Winter Park Apartments for Rent - 81 rentals

Remarks: Nestled beside Cady Way Park & Trail, this charming home offers an unbeatable location in a quiet, established neighborhood on a peaceful tree-lined cul-de-sac. Enjoy easy access to top-rated Winter Park schools, Winter Pines Golf Club, Showalter Field, AdventHealth Winter Park, Baldwin Park, Downtown Winter Park, and a wide variety of shopping, dining, and entertainment. Inside, you’ll find beautiful terrazzo floors throughout much of the home, with ceramic tile in the spacious family room. The bright kitchen features a window overlooking the large backyard, solid wood cabinetry, and a cozy eat-in dining area. Tastefully updated bathrooms add a fresh, modern touch. The flexible floor plan includes: * Living room * Dining area * Eat-in kitchen * Expansive family room with French doors leading to an outdoor deck and large fenced backyard. Zoned for highly sought-after schools: * Brookshire Elementary * Glenridge Middle School * Winter Park High School This home combines a prime location, comfortable living spaces, and excellent schools—making it a wonderful place to call home.

Listing is courtesy of: LOVEJOY PROFESSIONAL REALTY, INC (321-614-0588)

Listing Agent: Paul Chisholm (407-590-2997)

Remarks: Welcome to the heart of Winter Park! This beautiful first floor condo is located in one of the town’s most iconic buildings, Park Aire. Nestled between the famous Winter Park Golf Course and downtown area where shopping and dining are a must! Other close by attractions include, the Morse Museum, Central Park, Hannibal Square and Scenic Boat Tours. This updated condo features beautiful wood floors, updated kitchen, and nice view from oversized windows. Park Aire has a beautiful private pool area and lush garden area as well as reserved underground parking. This is a great opportunity to live on one of the most well known streets in Central Florida! Call for your showing today! Water and basic internet included. NO PETS and NO SMOKING

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Flory Clark (321-228-2873)

Remarks: Welcome home to this beautifully maintained rental in one of Winter Park's most desirable neighborhoods, zoned for top-rated schools! This spacious 3-bedroom, 2-bath residence features a desirable split-bedroom floor plan, a 2-car garage, and an indoor laundry room complete with a brand-new washer and dryer. The interior has been freshly painted, giving the home a bright, clean, and move-in-ready feel. Designed for both comfortable living and entertaining, the home offers separate formal living and dining rooms, along with a spacious family room featuring a cozy fireplace. The kitchen boasts ample cabinet and counter space, a breakfast nook, and opens seamlessly to the family room, creating the perfect gathering space for family and friends. Step outside through the sliding glass doors to the oversized 23' x 12' screened porch overlooking a fully fenced backyard—ideal for relaxing, entertaining, or enjoying Florida's beautiful weather. Pets are welcome! Conveniently located just minutes from shopping, dining, Rollins College, Full Sail University, Downtown Winter Park, major roadways, parks, and everything Central Florida has to offer. Don't miss this exceptional rental opportunity! Schedule your private showing today, homes in this highly sought-after Winter Park location lease quickly.

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

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

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: 2 bedroom, 1 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New tile floor was installed and freshly painted. Washer & Dryer in the unit. No min credit score is required. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a pool, dog park, and mature landscaping. Convenient access to I-4 and major employment centers. Please use showing instructions.

Listing is courtesy of: MTRE GROUPE LLC (786-282-9992)

Listing Agent: Mauricio Toro (786-282-9992)

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: 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: 2br 2.5ba UPDATED home in Hidden Oaks, Winter Park!!! Kitchen UPDATED with GRANITE counters and solid wood cabinets, upgraded toilets throughout, updated sinks & faucets in all baths. TILE FLOORS downstairs with neutral tone carpet on stairs and second floor. Dry bar area in living room. Both bedrooms are upstairs, each with their own full bathroom! Half bath downstairs off the living/dining room combo. Eating space in kitchen. PRIVATE PATIO in rear, and no rear neighbors! Washer and dryer included. Location in WINTER PARK allows for easy access to University Blvd, FL-408. Short commute to DOWNTOWN ORLANDO. Community pool and playground area. Sorry, no pets. Tenant to register with HOA and purchase parking decal(s) at tenant's expense. Don't wait! Schedule your appointment TODAY. Tenants will be required to obtain renter's insurance that includes $300,000 of liability coverage.

Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P (407-774-9858)

Listing Agent: Greg Mann (407-435-0826)

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: Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a table with 4 chairs - picnic in your own park like back yard. Ready to move in on September 1, 2026.

Listing is courtesy of: BLACKFIN REALTY LLC (407-947-9722)

Listing Agent: Scott Banta (407-947-9722)

Remarks: Welcome home to Winter Park living at its finest in this beautifully updated one-story home where comfort, convenience, and charm come together. From the moment you enter, you'll notice the bright, freshly painted interior, spacious layout, and modern touches throughout—including new updated bathrooms, landscaping enhancements and brand-new stainless-steel appliances. The attached two-car garage adds everyday ease, while the included washer and dryer. Step outside to your private backyard retreat, where a peaceful water view and inviting fire pit creates the perfect setting for morning coffee, weekend gatherings, or quiet evenings under the stars. Professional landscaping and pest control are also included, so you can spend less time on upkeep and more time enjoying your home. Ideally located near Downtown Winter Park, Park Avenue, local coffee shops, restaurants, grocery stores, entertainment, and daily conveniences, this home also offers quick access to Maitland, Casselberry, Orlando, I-4, and SR-417. Zoned for Seminole Country Schools. If you're searching for a stylish, low-maintenance rental in a prime location, this Winter Park home is ready to welcome you. Schedule your showing today!

Listing is courtesy of: CENTRAL FLORIDA REALTY MANAGEMENT LLC (407-542-4403)

Listing Agent: Kevan Patel (407-491-3559)

Remarks: For Rent – Beautifully Updated Home Near Lake Killarney! Located just minutes from Downtown Winter Park, Park Avenue, I-4, and Maitland, this beautifully updated home offers convenient access to nearby shops and dining. The 3-bedroom, 3-full-bath layout features open living spaces and modern finishes throughout. LVP flooring flows through the entire home, complemented by fresh paint, abundant natural light, and designer fixtures. The kitchen boasts a large island and nicely appointed stainless steel appliances, perfect for everyday living and entertaining alike. The primary bedroom offers plenty of space and direct access to the covered patio. Its en suite bath is a true spa retreat, featuring a floating vanity, luxurious soaking tub, walk-in shower, and an expansive walk-in closet. Two comfortably sized guest bedrooms share an updated hall bath. Situated on a spacious quarter-acre lot, the home includes a large fenced backyard with a deck, ideal for outdoor entertaining and relaxation. Lawncare is included. Available August 1, 2026. Rent is $4,500/month with a $5,000 security deposit. Pets will be considered and are subject to owner approval; a $500 non-refundable pet deposit is required. Application fee is $50 per adult. Schedule your showing today!

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

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

Remarks: Freshly remodeled and move-in ready, this 3-bedroom, 2-bath townhome offers comfortable living in a highly desirable Winter Park location. The open-concept living and dining areas create a welcoming space for everyday living and entertaining, while the convenient pass-through window connects the kitchen and dining room for added functionality. The brand-new kitchen remodel features granite countertops and all-new stainless steel appliances. The spacious primary suite includes a walk-in closet and private en suite bath with a walk-in shower. Two additional bedrooms and a full bath offer ample room for everyone. Tile flooring throughout provides easy maintenance and durability. Enjoy time relaxing outdoors on the covered patio in the privacy of the fenced backyard. Additional recent updates include a new roof, all-new Low-E energy-efficient windows, and a new vanity, toilet, and faucets in the guest bath. Residents enjoy access to the community pool and clubhouse, along with a prime location close to shopping, dining, entertainment, and major roadways. EV parking with outlet for your charger. With its combination of recent upgrades, community amenities, and sought-after Winter Park address, this is the perfect place to call home.

