Apartments for Rent Near West Orange High in Winter Garden - 25 rentals

Remarks: Beautiful and well-maintained rental home located in the highly desirable Waterleigh community in Winter Garden! This spacious home features a bright and modern interior with light-tone cabinetry in the kitchen and bathrooms, creating a clean and elegant atmosphere throughout. The first floor offers durable ceramic tile flooring, while the second floor provides the comfort of carpeting in all bedrooms and additional living areas upstairs. Enjoy an open-concept layout perfect for everyday living and entertaining. Residents will have access to Waterleigh’s outstanding resort-style amenities, including pool, fitness center, playgrounds, walking trails, parks, and beautifully maintained recreational areas designed for relaxation and an active lifestyle. Conveniently located near shopping, dining, major highways, and world-famous attractions, this home offers the perfect combination of comfort, convenience, and community living. Don’t miss this opportunity to lease a home in one of Winter Garden’s most sought-after communities!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Jean Dadam (407-961-2182)

Remarks: Modern Comfort Meets Effortless Living! BRAND NEW KITCHEN APPLIANCES INCLUDING DISHWASHER!!! Welcome to this beautifully maintained and spacious 2-story townhome featuring 3 bedrooms, 2.5 bathrooms, and a 2-car garage—designed for both comfort and functionality. Step inside to an inviting open-concept layout filled with natural light, high ceilings, and seamless flow between the living, dining, and kitchen areas—perfect for entertaining or everyday living. The neutral tones and bright spaces create a warm, modern ambiance you’ll love. House was recently painted (all interior) and brand new carpet. Upstairs, retreat to your private primary suite, complemented by two additional well-sized bedrooms and a full bath—ideal for family, guests, or even a home office setup. Come check it out! Please use the following RentSpree link for application: https://apply.link/_ZzvQXU

Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)

Listing Agent: Emilia Rivero (412-944-3471)

Remarks: Complete application required with copy of applicant's driver's license. Complete credit reports for all adults required, proof of income (last two paystubs, last 2 months bank statements). Only 1 pet permitted. Located in Stoneybrook West community. Water view!

Listing is courtesy of: SUSANA JORDAN STUTSMAN (321-278-0334)

Listing Agent: Susana Stutsman (321-278-0334)

Remarks: One or more photo(s) has been virtually staged. AMAZING LOCATION - GREAT PRICE - VERY NICELY UPDATED UNIT! SCREENED IN BALCONY PATIO! 2 Bedroom + 2 Bath condo just 3 minutes from Plant Street in Winter Garden. Kitchen has been beautifully updated and unit has stylish flooring throughout (no carpet). Wonderful split floor plan: the 2 bedrooms are separated by open concept kitchen/ living room combo and each has their own bathroom. Community has private pool area, basketball courts, and plenty of green space for outdoor activities. Application process and fees apply. Call today for your private showing.

Listing is courtesy of: ROMAN REALTY GROUP, LLC (407-876-1990)

Listing Agent: Brian Lemay (321-314-5412)

Remarks: Beautiful 2-bedroom, 2-bath condo in the desirable Southern Pines community of Winter Garden. This second-floor unit features a bright open floor plan with a spacious living area that flows into a light-filled solarium—ideal for a home office, reading nook, or additional sitting area. The kitchen is centrally located with ample cabinet and counter space, adjacent to a dedicated dining area. The split-bedroom layout offers privacy, with the primary suite featuring a walk-in closet and private bath, while the second bedroom is generously sized with easy access to a full bathroom. Enjoy low-maintenance living with access to community amenities including pool, fitness center, playground, and tennis courts. Conveniently located near shopping, dining, major highways, and top-rated schools. Unassigned common parking available with a maximum of 2 vehicles per unit. Unit currently tenant-occupied through 5/30. Carpets will be steam cleaned and interior paint will be professionally touched up prior to move-in.

Listing is courtesy of: AFT PROPERTY LLC (407-900-0056)

Listing Agent: Seyed Azimi (407-900-0056)

Remarks: AVAILABLE NOW! Beautiful 3-bedroom, 2-bath townhome available for rent in the heart of Winter Garden! This 1,180 sq. ft. home features brand-new windows, a new microwave, a brand new AC, new roof, a new sliding glass door, an updated electrical panel, offering comfort, efficiency, and peace of mind. FIRST FLOOR BEDROOM with ensuite bathroom, then remaining 2 bedrooms upstairs. The interior boasts bright, open living spaces with a functional layout ideal for everyday living and entertaining. Screen room is tiled with artificial turf in the fenced backyard. Enjoy a prime location just minutes from Historic Downtown Winter Garden, where you’ll find the popular Plant Street Market, a weekly farmers market, boutique shopping, and local dining. Winter Garden offers a charming small-town atmosphere with convenient access to major highways and top-rated schools. Plus, you’re just a short drive from Walt Disney World and other Central Florida attractions—making this an ideal place to call home.

