Winter Park Apartments for Rent - 76 rentals

Remarks: Resort Style Pool Home in KENILWORTH ESTATES! Conveniently located in Winter Park with a walking distance to Baldwin Park, Advent Health, Cody trail park! A short drive to Renown Rollin College, Park Ave, Full Sail University, downtown Orlando, theme parks, and UCF! Close to restaurants, shopping centers, bars, Publix, CVS and gas stations. Welcome Home! through the main door, you will be amazed by its modern and spacious floor plan! A lovely living room with a fireplace, an extra room for home gym or office, on the right, a sparkling pool in front of your eyesight through a modern glass sliding door, sitting under porch, enjoying family gathering in this resort style garden! There has a plenty closet space for storage. Spacious kitchen cabinets for cooking supplies. Be ready to live in a luxury and breath-taking Winter Park Pool home, while enjoying all Florida sunshine and outdoor biking, jogging and golfing at Winter Park Pine. Move in today!

Listing is courtesy of: EXPLORE FLORIDA REALTY SERVICES LLC (407-982-9709)

Listing Agent: Shannon Lee (407-982-9709)

Remarks: This Winter Park condo features two bedrooms and three bathrooms, with an attached garage for convenient parking. The entrance welcomes you with a charming foyer. At the heart of the spacious open great room is the kitchen—highlighted by custom cabinets, quartz countertops, and stainless-steel appliances, all thoughtfully arranged on the first floor. An oversized counter provides space for dining, and the combined dining and living area provide access through French doors to the enclosed rear porch. The living room is enhanced by a decorative built-in electric fireplace. Upstairs you'll find two bedrooms, each with en suite baths. The master bedroom stands out with custom closets, a large window that fills the space with natural light and raised ceilings that add dimension. Two-tone contrasting colors create a cozy and inviting atmosphere, and the master bath includes a double sink vanity, walk-in shower, and linen closet. The second bedroom also boasts raised ceilings, custom closets, and its own private bathroom. Lazy Oaks Condominium is a highly sought-after community in Winter Park, located off Old Howell Branch Road. Residents enjoy amenities such as monthly pest control, guest parking, curbside garbage collection, and private mailboxes.

Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)

Listing Agent: Joyce Gary (407-782-3276)

Remarks: Welcome to this beautiful 3-bedroom, 2.5-bath townhome featuring modern finishes and a serene setting. Enjoy cooking in the kitchen with elegant granite countertops, durable tile flooring downstairs, and stylish luxury vinyl plank flooring upstairs. Step outside to your private fenced patio with peaceful conservation views, perfect for relaxing or entertaining. Water is included! Available NOW! **All Remi Emerson Residential tenants are enrolled in the Resident Benefits Package (RBP) for an additional $50 a month which includes your $100,000 tenant liability insurance, quarterly HVAC air filter delivery, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, plus on-demand pest control! If you have an animal/pet you must click on the Pet Screening link in the application.**Security deposit is due upon lease signing. The first full month's rent is due 1 week prior to move in date. The 2nd month of rent is prorated. Every person 18 yrs or older must fill out an application. Please upload your last 2 months of paystubs in your application. Only complete applications will be considered. A one time admin fee of $250 due upon approval. A lease renewal fee of $125 after 1 year.**

Listing is courtesy of: REMI EMERSON RESIDENTIAL (407-490-1848)

Listing Agent: Shelley Davis (407-625-3489)

Remarks: This beautiful 3 bedroom, 2 bathroom home is located in the heart of Winter Woods in desirable Winter Park. This home offers a spacious split floor-plan with an open living/dining area. Features include tile throughout, a fenced-in backyard with patio area, 2 car garage, washer/dryer hookups, and is convenient to schools, recreational parks, restaurants, & the lovely downtown Winter Park. Please note the outdoor hot tub/spa does not work and will not convey. Pets under 50 lbs. 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)

