Winter Park Apartments for Rent - 86 rentals

Remarks: Welcome to this charming and well-maintained rental located in a quiet, centrally situated community in the highly desirable Maitland/Winter Park area. This spacious 2-bedroom, 2.5-bathroom home offers comfort, convenience, and a low-maintenance lifestyle. Inside, you’ll find a bright and open floor plan with a generous living and dining area that flows seamlessly into the kitchen, which is equipped with brand new appliances. The layout provides plenty of natural light, along with ample closet space and storage throughout. Step outside to enjoy a private backyard space—perfect for relaxing or entertaining. Residents of this community enjoy access to a sparkling pool, beautifully maintained grounds, and the ease of included exterior and yard maintenance. Assigned parking is available, along with additional guest parking for visitors. Ideally located just minutes from Park Avenue, this home offers quick access to popular dining, shopping, grocery stores, and entertainment options, as well as nearby parks and major roadways for easy commuting. Zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High School. This is a great opportunity to enjoy a comfortable rental with the feel of a townhome in a prime location—don’t miss it!

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Brian Hyser (407-951-2472)

Remarks: Winter Park Lakefront Community. Lakefront Deck, Dock, Grill, Community Building, Heated Pool and Sauna. Immaculate 2 Bedroom 2 Bath First Floor Unit. Upgraded Kitchen with Raised Ceiling, Maple Cabinets and Granite Counters. Cabinets (matching Kitchen Cabinets) and Counters built in Dining Room for extra Storage. Recently Painted. New Carpets in Bedrooms. Bathroom Vanities and Commodes have been replaced. New Storage Cabinet in Hall. Windows have been replaced. A/C approximately 10 years old with regular servicing. Walking Distance to shopping Centers. Minutes to Downtown Park Ave. Look no further! You have found the perfect unit for rent! Unit also available for sale! (See MLS#65376215)

Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)

Listing Agent: Janice Erickson (407-621-6856)

Remarks: Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Yigit Orer (407-948-5347)

Remarks: One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional bedrooms, a versatile loft, and a conveniently placed laundry room. A first-floor guest suite adds flexibility for visitors or a dedicated workspace. Outside, a spacious backyard and custom gazebo create an inviting place to unwind. Zoned for Princeton Elementary and positioned for quick, easy access to everything College Park and Winter Park have to offer, this home delivers rare quality and exceptional value for 32789. This home is available immediatly.

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

Listing Agent: Kris Kennedy (813-947-3509)

Remarks: Winter Park Pines home,4 bed/2 bath ready for a new resident. On a quiet cul-de-sac, this renovated home offers a blend of modern amenities with a fantastic location. It features a brand new kitchen & bathrooms with quartz countertops, updated brushed brass fixtures, with lots of custom touches. It features engineered wood flooring in the living areas and primary bedroom, a convenient indoor laundry room, new windows and sliding doors that let in tons of natural light. Other upgrades include new doors, trim, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system, lawncare is included in the rent. This home also has a new roof, garage door, and a HVAC system. This home is also next to the scenic Cady Way trail, ideal for biking, walking, and running. Zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Call for your showing today! Sorry NO PETS.

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

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

Remarks: Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete with a cozy firepit and large privacy bushes that create a secluded, tranquil retreat—ideal for relaxing evenings or entertaining guests. With a deeded dock and boat lift, you’ll have direct access to the Lake Killarney lifestyle you’ve been dreaming of. Come see this special home and start enjoying the lake life you deserve!

Listing is courtesy of: COLONIALTOWN REALTY (407-896-7300)

Listing Agent: Alexander Scures (407-925-5338)

Remarks: Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *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. Pet friendly home (w. approval and non-refundable pet fee).

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

Listing Agent: Mo Jabr (407-571-1441)

Remarks: 1 Bedroom/1 Bath condo in Winter Park's Parkview Village! Situated just off of 436/South Semoran Blvd & so convenient to UCF, Full Sail University, 417 & more! The living room, dining & kitchen layout flows easily with sliding doors that lead to the screened patio! Fresh interior paint, washer & dryer. Parkview Village offers a pool, clubhouse. Take a look today!

