Winter Park Apartments for Rent - 83 rentals

Remarks: Special of the month! $2100 for the first 2 months then $2350. Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes from I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and shed. Don't miss this opportunity!

Listing is courtesy of: 365 REALTY, INC. (407-944-1365)

Listing Agent: Vanessa Rivera Laboy (407-766-8093)

Remarks: Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! Landscape/Lawn Care and Reclaimed Water Bill are paid by landlord. UV sanitizing lights installed in all bathrooms. Water filter system installed in kitchen sink. This 4 bed 3.5 bathrooms plus an office and second floor loft is ready to move-in . When you enter the home, an open concept floor plan leads you to the family room, the kitchen / nook area combined. 20-foot high ceiling family room with wide sliding doors to the back patio and high windows gives you plenty of natural sunlight. The large covered lanai would be great for a morning coffee, evening wine, of course family gatherings and BBQ. The Master bedroom is located on first floor. The community is just a few minutes to Costco, Super Target, Publix, Trinity Prep School, and Full Sail University. Located along the southern shores of beautiful Lake Howell, Hawk's Crest provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Ave and Winter Park Village. As you enjoy convenience location, you will benefit from these wonderful amenities within the community: Community pool, Clubhouse, Party Room, Dog Park, Free Gym, Grilling Area, Kid's Splash Pad, Lake Park Picnic Tables, Playground, Cabana, Play Lawn, Lakeside Dock and Future Kayak Access. Come and see your new home today, don't miss this chance.

Listing is courtesy of: EAST PEARL REALTY (407-802-6859)

Listing Agent: Yan Zuo (407-435-3142)

Remarks: STYLISH, STUNNING AND RENOVATED TO THE NINES. This 3-bedroom, 2.5-bath Winter Park home has great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all new interior spaces, this fantastic home is almost totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. In addition to the 3 upstairs bedrooms, the downstairs has a bonus room which is perfect for a den or playroom and a convenient interior laundry room. The lot is 6,750 sqft and is fenced and gated offering a nice new patio of clay pavers, a carport, and large backyard. This 1,774 sqft of living space is perfect for the tenant who wants quality, style and convenient location. This one is MOVE IN READY AND WAITING FOR YOU. There is a $99 per adult application fee and once approved the first & last month’s rent will be due along with the security deposit and any applicable pet fee and deposit.

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

Listing Agent: Johnny Hurlburt (407-579-3168)

Remarks: Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior designed for today’s renter, delivering comfort, functionality, and style in a true turnkey living experience. Ideally located just minutes from Park Avenue, Rollins College, and Winter Park’s premier dining, shopping, and entertainment, this property places tenants in the center of one of Orlando’s most vibrant communities while still offering a sense of neighborhood charm and convenience. Its proximity to major roadways and local amenities makes it especially attractive for professionals, families, and relocation clients seeking both accessibility and quality living. This is a high-demand rental opportunity in a low-inventory pocket of Winter Park, and clean, updated homes in this location do not last. Agents are encouraged to bring qualified tenants ready to move quickly. Now accepting applications with expedited approvals available for well-qualified applicants.

Listing is courtesy of: KELLER WILLIAMS GAINESVILLE REALTY PARTNERS (352-240-0600)

Listing Agent: Fredrick Jacobs (352-790-1088)

Remarks: Rarely available neighborhood for rentals, this 2 bedroom 1 and a half bath house is surrounded by multi-million dollar homes. Large back yard is totally fenced for pets. Zoned for Winter Park's finest schools and located just off Park Avenue for easy access to shopping and restaurants. Flexible lease terms from 6-12 months. All appliances are in place, including washer/dryer. Don't miss this quaint home on a picturesque brick lined street.

Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)

Listing Agent: Jacob Johnson (407-353-0106)

Remarks: Fantastic bungalow in sought-after Winter Park. Great location, close to Advent Hospital Winter Park, Park Avenue, 10 minutes to I4. Large, fenced-in backyard, original hardwood floors in living area & bedrooms. Stainless appliances, granite countertops in kitchen, one car garage. Tons of natural light, indoor laundry.

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

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

Remarks: Fully furnished and Turnkey/Renovated in-town home. Close to downtown Winter Park, Advent and Orlando Health. Newly renovated kitchen with Sub-Zero/Cafe appliances. Monthly rental only…2 bedrooms sleeps 4. Nice covered/screened porch. Available now. Weekly to monthly rental.

