Apartments for Rent Near West Orange High in Winter Garden - 29 rentals

Remarks: Welcome to this stunning townhome located in the highly sought after gated community of Hickory Hammock in Winter Garden. This beautifully maintained 3-bedroom, 2.5 bath residence with a 2-car garage offers a spacious and functional layout with designer finishes throughout. Step inside to find tile flooring that flows through the entire first floor. The entry level features an open great room with a ceiling fan and sliding glass doors leading to the patio. The kitchen is a chef’s dream, complete shaker-style design with light beige granite countertops , dark cherry stained wood cabinets , stainless steel appliances, tile backsplash, a walk-in pantry, and an inviting eat-in dining area. Upstairs, a spacious loft offers flexible living space, perfect for a media area or playroom. Two guest bedrooms, each with ceiling fans and ample closet space, share a full bathroom featuring tile floors, double sinks with quartz counters, and a tiled shower/tub combination. The primary suite is a true retreat ceiling fan, and a spa like ensuite bath featuring tile floors, dual quartz vanities, a glass-enclosed tile shower, garden tub, and a large walk-in closet. The laundry room, complete with washer and dryer, adds convenience. In addition to the 2-car garage, the townhome enjoys an ideal location bordered by extra parallel parking and a spacious green area with mature trees, perfect for playtime or walking your dog. Residents of Hickory Hammock enjoy resort-style amenities including a zero entry community pool, clubhouse, fitness center, tennis and volleyball courts, fishing pier, playgrounds, parks, walking trails, and a dog park. With top rated schools, close proximity to downtown Winter Garden, Winter Garden Village, and just 20 minutes to Disney and 30 minutes to the airport, this home combines luxury, comfort, and convenience offering the best of Central Florida living.

Listing is courtesy of: WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC (407-922-9169)

Listing Agent: Ricardo Diaz (407-922-6196)

Remarks: Luxury lease opportunity in the gated community of Canopy Oaks, offering an exceptional combination of space, privacy, and convenience in one of Winter Garden's most desirable locations. Ideally situated near major healthcare facilities, business centers, Downtown Winter Garden, Winter Garden Village, and Orlando's attractions and entertainment destinations, this A.R. Bailey Homes Delray model is designed for those seeking luxury living with easy access to everything Central Florida has to offer. Nestled within an intimate community of just 49 homesites, this impressive residence showcases timeless architecture and thoughtful design throughout. A striking exterior presentation features a paver driveway, concrete tile roof, stone-accented elevation, wood-look garage doors, and grand solid wood double-entry doors. Inside, expansive living spaces are filled with natural light and enhanced by architectural ceilings, elegant finishes, and a versatile floor plan designed for both everyday living and entertaining. The chef-inspired kitchen serves as the heart of the home, featuring a natural gas cooktop with exterior venting, built-in oven, upgraded appliances, pot filler, 42-inch cabinetry with crown molding, under-cabinet lighting, tile backsplash, walk-in pantry, and an oversized island overlooking the spacious great room with coffered ceilings. A gated wine cellar adds a distinctive feature rarely found in comparable properties. The first-floor primary suite offers a private retreat complete with dual granite vanities, a soaking tub, oversized walk-in shower with dual shower heads and bench seating, and a custom-designed closet system. A separate first-floor en-suite bedroom provides flexibility for guests, extended family, or a private office. Upstairs, the home continues to impress with a second primary suite, two additional en-suite bedrooms, a spacious loft, guest powder bath, and a covered balcony, creating multiple private living areas throughout the residence. Designed to embrace Florida's indoor-outdoor lifestyle, dramatic corner-opening glass walls and expansive stackable sliding doors create a seamless connection to the covered lanai, enhanced by a motorized retractable screen. The oversized backyard offers privacy and abundant space for outdoor enjoyment. Additional features include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, a mudroom, reading nook, and extensive storage throughout. Residents enjoy access to community walking trails and a playground while benefiting from convenient access to healthcare facilities, shopping, dining, recreation, and major transportation corridors including the Florida Turnpike, SR 429, SR 408, and Interstate 4. Property is currently offered for sale (MLS# O6394059) and lease. Availability and terms are subject to change. Virtual pool rendering shown for illustrative purposes only. No pool currently exists on the property. Any depicted pool or outdoor improvements are conceptual and subject to design, permitting, and approval requirements.

