Winter Park Apartments for Rent - 80 rentals

Remarks: DO not miss out on this thoughtfully designed townhome! This gorgeous end unit Marigold two-story townhome has no direct rear neighbors, water view and features a Craftsman exterior. Townhome offers 3 bedrooms, 2 full bathrooms, a powder room, a two-car garage and a covered lanai. The kitchen is fully equipped with a pantry, modern gray cabinetry, a Suite Arabesque ceramic tile backsplash, Lagoon quartz countertops and beautiful Positano Blanco porcelain tile flooring. Upstairs the primary Suite features a spacious walk-in closet, and the primary bathroom offers a double sink quartz-topped vanity, a linen closet, private water closet and walk-in shower. Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off Howell Branch Road! This neighborhood has gated access, a resort-style pool with cabana and 1GB high-speed fiber optic internet, along with 75 streaming cable and music channels included in rent!!! Schedule your showing today!

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

Listing Agent: Nicole Howell (321-217-7918)

Remarks: This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 lbs. 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 lease in the desirable Autumn Glen community of Winter Park. This spacious and well-maintained 4-bedroom, 2-bathroom single-family home offers comfort, space, and serenity in a peaceful neighborhood setting. Thoughtfully landscaped with lush greenery and tranquil water views, the home features an oversized kitchen with stainless steel appliances, ample storage, and a pass-through opening to the main living area. Enjoy multiple living and entertaining spaces including a formal dining room, a family room, and a cozy living room with a wood-burning fireplace. The primary suite is oversized with a walk-in closet and a private ensuite bath featuring double sinks, a garden tub, and separate shower. Additional features include recessed lighting throughout, carpeted bedrooms, a laundry room with utility sink, and a breakfast nook. Step into your own private oasis with a spacious enclosed patio that’s perfect for year-round entertaining. An expansive in-ground hot tub with powerful Jacuzzi- type jets, comfortably seating up to 10 guests. Whether you’re hosting a summer soirée or enjoying a quiet evening under the stars, the optional heat setting makes it the ideal retreat in any season." The side-entry garage and whole-house water filtration system add everyday convenience. Community amenities include two tennis courts, a tot lot, and a scenic walking path around the pond—ideal for active and leisurely lifestyles alike. With easy access to I-4, 408, and 417—and just 15 minutes to Downtown Winter Park and the iconic Park Avenue—you’re never far from top-tier dining, shopping, and entertainment. Don’t miss the opportunity to lease this gem in one of Central Florida’s most desirable areas. Schedule your private tour today!

Listing is courtesy of: METRO CITY REALTY (407-237-3331)

Listing Agent: Beatrice Miranda (407-592-4448)

Remarks: Experience effortless Winter Park living in this stylish, top-floor condo in the charming Stratford community. This move-in-ready gem features modern wood-look tile, a private balcony with serene landscape views, and the convenience of an in-unit washer/dryer. Enjoy resort-style perks like a sparkling pool, fitness center, and tennis courts. Perfectly situated just 10 minutes from the upscale dining of Park Avenue and major campuses like Rollins and Full Sail, this home offers the ideal blend of relaxation and location. Schedule your showing today before this Winter Park beauty is gone! Credit and background check needed. 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: Very clean 1/2 duplex near Full Sail University. 2 initial bedrooms with third bedroom built out into the insulated and air conditioned garage. There is storage space in the garage but not enough to park a car. Located off of Forsythe Rd near University Blvd, this home is ideal for a student at Full Sail University or UCF. Very close to major roadways of Semoran Bv (SR436) and University Bv. Also, shopping, banking, restaurants within walking distance. Flooring is all ceramic tile with no carpet. The back yard is fully fenced.

Listing is courtesy of: CLASSIC 1 REALTY INC (407-281-1490)

Listing Agent: Joe Thomas (407-281-1490)

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 (239-486-9939)

Remarks: Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

Listing is courtesy of: METRO CITY REALTY (407-237-3331)

Listing Agent: Bobby Mills (321-946-1119)

Remarks: This first floor, 2 bedroom, 1 bathroom condo is located in the heart of Winter Park. Enjoy all of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include an open main living area, lovely kitchen with granite countertops and stainless steel appliances, spacious bedrooms, and upgraded bathroom. This boutique community includes an on-site laundry facility. Pets under 40 lbs may be considered. Photos shown are of a comparable unit with a similar floor plan and finishes; minor variations in layout, fixtures, colors, views, and other features may exist. 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: Beautifully Updated 2-Bed/2-Bath Condo Near UCF & Full Sail! Step into this stylish and freshly updated second-floor condo, featuring two spacious bedrooms and two modern bathrooms. You'll love the new luxury vinyl plank flooring and fresh paint throughout, creating a clean, contemporary feel. Enjoy the light and airy open-concept living space, filled with natural sunlight and perfect for both relaxing and entertaining. The kitchen shines with updated white shaker cabinets and elegant marble-look countertops. Conveniently located just minutes from UCF and Full Sail University, this home is perfect for students, professionals, or anyone seeking easy access to everything East Orlando has to offer. Residents of Lancelot Condominiums enjoy access to a sparkling community pool.

