Apartments for Rent Near Winter Park High in Winter Park - 21 rentals

Remarks: Welcome home to this charming, move-in-ready residence in the heart of Winter Park! Ideally located near top-rated public schools, shopping, dining, and healthcare facilities, this beautifully updated 3-bedroom, 2-bath home offers approximately 1,450 square feet of comfortable living space. The remodeled kitchen features modern cabinetry, updated appliances, and plenty of space for cooking and gathering. Both bathrooms have been tastefully renovated with stylish fixtures and finishes. Tile flooring extends throughout the main living areas, while the bedrooms feature durable vinyl flooring for added comfort and easy maintenance. Additional highlights include a spacious laundry room, a large tiled Florida room that provides flexible living space, and a fully fenced backyard—perfect for pets, outdoor entertaining, or simply relaxing. Call today for a showing!

Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)

Listing Agent: Alisa Hildebrand (407-310-8962)

Remarks: Beautiful and affordable 2-bedroom, 2-bath condominium for rent in desirable East Winter Park! This renovated and move-in-ready unit features an open floor plan with modern plank-style tile flooring throughout the living areas, neutral colors, and plenty of natural light. The updated kitchen offers newer cabinets, countertops, appliances, and a stylish backsplash, creating a modern and functional space. Both bathrooms have been upgraded with newer vanities and finishes. The carpet was replaced in 2020 for added comfort. The spacious primary bedroom includes a large walk-in closet and a private en-suite bathroom. A stackable washer and dryer, only one year old, are also included for your convenience. Located just steps from the community pool, this well-maintained community is conveniently close to Full Sail University, Valencia College, and University of Central Florida. Enjoy easy access to major highways, shopping, dining, and entertainment, while being only a short drive from Park Avenue. Zoned for highly sought-after Winter Park schools.

Listing is courtesy of: DOUGLAS EDMUND REAL ESTATE LLC (407-853-4402)

Listing Agent: Yuly Rodriguez (407-879-0720)

Remarks: Occupied until July 31 2026. [August 1st 2026 house will be available for in-person showings and Vacant on SentriKey.] Beautiful 4 Bedroom Furnished House with a Pool! This home has an Eat-In Updated Kitchen. There are 3 bedrooms and a bathroom on one side and a large master suite on the other side with a fireplace. The master bathroom has an extra large walk-in shower with a double mirrored dressing area. There is a family room/ FLex Space/ Office Area with a Roku TV, Desk, and Wi-Fi. There is no garage. It has 2 sheds for storage in the back. The neighborhood is nice and quiet. It is conveniently located near Hospitals, Businesses, Restaurants, Schools and Shopping.

Listing is courtesy of: A +ROI PROPERTY (407-718-7994)

Listing Agent: Rene Fossey (407-718-7994)

Remarks: Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms with brand-new carpeting and easy access to the spacious backyard, offering plenty of room to relax or entertain outdoors.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jordan Heidrich (407-223-3495)

Remarks: Experience the best of Winter Park waterfront living in this beautifully updated ground-floor residence at Perle du Lac, ideally located just a short stroll from the boutiques, restaurants, and cafés of Park Avenue. Even more rare, this exceptional residence includes a private covered boat slip on the pristine waters of Lake Virginia, offering direct access to the renowned Winter Park Chain of Lakes. Offering just over 2,700 square feet of thoughtfully designed living space, the home features freshly painted interiors, hardwood and travertine flooring, and elegant custom millwork throughout. The gourmet kitchen is equipped with custom cabinetry, hardwood countertops, and premium Sub Zero, Wolf, Dacor, and Bosch appliances. A versatile library with custom built ins provides the perfect space for a home office, reading room, or additional living area. The spacious primary suite is a peaceful retreat featuring picturesque lake views and a spa inspired bath with dual vanities, a soaking tub, walk in shower, private water closet, and a generous walk in closet. Two additional bedrooms, two full bathrooms, a powder room, and a dedicated laundry room are thoughtfully situated on the opposite side of the residence, offering exceptional privacy for family and guests. Just off the living room, a covered lakeside patio provides the perfect setting for morning coffee or evening sunsets overlooking Lake Virginia. From here, enjoy easy access to your private covered boat slip, making it effortless to spend the day exploring the Winter Park Chain of Lakes. Additional highlights include two assigned garage parking spaces, a private storage room, and access to Perle du Lac's exceptional amenities, including a heated pool, hot tub, beautifully landscaped grounds, and double gated security. Combining the convenience of a walkable Park Avenue lifestyle with the luxury of private lakefront boating, this residence offers one of Winter Park's most desirable living experiences.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jennifer King (407-595-3272)

