Winter Park Apartments for Rent - 84 rentals

Remarks: Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals, airports, Winter Park's cultural gems, and the scenic Chain of Lakes, this home is perfect for professionals, creatives, and families seeking a refined long-term stay. The neighborhood offers an exceptional lifestyle with walking trails, pickleball and tennis courts, playgrounds, dog parks, proximity to Baldwin Park, and Winter Park Pines Golf Club.

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

Listing Agent: Benjamin Cole Iv (407-399-0629)

Remarks: Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

Listing is courtesy of: LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV (407-207-2220)

Listing Agent: Smith Salomon (407-724-9127)

Remarks: Who wouldn’t want to live on a street called LOTAFUN? This one-story Winter Park home has 3-bedrooms, 2.5-baths with great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all new interior spaces, this fantastic home is totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. Located at the end of a dead end street, the privacy is just one of its best features; with partial views of Lake Killarney from the dining area, kitchen, family room, and side yard as a close second. Spacious bedrooms, interior laundry closet and large side yard are also special features offered. This 1,534 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 pet deposit.

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

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

Remarks: Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act now! This one won't last long! All applicants are required to do 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: Newer home for rent in the gated new community of Hawks Crest. The home offers both style and flexibility. The first floor is graced with an openness that invites you in and makes you feel welcome. The plan features options to help you personalize the home to your needs and preferences. Entering the home, you walk into an expansive space. A flex room with 2-story ceiling can be used as a formal living room if you like. This room leads to the dining room, which looks out to a lanai. The kitchen opens to both rooms, as well as the gathering room at the back of the home. Spending time in the kitchen is a pleasure. The plentiful counter space lets you spread things out when preparing a meal. U-shaped, one arm of the counter holds the sink and looks into the gathering room. The kitchen offers gourmet upgrades, built in brand new appliances, granite counter top, touchless faucet. The upstairs layout is split, with the owner’s suite on one side and the three additional bedrooms with shared bathroom on the other. The suite features a bedroom, huge walk-in closet and bathroom with dual sinks, private commode, soaking tub and separate shower. Transform the suite into a retreat with the addition of a sitting room. Gated community with access to lake Howell, gym, swimming pool, clubhouse and playground.

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

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

Remarks: Check out this Winter Park gem near Lake Sue! This 3BR/2BA home features a modern kitchen with granite and stainless steel, wood floors, and a private backyard oasis (landscaping included). Perfect for commuters or remote workers, it boasts an oversized 3rd bedroom/office and is minutes from Park Ave and Audubon Park. Zoned for Audubon K-8 and Winter Park High. Every applicant should apply separately. 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: Welcome to the Four Seasons Condominiums! This great PARTIALLY FURNISHED 2 bedroom, 1.5 bath townhouse condo has much to offer. This completely uniquely designed townhouse features a sunken living room with glass sliding door that open to the private covered patio area, dining room , generous modern kitchen with a colorful glass subway tile backsplash , stainless steel appliances and quartz countertops. First floor also features entry way and half bath for guest. Upstairs features a split bedroom floor plan with two ample bedrooms with loads of closet space. Also upstairs is the modern style full bath with a large vanity and back lit mirror.medicine cabinet. Added features are the washer/dryer combo, laminate floor through out, Ecobee thermostat, new windows and glass doors, window treatments, one assigned carport space with extra open parking, and designer color scheme. Tenant will have access to the pool areas, tennis courts etc. Walk out your door with steps away to the Ward Memorial Park. Association approval is required. Water , sewer and trash is included. Owner will consider pet. Looking for a minimum of a years lease. Available JUNE 2026 SHOWINGS BY APPOINTMENT ONLY. ADVANCED NOTICE NEEDED.

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: John Abbott, Jr (407-398-2330)

Remarks: Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area with small private courtyard. Cozy fireplace in the living room, lots of windows bring in the natural light of the Florida sunshine. Water/sewer is included in rent. Community pool and fitness room at the clubhouse only 2-3 minutes walking distance from the unit. Condo conveniently located near Colleges, Shopping and dining. Pets welcomed! (some restrictions apply)

Listing is courtesy of: JEXOR LLC (407-587-5701)

Listing Agent: Carolina Barriento (407-587-5701)

Remarks: Welcome to this beautifully refreshed townhome nestled in a quiet cove community in the heart of Winter Park. Thoughtfully updated throughout, this light-filled home features new flooring downstairs, fresh carpet on the stairs, new paint throughout, and new light fixtures — move-in ready and waiting for you. The open floor plan flows seamlessly from the living and dining combination into the kitchen, where granite countertops, a charming bay window with bench seating, and a convenient pass-through to the dining area make everyday living a pleasure. A powder room is conveniently located on the main level, and the family room opens into an enclosed sunroom — a versatile bonus space perfect for a home office, playroom, or quiet retreat. A decorative fireplace and ceiling fans add warmth and comfort throughout. Upstairs, the spacious primary suite offers a private en suite with walk-in shower and a walk-out balcony — your own personal escape. A second bedroom on the upper level enjoys its own private bath with tub/shower combo. The third-floor bedroom is a standout, complete with a full bath featuring a walk-in shower and an oversized walk-in closet. High ceilings throughout give the entire home an airy, expansive feel. Residents enjoy access to a community pool and are zoned for an exceptional A-rated school corridor — Dommerich Elementary, Maitland Middle, and Winter Park High School. The location is equally impressive, with easy access to major roads, shopping, and dining, plus walking distance to Howell Branch Preserve Park. Available now at $2,200/month. Security deposit of $2,200 required. Application fee of $50 per adult. No pets. No smoking.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Dee Morgan (407-616-5526)

Remarks: REMODELLED - new flooring and freshly painted. Welcome home to this beautiful townhome centrally located in Winter Park, 15 miles away from Park Avenue, just outside of Baldwin Park. Enjoy beautiful water views on the back patio. This home is fresh ready to move in. Available for rent April 15 or later. Top schools, Glenridge middle school, Winter Park high school and Brookshire elementary school. Quiet neighbors. The home comes unfurnished. Amenities - dog park and kids play area. Walking distance to Walmart and 5 minutes away to Costco, Publix and shopping and dining. 20 minutes drive to downtown Orlando. All applicants are subject to credit, background, income, and rental history verification. Minimum income, credit, and HOA requirements (if applicable) must be met for approval, and additional documentation may be requested during the screening process. A security deposit is required at lease signing, and first month's rent is due prior to move-in. Approval is not guaranteed, and all terms, fees, and availability are subject to change without notice.

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

Listing Agent: Livia Petraru (407-269-4556)

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: 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)