Winter Park Apartments for Rent - 77 rentals

Remarks: Welcome to Lazy Oaks condominium. This townhome features two levels with an open floor plan that consist of 2 bedrooms, 2.5 bathrooms, and a Florida Room. Over 1200 sqft of living space awaits you with an upgraded laminate flooring, baseboards, lighting, and ceiling fans. A prime location that is nestled near Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando International Airport. Home is available furnished at $2,100/mo. Schedule your showing today!

Listing is courtesy of: MAYERS REAL ESTATE LLC (407-717-0105)

Listing Agent: Damon Mayers (407-717-0105)

Remarks: This beautiful 2 bed / 1 bath 1,029 square foot home in Winter Park is totally refurbished and available for immediate occupancy. Newer kitchen cabinets. Newer bathroom. With a single car carport. This property features wood floors throughout, tile floors in the kitchen, dining room and bathroom, large open yard. Washer/dryer, shed & lawn care included! Application Fee: $50 each adult (18+) **Full Credit/Skip/Eviction/Background check is done on all applicants. **Please have the following documents ready to attach as JPEG or PDF: - Drivers License - (3) Pay Stubs

Listing is courtesy of: PREMIER MANAGEMENT GROUP INC (407-370-4400)

Listing Agent: Ken Warren (407-370-4400)

Remarks: Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an oversized walk-in closet, while the living room includes a nook overlooking the lake, ideal for a home office or reading area. The generous kitchen offers a pantry and eat-in dining space, seamlessly connecting to the living and dining areas. Sliding glass doors invite natural light and lake breezes throughout. A private laundry room and secured garage parking add everyday convenience. This residence includes a deeded boat slip, providing direct access to Winter Park’s iconic chain of lakes. A community elevator offers access to the third floor. High-end modern finishes, ample storage and refined living spaces make this offering exceptional in both quality and location. Please note: At least one resident must be 55 years of age or older. All additional residents must be at least 21. Lease includes one assigned garage parking space and a deeded boat slip. Annual lease only. Application and association approval required.

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

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

Remarks: 2-bedroom, 1.5-bathroom, two-story townhouse in Four Seasons Condos of Winter Park. This well maintained townhouse includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets, and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with built-in blinds that open to a fenced patio. You will find a neutral color palette throughout the townhouse. Open and fenced-in patio located in the back of the unit. The second floor includes both bedrooms, full bathroom, and rear door to exterior staircase. Water, sewer, and landscaping are included. This unit also comes with covered carport space. The Four Seasons Condos are located within the city limits of Winter Park. Community pool and laundry facilities available at the Clubhouse. Close to shopping, restaurants, the Winter Park Medical Center, Cady Way recreational trail and more. Approximate living and total sq ft is 1219. This is a non-smoking unit. Additional HOA application and approval is required. All tenants are enrolled in a Resident Benefit Package for an additional $50/month (details available below). Don’t miss out, contact us today! All information is deemed reliable, but not guaranteed. Listing Brokerage does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. All residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month as additional rent, which includes renters insurance, credit building to help boost your credit score with timely rent payments, our best-in-class resident rewards program, $1M Identity Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, online resident portal for easy online rent payments & maintenance reporting, HVAC air filter delivery (for applicable properties), and much more! More details available upon application.

Listing is courtesy of: WILSON MANAGEMENT GROUP (407-896-1200)

Listing Agent: Amy Spano (407-896-1200)

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 kids or pets. Zoned for Winter Park's finest schools and located just off Park Avenue for easy access to shopping and restaurants. Shorter term lease is negotiable. 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: Welcome to 2372 Shadowland Loop – Comfort, Style & Location in the Heart of Winter Park Step into this beautifully maintained rental home located in one of Winter Park’s most desirable and convenient areas. From the moment you walk in, you’ll appreciate the open layout, natural light, and inviting living spaces designed for both relaxing and entertaining. The spacious living and dining areas flow seamlessly into a well-appointed kitchen, featuring ample cabinet space and a functional layout perfect for everyday living. Whether you're hosting guests or enjoying a quiet night in, this home offers the flexibility and comfort you’re looking for. The primary suite provides a private retreat with generous closet space and an en-suite bathroom, while additional bedrooms offer versatility for guests, a home office, or family living. Step outside to enjoy your outdoor space—ideal for morning coffee, evening relaxation, or weekend gatherings. Location is everything, and this home delivers. Conveniently situated just minutes from shopping, dining, major roadways, and top-rated schools, you’ll have easy access to everything that makes Winter Park one of Central Florida’s most sought-after communities. ? Spacious, open floor plan ? Bright and inviting living areas ? Private primary suite ? Flexible secondary bedrooms ? Convenient Winter Park location Available now—schedule your private showing today and experience the lifestyle this home has to offer.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: William Grim, Iii (407-314-9784)

Remarks: Experience the rare luxury of a high-performance, meticulously updated 3-bedroom sanctuary in a quiet Winter Park cul-de-sac, offering the perfect blend of modern utility and suburban serenity. Zoned for Winter Park High School, this versatile floor plan features both a dedicated private office for the remote professional and an expansive game room for premier entertaining. Every major system has been addressed for total peace of mind, including a BRAND NEW ROOF (2026), high-efficiency AC (2025), and a fresh 2026 interior refresh. The heart of the home is a light-filled living area anchored by a magnificent wood-burning stone fireplace, leading to a chef’s kitchen outfitted with premium Quartz countertops, new cabinetry, and a new dishwasher. Experience a seamless flow with brand-new luxury vinyl plank flooring throughout—no carpet—and spa-inspired bathrooms featuring a new walk-in primary shower and pristine guest bath updates. Situated on an oversized .33-acre lot, this property provides exceptional privacy and space rarely found in a rental. Enjoy the convenience of being just 5 minutes from Costco and major retail hubs, 15 minutes from Park Avenue’s world-class dining, and offering swift access to UCF and the 417. This is more than a rental; it is a meticulously modernized retreat ready for immediate move-in.