Listing is courtesy of: INDEPENDENCE REALTY GROUP LLC (407-408-6662)

Listing Agent: Gabriella Philippone (407-902-4237)

Remarks: Great location in Winter Garden. Beautiful and charming townhouse, well-maintain 2 bedrooms, 2.5 bath with 1234 sq ft. Step inside to a cozy living room, modern kitchen with granite countertop, stainless-steel appliances, nice dining room, patio and 1car garage. In second level we have all hardwood floors, 2 spacious bedrooms each with its own bath, and walk in closets. Laundry room located in the second floor. Internet and Cable are included. Gated community offers a playground, pool, gym, club house, walking and biking trail. Conveniently located near to many restaurants, stores, historic downtown Winter Garden. Easy access to 429 and Florida Turnpike.

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

Listing Agent: Betty Medina (407-587-5535)

Remarks: Available to rent in the heart of Winter Garden! This 3-bedroom, 2-bathroom condo is located in the Townhomes of Winter Garden community that features a community pool, quick access to major roadways, minutes from the charm and dining of Downtown Winter Garden and the scenic West Orange Trail, perfect for biking, walking, and outdoor recreation.

Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)

Listing Agent: Kevin Sullivan (321-663-3457)

Remarks: Welcome to the spectacular neighborhood of Regency Oaks in Winter Garden! This home has just been renovated with a quartz countertop, new stainless steel appliances, and beautiful laminate flooring. It is zoned for all A-rated schools and is close to the Groves Shopping Center, great restaurants, and has easy access to the 429. As you enter, the home opens up to a long formal dining room and sitting room combo, with the informal family room to the rear, both separated by the spacious kitchen. The Master Suite is situated on the right side of the home, making this a great split floor plan. The Master Bath includes a Roman tub, standalone shower, double vanity, and walk-in closet Well planned 4 bedroom 2 Bath, . Kitchen opens to the family room. Pets allowed. Close to Winter Garden Village and Historical Downtown Winter Garden, Restaurants and shopping

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Reynaldo Izaguirre, Pa (407-683-0998)

Remarks: Prime Location & Resort-Style Living! Welcome home to this beautifully appointed first-floor, 2-bedroom, 2-bath condo in the highly sought-after GATED community of Southern Pines. The desirable open, split floor plan offers both space and privacy, enhanced by wood laminate flooring throughout the living, dining, and kitchen, tile in the baths, and plush carpeted bedrooms. The kitchen features granite countertops, and the home includes an in-unit washer and dryer for added convenience. Relax year-round in the bright solarium just off the living room—perfect for morning coffee or unwinding after a long day. Water, sewage, basic cable, and internet are all included, making this home as practical as it is comfortable. Enjoy resort-style amenities right outside your door, including a community pool, fitness center, indoor basketball court, tennis court, sand volleyball, playground, business center, game room with pool table, gas grilling area, and a private movie theater. Ideally located close to everything, but tucked away from the hustle and bustle. Located just minutes from the Florida Turnpike, SR-408, Winter Garden Village, and historic downtown Winter Garden, this condo offers the perfect blend of convenience, comfort, and community living.

Listing is courtesy of: MARTI PURDY PROPERTIES INC (407-614-6177)

Listing Agent: Marti Purdy (407-761-0848)

Remarks: One or more photo(s) has been virtually staged. one or more photos have been digitally edited. WHERE MODERN MEETS ELEGANCE. AMAZING TOWNHOUSE in Winter Garden, FL. 3 BEDS, 2.5 BATHS, 2 CAR GARAGE, WITH LOFT. The LARGEST FLOOR PLAN in The Westbrook Community . GRANITE AND STAINLESS STEEL in the kitchen. Gorgeous Farm style sink. Very spacious bedrooms. Oversized master bedroom with 2 walk in closets and the master bath features double sinks and a walk in shower. The unit also features a loft or bonus room on the second floor which can be used as an office or a second living room. LOTS OF STORAGE. COMMUNITY POOL. From your rear porch, you can access the pool just crossing the street. WATCH VIDEO LINK below the pictures

Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)

Listing Agent: Maria Ubillus (954-242-7900)