Remarks: Wonderful 3 bedroom, 2 bath rental in the heart of Winter Park. Location is amazing! Central to Rollins College, UCF, Winter Park Schools, Baldwin Park, and more! Be sure to schedule a private showing.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Brian Rotenberger (407-948-8478)

Remarks: Enjoy comfortable living in the highly sought-after Winter Park area! Close to shopping, dining, and major roadways, this well-located rental provides exceptional value in one of Central Florida's most desirable communities. This first-floor condo is ideally located just steps from the community pool and on-site laundry facilities, offering convenience and easy access to everyday amenities. Don't miss this opportunity to make it your next home.

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

Listing Agent: Leticia Morales (407-515-0318)

Remarks: Welcome home to this beautiful, bright, and well maintained rental in Winter Park. Enjoy a comfortable layout, plenty of natural light, and a warm, inviting feel from the moment you walk in. Conveniently located near shopping, dining, UCF, Full Sail University, and major highways. This is a place you'll love coming home to. Schedule your showing today!

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

Listing Agent: Yigit Orer (407-948-5347)

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: Beautifully renovated 3 bedroom, 2 bath pool home in one of Winter Park's most desirable neighborhoods. Designed with an open floor plan, this home features wood flooring throughout the main living areas, crown molding, and an incredible chef's kitchen with Quartz countertops, a large breakfast bar, custom cabinetry, floating wood shelves, gas range, stainless steel appliances, and abundant storage. The spacious Florida room overlooks a private backyard complete with a sparkling pool, expansive deck, covered seating area, mature landscaping, and a fully fenced yard. Mango and lime trees, landscape lighting, and a powered storage shed with workbench make the outdoor space just as enjoyable as the inside. Additional features include hurricane impact windows, plantation shutters, updated lighting and ceiling fans, a Nest thermostat, surround sound, and a circular paver driveway. Ideally located just minutes from Park Avenue, Rollins College, the Winter Park Racquet Club, Winter Park Golf Club, Phelps Park, and the YMCA, with easy access to top rated schools, dining, shopping, and everything charming about Winter Park.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jennifer King (407-595-3272)

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.

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

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

Remarks: Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a reclaimed Chicago brick fireplace and full-length sliders opening to a resort-style lanai with summer kitchen, wood ceiling, and recessed lighting. Step outside to a private backyard oasis with a sparkling pool, outdoor kitchen area, and no rear neighbors—perfect for entertaining. The first-floor primary suite offers complete privacy with a spa-inspired bath, soaking tub, walk-in shower, and dream closet. The main level also includes a private office, full bath, dining room, laundry room, and generous living spaces. Upstairs features a large loft, rumpus room, four additional bedrooms, and two beautifully designed baths. The oversized two-car garage provides high ceilings, storage, and a flex space ideal for bikes, fitness, or workshop use. Located minutes from Park Avenue dining, shopping, and entertainment, this home delivers luxury, comfort, and an unbeatable Winter Park lifestyle. Professionally managed with exceptional service.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Tab Bish Llc (855-450-0442)