Listing is courtesy of: NEXTHOME NEIGHBORHOOD REALTY (407-377-7735)

Listing Agent: Brenden Rendo (407-710-8720)

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: 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: Beautifully renovated private studio unit (1 bed / 1 bath) located in the rear of the property in a highly desirable area near Winter Park and Downtown Orlando. This cozy detached unit offers a comfortable living space with a private bathroom, ideal for a single professional or student looking for convenience and privacy. Water and electricity are included in the rent, making it an easy and budget-friendly option. The main house and the additional front unit are currently occupied, while this rear studio offers its own separate and peaceful setting. Excellent location with easy access to I-4, Downtown Winter Park, Downtown Orlando, shopping, dining, and Dubsdread Golf Course.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Andres Ospina Rivera (321-821-8446)

Remarks: Meticulously maintained home with a Highly-Flexible floor plan offering 4 bedrooms, two bonus room areas that would be perfect for a home gym, nursery or media room. In one of Winter Park's most sought after areas. Enjoy the enjoyment of local parks, restaurants, convenient shopping, easy commutes and some of the best walkability around. This traditional home sits on a very private corner lot. Features front covered patio and sitting area. Lots of natural light in the oversized great room and it’s the perfect entertaining space. It has a true chef’s kitchen including solid wood custom cabinetry, 5 burner gas stove with pot filler, Sub-Zero refrigerator, Fisher & Paykel double drawer dishwasher and so much more. The primary suite is upstairs and offers a luxurious secluded environment to relax. The oversized suite has its own private balcony that looks out over the beautiful private backyard and pool space. The master bath has a large jetted tub, walk in shower, double vanities with tons of counter space PLUS a 16x13 Custom Designed Walk-in closet...and so MUCH more! Call for your private viewing today!

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

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

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: Welcome to 870 Carver Street, a one-of-a-kind rental offering two distinct, private residences on a single fully fenced property in the heart of Winter Park. The main home is a 2 bedroom, 2 bath retreat featuring vaulted ceilings with exposed rafters, warm wood finishes, and industrial-inspired black metal ductwork. The open living area is anchored by a well-appointed kitchen with solid wood cabinetry, under-cabinet lighting, and a substantial island with seating for four. Black aluminum-framed windows flood the space with natural light. The primary suite includes a floating wall closet system, in-suite laundry, and a spa-style bath with dual-sink floating vanity and glass-enclosed walk-in shower. The second bedroom features an en-suite full bath with a tub-shower combination. The second residence is a self-contained 1 bedroom, 1 bath unit with its own private entrance and dedicated driveway on Carver Street, completely separate from the main home. Inside, vaulted ceilings, tile flooring, a full kitchen, en-suite bath, private laundry, and white oak stairs lead to a bright, cohesive living and dining area. The two residences share a fully fenced yard with a rear garden courtyard but are otherwise independent, making this an ideal arrangement for roommates, a home office, a live-in guest, or simply extra space on your own terms. Outdoor spaces include covered entries and an expansive front porch with warm wood architectural detailing. An oversized garage with extra depth for storage is accessed via a sliding steel-framed, wood-clad gate along Railroad Avenue. Just a short distance from Park Avenue, Winter Park Village, Whole Foods Market, the Winter Park Golf Course, and the SunRail and Amtrak stations... everything Winter Park has to offer is right at your door!

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

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

Remarks: Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a talbe with 4 chairs - picnic in your own park like back yard. Ready to move in immediately.

Listing is courtesy of: BLACKFIN REALTY LLC (407-947-9722)

Listing Agent: Scott Banta (407-947-9722)

Remarks: This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, island, and pantry with plenty of storage. Upstairs you will find the carpeted bedrooms and primary suite with dual sinks, walk in shower, and a walk-in closet. Additional features include a 2 car garage, patio with quiet backyard area, and utility closet for the washer/dryer. Community features include a pool and cabana, park, and playground. 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: 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: 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: 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: Cozy one-story villa located in desirable Winter Park. This home features two bedrooms and two full bathrooms, a bright living room–dining room combo, and a charming fireplace. Enjoy outdoor living on the private patio. Washer and dryer are included in the rent for added convenience. Pets are welcome (with some restrictions). Excellent location close to shopping, major highways, and local colleges.

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

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

Remarks: Bright and freshly updated ground-floor 2-suite condo in a peaceful, well-kept community. This move-in-ready home features new interior paint, new water heater, granite countertops, and durable vinyl plank flooring throughout. The split-suite layout offers privacy and flexibility for roommates or professionals. Zoned for Cheney Elementary, with convenient access to A-rated middle and high schools, plus minutes to Full Sail University and UCF. A perfect blend of comfort, convenience, and value.

Listing is courtesy of: NOBSKA REAL ESTATE LLC (689-276-1593)

Listing Agent: Jiny Lee (407-920-0702)