Winter Park Apartments for Rent - 80 rentals

Remarks: Live in the heart of Winter Park, just steps from the city’s most loved restaurants, cafés, yoga studios, and boutique shops. This beautifully renovated unit offers the perfect blend of walkability, comfort, and style. Zoned for top-rated Winter Park schools and within walking distance to a renowned private school, the location alone makes this an exceptional find. Inside, the home features a double-master layout, ideal for roommates, families, or anyone wanting extra space and privacy. Enjoy the convenience of in-unit laundry and the peace of mind that comes with a fully renovated, move-in-ready interior. With no carpet anywhere, the home is easy to maintain—especially if you have pets. Modern finishes, clean lines, and thoughtful updates make this a standout property in one of Central Florida’s most desirable neighborhoods. Schedule your appointment today—this Winter Park gem won’t last.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Farzana Zalil (407-617-3258)

Remarks: Available for lease in the desirable Autumn Glen community of Winter Park. This spacious and well-maintained 4-bedroom, 2-bathroom single-family home offers comfort, space, and serenity in a peaceful neighborhood setting. Thoughtfully landscaped with lush greenery and tranquil water views, the home features an oversized kitchen with stainless steel appliances, ample storage, and a pass-through opening to the main living area. Enjoy multiple living and entertaining spaces including a formal dining room, a family room, and a cozy living room with a wood-burning fireplace. The primary suite is oversized with a walk-in closet and a private ensuite bath featuring double sinks, a garden tub, and separate shower. Additional features include recessed lighting throughout, carpeted bedrooms, a laundry room with utility sink, and a breakfast nook. Step into your own private oasis with a spacious enclosed patio that’s perfect for year-round entertaining. An expansive in-ground hot tub with powerful Jacuzzi- type jets, comfortably seating up to 10 guests. Whether you’re hosting a summer soirée or enjoying a quiet evening under the stars, the optional heat setting makes it the ideal retreat in any season." The side-entry garage and whole-house water filtration system add everyday convenience. Community amenities include two tennis courts, a tot lot, and a scenic walking path around the pond—ideal for active and leisurely lifestyles alike. With easy access to I-4, 408, and 417—and just 15 minutes to Downtown Winter Park and the iconic Park Avenue—you’re never far from top-tier dining, shopping, and entertainment. Don’t miss the opportunity to lease this gem in one of Central Florida’s most desirable areas. Schedule your private tour today!

Listing is courtesy of: METRO CITY REALTY (407-237-3331)

Listing Agent: Beatrice Miranda (407-592-4448)

Remarks: This beautiful corner-unit townhouse offers comfort, space, and convenience in a highly desirable location. This home features 3 bedrooms and 2.5 bathrooms, providing plenty of space for families and professionals. The kitchen flows seamlessly into the living, dining áreas and private patio offering a practical design for everyday living. All bedrooms are located upstairs for added privacy, including a comfortable primary suite with its own private bathroom.Conveniently situated near shopping, dining, schools, colleges and roadways, this property offers both comfort and accessibility to everything you need while still providing a peaceful residential setting.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Nelly Kilzi De Khabaze (786-925-3470)

Remarks: Enjoy comfortable living in this well-maintained condo in a highly desirable Winter Park location. The home offers 2 spacious bedrooms and 2 full bathrooms, making it a great fit for families, professionals, or roommates. The bright open living and dining area creates a welcoming space for relaxing or entertaining. The kitchen includes all appliances, plus a washer and dryer for added convenience. Water is included in the rent, adding extra value. Both bedrooms offer generous space, natural light, and ample closet storage. The thoughtful layout provides privacy between the bedrooms, which is ideal for remote work or shared living. Located near Full Sail University, UCF, major highways, shopping, and everyday conveniences, the condo also offers easy access to Downtown Orlando. Residents can enjoy a community pool and fitness center in a quiet, private community. This property combines comfort, convenience, and a great location. It is an excellent rental opportunity in Winter Park.

Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)

Listing Agent: Robert Arnold, Jr (407-389-7318)

Remarks: Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard that may become your favorite spot to watch the sunset or skip your morning coffee. The kitchen comes fully equipped with microwave, dishwasher, range/oven, and refrigerator. Good size closets provide lots of storage and a 1 car garage is perfect for big boy toys or an expensive auto. The home is conveniently located near top rated schools... Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High. Don't miss out, act now. All measurements are estimated

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Bernardo Reynoso (561-702-4559)

Remarks: Beautiful and very spacious 3BR/2.5BA with 2 car garage, large upstairs balcony, fenced patio, New wood flooring throughout the unit, all appliances including side by side refrigerator and full size washer and dryer. This property is centrally located in winter park FL,walking distance to shopping, restaurants, bars, coffee shops, Publix Supermarket, short driving distance to downtown Orlando and Advant Health Orlando hospital and close proximity to Park Ave Won't last long , please call to schedule your appointment today.

Listing is courtesy of: HPL REALTY INVESTMENTS (407-601-6057)

Listing Agent: Moshe Sheffi (321-945-2367)

Remarks: Fantastic end corner unit with Seminole County Winter Park address. Gated community, 3/2.5 - 2 story townhome with open floor plan. Very convenient location just off Semoran Blvd, with Walmart super center, Publix and abundant of shopping and dining facilities nearby.

Listing is courtesy of: HONEST REAL ESTATE COMPANY (407-417-1314)

Listing Agent: Kevin Song (407-234-8430)

Remarks: Beautifully renovated 3 bedroom, 2 bath pool home in one of Winter Park's most desirable neighborhoods. Designed with an open floor plan, this home features wood flooring throughout the main living areas, crown molding, and an incredible chef's kitchen with Quartz countertops, a large breakfast bar, custom cabinetry, floating wood shelves, gas range, stainless steel appliances, and abundant storage. The spacious Florida room overlooks a private backyard complete with a sparkling pool, expansive deck, covered seating area, mature landscaping, and a fully fenced yard. Mango and lime trees, landscape lighting, and a powered storage shed with workbench make the outdoor space just as enjoyable as the inside. Additional features include hurricane impact windows, plantation shutters, updated lighting and ceiling fans, a Nest thermostat, surround sound, and a circular paver driveway. Ideally located just minutes from Park Avenue, Rollins College, the Winter Park Racquet Club, Winter Park Golf Club, Phelps Park, and the YMCA, with easy access to top rated schools, dining, shopping, and everything charming about Winter Park.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jennifer King (407-595-3272)

Remarks: Beautiful pool home for rent in Winter Park located in the established Eastbrook community with NO HOA. This home offers 3 bedrooms plus a versatile bonus room, 2 bathrooms, approximately 1,770 sq ft of living space, a 2-car garage, extended driveway, and a private screened pool with fully fenced backyard. Inside, you’ll find a bright and functional layout with comfortable living and dining areas, updated kitchen with granite countertops and modern cabinetry, plus updated bathrooms with clean finishes. The bonus room offers flexibility for a home office, gym, playroom, or additional living space. Major updates include roof replaced in 2018, fully paid solar panels installed in 2020, water heater 2019, and A/C replaced in 2013. Conveniently located near Park Avenue, Rollins College, Full Sail University, University of Central Florida, shopping, dining, and major highways. First month’s rent, last month’s rent, and security deposit required prior to move in. Background and credit check required through RentSpree at tenant expense ($50 x adult over 18 years old). Preferred credit score 550+. No prior evictions. Pet restrictions apply.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: Don't miss this opportunity! Beautiful apartment located in Winter Park, one of the most convenient and desirable areas in the Orlando region. Conveniently located near Full Sail University, Rollins College, shopping centers, restaurants, entertainment, and major highways. Enjoy the comfort of a well-maintained community featuring a swimming pool and common areas for relaxation. This apartment offers an excellent combination of location, comfort, and quality of life. Pets are welcome, subject to size restrictions and approval. Properties in this area rent quickly, so schedule your showing before it's gone!

Listing is courtesy of: HOME PRIME REALTY LLC (813-497-4441)

Listing Agent: David Carballo (813-767-4897)

Remarks: This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the living area, creating an open and airy feel. Tile flooring graces the foyer, formal dining room, and kitchen, while the eat-in kitchen includes a bright breakfast nook enveloped by bay windows for abundant natural light. The private backyard oasis features a large screened porch, mature shade trees for natural privacy, an automatic irrigation system, and beautifully established landscaping that minimizes maintenance. Residents enjoy an exceptional lifestyle without leaving the neighborhood. Relax by the community pool, take leisurely strolls through the park, or visit the nearby playground. The community also provides direct access to the pristine waters of Lake Burkett (approximately 75 acres) and the connected Lake Martha chain (approximately 30 acres), ideal for boating, fishing, and recreation. Trinity Bay is conveniently located adjacent to Trinity Preparatory School, the location is zoned for highly rated Seminole County public schools and offers easy access to major roadways, including SR 417, as well as proximity to the University of Central Florida (UCF), Full Sail University, premier shopping, and fine dining. This well-maintained residence offers a rare combination of character, comfort, and community amenities in a prime Winter Park location.

