Winter Park Apartments for Rent - 70 rentals

Remarks: Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer generous space, with a private primary suite that includes an en-suite bathroom and ample closet storage. Step outside to enjoy serene surroundings or take advantage of community amenities, all just moments from shopping, dining, and entertainment. Ideally located near Downtown Winter Park, Park Avenue, and with convenient access to Interstate 4, this condo offers the perfect blend of comfort, convenience, and lifestyle. Don’t miss your opportunity to call this charming property home!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: David Drawdy, Jr. (407-629-4420)

Remarks: SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!! PRIME LOCATION! JUST STEPS FROM PARK AVENUE, WALKING DISTANCE TO EVERYTHING! This beautiful TOWNHOME is located in the exclusive 400 West community, just moments from Park Avenue. It offers a PERFECT COMBINATION OF SUPERIOR CRAFTSMANSHIP, ELEGANT INTERIORS, and GREAT WALKABILITY. You can enter via the PRIVATE GARAGE or the charming garden-style front path. The main level is BRIGHT and OPEN, with HIGH-END FINISHES like large porcelain tiles and designer lighting. The CHEF'S KITCHEN features POLISHED CHROME HARDWARE, QUARTZ COUNTERTOPS, and STAINLESS-STEEL APPLIANCES, including a Whirlpool French door refrigerator. Ample STORAGE, MOTORIZED Lutron window shades, and a STYLISH POWDER BATH with under-stair storage add FUNCTIONALITY. UPSTAIRS, TWO SPACIOUS PRIMARY SUITES with HARDWOOD FLOORS and LARGE WINDOWS fill the rooms with NATURAL LIGHT. Spa-like en-suite bathrooms have LARGE PORCELAIN TILES, FRAMELESS GLASS SHOWERS, and MODERN VANITIES with CHROME FIXTURES. The primary bath includes a DOUBLE-SINK VANITY, private water closet, and built-in shower bench. A large WALK-IN CLOSET and a full LAUNDRY ROOM with Samsung washer and dryer complete this level. The THIRD FLOOR offers FLEXIBILITY with two additional bedrooms or versatile spaces, each with walk-in closets and a JACK-AND-JILL BATHROOM—perfect for GUESTS, HOME OFFICES, GYMS, or STUDIOS. Recent updates include INTERIOR REPAINT (2025), BLACKOUT SHADES, CLEANED CARPETS AND TILE, and SMART HOME features like NEST THERMOSTAT and RING DOORBELL. Guest PARKING is convenient on-site and nearby. BLENDING TIMELESS QUALITY with MODERN AMENITIES, this LOW-MAINTENANCE, THREE-LEVEL HOME offers PRIVACY and FLEXIBILITY in a QUIET, LOW-DENSITY COMMUNITY. Located just STEPS from everything Winter Park has to offer, it’s an EXCEPTIONAL OPPORTUNITY for a permanent residence or a LOCK-AND-LEAVE retreat in the HEART OF THE CITY. This property is eligible for alternative coverage in lieu of a security deposit. Eligibility requirements apply. For details and enrollment, please contact our leasing team and enjoy a deposit-free renting experience! All Specialized Property Management residents are automatically enrolled in our Resident Benefits Package (RBP) for $49/month. This package includes tenant legal liability insurance, HVAC air filter delivery (where applicable), credit reporting, a renter rewards program, and more! Specialized Property Management residents are enrolled in the Resident Benefits Package (RBP) for $49.00/month which includes tenant legal liability insurance, HVAC air filter delivery (for applicable properties), credit reporting, renter rewards program, and much more! Additionally, most homes feature high-speed internetup to 1 Gigat a special group rate. This includes premium support and professional setup powered by Second Nature, ensuring youre connected quickly at move-in. The group-rate internet is $64/month and is a required part of the program. Full details will be provided during the application process

Listing is courtesy of: SPECIALIZED PROPERTY MANAGEMENT (407-682-3355)

Listing Agent: Nancy Guadagnino (407-705-8559)

Remarks: One or more photo(s) has been virtually staged. The 1 bed, 1 bath unit is ideally located in Winter Park, close to Full Sail and UCF. Rent includes water, and all appliances including washer & dryer. A spacious Living/Dining space and a Huge bedroom make this the best one bed/one bath you'll find. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room.

Listing is courtesy of: BENCHMARK REAL ESTATE GRP INC (321-422-4729)

Listing Agent: Torey Eisenman (407-743-6593)

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: Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Troy Hensley (407-406-5300)

Remarks: Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the vibrant Winter Park area has to accord. Don't miss the opportunity to make this your new home!

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops, stainless steel appliances, self-closing cabinets, and stylish finishes that reflect quality and fresh design. Newer insulated windows including large sliding doors bring energy efficiency to this to this immaculate home. Gorgeous views and spectacular sunsets over Lake Killarney you can enjoy from the lakefront pool, picnic & shuffleboard areas. Access to lake amenities including a private community boat ramp, dock, and fishing. Prime location: just minutes from Winter Park Village. Literally right next door to Trader Joe’s! Very convenient to Whole Foods, great dining, boutique shopping, and more. Commuting is a breeze with easy access to major roads This condo delivers more than just a home — it offers a lifestyle. If you value charm, ease, and access to nature plus city conveniences, this is the perfect pick. Whether you’re starting out, downsizing, or just wanting a beautiful place to come home to. some photos virtually staged*

Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)

Listing Agent: Elizabeth Fowler (863-441-5304)

Remarks: Winter Park 4 Bedrm Home for Rent! Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application results. Pets: OK (Dangerous Pets are not permitted, Pit Bulls, etc.) Priced $2,099.00 for the first 4 months, $2,199.00 for the remaining 8 months (Average: $2,167.00/mo). AVAILABLE: May 19, 2026

Listing is courtesy of: ORLANDO REALTY & PROPERTY MGNT (407-641-5782)

Listing Agent: Jay Myers (407-641-5782)

Remarks: 1

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

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

Remarks: Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are welcomed by an abundance of natural light filling the entryway, dining room and formal living room. The inviting family room includes a stylish wood burning fireplace and French doors that lead out to the backyard. Cook and enjoy your favorite meals in the home’s gourmet kitchen and dinette area. Right off the large 2-car garage is a walk-in laundry room and a lovely half bathroom. Upstairs is the spacious master bedroom and master bathroom including a large soaker tub and walk-in shower. Experience gorgeous Florida outdoor living in the impressive second floor deck that can be accessed through the master bedroom or backyard. Enjoy the lime and pineapple trees in this well-maintained backyard. The home is conveniently located in close proximity to Winter Park’s Park Avenue restaurants and shops and incredible schools. Landscaping/Lawn Care will be provided by landlord.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Lisa Gould (407-721-7612)