Winter Park Apartments for Rent - 81 rentals

Remarks: Stunning 3 beds/2.5 bath/1car garage townhome ready to move-in June at Grayson Square, Winter park. RENT INCLUDES high-speed 1GB fiber optic internet & 75 streaming cable and music channels. The first floor is efficiently laid out with the kitchen, powder room, and spacious gathering room perfect for entertaining with a sliding glass door that opens to the covered lanai and patio that overlooks a pond. Enjoy indoor/outdoor entertaining in your new home. Well-appointed kitchen with top-of-the-line stainless steel appliances and a large quartz countertop. Ample storage throughout. Upstairs you will find a master suite with a spacious walk-in closet. Luxurious ensuite bathroom with glass-door shower and quartz countertop and double sinks. 2 additional bedrooms and a laundry closet with washer and dryer. Grayson Squares offers: Community Pool with Cabana, Zoned for Seminole County Schools, Gated Entry, Near Major Roadways Providing Easy Daily Commutes, Minutes to Shopping and Dining Options on Park Ave. in Downtown Winter Park, 3 Miles to SR 417, 20 Minutes to Downtown Orlando and Orlando Area Attractions. Welcome Home! Equal Housing Opportunity

Listing is courtesy of: P & C PROPERTIES (407-233-1372)

Listing Agent: Fabian Berastegui (407-233-1372)

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: In the heart of Winter Park on a quiet cobbled street, this Mediterranean style 3-bedroom, 3-bathroom house is available to rent today. With beautiful Travertine floors throughout the downstairs of the home, granite countertop kitchen, marble countertop bathrooms, and limestone ornate pillars throughout the home, this home boasts character. Upstairs the home enjoys three bedrooms, two bathrooms, two balconies, and an upstairs utility room. The powder room is downstairs, and patio and a nice size back garden that the tenant can tend to as their own. The front of the house is a brick courtyard. New stainless-steel fridge 2023. 0.9 miles from Rollins College. Perfect for three tenants. Call today Weeks and Months Available

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

Listing Agent: Moire Mckibbin (407-361-1139)

Remarks: Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix, Trader Joe's, Regal Movie Theater, and a variety of restaurants and bars. Join this vibrant community and make this beautiful condo your new investment property or dream home!

Listing is courtesy of: FLORIDA DREAMS REALTY GRP INC (407-654-9992)

Listing Agent: Adriana Montes (407-654-9992)

Remarks: Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area with small private courtyard. Cozy fireplace in the living room, lots of windows bring in the natural light of the Florida sunshine. Water/sewer is included in rent. Community pool and fitness room at the clubhouse only 2-3 minutes walking distance from the unit. Condo conveniently located near Colleges, Shopping and dining. Pets welcomed! (some restrictions apply)

Listing is courtesy of: JEXOR LLC (407-587-5701)

Listing Agent: Carolina Barriento (407-587-5701)

Remarks: REMODELLED - new flooring and freshly painted. Welcome home to this beautiful townhome centrally located in Winter Park, 15 miles away from Park Avenue, just outside of Baldwin Park. Enjoy beautiful water views on the back patio. This home is fresh ready to move in. Available for rent April 15 or later. Top schools, Glenridge middle school, Winter Park high school and Brookshire elementary school. Quiet neighbors. The home comes unfurnished. Amenities - dog park and kids play area. Walking distance to Walmart and 5 minutes away to Costco, Publix and shopping and dining. 20 minutes drive to downtown Orlando. All applicants are subject to credit, background, income, and rental history verification. Minimum income, credit, and HOA requirements (if applicable) must be met for approval, and additional documentation may be requested during the screening process. A security deposit is required at lease signing, and first month's rent is due prior to move-in. Approval is not guaranteed, and all terms, fees, and availability are subject to change without notice.

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

Listing Agent: Livia Petraru (407-269-4556)

Remarks: Discover modern living in this beautifully designed townhome located in the heart of Winter Park. This residence has a spacious layout with contemporary finishes, high ceilings, modern light fixtures and shades, and abundant natural light. Enjoy the convenience of a well-appointed kitchen, an inviting living area, and a private patio for relaxing, and private access to the community pool! The property provides access to community amenities and is situated near local shops, dining, and entertainment venues. Experience the vibrant lifestyle Winter Park has to accord.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

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: Charming 3BR/2.5BA single-family home in desirable Winter Park! Interior features include ceramic tile & laminate flooring, ceiling fans, and a bright kitchen with breakfast bar/kitchen island and stainless-steel appliances. Washer/dryer and major kitchen appliances included. Conveniently located near Hannibal Square, Park Ave, Central Park, Rollins College, the Winter Park Community Center, and the Farmers’ Market. Enjoy classic Florida curb appeal with a welcoming front porch and balcony, plus a functional layout perfect for everyday living and entertaining. Lease term 12 months. $75 application fee each adult. Pets considered with owner approval (pet fees/deposit may apply). Renters Insurance required. Great opportunity to live in one of Central Florida’s most desirable areas. Schedule your showing today!