Remarks: Fantastic 3 bedroom 2 home in Stoneybrook West! INTERNET and CABLE TV INCLUDED!!! TOP RATED SCHOOLS!!! This wonderful home is located less than 3 miles from the popular Winter Garden Fowlers Grove shopping mall, numerous restaurants and is just minutes from the Turnpike, 408, and 429. The community of Stoneybrook West features resort style amenities such as 24 hour guarded gates for maximum security, large community pool with views of SPRING FED Lake, fitness center/gym, in-line skating rink, large playground area, basketball courts and a dock for fishing

Listing is courtesy of: KARDOSH REALTY (407-499-4466)

Listing Agent: Frederico Hexsel (407-745-8841)

Remarks: Welcome to an awesome 2-bedroom, 1-bath condo with an attached garage. Just steps away from the car wash in the beautiful gated community of Southern Pines. The community has a fully equipped state-of-the-art gym, indoor basketball and racquetball courts. BBQ Pavilion for entertaining friends and family with three grills. Pool table and computer room for residents. A theatre with surround sound and vibrating recliners.

Listing is courtesy of: HOMESMART (407-476-0451)

Listing Agent: Maria Lloret (407-929-1994)

Remarks: One or more photo(s) has been virtually staged. Welcome to 1226 Portmoor Road in the highly sought-after, manned-gated Golf community of Stoneybrook West! This stunning 5-bedroom, 3-bath golf-view home offers over 2,800 square feet of beautifully updated living space. No Carpets!!! Designed for both comfort and entertaining, the home features formal living and dining rooms, a spacious family room, and a desirable first-floor guest bedroom with a full bath. The chef’s kitchen shines with granite countertops, stainless steel appliances, and an extra refrigerator in the garage. Upstairs, enjoy new laminate flooring, generously sized bedrooms, and a luxurious primary suite with tray ceilings and a private balcony overlooking the course. Step outside to your upgraded screened lanai and low-maintenance turf backyard—perfect for relaxing or hosting gatherings. Residents enjoy a Jr. Olympic pool, fitness center, clubhouse, dock, tennis, basketball, playground, high-speed internet, cable, and discounted golf—all minutes from Winter Garden Village, major highways, hospitals, theme parks, and Orlando International Airport. Schedule your showing today!

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Shirley Botansky (407-704-0874)

Remarks: Must see!! Welcome Home, beautiful property with a lots of upgrades, freshly painted. Four ample bedrooms, separated Living and Dining, kitchen with granite counter tops. All appliances are included. Master suite with a large walking closet, and separate upgraded master bathroom with skylights. Big patio fenced. Conveniently Gated Community with Security Guard 24 hrs, closed Shopping centers, restaurants, and Theme Parks. Golf Community with amenities such as Pool, Tennis court, Lakefront, Fitness Center, Boating, basketball, Fishing pier, hockey, beach volleyball, and playground. Call today to request your showing.

Listing is courtesy of: REALTY ONE GROUP EVOLUTION (786-477-4715)

Listing Agent: Milena Nunez (407-247-1814)

Remarks: Beautifully maintained 2-bedroom, 2.5-bath townhome available for rent in a gated Winter Garden community. This home offers a smart, functional layout with an open-concept living and dining area on the main floor—perfect for everyday living and entertaining. A convenient half bath is located downstairs for guests. Upstairs, both bedrooms feature private en-suite bathrooms and spacious walk-in closets, creating two comfortable and well-appointed suites. The laundry room is also located upstairs and includes a linen closet for added storage and convenience. Enjoy your own private, fenced-in patio situated between the home and the rear-loading garage—an ideal space for relaxing outdoors or hosting small gatherings. Residents have access to fantastic community amenities, including a resort-style pool, fitness center, and playground. Rent includes cable, high-speed internet, phone service, and an alarm system, offering exceptional value and a truly move-in-ready experience. Located in highly desirable Winter Garden, this home is just minutes from Historic Downtown Winter Garden, shopping, dining, entertainment, and major roadways, including the Turnpike and SR-429. Easy commute to downtown Orlando and Disney. This townhome offers comfort, privacy, and convenience in a prime location—an excellent rental opportunity.