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

Listing Agent: Melissa Vance (407-489-5166)

Remarks: This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and local shops, restaurants, and schools. Features include an open floor plan with tile flooring throughout the downstairs main living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, tiled back splash, an island, and walk-in pantry. Upstairs you will find the carpeted bedrooms and primary suite with dual sinks, walk-in shower, and 2 walk-in closets. Additional home features include a 2 car garage, patio with quiet backyard area, and laundry closet. Sorry, no students. Pets under 50 lbs. 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 Sandlewood Trail Condo. No Pets

Listing is courtesy of: NOELKE REALTY (407-607-7166)

Listing Agent: Tom Noelke (407-607-7166)

Remarks: FOR RENT - 648 W. SWOOPE AVENUE, WINTER PARK | OFFERED AT $2,700/MO - Stunning Home, Completely Remodeled, and Professionally Designed! Super cute 3 bedroom, 1 bath home in downtown Winter Park. Updated flooring, paint, windows, newer HVAC unit, updated kitchen cabinets, stainless steel appliances, Quartz countertops, beautiful bathroom tile work & fixtures, and interior washer/dryer. Open floorplan. Living/Dining room combo. Designer light fixtures. Fenced backyard. Located within walking distance to Park Avenue, Hannibal Square, the Winter Park Village, Rollins College and more. No smoking. Pets will be considered with an additional, non-refundable pet deposit. Move-in ready and available for occupancy July 1, 2025. Background and Credit Check required. $50 application fee. First month's rent + $3,000 security deposit. Tenant must carry renter's insurance. Lawn care and pest control included. Owner will consider pets.

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

Listing Agent: Kelly Price (407-645-4321)

Remarks: Behind a gated courtyard entrance in the Vias of Winter Park, just around the corner from Kraft Azalea Garden on the shores of Lake Maitland, this move-in ready residence offers privacy, thoughtful design and exceptional indoor-outdoor living. Surrounded by mature landscaping and accessed from both front and rear driveways, the property provides a rare sense of seclusion while remaining minutes from Park Avenue, Winter Park Racquet Club, dining, shopping and top-rated schools. Designed to maximize natural light, the home features vaulted ceilings, skylights, walls of windows and seamless connections to multiple outdoor living areas. The main level includes formal living and dining rooms, a spacious family room, dedicated home office and powder bath. Custom built-ins, extensive storage and carefully planned living spaces support both everyday living and entertaining. The chef's kitchen is appointed with custom wood cabinetry, stone countertops, premium appliances, a large center island with seating and generous preparation space. Open sightlines and direct access to outdoor gathering areas create a natural flow throughout the home. Upstairs, three bedrooms and two full baths include a spacious primary suite featuring vaulted ceilings, hardwood flooring, private balcony access and a renovated bath with marble finishes and a walk-in shower. Additional storage throughout the second level enhances functionality and organization. Outdoor living is a defining feature of the property. Multiple gathering spaces include a welcoming front courtyard, fire pit area and a fully equipped outdoor kitchen and dining space featuring a Wolf grill, brick pizza oven and market lighting. Mature hedges and professionally designed landscaping create privacy throughout the grounds. Additional highlights include hardwood flooring, an oversized garage with substantial storage capacity, dedicated utility room with laundry and utility sink, rear motor court access and multiple outdoor entertaining areas designed for year-round enjoyment. Available for a one-year lease. Unfurnished. Pets considered on a case-by-case basis subject to landlord approval.

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

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

Remarks: Beautiful and very spacious 3BR/2.5BA with 2 car garage, large upstairs balcony, fenced patio, New wood flooring throughout the unit, all appliances including side by side refrigerator and full size washer and dryer. This property is centrally located in winter park FL,walking distance to shopping, restaurants, bars, coffee shops, Publix Supermarket, short driving distance to downtown Orlando and Advant Health Orlando hospital and close proximity to Park Ave Won't last long , please call to schedule your appointment today.

