Winter Park Apartments for Rent - 83 rentals

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)

Remarks: FOR RENT in Winter Park! Experience comfortable living in this beautiful 3-bedroom, 2.5-bathroom townhome located in the gated community of Grayson Square. Rent includes high-speed internet and cable, offering great value and convenience. The home features a bright open floor plan with abundant natural light, a modern kitchen with quartz countertops and stainless steel appliances, and sliding glass doors leading to a covered patio. Enjoy peaceful views with water, fountain features, and no rear neighbors, creating a relaxing and private outdoor setting that can be enjoyed from the living room, kitchen, and primary bedroom. Upstairs, you will find the spacious primary suite with a walk-in closet and an en-suite bathroom with dual vanities and a glass-enclosed shower. Two additional bedrooms share a full bathroom on the second floor.  A washer and dryer are included for added convenience. Residents of Grayson Square enjoy access to the community pool and playground. The property is conveniently located off Howell Branch Road, minutes away from downtown Winter Park, with easy access to major highways, shopping, dining, and entertainment.

Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)

Listing Agent: Vildan Nigro (352-988-3824)

Remarks: newly updated 3 bedroom 2 bath with flex room for home office. new appliances and ready for move-in.

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

Listing Agent: Mike Wang (631-748-6708)

Remarks: Beautiful townhouse in a pool community, near to supermarket and Costco, good school area. High and trey ceiling in the master bedroom with high loft and living room. Beautiful tile floor on first floor

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

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

Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home located in the heart of Winter Park. Filled with abundant natural light throughout and thoughtful upgrades, this home offers a warm and inviting atmosphere that would be perfect for your family. Highlights: -Primary suite featuring a walk-in closet and private ensuite bathroom -Classic terrazzo flooring -Recently remodeled kitchen with brand-new appliances -Solid wood cabinetry -Fully fenced backyard -2-car parking space -Washer and dryer included -Lawn Service Included Enjoy living in a prime Winter Park location close to shopping, dining, parks, and top-rated schools. This home blends modern updates with timeless charm, definitely a must-see! 12-month Minimum Lease $85 Non-Refundable Application Fee (18+) All Belmont Management Group residents are enrolled in the Resident Benefits Package (RBP) for $50.00/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. Please note, that we require all applicants to have - a combined monthly, net household income of 3X the monthly rent, - good standing credit - minimum score of 650, No accounts in collections - and no prior evictions or collections from any apartment complexes Along with your application, please include a copy of your photo ID as well as two consecutive months of your most recent pay stubs or other proof of income. We will not accept W2s as proof of income. The application includes full background, credit check as well as eviction judgments Pets are allowed on a case-by-case basis via the owner's instructions.

Listing is courtesy of: BELMONT REALTY (407-745-0696)

Listing Agent: Summer Hornburg (407-495-8134)