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

Listing Agent: Lisa Rutkowski (407-793-2416)

Remarks: Spacious and beautifully designed 5-bedroom, 3-bathroom home with a 3-car garage located in the heart of Winter Garden. Offering approximately 3,462 square feet of living space, this home features a versatile floor plan perfect for families of all sizes. The first floor includes a formal dining room, a spacious family room, a separate sitting room, and a well-appointed kitchen with granite countertops, ample cabinet space, and a breakfast nook. A full bedroom and bathroom are conveniently located downstairs, making it ideal for guests, extended family, or a home office. Upstairs, you'll find a large loft area, four additional bedrooms, and two full bathrooms. The oversized primary suite offers a spacious retreat complete with dual vanities, a garden tub, a separate shower, and generous closet space. Ideally located near top-rated schools, shopping, restaurants, major highways, and just minutes from downtown Winter Garden. Enjoy easy access to Walt Disney World, other world-famous Central Florida attractions, and all the conveniences the area has to offer. Don't miss the opportunity to make this spacious Winter Garden home your next residence. Schedule your showing today!

Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)

Listing Agent: Amanda Yuan (407-353-2867)

Remarks: Charming 1-bedroom, 1-bathroom apartment with a private 1-car garage, ideally located just minutes from the heart of Downtown Winter Garden. This inviting home features a functional layout, a private garage for convenient parking and additional storage, and an unbeatable location in one of Central Florida's most desirable communities. Enjoy being just minutes from local restaurants, coffee shops, boutiques, the West Orange Trail, the award-winning Winter Garden Farmers Market, and year-round community events. With easy access to major highways, Winter Garden Village, and downtown Orlando, this property offers the perfect combination of comfort, convenience, and location. Don't miss the opportunity to make this charming Winter Garden property your next home. Contact us today for more information or to schedule your private showing.

Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)

Listing Agent: Michele Saenz (720-391-9004)

Remarks: Amazing opportunity in the resort-style Southern Pines Condos in Winter Garden! Freshly painted 1-bedroom, 1-bath condo, ready for move-in. Laminate flooring in the dining area, living room, and bedroom, with ceramic tile in the kitchen and bathroom. The spacious bedroom features a walk-in closet and a dual-entry bathroom that also serves as a guest bath. The kitchen includes a separate dining area and a bonus/flex room. Additional features include a laundry closet, extra storage closets, and no carpet throughout. This gated community boasts a multi-million-dollar clubhouse with a resort-style pool, hot tub, private bar, grilling area, fitness center, indoor basketball and racquetball courts, a dog park, and more. The clubhouse also features a business center, game room, and theater. Enjoy tennis courts, centralized mailboxes, and a car wash area. Resort living at its finest! HOA application and background screening required. The HOA charges a $100 application fee per adult or married couple. Prior eviction or criminal history will be assessed as part of the screening process. Minimum 1-year lease. Renters insurance required. $54/month Spectrum high-speed internet and cable package (exclusive community rate valued at over $200/month). Pets allowed (maximum 2 pets, 30 lbs combined adult weight limit, $250 pet deposit, and $25/month pet fee per pet). A $125 lease processing fee is due after approval and lease signing.