Listing is courtesy of: MNT INTERNATIONAL (844-668-7589)

Listing Agent: Mostafa Boulhanna (407-536-1484)

Remarks: Cute 2 bedroom, 2 bathroom, freshly painted condo in Winter Park. Amenities include a swimming pool, fitness center, clubhouse/conference room, well-maintained grounds, and ample parking. This property offers easy access to Full Sail University, University of Central Florida, Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Shopping, dining, entertainment, parks and grocery stores are all nearby. Major highways SR-417 and SR-408 are easily accessible. There is a washer and dryer in the condo and new carpet throughout bedrooms and main living areas. There is a screened in back patio with storage closet.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Meg Dolan (321-948-0701)

Remarks: Fabulous rental opportunity in the sought-after Winter Park School District. This 4-bedroom, 2.5-bath, 2219-square-foot home also boasts glorious lake views from the massive 1,000-square-foot Florida room, ideal for entertaining and enjoying the Florida lifestyle on an expansive ½ acre lot. Ready for move-in, the home is full of natural light pouring in and shining onto the wood flooring throughout the home. There are opportunities to create a multitude of spaces that serve your needs for a home office, craft room, or playroom. The updated open kitchen offers views of the family room, Florida room, and the dining room with solid maple cabinets, granite counters,china-front cabinetry, custom tile backsplash, and stainless steel appliances. The kitchen also has programmable “smart lights”. The master bedroom offers ample storage space, a walk-in shower, and a walk-in closet. There are three additional bedrooms and an additional bathroom. There is a large storage shed and well/pump system for irrigation and a massive backyard for a variety of activities. The 8-zone irrigation system is run by a ground well and pump system, which will equate to savings on the water bill. Start enjoying life in the quiet community known as Arrowhead Cove with Winter Park Schools, as well as charter and private schools in the area, including Trinity Prep, Full Sail, and UCF.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Julia Magnani (305-610-1876)

Remarks: Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms with brand-new carpeting and easy access to the spacious backyard, offering plenty of room to relax or entertain outdoors.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jordan Heidrich (407-223-3495)

Remarks: Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storage and an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped grounds. Perfectly situated near Park Avenue, Rollins College, I-4, and Downtown Orlando, this home offers the best of Winter Park living.

Listing is courtesy of: RE/MAX VANTAGE (407-745-4980)

Listing Agent: Rustina Gibson (407-808-7127)

Remarks: Virtually Staged. Brand-New Luxury Home for Lease in Winter Park's Most Walkable Neighborhood Live in one of Central Florida's most desirable communities without compromising on space, style, or location. This brand-new, never-lived-in home by Nautilus Homes offers 4 bedrooms, 4 full bathrooms, a private office, and over 3,000 square feet of refined living, all in the heart of Winter Park, steps from everything that makes this city special. The moment you walk in, the difference is obvious. Crème Brûlée wide-plank wood flooring flows throughout, setting a warm, elevated tone that carries into every room. The open-concept living area is anchored by a built-in wine and coffee bar, perfect for morning routines and evening wind-downs alike. The chef's kitchen is the heart of the home, featuring custom ceiling-height cabinetry, a handcrafted wood range hood, and high-end finishes designed for serious cooking and effortless entertaining. Just off the kitchen, a beautifully appointed butler's pantry finished in statement Kit-Kat tile connects seamlessly to the formal dining room, a layout that makes hosting feel natural, not stressful. The floor plan gives everyone their own space. A private office and a full en-suite bedroom on the main level offer flexibility for working from home, hosting guests, or accommodating multigenerational living. Upstairs, three additional bedroom suites each feature walk-in closets and their own beautifully finished bathrooms, no sharing, no compromising. The primary suite is in a category of its own. A spa-inspired bathroom with a freestanding soaking tub, an oversized 9-foot walk-in shower with dual sprayers, a frameless glass enclosure, and sleek linear drainage make every morning feel intentional. The walk-in closet is generously sized and thoughtfully designed. Additional features include a 2-car attached garage, central air and heating, an irrigation system, wood flooring throughout, and electric dryer hookup, everything you'd expect in a home at this level, with nothing left out. Outside, you're minutes from Park Avenue, Winter Park Village, East End Market, and a tight-knit community known for tree-lined streets, top-rated schools, and a pace of life that feels a world away from the rest of Orlando. This is the rare rental that actually lives up to the photos. Reach out today, homes like this don't stay available long.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Christina Fata (407-917-8946)