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

Listing Agent: Olga Recean (253-285-2595)

Remarks: Within the gated community of Southern Pines you will enjoy the FLORIDA LIFESTYLE everyday! Soak up the sun by the resort-style pool and spa. What's your pleasure? Enjoy the tennis courts, a volleyball court, or indoor racquetball, basketball courts and full fitness center with a kiddie playroom. The clubhouse feature a media room, theatre room, computer terminals with free internet and then there's the playground, barbecue areas and even a car wash. This is the LARGEST one-bedroom unit available with a BONUS/ SUNROOM. It is a two-story condo with your own private entrance. NEWLY REMODELED with NO CARPET. Tile floors in the kitchen & in the FULLY REDESIGNED LUXURY BATH. Large TILE WALK-IN SHOWER w/GLASS ENCLOSURE & NEW STONE counters. The main living/dining areas, stairs and the bedroom feature the NEW HYBRID Plank Flooring (better than Luxury Vinyl or laminate). Crown moldings throughout. Close to everything...Winter Garden Village shopping and restaurants, hospitals, easy access to downtown, Disney, or almost anywhere via SR 429, FL. Turnpike, I-4. Must see! All rentals include the Claire Schwartz & Associates Resident Benefits Package (RBP) which delivers savings and convenient, professional services that make taking care of your home second nature. All as a part of your cost of $35/month, payable with Rent. APPLY FOR THIS HOME ON OUR WEBSITE. LOOK FOR THE LINK TO "OUR RENTAL LISTINGS/APPLY HERE" & OPEN YOUR HOME BY CLICKING ON IT AND "APPLY HERE" OR CALL YOUR REALTOR TO VIEW.

Listing is courtesy of: CLAIRE SCHWARTZ & ASSOCIATES (407-352-5244)

Listing Agent: Claire Schwartz (321-439-6995)

Remarks: Location, Location, Location! Exceptional opportunity in Winter Garden, just 4 minutes from Hamlin Town Center, in one of the fastest-growing areas in Central Florida. This unique property features approximately 2.5 acres of land, delivering something increasingly rare in today’s market: space, privacy, and flexibility of use. The home includes 3 bedrooms, 2 bathrooms, and a bonus room, with a functional layout and spacious living areas ideal for comfort and versatility. The standout feature is the expansive lot—perfect for hosting family and friends, enjoying gatherings, and making the most of group living without the usual limitations of close neighbors. The property provides ample parking and vehicle circulation space, easily accommodating multiple guests. In addition, this is truly a “country-style setting within the city”—you get the benefits of a rural feel with space, tranquility, and privacy, while remaining just minutes from urban conveniences, including shopping, dining, and everyday services. Located in the Horizon West area, the property is near highly regarded schools such as Hamlin Elementary School, Hamlin Middle School, and West Orange High School, and is surrounded by modern infrastructure and ongoing growth. Whether for personal use, long-term value, or a lifestyle centered on space and freedom, this property stands out in a high-demand, appreciating area. Contact us for more information and to schedule a private showing.

Listing is courtesy of: REIS E SILVA REALTY GROUP LLC (407-274-8510)

Listing Agent: Mara Brasil (407-970-9935)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful home in the desirable Mezzano community of Winter Garden, offering a spacious multi-level floor plan designed for both comfort and functionality. Inside, you’ll find bright, open living areas with modern finishes that create a warm and inviting atmosphere. The main living space flows seamlessly into the dining area and kitchen, making it perfect for entertaining or family gatherings. The kitchen features stylish cabinetry and well-planned workspaces, while the bedrooms provide privacy and relaxation with ample room to suit different needs. Bathrooms are finished with contemporary details, adding a touch of sophistication. Beyond the interior, residents enjoy access to community amenities including a pool, recreational facilities, and landscaped grounds. Conveniently located near shopping, dining, and major highways, this home is also zoned for Summerlake Elementary, Hamlin Middle, and West Orange High School, making it an excellent choice for families seeking quality education and a vibrant neighborhood lifestyle.

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Cesar Sanchez (689-339-3803)

Remarks: Welcome to this charming and well-located rental in the heart of Winter Garden! Situated on historic Plant Street, this inviting property offers the perfect blend of character, convenience, and lifestyle. This home features a bright and functional layout with comfortable living spaces, ideal for relaxing or entertaining. Large windows bring in plenty of natural light, creating a warm and welcoming atmosphere throughout. The kitchen is thoughtfully designed with ample cabinet space, making everyday living easy and efficient. Step outside and enjoy being just moments from the vibrant downtown Winter Garden district. You’ll have easy access to local shops, dining, the popular farmers market, and the scenic West Orange Trail—perfect for biking, walking, or enjoying Florida’s beautiful weather. Additional highlights include convenient parking, quick access to major roadways for commuting to Orlando and surrounding areas, and enrollment in a Residents Benefits Package offering HVAC filter delivery, renters insurance, and more for $39.95/month. Whether you’re looking for a cozy place to call home or a location that keeps you connected to everything, this rental offers the best of both comfort and convenience. Don’t miss your chance to live in one of Winter Garden’s most sought-after areas—schedule your showing today!

Listing is courtesy of: WATSON REALTY CORP., REALTORS (352-243-7374)

Listing Agent: Robert Pringle (407-436-2142)