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

Listing Agent: Barry Stephens (407-547-6500)

Remarks: This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home is the in-unit washer and dryer a rare item within the complex. Community also has an additional laundry facility of it own. From the living room you can Step outside onto the nice open patio….whether it's for morning coffee or evening cookouts with family and friends. The community pool is walking distance and accessible to all residents. Unit has two parking spaces and plenty of additional guest parking. The condo is ideally located, with plenty shopping and dining nearby. Full Sail University and a newly built HCA Emergency room are minutes away. Commuting is made easy with access onto 436, and the 408 which makes it easy to travel to Downtown Orlando or Winter Park

Listing is courtesy of: KIMBRIDGE REALTY, LLC (407-755-7367)

Listing Agent: Scott Butts (321-239-8509)

Remarks: Gorgeous Modern Home with 4 bedrooms + 3 and a half bath home with numerous upgrades throughout located in desirable Winter Park. This house has a large kitchen that opens to the family room for entertaining. Fantastic kitchen with solid wood cabinets, granite counters, walk-in pantry, stainless appliances, Gas 5 burner stove, built-in microwave, large island, big windows emanating a lot of natural light. The home features hardwood floors throughout the main living area, stairs, upstairs bonus loft, and Primary bedroom. The living room offers a gas decorative fire feature, a separate dining room and a large sliding glass door allowing additional natural light, that leads out to a covered patio and private fenced yard. The downstairs living space also has a fourth bedroom and full bath, an indoor laundry room, and a guest half bathroom. At the top of the stairs is a bonus loft for more living space, 2 bedrooms with a jack-and-jill bathroom, and closets with shelving. Upstairs also has the large primary bedroom with double door entrance, wood floors, plantation shutters on windows as well as the large sliding glass doors that lead out to the private balcony, the walk-in closet has custom built-in shelving, the big bathroom has two separate sinks, large walk-in shower and a separate soaking tub and a toilet closet. Wonderful home for the family and one of the best school districts. The surrounding area offers grocery stores, shopping, parks, easy access to highways, and moments away from Park Ave shopping and entertainment, farmers market, boat tours and so much more.

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

Listing Agent: Wendy Calvet (407-276-5024)

Remarks: Welcome to this fully renovated residence in the heart of Winter Park, where modern upgrades meet timeless charm in one of Central Florida’s most desirable communities. Thoughtfully updated throughout, this home offers a fresh, move-in-ready living experience with stylish finishes and enhanced comfort. Ideally situated near Full Sail University and Rollins College, this property is well-suited for students, faculty, and professionals alike. Zoned for highly regarded schools including Aloma Elementary, Glenridge Middle, and Winter Park High School. Enjoy a vibrant lifestyle with easy access to nearby parks and outdoor destinations such as Kraft Azalea Garden and Mead Botanical Garden perfect for relaxing walks and enjoying nature. The renowned Park Avenue is also just a short drive away, offering boutique shopping, dining, and cultural experiences. Conveniently located with quick access to major roadways, downtown Orlando, and Orlando International Airport, this home also places you within reach of Florida’s beautiful east coast beaches, including Cocoa Beach and New Smyrna Beach ideal for weekend getaways. This fully renovated home offers the perfect combination of location, lifestyle, and modern living, making it an exceptional leasing opportunity in Winter Park. Water is included in the rent. Apply here: https://apply.link/oQ8t72Y

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

Listing Agent: Betsy Breton-Garcia, Pa (407-580-5350)

Remarks: Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a reclaimed Chicago brick fireplace and full-length sliders opening to a resort-style lanai with summer kitchen, wood ceiling, and recessed lighting. Step outside to a private backyard oasis with a sparkling pool, outdoor kitchen area, and no rear neighbors—perfect for entertaining. The first-floor primary suite offers complete privacy with a spa-inspired bath, soaking tub, walk-in shower, and dream closet. The main level also includes a private office, full bath, dining room, laundry room, and generous living spaces. Upstairs features a large loft, rumpus room, four additional bedrooms, and two beautifully designed baths. The oversized two-car garage provides high ceilings, storage, and a flex space ideal for bikes, fitness, or workshop use. Located minutes from Park Avenue dining, shopping, and entertainment, this home delivers luxury, comfort, and an unbeatable Winter Park lifestyle. Professionally managed with exceptional service.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Tab Bish Llc (855-450-0442)

Remarks: Are you looking for a spacious 1 bedroom 1 bathroom unit to call home? This home features its own washer and dryer, a large bedroom and living room, a spacious kitchen with ample countertop space, plenty of cabinets. The back sunroom would make a great office or a bright sitting area. The home is located 1 mile from Park Avenue. In addition, the home is located within walking distance of restaurants and shopping.