Remarks: Welcome home to this beautifully updated Cherokee Park townhome, where modern elegance meets comfort in the heart of highly desirable Winter Park. Perfectly situated near some of the area’s best dining, shopping, and entertainment, this home offers both luxury and convenience in one exceptional location. Step inside to a bright and airy open-concept living space featuring wood-style flooring, soaring vaulted ceilings, and a sleek modern fireplace that creates a warm yet contemporary focal point. Large windows throughout flood the home with natural light, including a stunning arched window overlooking lush greenery for a peaceful and inviting atmosphere. The thoughtfully updated kitchen and bathrooms feature clean contemporary finishes, stone countertops, designer lighting, and premium frameless glass showers. Fresh interiors, updated fixtures, and organized closet shelving make this home completely move-in ready with both style and functionality in mind. Upstairs, spacious bedrooms offer comfort and privacy with abundant natural light and spa-inspired bathrooms designed for relaxation. Step outside to your own private backyard retreat featuring low-maintenance luxury landscaping, pristine white stone accents, and premium artificial turf that keeps the outdoor space vibrant year-round. The fully fenced yard is perfect for relaxing evenings, entertaining guests, or enjoying peaceful mornings outdoors. Located just minutes from the renowned shops and restaurants of Park Avenue, residents will enjoy easy access to boutique shopping, fine dining, local cafés, and everyday conveniences including Trader Joe's. You’re also close to scenic parks, Lake Virginia, and Rollins College, making this location ideal for those seeking an active and connected lifestyle. Zoned for highly rated Winter Park schools and professionally managed by Atrium Management, this home offers the perfect combination of style, location, and convenience.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Raquel Elliott (407-921-3772)

Remarks: Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a table with 4 chairs - picnic in your own park like back yard. Ready to move in immediately.

Listing is courtesy of: BLACKFIN REALTY LLC (407-947-9722)

Listing Agent: Scott Banta (407-947-9722)

Remarks: Welcome to this charming 3-bedroom, 2-bathroom home located in a well-established Winter Park neighborhood. This property offers a comfortable single-story layout with inviting living spaces, ideal for everyday living and entertaining. The home features a functional floor plan with a bright living area, an eat-in kitchen, and well-sized bedrooms, including a primary suite with a private bath. Additional upgrades and features include a whole-home water softener, premium appliances, spa-like showers, wood and tile flooring throughout, an efficient HVAC system, and pest control service included for added convenience. Step outside and enjoy the large patio area with pavers and a pergola, perfect for relaxing or entertaining guests. Additional highlights include central air conditioning, a spacious driveway, and a garage for added convenience. Enjoy a generous yard with plenty of space to relax or host gatherings, all within a quiet residential setting. Act now! This one won't last long! All applicants are required to complete a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The backyard also has a gazebo, is totally fenced in and has lots of room to roam. Conveniently located between Baldwin Park and Winter Parks Park Avenue. Winter Park School district. Sorry, no pets.

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

Listing Agent: Jackie O'Leary (407-718-0887)

Remarks: Welcome to Sandlewood Trail Condo.

Listing is courtesy of: NOELKE REALTY (407-607-7166)

Listing Agent: Tom Noelke (407-607-7166)

Remarks: Welcome to this charming 3-bedroom, 2-bathroom house located in the heart of Winter Park. This lovely home features a spacious back yard and patio perfect for enjoying the outdoors. The kitchen and bathrooms have been remodeled. It is a convenient 4 minute walk to Rollins College, and a 10 minute walk to local shops and restaurants on Park Avenue.

Listing is courtesy of: ALFANO PROPERTY MANAGEMENT (407-616-5343)

Listing Agent: Rafael Pierluisi (407-221-2185)

Remarks: LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park , that just had a new roof put on.. At just a ten minute drive from Orlando, this home is in a very convenient location for anyone who wants to be in and out of the city whenever they'd like. Beautiful interior, with original wood flooring throughout. Tile in the spacious open kitchen that opens into the living room, giving this home a wide-open layout. Enjoy, the peaceful, secluded feeling when lounging on the deck in the generous backyard during warm summer nights. Large, fenced backyard. Lake Killarney access for kayaking and canoeing.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Vincent Paige, Pa (407-256-8190)

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 spacious 4-bedroom, 2-bath home offers serene golf course views from your privately screened pool and patio. As you enter the home, you are welcomed by an open living area that flows seamlessly into the kitchen. The kitchen features a breakfast bar, high-end countertops, and large windows overlooking the enclosed patio and pool area. This outdoor space is perfect for relaxing or entertaining while enjoying scenic golf course views. The primary bedroom includes a spacious en suite bathroom with dual vanities and a tiled shower. Additional features include a two-car garage, with washer/dryer hook-ups. Conveniently located near the Crosby Wellness Center, Ward Park, Cady Way Trail, Park Avenue, Winter Park Village, and major roadways, this home offers easy access to shopping, dining, and entertainment. This property includes pool service and is approximately 2,779 total square feet (1,961 under air). Pets subject to owner approval. Schedule your showing today! All information is deemed reliable, but not guaranteed. Listing Brokerage does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. All residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month as additional rent, which includes renters insurance, credit building to help boost your credit score with timely rent payments, our best-in-class resident rewards program, $1M Identity Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, online resident portal for easy online rent payments & maintenance reporting, HVAC air filter delivery (for applicable properties), and much more! More details available upon application.