Listing is courtesy of: HAVEN PROPERTY GROUP LLC (407-928-3894)

Listing Agent: Jerry Agan (678-873-4463)

Remarks: Virtually Staged. Welcome to Park Aire, a small iconic condo community located on Park Avenue by the WP9 golf course. 1st floor unit with oversized window views of the golf course and Casa Feliz. This one bedroom unit has an updated kitchen and bath. Amenities include a covered parking space, swimming pool, social room, a guest room for rent, open air patios on the third floor, under building covered parking spot and laundry in building garage and 2nd floor. You are close by for shopping and dining along Park Ave area.

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

Listing Agent: Andy Holland (407-948-7172)

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: Jennifer Linton (407-488-9392)

Remarks: Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

Listing is courtesy of: COLONIALTOWN REALTY (407-896-7300)

Listing Agent: Alexander Scures (407-925-5338)

Remarks: MOVE-IN SPECIAL-$230 OFF THE 1ST MONTH'S RENT!!!! Welcome home to this beautiful 3-bedroom, 2.5-bath end-unit townhome with a one-car garage, located in the highly desirable gated community of Vistas at Lake Howell in Winter Park. This rare rental opportunity offers a spacious and inviting floor plan with a large living room featuring laminate flooring and a built-in entertainment center. The fully equipped kitchen includes stainless steel appliances, solid-surface countertops, and solid wood cabinetry. All bedrooms are located upstairs for added privacy. The spacious primary suite features a large walk-in closet. The versatile third bedroom can serve as a traditional bedroom, home office, guest room, or flex space to suit your lifestyle. The upstairs laundry closet adds everyday convenience by keeping everything on one level. All Keller Williams residents are enrolled in the Resident Benefits Package (RBP). The RBP includes HVAC air filter delivery, renters' insurance, credit building to help boost your credit score with timely rent payments, $1M Identity Protection, utility concierge service to make utility connections a breeze during your move-in, our best-in-class resident rewards program, and much more. More details are available upon application. Renters' insurance is required, and proof of coverage must be provided. Conveniently located near shopping, dining, Full Sail University, Rollins College, and UCF, with easy access to SR 408, SR 417, SR 426 (Aloma Avenue), and SR 436 (Semoran Boulevard), making commuting throughout Central Florida quick and convenient. This exceptional townhome won't last long!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Kelly Popchock (863-207-7552)

Remarks: Gorgeous FULLY FURNISHED 1 Bedroom/1 Bath apartment with private entrance, in Winter Park. This attached apartment has been thoughtfully renovated with beautiful Luxury European Design. This apartment features a private courtyard and private entrance. Upon entering you will be greeted by a spacious living room fitted with a sofa chase, 55” Flat Screen Television, a small dining table/desk, modern storage cabinetry and a mini-split AC system. The kitchenette features Refrigerator/Freezer (located in an alcove), 2 burner hot plate, full-size sink, cookware and dinnerware, microwave, Keurig coffee maker, plenty of cabinet space and a full-size LG Thin Q Washer Dryer Unit. The master bedroom provides ample space including 2 Wardrobers with Drawers, King Size Bed, Antique English Desk/Hutch and a separate Mini-Split AC for maximum comfort. The Private Bath features luxurious finishes including a beautiful soaker tub, double vanity and shower with dual rain shower with body jets, sprayers and ample storage for linens. This location provides easy access to Baldwin Park, Downtown Winter Park, local walking trails, restaurants and more!!! Call today to schedule your private viewing.

Listing is courtesy of: GATE PROPERTIES & MANAGEMENT INC (407-704-7904)

Listing Agent: Nicholas Wild (407-704-7904)

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: One story Winter Park home with 3 Bedroom , 2 full bath. AVAILABLE now ! Great accessible location close to shopping, major roadways, schools and a short drive to Downtown Orlando. This Home has tile and laminate flooring throughout, easy maintenance clean modern appearance. Kitchen comes with all major appliances, large family room with high ceilings. Unit Feature an in-unit washer and dryer. Primary suite with his & hers closets and private bathroom. Property is on a large corner lot with a great deal of outdoor space, a screened/cover rear patio. Community offer quite atmosphere and a community pool . Conveniently located just off 436 in Winter Park, this home offers the perfect mix of comfort, convenience, and community living. Easy to see call today

Listing is courtesy of: KIMBRIDGE REALTY, LLC (407-755-7367)

Listing Agent: Scott Butts (321-239-8509)