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

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

Remarks: One or more photo(s) has been virtually staged. Beautifully mainted and move-in ready home available for rent in a convenient location. This property features a bright and inviting interior with functional layout, spacious living areas, and well-sized bed rooms. The home offers a clean feel with plenty of natural light throughout, creating a comfortable and welcoming environment. Enjoy a private outdoor space perfect for relaxing or entertaining. Conveniently located near major roadways, shopping, dining, and everyday amenities. Available for immediate occupancy! Schedule your showing today.

Listing is courtesy of: PRIMAC GROUP, INC (407-889-7075)

Listing Agent: Paula Wells (407-463-8792)

Remarks: Welcome Home to Waterfall Cove in Winter Park! This spacious 3-bedroom, 2-bath ground floor corner unit is move-in ready with fresh paint and brand new carpet throughout. Corner placement means extra natural light and a layout that lives even larger than its generous footprint. Community Perks include a sparkling pool just in time for summer, secured building access, and a peaceful, park-like setting complete with mature landscaping. Tucked into the heart of Winter Park, one of Central Florida's most charming and sought-after communities. You're steps from Winter Park Village, a premier open-air lifestyle center with upscale shopping, Publix, Regal Cinemas, and top-tier dining. Basic internet and cable TV. Tenant responsible for water and electricity only. Easy showing — call us today and move in tomorrow!

Listing is courtesy of: ZEAL REALTY (407-789-2051)

Listing Agent: Ryan Hoppe (321-247-1098)

Remarks: Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for an indoor herb garden. A formal dining area sits just off the kitchen, creating the perfect space for entertaining.Down the hallway, you’ll find a full-size washer and dryer — INCLUDED in the rent — along with a generously sized laundry room offering ample storage space. The guest bathroom is conveniently located next to the laundry area and the second bedroom. The primary suite features a private en-suite bathroom and a large walk-in closet for added comfort and privacy.Enjoy relaxing evenings on the screened porch just off the living room.Pet-friendly! Pets under 40 lbs are welcome with a $350 pet deposit. Limit one Pet.Residents of Parkview Village enjoy access to a community pool and a prime location just south of University off Semoran Boulevard (SR 436). Conveniently located:Winter park Village and Park ave Winter Park are under 10 minutes away. The unit is also 10 minutes to Florida State Road 417, 12 minutes to Florida State Road 408 (East/West Expressway) Making your downtown commute quick and easy!Don’t miss this opportunity — schedule your showing today!

Listing is courtesy of: JML REALTY INVESTMENTS LLC (407-921-9635)

Listing Agent: Jacqueline Ramos (407-921-9635)

Remarks: Adorable mid century modern bungalow in Winter Park! This 3 bedroom, 1 bathroom home has been beautifully updated with new tile wood floors in the main living area. The kitchen features white appliances and tasteful white cabinetry. The updated bathroom features a new vanity and classic mosaic tile floor. Enjoy the spacious backyard with wooden deck! Washer, dryer and lawn care is included! This property is available May 2026.

Listing is courtesy of: GATE PROPERTIES & MANAGEMENT INC (407-704-7904)

Listing Agent: Nicholas Wild (407-704-7904)

Remarks: One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.

Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)

Listing Agent: Donna Peebles (321-229-6085)

Remarks: A absolutely stunning 3 Bedroom 2 Bath single family home, with upgrades galore, this is not your typical rental home. The owners have totally transformed this very unique home into a stunning retreat. From the minute you pull up to this home, you are wowed by the great curb appeal, brick paver driveway and manicured garden. You are welcomed by gorgeous wooden double doors, leading into a reception area in the heart of the home. Which in turn leads into a formal living room, formal dining room and a stunning state of the art kitchen. This new kitchen has it all, beautiful stainless appliances, with built in oven and microwave, double door fridge, quartz counter tops, with eating space. All leading into the family room, with wood burning fireplace and French doors leading to a screened, Spanish tiled sunroom, which in turns leads to a large deck for entertaining and a meandering garden with such a calming surreal feel. Large Master bedroom with spa like bathroom, double sinks with quartz counters, one of a kind shower with seat. Two additional generous bedrooms and second upgraded bathroom with tub complete this unique home. Inside laundry room including washer & dryer, double garage with opener. Includes lawn care, pest control and alarm. This home is situated in the much sought after Brookshire school district, close to shopping, restaurants and major hwys. On a quiet low traffic street close to the Winter Park Pines Golf course. Home will be available for a June 1st move in.

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

Listing Agent: Sarah Gholami (352-346-7857)

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)