Remarks: Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility. Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal entertaining and casual gatherings. The gourmet kitchen is a chef's dream, complete with an enormous walk-in pantry, high-end appliances, and seamless flow into the dining area. Entertain in style with a wet bar and food service station, perfect for hosting elegant dinners or festive celebrations. Master Suite is an expansive sanctuary that features a spa-like bathroom equipped with a soaker tub, walk-in shower, His and Her vanities Step outside to your private heated lap pool, perfect for fitness or relaxation. The backyard retreat is surrounded by lush landscapingan ideal oasis for quiet relaxation or sunny Florida afternoons. A first-floor bedroom with en-suite bath adds convenience for guests or multi-generational living. Perfectly situated near Audubon Park and Baldwin Park, this home offers unbeatable access to top-rated schools, including Audubon Park K-8 & Winter Park H.S. Ideally situated near Downtown Orlando, Rollins College, hospitals, renowned restaurants, and boutique shopping, making it a prime location for those seeking convenience and accessibility. Explore numerous community parks, perfect for those who enjoy an active outdoor lifestyle. An area rich in culture with nearby museums to explore and learn. This is more than just a homeit's a lifestyle. Experience the best of Winter Park living: elegant, elevated, and effortlessly connected. Pets negotiable with owner approval. Additional fees may apply.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Raquel Elliott (407-921-3772)

Remarks: Look no further, this luxury Modern Townhome offers premium location just minutes from Park Avenue, restaurants, shopping, Hannibal Square, and Rollins College just to name a few! Through the front door you are met with 13-foot ceilings, Modern finishes, Pella double windows, and wood flooring throughout. The Chef’s gourmet kitchen is complete with high-end flat panel cabinetry, Quartz countertops, Wolf gas cooktop, and Subzero appliances! On the second floor there are three bedrooms, 2 full bathrooms, utility room and the spacious primary bedroom is equipped with an oversized walk-in closet, opulent tub, walk-in shower, and Quartz countertops. Schedule your private 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: Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access to everything Orlando. Featuring new flooring and a clean, fresh interior, it is ideal for any lifestyle.

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

Listing Agent: Angel Ramirez (407-967-5368)

Remarks: This 2/2, 1,018 sq. ft. second story condo in Parkview Village features a living room & dining room combo! Screened in balcony, inside utility closet. This unit is close to community pool! Water/Sewer Included! Sorry, No Pets!! Application Fee: $50 / 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 & Pay Stubs (3)**

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

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

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: Winter Park Pines home,4 bed/2 bath ready for a new resident. On a quiet cul-de-sac, this renovated home offers a blend of modern amenities with a fantastic location. It features a brand new kitchen & bathrooms with quartz countertops, updated brushed brass fixtures, with lots of custom touches. It features engineered wood flooring in the living areas and primary bedroom, a convenient indoor laundry room, new windows and sliding doors that let in tons of natural light. Other upgrades include new doors, trim, fresh interior and exterior paint, and a beautiful paver patio. Outside, enjoy all-new landscaping with fresh sod and a new irrigation system, lawncare is included in the rent. This home also has a new roof, garage door, and a HVAC system. This home is also next to the scenic Cady Way trail, ideal for biking, walking, and running. Zoned for highly rated Winter Park schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Call for your showing today! Sorry NO PETS.

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

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

Remarks: Welcome to this fully renovated residence in the heart of Winter Park, where modern upgrades meet timeless charm in one of Central Florida’s most desirable communities. Thoughtfully updated throughout, this home offers a fresh, move-in-ready living experience with stylish finishes and enhanced comfort. Ideally situated near Full Sail University and Rollins College, this property is well-suited for students, faculty, and professionals alike. Zoned for highly regarded schools including Aloma Elementary, Glenridge Middle, and Winter Park High School. Enjoy a vibrant lifestyle with easy access to nearby parks and outdoor destinations such as Kraft Azalea Garden and Mead Botanical Garden perfect for relaxing walks and enjoying nature. The renowned Park Avenue is also just a short drive away, offering boutique shopping, dining, and cultural experiences. Conveniently located with quick access to major roadways, downtown Orlando, and Orlando International Airport, this home also places you within reach of Florida’s beautiful east coast beaches, including Cocoa Beach and New Smyrna Beach ideal for weekend getaways. This fully renovated home offers the perfect combination of location, lifestyle, and modern living, making it an exceptional leasing opportunity in Winter Park. Water is included in the rent. Apply here: https://apply.link/oQ8t72Y

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Betsy Breton-Garcia, Pa (407-580-5350)