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Alessandra Oliveira (305-788-0825)

Remarks: Enjoy comfortable Winter Park living in this freshly painted 3-bedroom, 2.5-bath townhome located in the gated community of Grayson Square. Thoughtfully designed for everyday living, this home features a spacious open-concept living and dining area, perfect for entertaining, with direct access to a covered lanai for relaxing outdoors. The kitchen offers stainless steel appliances, quartz countertops, and ample cabinet space for storage and functionality. Upstairs, the owner’s suite includes a large walk-in closet and a private bathroom with dual sinks, quartz counters, and a glass-enclosed shower. A washer and dryer are also included for added convenience. Additional highlights include a two-car garage with epoxy floors and ceramic tile flooring throughout the main living areas, providing both style and easy maintenance. Residents of Grayson Square enjoy gated access, a community pool with cabana, and 1GB high-speed fiber optic internet included in the rent, along with 75 streaming cable and music channels. Ideally located near downtown Winter Park, this home offers easy access to Howell Branch Road, 436, 434, and 417. Starbucks, Publix, and Walmart are just minutes away, while the shopping and dining of Park Avenue are approximately 15 minutes away. Top-rated Seminole County schools are also nearby. A wonderful opportunity to lease a well-maintained home in a convenient Winter Park location. ¡Hablo Español!

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

Listing Agent: Denise Del Castillo (321-960-3110)

Remarks: Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete with a cozy firepit and large privacy bushes that create a secluded, tranquil retreat—ideal for relaxing evenings or entertaining guests. With a deeded dock and boat lift, you’ll have direct access to the Lake Killarney lifestyle you’ve been dreaming of. Come see this special home and start enjoying the lake life you deserve!

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

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

Remarks: Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

Listing is courtesy of: LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV (407-207-2220)

Listing Agent: Smith Salomon (407-724-9127)

Remarks: Welcome to the Four Seasons Condominiums! This great PARTIALLY FURNISHED 2 bedroom, 1.5 bath townhouse condo has much to offer. This completely uniquely designed townhouse features a sunken living room with glass sliding door that open to the private covered patio area, dining room , generous modern kitchen with a colorful glass subway tile backsplash , stainless steel appliances and quartz countertops. First floor also features entry way and half bath for guest. Upstairs features a split bedroom floor plan with two ample bedrooms with loads of closet space. Also upstairs is the modern style full bath with a large vanity and back lit mirror.medicine cabinet. Added features are the washer/dryer combo, laminate floor through out, Ecobee thermostat, new windows and glass doors, window treatments, one assigned carport space with extra open parking, and designer color scheme. Tenant will have access to the pool areas, tennis courts etc. Walk out your door with steps away to the Ward Memorial Park. Association approval is required. Water , sewer and trash is included. Owner will consider pet. Looking for a minimum of a years lease. Available JUNE 2026 SHOWINGS BY APPOINTMENT ONLY. ADVANCED NOTICE NEEDED.

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: John Abbott, Jr (407-398-2330)

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: Beautifully renovated private studio unit (1 bed / 1 bath) located in the rear of the property in a highly desirable area near Winter Park and Downtown Orlando. This cozy detached unit offers a comfortable living space with a private bathroom, ideal for a single professional or student looking for convenience and privacy. Water and electricity are included in the rent, making it an easy and budget-friendly option. The main house and the additional front unit are currently occupied, while this rear studio offers its own separate and peaceful setting. Excellent location with easy access to I-4, Downtown Winter Park, Downtown Orlando, shopping, dining, and Dubsdread Golf Course.

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

Listing Agent: Andres Ospina Rivera (321-821-8446)

Remarks: Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

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

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

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: This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home is the in-unit washer and dryer a rare item within the complex. Community also has an additional laundry facility of it own. From the living room you can Step outside onto the nice open patio….whether it's for morning coffee or evening cookouts with family and friends. The community pool is walking distance and accessible to all residents. Unit has two parking spaces and plenty of additional guest parking. The condo is ideally located, with plenty shopping and dining nearby. Full Sail University and a newly built HCA Emergency room are minutes away. Commuting is made easy with access onto 436, and the 408 which makes it easy to travel to Downtown Orlando or Winter Park

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

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

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)

Remarks: One or more photo(s) has been virtually staged. Lovely home in Winter Park school district. Closet to downtown Winter Park. Updated kitchen and baths on a Quiet street. Lawncare included.

Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)

Listing Agent: Donna Peebles (321-229-6085)