Remarks: ***New residents will receive three (3) complimentary months of the Resident Benefits Package (RBP). Take advantage of this exclusive offer and enjoy added benefits at no cost for your first three months!*** This property will not last long! Schedule a showing today! Winter Park Two Story 2/2.5 Townhome located in the Private - Gated Community of Vistas at Lake Howell. All Stainless Steel Kitchen Appliances Included (Dishwasher, Range, Refrigerator, and Microwave). Living & Dining Room Combo. All bedrooms are located on the second floor. Primary Bedroom has custom closet design and ensuite bathroom. Ceiling Fans in Many Rooms. Half Bathroom Downstairs. Screened in Private Back Patio/Porch. Attached One Car Garage. Convenient to SR-436 & I-4. Laundry Room is upstairs near bedrooms. Washer and Dryer Convenience Only. Separate HOA Application & Approval Required. Schedule a showing today! All our residents are enrolled in our Resident Benefits Package for $55.00 per month, charged as additional rent. This package includes Pest Assurance powered by Pest Share, access to an online resident portal, and availability of a dedicated 24/7 maintenance portal. Additionally, it offers monthly reporting of rental payments to Experian RentBureau, bi-monthly home delivery of replacement HVAC filters, and the use of resident-completed inspection technology. Residents are entitled to one late fee waiver during their residency and have access to concierge utility services

Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC (407-557-3164)

Listing Agent: Elizabeth Santiago Moyet (321-231-2105)

Remarks: FULLY FURNISHED and move in ready elegant home.A rare find in Winter Park. 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a picturesque street, the property boasts inviting curb appeal with mature landscaping and a welcoming entrance. Inside, thoughtfully designed living spaces feature abundant natural light, an open and functional layout, and seamless flow ideal for both everyday living and entertaining. The private backyard provides a serene retreat with ample space for relaxing or hosting gatherings. Step outside to your fully fenced backyard, complete with a private hot tub and spacious patio, ideal for relaxing evenings or casual get togethers. With no pool to maintain, you'll enjoy low maintenance outdoor living in a peaceful setting.1 time cleaning per month and wifi included. Schedule your showing today! Located near top-rated schools, parks, and cultural attractions, 2075 Jewel Avenue presents a rare opportunity to enjoy refined living in one of Florida’s most prestigious neighborhoods. Mid term lease available.

Listing is courtesy of: URBANISTA BROKERS (407-619-7272)

Listing Agent: Paul Jimenez (407-276-3516)

Remarks: Located in the highly sought-after Winter Park High School district, this beautifully maintained 3-bedroom, 2-bath home in Laurel Springs provides comfort, space, and convenience. The bright and inviting living area features tile and an open, welcoming feel. Enjoy year-round indoor-outdoor living in the expansive 400+ sq. feet. enclosed patio overlooking a fully fenced backyard—perfect for entertaining, relaxing, or family gatherings. Ideally situated with easy access to shopping, dining, parks, and major highways. Move-in ready!!!!

Listing is courtesy of: JOY ESTATE ENTERPRISE INC (321-754-9131)

Listing Agent: Liu Zhang (917-892-2868)

Remarks: This first floor, 2 bedroom, 1 bathroom condo is located in the heart of Winter Park. Enjoy all of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include an open main living area, lovely kitchen with granite countertops and stainless steel appliances, spacious bedrooms, and upgraded bathroom. This boutique community includes an on-site laundry facility. Pets under 40 lbs may be considered. Photos shown are of a comparable unit with a similar floor plan and finishes; minor variations in layout, fixtures, colors, views, and other features may exist. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.

Listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY (407-897-3366)

Listing Agent: Matthew Kirsch (407-897-3366)