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

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

Remarks: Amazing opportunity in resort style Southern Pines Condos, Winter Garden! The primary bedroom has ample space, a walk-in closet, and a bathroom that doubles as a guest bath with double entry doors. Gourmet kitchen with separate dining area and bonus/flex room. Additional features include a laundry room, extra closets, and no carpet throughout. This gated community boasts a multi-million-dollar clubhouse with a resort-style pool, hot tub, private bar, grilling area, fitness center, indoor basketball and racquetball, gyms, and more. The clubhouse also has a business center, game room, and theater. Enjoy tennis courts, centralized mailboxes, and a car wash area. This is resort living at its finest! * Minimum 1 year lease * Renters insurance mandatory * $54 monthly Spectrum high speed internet and cable service (exclusive deal worth over $200 per month!) * Pets allowed (up to 2 pets, 30 lbs total weight limit, $250 pet deposit, $25 pet fee per month per pet) * No prior evictions or criminal records * Once approved and the lease is signed, there is a $125 Lease Processing Fee to be paid. Unit currently tenant-occupied through 8/13 (pet dog on site). 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: 2 bedrooms, 1 Bath condo with an attached garage. No carpets, all vinyl flooring, including the stairs. Excellent location, end unit. Excellent second bedroom for someone who works from home or for a growing family. Stainless steel appliances in the kitchen.

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

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

Remarks: Virtually Staged. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom, 2500 sq ft ranch-style home, ideally located within a 5-minute walk to historic downtown Winter Garden in the heart of the Golf Cart District. Situated on a spacious corner lot, this home blends classic charm, thoughtful upgrades, and everyday functionality—perfect for families, snowbirds, or anyone seeking a relaxed yet connected lifestyle. Step inside to an open and airy floor plan featuring wood flooring in the main living areas and tile in the kitchen and bathrooms. The generously sized kitchen serves as the heart of the home, offering abundant counter space, ample storage, and natural light—ideal for cooking, entertaining, or casual dining. The fully fenced backyard provides privacy and space for outdoor living, pets, or play. A rare find, the 2-car garage includes a pass-through rear door that opens to an additional parking pad—perfect for a trailer, golf cart, or extra vehicle. You’ll also find a small air-conditioned room inside the garage, ideal for a home office, workout space, hobby room, or climate-controlled storage. Located in one of Winter Garden’s most desirable areas, you’re just a quick walk from local shops, yoga studios, restaurants, the farmers market, and community events. With no HOA and a layout built for both comfort and convenience, this home offers a unique opportunity to enjoy both peace and a vibrant, walkable lifestyle. Flexible Lease Term. Perfect if you are Building a home in Winter Garden. Yard care included.

Listing is courtesy of: LISA REALTY PARTNERS (407-500-5472)

Listing Agent: Lisa Pownall (407-927-1698)

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: Virtually Staged. This 2 bedroom and 2 bath condo is located on the FIRST FLOOR and it comes with tiled flooring throughout, all appliances, and fresh paint. Two assigned parking spaces for your convenience and beautiful amenities like pool, and basketball courts. Located at closed proximity to Downtown Winter Garden, shopping, public transportation, and restaurants. Clean and ready for you! There is a two vehicle max per HOA Rules and Regs. Two parking spots are assigned and residents are only permitted to park in their assigned spots. **RESIDENTS BENEFIT PACKAGE Residents are enrolled in the Resident Benefits Package (RBP). There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. RBP includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application. **RENTERS INSURANCE REQUIRED. Tenant is required to carry a minimum of $100k liability coverage. Personal property coverage is optional.

Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)

Listing Agent: Francisco Nieves-Taranto (321-248-4149)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bathroom townhome in the heart of Winter Garden. This inviting home features an open-concept floor plan with abundant natural light, tile flooring throughout the main living areas, and a spacious kitchen complete with ample cabinet space, breakfast bar, and included appliances. The primary suite offers a private bath, while the additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the convenience of an in-unit washer and dryer, a private fenced patio, and easy, low-maintenance living. Ideally located near shopping, dining, top-rated schools, major highways, and all that Winter Garden offers. Don't miss this opportunity—schedule your showing today!