Listing is courtesy of: HPL REALTY INVESTMENTS (407-601-6057)

Listing Agent: Moshe Sheffi (321-945-2367)

Remarks: Fabulous rental opportunity in the sought-after Winter Park School District. This 4-bedroom, 2.5-bath, 2219-square-foot home also boasts glorious lake views from the massive 1,000-square-foot Florida room, ideal for entertaining and enjoying the Florida lifestyle on an expansive ½ acre lot. Ready for move-in, the home is full of natural light pouring in and shining onto the wood flooring throughout the home. There are opportunities to create a multitude of spaces that serve your needs for a home office, craft room, or playroom. The updated open kitchen offers views of the family room, Florida room, and the dining room with solid maple cabinets, granite counters,china-front cabinetry, custom tile backsplash, and stainless steel appliances. The kitchen also has programmable “smart lights”. The master bedroom offers ample storage space, a walk-in shower, and a walk-in closet. There are three additional bedrooms and an additional bathroom. There is a large storage shed and well/pump system for irrigation and a massive backyard for a variety of activities. The 8-zone irrigation system is run by a ground well and pump system, which will equate to savings on the water bill. Start enjoying life in the quiet community known as Arrowhead Cove with Winter Park Schools, as well as charter and private schools in the area, including Trinity Prep, Full Sail, and UCF. 7864 Broken Arrow Trail is a house located in Orange County and the 32792 ZIP Code. This area is served by the Orange County Public Schools attendance zone.

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

Listing Agent: Julia Magnani (305-610-1876)

Remarks: 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: 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: Beautiful pool home for rent in Winter Park located in the established Eastbrook community with NO HOA. This home offers 3 bedrooms plus a versatile bonus room, 2 bathrooms, approximately 1,770 sq ft of living space, a 2-car garage, extended driveway, and a private screened pool with fully fenced backyard. Inside, you’ll find a bright and functional layout with comfortable living and dining areas, updated kitchen with granite countertops and modern cabinetry, plus updated bathrooms with clean finishes. The bonus room offers flexibility for a home office, gym, playroom, or additional living space. Major updates include roof replaced in 2018, fully paid solar panels installed in 2020, water heater 2019, and A/C replaced in 2013. Conveniently located near Park Avenue, Rollins College, Full Sail University, University of Central Florida, shopping, dining, and major highways. First month’s rent, last month’s rent, and security deposit required prior to move in. Background and credit check required through RentSpree at tenant expense ($50 x adult over 18 years old). Preferred credit score 550+. No prior evictions. Pet restrictions apply.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: FULLY FURNISHED 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a picturesque street, the property boasts inviting curb appeal with mature landscaping and a welcoming entrance. Inside, thoughtfully designed living spaces feature abundant natural light, an open and functional layout, and seamless flow ideal for both everyday living and entertaining. The private backyard provides a serene retreat with ample space for relaxing or hosting gatherings. Step outside to your fully fenced backyard, complete with a private hot tub and spacious patio, ideal for relaxing evenings or casual get togethers. With no pool to maintain, you'll enjoy low maintenance outdoor living in a peaceful setting.1 time cleaning per month and wifi included. Located near top-rated schools, parks, and cultural attractions, 2075 Jewel Avenue presents a rare opportunity to enjoy refined living in one of Florida’s most prestigious neighborhoods. Mid term lease available.

Listing is courtesy of: URBANISTA BROKERS (407-619-7272)

Listing Agent: Paul Jimenez (407-276-3516)

Remarks: This beautiful new two-story home, high ceiling and fully equipment kitchen, located in Winter Park’s exclusive gated community of Hawk’s Crest. Community has lake access with canon launch. This home was build by Taylor Morrison comes with 4-bedroom, 2.5 bathroom home has a great open floor plan that features open dining and living rooms that look out to the lanai and backyard. Home comes all premium appliances, chandeliers light fixtures with tractable fans in every room as well as smart home Alexa control switches. All of the existing security cameras and alarms can convey to you. Extended backyard with screened patio overseas a beautiful fountain pond view. The community features a resort style swimming pool, fitness center, splash pad, clubhouse, playgrounds, dog park, and access to a dock on Lake Howell where you can enjoy fishing and kayaking. Rental fee includes lawn care and irrigation for the best of maintenance free living. Come take a look.

Listing is courtesy of: HONEST REAL ESTATE COMPANY (407-417-1314)

Listing Agent: Elaine Zheng (407-417-1314)