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

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: 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: 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: Welcome to 224 Faulkner St, a well-maintained 3-bedroom, 2-bathroom single-story home located within the golf cart district of desirable Winter Garden. As you enter the home, you're welcomed into a spacious living and dining area featuring vaulted ceilings, abundant natural light, and direct access to the backyard. The kitchen includes a breakfast bar, refrigerator, oven, and dishwasher, and flows conveniently into the dining space. The primary suite is privately positioned to the right side of the home and features an ensuite bathroom with dual vanities, a separate shower and toilet area, and a walk-in closet. Two additional bedrooms are generously sized and share a full family bathroom. Additional features include a dedicated laundry room with a washer and dryer, interior access to the two-car garage, and a driveway with ample parking. Outside, the home offers a spacious yard perfect for enjoying Florida living. Conveniently located approximately half a mile from Plant Street, this home offers easy access to downtown Winter Garden's shopping, dining, farmers market, and local events.

Listing is courtesy of: WINTER GARDEN REAL ESTATE (407-910-1066)

Listing Agent: Anthony O'Reilly Brookes (407-910-1066)

Remarks: Ready to move-in One-bedroom, one Jack-n-Jill bath. Fully renovated with fresh paint from top to bottom. Luxury Vinyl floors from stairs thru out the unit. the Bathroom has ceramic tile. The unit features a study/den perfect if you have a home office or need a craft room.

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

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

Remarks: STUNNING GATED TOWNHOME IN WINTER GARDEN – AVAILABLE NOW! ? Welcome home to this stylish 2-story, 3-bedroom, 2.5-bathroom townhome featuring an attached 2-car garage. Tucked inside the highly desirable, gated community of Tucker Oaks in the heart of Winter Garden, this home offers 1,544 sq. ft. of bright, open living space designed for easy everyday living and effortless entertaining! HOME HIGHLIGHTS Bright & Airy: Open-concept main level with abundant natural light and warm wood-tone flooring. Chef's Kitchen: Spacious layout featuring full-size appliances, ample cabinetry, and a connected dining area. Upstairs Oasis: Three generous bedrooms located upstairs, including a private, spacious primary suite. In-Unit Laundry: Dedicated washer and dryer hookups for your everyday convenience. Parking Galore: Attached 2-car garage with a private driveway. Year-Round Comfort: Central A/C and forced-air heat keep you perfectly comfortable. Guest-Friendly: Convenient half-bath located on the main floor. THE COMMUNITY & LOCATION Tucker Oaks is a beautifully maintained, gated community in the West Orange corridor. You are just minutes away from: Downtown Winter Garden (Charming shops, local dining, and weekly farmers market) West Orange Trail (Miles of paved walking and biking trails) Hamlin Town Center & Disney theme parks Easy Commutes: Quick access to SR-429 and the Florida Turnpike to get anywhere in Central Florida fast! TOP-RATED SCHOOLS Elementary: Sunridge Elementary Middle: Lakeview Middle High: West Orange High School LEASE DETAILS & FEES Lease Term: 12 Months (Available Immediately!) Pet Policy: NO PETS, please. Utility & Maintenance Reduction Program: $15/month (Includes high-quality AC filters shipped directly to your door for hassle-free replacement). One-Time Move-In Admin Fee: $250 Please Note: Applicants may be subject to HOA application fees, deposits, rules, policies, and procedures. All County does not accept responsibility for HOA rental fees and/or board approval processes. Final security deposit amount may vary based on screening results and rental criteria. READY TO TOUR YOUR NEXT HOME? Don't wait! Schedule your self-guided showing today through Tenant Turner. Listed and professionally managed by: All County CFL Property Management 390 N. Orange Ave Suite 2300, Orlando, FL 32801

Listing is courtesy of: ALL COUNTY CFL PROPERTY MGMT (407-802-2379)

Listing Agent: Vicky Ramos (689-231-6171)

Remarks: Beautiful Fully Furnished, French Country model Home. This gorgeous pool home features 5 Bedrooms (2 Master Suites 1st and 2nd floor) plus an office/study with 4.5 baths, Cinema (with top of the line equipment and sound system, over $30K) with 3 car garage on a prime location in Winter Garden, nearby shopping, highway, hospital and Disney Parks. Canopy Oaks is a gated community, home of 49 beautiful Estates just between the Winter Garden Village and the quaint historic downtown Winter Garden, Orlando's most popular suburb! Location is a privilege. The Mediterranean style property features a pavered driveway, tropical taylored landscape, iron banister railings, arched wooden entry door, soffit and coach lights, plenty of tall windows with beautiful plantation shutters throughout, lots of natural light, This open floor plan offers a huge great room for gathering with family and friends flows easily into the kitchen, dining area, and out to the amazing pool area to a beautiful and fully equiped Summer Kitchen through the 3-panel stackable sliding doors onto a covered lanai equiped with an automated screen, creating a bigger indoor-outdoor space. Kitchen features the large granite island which can easily seat 5 guests, stainless steel appliances, custom cabinetry, and pendant lights. The luxurious second floor features a large family room which opens through stackable sliding glass doors overlooking a lovely porch overlooking the pool area. Master suite is gorgeous with tray ceiling, wet bar with a kitchenAid Wine Cooler/coffee station, an expansive master closet, and an impressive curved dual walk-in shower and a free-standing soaking tub, Master also have a private entrance to the upstairs balcony. This community has a park and walking trail around a small pond. Easy access to 429, 408, Highway 50, turnpike, Disney World, and Universal. Schedule a showing quick, you don't want to miss this one!

Listing is courtesy of: B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE (407-217-7573)

Listing Agent: Oscar Rodriguez (321-297-7264)

Remarks: Welcome to your dream home in the heart of Winter Garden, Florida! This beautifully maintained 6 -bedrooms, 3-bathrooms residence in the Alexander Ridge community offers the perfect blend of comfort, style, and modern living. Step inside to an inviting open-concept floor plan filled with natural light and thoughtful upgrades. The spacious living area. The kitchen is a chef’s dream with stainless steel appliances, granite countertops, a large island, and ample cabinet space. The primary suite provides a peaceful retreat with a walk-in closet and a luxurious in-suite bath complete with dual vanities, a soaking tub, and a separate glass-enclosed shower. Five additional bedrooms offer flexibility for family, guests, or a home office. Enjoy outdoor living with a covered patio, perfect for morning coffee or weekend BBQs. Just steps away, the resort-style community pool offers a great place to cool off and connect with neighbors. Located in a vibrant, family-friendly neighborhood just minutes from historic Downtown Winter Garden, top-rated schools, local shops, dining, and major highways — this home has it all. Don’t miss your chance to live in this beautiful home — schedule your private showing today!

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

Listing Agent: Claudia Montes (407-484-5261)