Winter Park Apartments for Rent - 79 rentals

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 an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility. Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal entertaining and casual gatherings. The gourmet kitchen is a chef's dream, complete with an enormous walk-in pantry, high-end appliances, and seamless flow into the dining area. Entertain in style with a wet bar and food service station, perfect for hosting elegant dinners or festive celebrations. Master Suite is an expansive sanctuary that features a spa-like bathroom equipped with a soaker tub, walk-in shower, His and Her vanities Step outside to your private heated lap pool, perfect for fitness or relaxation. The backyard retreat is surrounded by lush landscapingan ideal oasis for quiet relaxation or sunny Florida afternoons. A first-floor bedroom with en-suite bath adds convenience for guests or multi-generational living. Perfectly situated near Audubon Park and Baldwin Park, this home offers unbeatable access to top-rated schools, including Audubon Park K-8 & Winter Park H.S. Ideally situated near Downtown Orlando, Rollins College, hospitals, renowned restaurants, and boutique shopping, making it a prime location for those seeking convenience and accessibility. Explore numerous community parks, perfect for those who enjoy an active outdoor lifestyle. An area rich in culture with nearby museums to explore and learn. This is more than just a homeit's a lifestyle. Experience the best of Winter Park living: elegant, elevated, and effortlessly connected. Pets negotiable with owner approval. Additional fees may apply.

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: 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: 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: 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: Look no further, this luxury Modern Townhome offers premium location just minutes from Park Avenue, restaurants, shopping, Hannibal Square, and Rollins College just to name a few! Through the front door you are met with 13-foot ceilings, Modern finishes, Pella double windows, and wood flooring throughout. The Chef’s gourmet kitchen is complete with high-end flat panel cabinetry, Quartz countertops, Wolf gas cooktop, and Subzero appliances! On the second floor there are three bedrooms, 2 full bathrooms, utility room and the spacious primary bedroom is equipped with an oversized walk-in closet, opulent tub, walk-in shower, and Quartz countertops. Schedule your private showing today!

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

Listing Agent: Nicole Howell (321-217-7918)

Remarks: Welcome home to Winter Park living at its finest in this beautifully updated one-story home where comfort, convenience, and charm come together. From the moment you enter, you'll notice the bright, freshly painted interior, spacious layout, and modern touches throughout—including new updated bathrooms, landscaping enhancements and brand-new stainless-steel appliances. The attached two-car garage adds everyday ease, while the included washer and dryer. Step outside to your private backyard retreat, where a peaceful water view and inviting fire pit creates the perfect setting for morning coffee, weekend gatherings, or quiet evenings under the stars. Professional landscaping and pest control are also included, so you can spend less time on upkeep and more time enjoying your home. Ideally located near Downtown Winter Park, Park Avenue, local coffee shops, restaurants, grocery stores, entertainment, and daily conveniences, this home also offers quick access to Maitland, Casselberry, Orlando, I-4, and SR-417. Zoned for Seminole Country Schools. If you're searching for a stylish, low-maintenance rental in a prime location, this Winter Park home is ready to welcome you. Schedule your showing today!

Listing is courtesy of: CENTRAL FLORIDA REALTY MANAGEMENT LLC (407-542-4403)

Listing Agent: Kevan Patel (407-491-3559)

Remarks: Nestled on a picturesque, tree-lined brick street, this charming 3-bedroom, 2-bath home offers an unbeatable location just minutes from Park Avenue, Rollins College, shopping, dining, and entertainment. Inside, you'll find a spacious floor plan featuring a formal living room, dining room, and family room, providing plenty of space for both relaxing and entertaining. The kitchen is equipped with all appliances and includes a breakfast bar along with a cozy eat-in dining area. Tile flooring runs throughout most of the home, with carpeting in one bedroom for added comfort. Additional features include an inside utility room with washer and dryer hookups, a large screened-in back porch perfect for enjoying Florida's beautiful weather, and a backyard storage shed for extra convenience. A two-car carport provides covered parking, and lawn care is included, making maintenance easy and worry-free.. All of our residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month, which includes renters insurance, *RentSpree applications will not be accepted. Residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month. More details upon application. This home combines charm, space, and convenience in one of the area's most desirable locations. Schedule your showing today!

Listing is courtesy of: WATSON REALTY CORP (407-359-2300)

Listing Agent: Tara Mason (407-501-1215)

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: 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: 2 bedroom, 2 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New tile floor was installed and freshly painted. Washer & Dryer in the unit. No min credit score is required. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a pool, dog park, and mature landscaping. Convenient access to I-4 and major employment centers. Please use showing instructions.

Listing is courtesy of: MTRE GROUPE LLC (786-282-9992)

Listing Agent: Mauricio Toro (786-282-9992)

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: DO not miss out on this thoughtfully designed townhome! This gorgeous end unit Marigold two-story townhome has no direct rear neighbors, water view and features a Craftsman exterior. Townhome offers 3 bedrooms, 2 full bathrooms, a powder room, a two-car garage and a covered lanai. The kitchen is fully equipped with a pantry, modern gray cabinetry, a Suite Arabesque ceramic tile backsplash, Lagoon quartz countertops and beautiful Positano Blanco porcelain tile flooring. Upstairs the primary Suite features a spacious walk-in closet, and the primary bathroom offers a double sink quartz-topped vanity, a linen closet, private water closet and walk-in shower. Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off Howell Branch Road! This neighborhood has gated access, a resort-style pool with cabana and 1GB high-speed fiber optic internet, along with 75 streaming cable and music channels included in rent!!! Schedule your showing today!

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

Listing Agent: Nicole Howell (321-217-7918)

Remarks: This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 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: 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: Very clean 1/2 duplex near Full Sail University. 2 initial bedrooms with third bedroom built out into the insulated and air conditioned garage. There is storage space in the garage but not enough to park a car. Located off of Forsythe Rd near University Blvd, this home is ideal for a student at Full Sail University or UCF. Very close to major roadways of Semoran Bv (SR436) and University Bv. Also, shopping, banking, restaurants within walking distance. Flooring is all ceramic tile with no carpet. The back yard is fully fenced.

Listing is courtesy of: CLASSIC 1 REALTY INC (407-281-1490)

Listing Agent: Joe Thomas (407-281-1490)

Remarks: Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

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

Listing Agent: Bobby Mills (321-946-1119)

Remarks: Beautifully Updated 2-Bed/2-Bath Condo Near UCF & Full Sail! Step into this stylish and freshly updated second-floor condo, featuring two spacious bedrooms and two modern bathrooms. You'll love the new luxury vinyl plank flooring and fresh paint throughout, creating a clean, contemporary feel. Enjoy the light and airy open-concept living space, filled with natural sunlight and perfect for both relaxing and entertaining. The kitchen shines with updated white shaker cabinets and elegant marble-look countertops. Conveniently located just minutes from UCF and Full Sail University, this home is perfect for students, professionals, or anyone seeking easy access to everything East Orlando has to offer. Residents of Lancelot Condominiums enjoy access to a sparkling community pool.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Melissa Vance (407-489-5166)

Remarks: This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and local shops, restaurants, and schools. Features include an open floor plan with tile flooring throughout the downstairs main living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, tiled back splash, an island, and walk-in pantry. Upstairs you will find the carpeted bedrooms and primary suite with dual sinks, walk-in shower, and 2 walk-in closets. Additional home features include a 2 car garage, patio with quiet backyard area, and laundry closet. Sorry, no students. 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)