Listing is courtesy of: WILSON MANAGEMENT GROUP (407-896-1200)

Listing Agent: Amy Spano (407-896-1200)

Remarks: Experience effortless Winter Park living in this stylish, top-floor condo in the charming Stratford community. This move-in-ready gem features modern wood-look tile, a private balcony with serene landscape views, and the convenience of an in-unit washer/dryer. Enjoy resort-style perks like a sparkling pool, fitness center, and tennis courts. Perfectly situated just 10 minutes from the upscale dining of Park Avenue and major campuses like Rollins and Full Sail, this home offers the ideal blend of relaxation and location. Schedule your showing today before this Winter Park beauty is gone! Credit and background check needed. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: This beautiful, furnished home on Lake Killarney offers a rare opportunity to lease a luxury property on a skiable lake, complete with a private dock for your boat and jet ski. Enjoy scenic rides to popular local dining spots like Hillstone's or Shake Shack, or simply unwind in your own backyard, lounging by the saltwater infinity pool and cozying up around the outdoor fire pit. Inside, the home features tile floors throughout, a chef-inspired kitchen with a propane gas stove, double oven, built-in coffee maker, and a wine fridge. The open-concept kitchen, living and dining area, with a gas fireplace, creates the perfect space for family gatherings or quiet evenings. Upstairs, you'll find a spacious bunk room with two queen beds and two twin beds—ideal for accommodating family and guests. For entertainment, the dedicated movie theater room is sure to impress, offering plush leather recliners, a popcorn machine, two refrigerators, and a selection of snacks for the ultimate movie night experience. The home is equipped with surround sound in key areas, including the living room, kitchen, primary bedroom and bathroom, as well as outside by the pool and fire pit. The flexible downstairs layout includes an office/bedroom with a Murphy bed and an expansive primary suite with a luxurious bathroom and walk-in closet. A water purification system ensures fresh, clean water throughout the home, while an app-controlled security system provides added peace of mind. Included in the rent are landscaping, pest control, and pool maintenance, making for a carefree, low-maintenance lifestyle. With easy access to Park Avenue, Winter Park Village, I-4, Publix, Trader Joe's, and more, this home offers the perfect blend of convenience and comfort. Pets are welcome.

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

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

Remarks: This beautiful new two-story home, high ceiling and fully equipment kitchen, located in Winter Park’s exclusive gated community of Hawk’s Crest. Community has lake access with canon launch. This home was build by Taylor Morrison comes with 4-bedroom, 2.5 bathroom home has a great open floor plan that features open dining and living rooms that look out to the lanai and backyard. Home comes all premium appliances, chandeliers light fixtures with tractable fans in every room as well as smart home Alexa control switches. All of the existing security cameras and alarms can convey to you. Extended backyard with screened patio overseas a beautiful fountain pond view. The community features a resort style swimming pool, fitness center, splash pad, clubhouse, playgrounds, dog park, and access to a dock on Lake Howell where you can enjoy fishing and kayaking. Rental fee includes lawn care and irrigation for the best of maintenance free living. Come take a look.

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

Listing Agent: Elaine Zheng (407-417-1314)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom townhome in the highly desirable area of Winter Park—perfect for renters seeking comfort, convenience, and a vibrant community lifestyle. Step inside to an open-concept layout designed for modern living, featuring stylish tile flooring and a spacious kitchen with granite countertops that flows effortlessly into the living and dining areas—ideal for entertaining or relaxing at home. The generous primary suite offers a private retreat with dual walk-in closets and an ensuite bathroom, while two additional bedrooms provide flexibility for roommates, guests, or a home office. Residents will love the resort-style community amenities, including tennis courts, pickleball courts, two sparkling pools, a playground, a putting green, and a clubhouse—giving you plenty of ways to unwind and stay active right at home. Location is everything, and this property delivers. You’ll be just 15 minutes from the shops, dining, and nightlife of Park Avenue, approximately 7 miles from University of Central Florida, and only 1.7 miles from Full Sail University—making it an excellent option for aspiring academics, faculty, or professionals alike. Don’t miss the opportunity to live in a well-appointed home with unbeatable amenities and a prime location!

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Samuel Kingsford (407-808-6633)

Remarks: One or more photo(s) has been virtually staged. Welcome to Park Aire, a small iconic condo community located on Park Avenue by the WP9 golf course. 1st floor unit with oversized window views of the golf course and Casa Feliz. This one bedroom unit has an updated kitchen and bath. Amenities include a covered parking space, swimming pool, social room, a guest room for rent, open air patios on the third floor, under building covered parking spot and laundry in building garage and 2nd floor. You are close by for shopping and dining along Park Ave area.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Andy Holland (407-948-7172)

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: 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)