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

Listing Agent: Dan Haber (321-624-0966)

Remarks: Great location in Winter Park! This 2-bedroom, 2-bath apartment offers comfortable living with easy access to everything you need. Open Parking in front and located close to Full Sail University, UCF, Valencia College, and major roads like University Blvd and SR-436 (Semoran Blvd). Enjoy being just minutes from shopping centers, grocery stores, coffee shops, and restaurants, including Publix, Walmart, Target, Starbucks, Chick-fil-A, and Winter Park Pines Golf Club. The area is safe and convenient, perfect location. Clean and ready to move in — don’t miss this opportunity to live in one of the best areas of Winter Park!

Listing is courtesy of: JCL REALTY INC (407-467-9411)

Listing Agent: Julio Lopez (407-467-9411)

Remarks: 1

Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)

Listing Agent: Maggie Walas (407-701-0144)

Remarks: Nestled along a quiet brick-lined street in Winter Park’s coveted Via’s neighborhood, 1041 Tuscany Place offers a rare blend of elegance, comfort, and breathtaking natural beauty. From nearly every room, this exceptional residence captures tranquil views of the private backyard and picturesque Lake Temple beyond. Inside, a thoughtfully designed open floor plan is enhanced by soaring vaulted ceilings and an abundance of natural light, creating a warm yet sophisticated atmosphere. The gourmet kitchen is beautifully appointed with premium Wolf appliances, a Sub-Zero refrigerator, quartz countertops, imported Italian cabinetry, and a striking mother-of-pearl mosaic backsplash. The primary suite serves as a peaceful retreat, complete with serene landscape views and a spa-inspired bath featuring a spacious walk-in shower with skylights, body jets, and an oversized 40-inch rainfall showerhead. Upstairs, two generously sized bedrooms share a well-appointed Jack-and-Jill bath, offering comfort and privacy for family or guests. Outdoor living is just as impressive. A spacious deck invites you to relax and entertain while overlooking the sparkling pool and hot tub, while the lower decks bring you into nature with an inviting fire pit overlooking the water. The expansive, beautifully landscaped backyard provides a private setting to enjoy the best of Florida living. Ideally located just minutes from the Winter Park Racquet Club, Interlachen country club, Lake Maitland, and the shops and dining of Park Avenue, this home offers an extraordinary lifestyle in one of Winter Park’s most desirable settings.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Bradford Barnett (407-227-0647)

Remarks: This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a gorgeous kitchen with quartz countertops, stainless steel appliances, and breakfast bar, a lovely primary suite with custom bathroom finishes, laundry closet, and a rear patio. Community amenities include a pool. Sorry, no pets. 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: Available for rent! Tucked onto a desirable corner lot just steps from Lake Killarney, this beautifully updated 3 bedroom, 2 bath single-family home puts you in one of the area's most sought-after spots. Walkable, quiet, and moments from the water. Inside, the home is move-in ready with a full suite of brand-new appliances (dishwasher, range, and refrigerator) plus washer/dryer hookups ready for your setup. Three comfortable bedrooms, two full baths, and bright, livable spaces make it easy to settle in from day one. Easy parking thanks to a covered carport and private driveway. Pets welcome on a case-by-case basis. Available now. Security deposit equal to one month's rent; move-in total is first month + security deposit. Tenant responsible for all utilities and minor maintenance (bulbs, filters); landlord handles major repairs and pest control.

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

Listing Agent: Zach Mitchell (407-920-6440)

Remarks: Beautifully Remodeled 2 Bed / 2 Bath Condo – Second Floor | Prime Location Charming and fully remodeled second-floor condo located just steps from the pool. Perfect for those seeking a low-maintenance lifestyle. This bright and inviting unit features fresh paint, new wood and ceramic tile flooring, and updated bathrooms and kitchen with granite countertops and new appliances, including a washer and dryer. The layout offers a comfortable living room, dining area, and a screened-in patio to relax and enjoy the outdoors. Community amenities include: Pool Sauna Clubhouse Ideally located within walking distance to Full Sail University and just minutes from UCF, Rollins College, and Valencia College, as well as shopping, dining, and major roadways. Note: Some images may be virtually staged.