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Paola Munoz (305-397-6164)

Remarks: Fully furnished rental, turnkey Urban retreat in Downtown Winter Garden — perfect for snowbirds, recent life-changes, divorcees, or anyone craving an active, walkable Florida lifestyle. This immaculate three-story townhome at Park Place offers 2,030 sq ft of stylish is ready for quality living with 3 beds, 3.5 baths and a custom elevator for easy access to every level. Why you’ll love it? Move-in ready: thoughtfully curated furnishings and decor — unpack, relax, entertain. Ideal for flexible living: private first-floor guest suite with full en-suite bath — perfect for in-laws, guests, or a live-work setup. Entertainer’s kitchen: chef-inspired with oversized island, breakfast bar, stainless appliances and gas range. Private primary level: spa bath with dual vanities, soaking tub and large walk-in shower. Comfortable modern features: natural gas, ceramic floors, plantation shutters, tankless water heater and rear-entry 2-car garage. Accessibility: custom elevator makes all three levels effortless. Location: You can live steps away from Winter Garden’s Plant Street scene — Plant Street Market, Crooked Can Brewing, Award winning Restaurants, Boutique shops, and the 22 mile long West Orange Trail. Enjoy yearly festivals, various superb dining, weekly farmers’ markets and nightlife within easy walking distance, plus quick access to major highways and all Orlando’s Theme Parks and Attractions. Perfect fit for: families/couples building a home and bridging the gap, tenants seeking low-maintenance seasonal living, those starting fresh after a divorce who want an elegant, turnkey sanctuary, or anyone who values design-forward, walkable downtown life. Schedule a tour and see how effortlessly this home fits your next chapter. Property is also For Sale.

Listing is courtesy of: BOARDWALK REALTY, LLC (321-241-5171)

Listing Agent: Marc Holland (407-408-4394)

Remarks: Charming two-story home for rent offering 3 bedrooms, 2.5 bathrooms, and a spacious loft, perfect for a home office, playroom, or additional living space. The main living area and upstairs loft feature durable bamboo flooring, while the kitchen offers appliances, tile flooring, a cozy eat-in dining area, and convenient access to the laundry room and two-car garage. All bedrooms are thoughtfully located on the second floor for added privacy. Step outside to enjoy a fully fenced backyard with no rear neighbors, providing a peaceful setting for relaxing or entertaining. Washer and dryer are included for added convenience. Ideally situated just minutes from Winter Garden Village and historic Downtown Winter Garden, you'll enjoy easy access to shopping, dining, entertainment, and one of the nation's top-rated farmers markets. Nearby AdventHealth Winter Garden and the Roper YMCA add to the home's exceptional location and everyday convenience.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Erica Sadelfeld (407-427-0398)

Remarks: Welcome to this extremely spacious 2-bedroom, 1 full-bathroom and 1 half-bath townhome, offering modern updates and a peaceful retreat in a quiet community. Step inside to find a bright and open floor plan with stylish finishes throughout. The fully updated kitchen features new cabinetry, sleek countertops, and stainless-steel appliances, making it a dream for cooking and entertaining. Enjoy the comfort and privacy of generously sized bedrooms, each having their own vanity the main bathroom upstairs, plus an additional half bath for guest's downstairs. The screened-in patio provides the perfect space to relax while overlooking the nicely sized fenced in backyard—ideal for outdoor gatherings or quiet moments of serenity. As a resident, you’ll have access to the community pool, offering a great place to unwind and enjoy the sunshine. With its prime location, modern updates, and tranquil setting, this townhome is a true gem. Don’t miss out on this incredible opportunity—schedule your showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Prentice Williams (321-438-8955)

Remarks: Stunning, brand-new luxury home available for rent in the highly desirable Winter Grove community of Winter Garden! This magnificent two-story residence features 4 spacious bedrooms, 3.5 bathrooms, a massive 3-car garage, and over 4,272 sq. ft. of pristine living space. The open-concept gourmet kitchen is a chef’s dream, fully equipped with high-end stainless steel appliances including a built-in oven, cooktop, microwave, refrigerator, and a dedicated dual wine fridge. Designed with a seamless kitchen-to-family room combo and soaring high ceilings, this layout maximizes natural light. The sprawling primary suite is located upstairs for ultimate privacy and boasts an expansive walk-in closet and a spa-like bathroom. A dedicated laundry room includes a full-size washer and dryer. Rent includes grounds care and property management for a stress-free lifestyle. Exceptional schools, dining, and shopping are just minutes away. Schedule your private tour today!

