overlooking conservation views. Enjoy durable tile flooring downstairs and stylish luxury vinyl plank upstairs. Perfect for relaxing or entertaining, this charming space offers comfortable living with modern finishes in a peaceful setting. Move-in ready from August 15, 2025, and dog-friendly for pet lovers.