Listing is courtesy of: CLARA HERRERA REALTY (407-921-1200)

Listing Agent: Clara Herrera (407-921-1200)

Remarks: Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from Interlachen Country Club and Winter Park Racquet Club, and is zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. Inside, natural light pours through windows in every room, giving the home a bright, airy feel throughout. The main living areas feature classic plantation shutters, while all bedrooms are fitted with blinds, a thoughtful touch that makes every space feel finished and move-in ready. Warm engineered hardwood floors, recessed lighting, and a flowing open layout connect the living room, dining area, and family room with ease. The chef's kitchen is the heart of the home, featuring granite countertops, a large center island, rich wood cabinetry, stainless steel appliances, and a professional-grade range hood, all opening into the spacious family room with its slate tile floors, wood-burning fireplace, built-in shelving, and French doors to the backyard. The primary suite overlooks the pool and rear yard, offering a serene and private feel. Its spa-inspired en suite bath features a dual-sink vanity, a walk-in tiled shower, and a private access directly to the backyard and pool, making it ideal for those who love to start or end the day outdoors. The second bedroom enjoys its own en suite bath. A third full bath serves the remaining bedrooms, beautifully updated with designer gold fixtures, modern vanity, and stylish lighting. The split bedroom layout offers privacy and flexibility for families, guests, or a dedicated home office. Out back, your private oasis awaits with a sparkling pool, concrete deck, lush lawn, and towering mature oaks creating that quintessential Winter Park canopy. Pool and lawn maintenance are included in rent, so you can simply enjoy. The attached 2-car garage includes laundry. No pets. No exceptions.

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

Listing Agent: Drew Henner (407-406-0662)

Remarks: Beautiful 4 Bedroom Furnished House with a Pool! This home has an Eat-In Updated Kitchen. There are 3 bedrooms and a bathroom on one side and a large master suite on the other side with a fireplace. The master bathroom has an extra large walk-in shower with a double mirrored dressing area. There is a family room/ FLex Space/ Office Area with a Roku TV, Desk, and Wi-Fi. There is no garage. It has 2 sheds for storage in the back. The neighborhood is nice and quiet. It is conveniently located near Hospitals, Businesses, Restaurants, Schools and Shopping.

Listing is courtesy of: A +ROI PROPERTY (407-718-7994)

Listing Agent: Rene Fossey (407-718-7994)

Remarks: Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The home truly shines outdoors, offering an abundance of entertaining space. Enjoy a screened-in pool, covered patio, and multiple seating areas including a tiled lounge space with a firepit, all set within a large, fenced backyard with both lush grass and low-maintenance turf. Whether hosting guests or enjoying a quiet evening, this home provides the perfect setting. Inside, the light-filled dining room overlooks the backyard from three sides, while the primary suite features a spacious closet and private en-suite bath. All bedrooms include newer carpet, and a generous utility room off the carport offers ample space for laundry and storage. Located in a highly rated school zone and just minutes from Rollins College, parks, shopping, dining, and everything Winter Park has to offer, this home delivers both lifestyle and convenience in one exceptional rental opportunity.

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Lianna Dangelo (321-446-3509)

Remarks: 3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and lawn service included. *Bonus Amenity Included* -All residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Shawn Beard (407-739-7722)

Remarks: Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step outside to your own private oasis — a fully fenced backyard with a sparkling private pool, perfect for relaxing or entertaining year-round. The property also includes an attached 2½-car garage and 4 additional driveway parking spaces, providing plenty of room for vehicles. Located in a prime Winter Park neighborhood, this home is close to parks, shopping, dining, and top-rated schools. Pets are welcome, making this a perfect home for the whole family. Don’t miss this opportunity to enjoy privacy, space, and convenience in one of Central Florida’s most sought-after areas.

Listing is courtesy of: THE REALTY MEDICS (321-947-7653)

Listing Agent: Jason Hamilton (321-947-7653)

Remarks: Welcome to 3038 Antique Oaks Circle #165, a well-maintained and inviting 2-bedroom apartment located in the desirable Winter Park area. This charming residence features a functional layout with abundant natural light, tile flooring throughout, and a warm, welcoming atmosphere. The unit offers a spacious living and dining area, along with a well-appointed kitchen equipped with newer appliances, including a refrigerator, washer, and dryer for your convenience. The comfortable-sized primary bedroom includes a private, recently renovated bathroom, providing both privacy and modern appeal. A second bedroom offers flexibility for guests, a home office, or additional living space. Residents can enjoy community amenities such as a sparkling pool and relaxing spa, perfect for unwinding and enjoying Florida living year-round. Ideally located directly across the street from Full Sail University and just minutes from University of Central Florida, as well as major roadways, shopping, dining, and entertainment options. Experience comfort, convenience, and a prime location—schedule your private showing today.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Edwin Rivera (407-394-7811)

Remarks: Two master bedrooms upstairs, one half bathroom and laundry room downstairs. one fenced patio on the back. Water is included. Two parking spaces belong to this property.

Listing is courtesy of: U S GLORY REALTY (407-222-7801)

Listing Agent: He Gao (407-955-0138)