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Rubens Aranha (407-308-9094)

Remarks: Beautiful 1 bedroom 1 bath condo on second floor in gated community of Southern Pines. Features additional office/solarium room. Open floor plan concept with carpeted living areas and tiled wet areas. Kitchen and bathroom both have granite counter tops. Master bedroom with walk in closet. Community features pool, tennis, basketball, fitness room, playground and more. Great location close to shopping restaurants, major roadways and just minutes from Disney. Easy move in terms first month rent plus one month security. Call today to schedule a viewing.

Listing is courtesy of: BANNER INT'L REAL ESTATE (407-574-5741)

Listing Agent: Nick Horton (407-733-7197)

Remarks: Welcome home to this bright and spacious 2-bedroom, 2-bath condominium in the desirable gated Southern Pines community. This second-floor residence offers approximately 1,276 square feet of comfortable living space with an open-concept floor plan, abundant natural light, and a functional split-bedroom layout that provides added privacy. The well-appointed kitchen features granite countertops, ample cabinetry, and a full appliance package, opening seamlessly to the living and dining areas—perfect for everyday living and entertaining. The spacious primary suite includes a walk-in closet and a private en-suite bath, while the second bedroom and full bath flexibility for guests, family, or a home office. Residents enjoy resort-style amenities including a swimming pool, fitness center, indoor basketball and racquetball courts, tennis courts, playground, clubhouse, and beautifully maintained grounds. Conveniently located just minutes from Winter Garden Village, historic Downtown Winter Garden, major highways including SR-429 and the Florida Turnpike, shopping, dining, and entertainment, this home offers the perfect blend of comfort, convenience, and lifestyle. Don't miss this opportunity to enjoy low-maintenance living in one of Winter Garden's most desirable communities.

Listing is courtesy of: FLORIDA SCANDI REALTY LLC (407-982-7224)

Listing Agent: Hans Tank (407-982-7224)

Remarks: An amazing opportunity has become available for you to become a resident of the guard-gated Stoneybrook West Golf Community. This pool home is located on a less travelled road to enjoy minimal traffic and peace and quiet. Get ready for the magic to begin with an amazing formal living room and dining room. The home then opens into the gourmet kitchen which will impress the chef of the family. A nice family room completes this area that leads to the pool. The backyard is a true highlight, featuring a spacious area, and screened private pool. Lush landscaping surrounds a generous green space, perfect for your enjoyment. An extended patio providing ample outdoor living space. When you’re ready to retire for the evening, this large, 4-bedroom split place allows everyone to have their privacy. Living in the Stoneybrook West community means enjoying resort-style amenities, including a community swimming pool, golf courses, a clubhouse with a fitness center, tennis courts, a pickle ball court, an inline skating rink, and basketball courts. Basic cable and internet are included in the HOA package. In addition to these amenities, the neighborhood is home to highly rated schools, with Whispering Oaks Elementary conveniently located just across the street from the main entry gate. Winter Garden offers excellent shopping and dining options at the Winter Garden Village Mall and nearby areas, with the trendy historic downtown Winter Garden and the West Orange bike trail just a short drive away. Make your private appointment today, while the opportunity still exists.

Listing is courtesy of: MBA REALTY GROUP, INC (407-291-4665)

Listing Agent: Sharon O'Malley (407-291-4665)

Remarks: Move-in ready 4-bedroom, 2.5-bath home located in a desirable Winter Garden/Oakland community. This spacious two-story residence features a functional floor plan with generous living areas, large bedrooms, and ample closet space throughout. Brand-new luxury vinyl flooring was installed on the entire second floor this month, while the main level offers easy-maintenance flooring and no carpet upstairs. The oversized bedrooms provide plenty of comfort and flexibility for families, guests, or a home office. Ideally situated in a well-maintained community, this home offers convenient access to shopping, dining, schools, major highways, and the many attractions of Winter Garden and Oakland. Clean, well-kept, and ready for occupancy, this is a wonderful opportunity to enjoy comfortable living in a great location.

Listing is courtesy of: POINTON REALTY INC (407-395-2860)

Listing Agent: Andrea Pointon (407-446-4414)

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)