Winter Park Apartments for Rent - 82 rentals

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: This cozy three-bedroom, two-bath home is close to downtown Orlando, College Park, Winter Park, hospitals, Orlando Science Center, restaurants, and shopping. The backyard is fenced, and landscaping is included. It is in an excellent school district. The owner is looking for good tenants to take care of the freshly painted and proudly maintained property.

Listing is courtesy of: INT'L PROFESSIONAL REALTY INC (407-699-7718)

Listing Agent: Lorena Ortega (407-256-3631)

Remarks: Characterized by its expansive layout and modern charm, 4571 Kawilla Crest Place in Winter Park, FL, offers an extraordinary living experience with six spacious bedrooms and five full bathrooms. Boasting a generous 3,676 square feet, this property is perfect for those who appreciate space and comfort. The open-concept design fosters a seamless flow between living areas, creating an inviting atmosphere for both relaxation and entertaining. Large windows throughout the home allow natural light to flood in, highlighting the elegant interior finishes. Each of the five bathrooms is thoughtfully designed with style and convenience, ensuring a comfortable experience for everyone. The well-appointed bedrooms provide ample space for rest and rejuvenation, making this home ideal for larger groups or families. In addition to the main living space, the home features a private mother in law suite with its own separate entrance. This self-contained suite includes a bedroom, bathroom, laundry area, and full kitchen, making it ideal for extended family, guests, or additional living space. Nestled in the serene setting of Winter Park, this residence offers a perfect balance of tranquility and accessibility. With its prime location, residents will enjoy proximity to local amenities, dining, and entertainment options. Embrace the opportunity to make this stunning property your next home, where spacious living meets unparalleled comfort. Discover the perfect blend of style and functionality at this remarkable address. Rent includes lawn, pool and pest care. The home is equipped with solar panels, which help keep electricity costs low. Prospects must view the home prior to applying. Tenant requirements include: minimum gross household income of 2.5x the monthly rent amount, a favorable background and credit screening, favorable rental history and references, proof of income/employment. A security deposit (same as rent) is due upon applicant approval to mark listing as Pending. First month rent and last month's rent are due 7 days prior to lease start date. The owner does not allow smoking in or around the home. Tenants are required to provide proof of renter's insurance. Tenants are responsible to pay all utilities and put in their name, where applicable. Please review these requirements BEFORE requesting a showing. After viewing, listing agent will provide application link, upon request. If a tenant-prospect chooses to apply for one of our rental properties, that DOES NOT guarantee that the prospect's application will be approved. The application fee is NON-REFUNDABLE. Tenant approval is contingent on a lease start date within 30 days of approval.

Listing is courtesy of: HOST MANAGEMENT GROUP LLC (407-680-1234)

Listing Agent: Lukasz Sokolowski (407-680-1234)

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: Welcome to this beautifully renovated 2-bedroom, 1-bathroom second-floor condo on picturesque Lake Killarney. This move-in-ready gem offers the perfect blend of modern conveniences and serene lakefront living. The stylish kitchen features granite countertops, a contemporary backsplash, and new stainless-steel appliances, including a dishwasher and a convenient combination washer/dryer. The bathroom is tastefully designed with a walk-in shower, while new luxury vinyl flooring flows seamlessly throughout the condo. A screened-in patio provides lake views, making it the perfect spot to enjoy your morning coffee or unwind in the evening. This property includes one designated parking space and ample visitor parking. Stunning lakefront sunsets are just steps away from your front door. The community offers exceptional amenities, including a lakefront pool, shuffleboard courts, and a park equipped with grills, picnic tables, and lounge chairs. A private boat dock and ramp provide access to Lake Killarney for fishing, canoeing, wakeboarding, or waterskiing, with canoe and kayak racks available for your convenience. Located within walking distance of Trader Joe's and Winter Park Village, and just five minutes from the renowned Park Avenue, this condo boasts a prime location. Rent includes water, sewer, trash, and access to all community amenities. This property is the perfect opportunity to embrace Florida’s lakefront lifestyle with modern comfort and unparalleled convenience.

Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)

Listing Agent: Monika Kenney (407-300-2941)

Remarks: Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 1,266 car garage and approximately 1,266 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated.

Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)

Listing Agent: Laidy Mataushek (844-874-2661)

Remarks: 3/1, Carport, Single Family Home, Living Room, Dining Room, Eat in Kitchen, Stainless Steel Appliances Included: Stove, Microwave, Refrigerator, Dishwasher, Disposal, Inside Utility Room with Washer and Dryer Hookups, Laminate Wood Flooring & Ceramic Tile Throughout, Fenced Backyard, Pets Ok Upon Owner's Approval, NO SMOKING, Year Built: 1957/1300 Sqft.

Listing is courtesy of: LEGENDS REALTY (407-333-1010)

Listing Agent: Tina Lopez (407-333-1010)

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: Welcome home to this charming residence tucked away on a quiet cul-de-sac in a welcoming neighborhood. Situated on an oversized 0.23-acre lot, this home offers plenty of outdoor space to relax, entertain, or simply enjoy the peaceful surroundings. Inside, the thoughtfully designed split-bedroom floor plan provides both comfort and privacy. The updated kitchen features beautiful granite countertops, stainless steel appliances, and a window overlooking the spacious backyard, making meal preparation both functional and enjoyable. The bathrooms have also been tastefully updated with granite finishes for a modern touch. The inviting living room is the perfect setting for movie nights or entertaining guests. Additional conveniences include a digital peephole at the front door, an epoxy-coated garage floor, and a powered storage shed offering extra space for hobbies, tools, or equipment. This well-maintained home combines modern updates with practical features in a desirable location, making it an excellent place to call home. Schedule your private showing today and discover everything this property provides.

Listing is courtesy of: D & D PROPERTY MANAGEMENT SOLUTIONS LLC (407-434-1693)

Listing Agent: Allan Dion (407-434-1693)

Remarks: STYLISH, STUNNING AND RENOVATED TO THE NINES. This 3-bedroom, 2.5-bath Winter Park home has great access to Interstate-4 and both Winter Park and Orlando downtown areas. With all interior spaces updated, this fantastic home is almost totally rebuilt with brand new electrical, plumbing, heating and air, ductwork, roof, flooring and Energy Star doors and windows. In addition to the 3 upstairs bedrooms, the downstairs has a bonus room which is perfect for a den or playroom and a convenient interior laundry room. The lot is 6,750 sqft and is fenced and gated (electronic with remotes) offering a nice new patio of clay pavers, a carport, and large backyard. This 1,774 sqft of living space is perfect for the tenant who wants quality, style and convenient location. This one is MOVE IN READY AND WAITING FOR YOU. There is a $99 for each adult application fee and once approved the first & last month’s rent will be due along with the security deposit and any applicable pet fee and deposit.

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

Listing Agent: Johnny Hurlburt (407-579-3168)

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: 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: 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: FURNISHED 6-12 month executive rental available immediately in Lake Killarney Condominiums. Perfect for one or two residents, this condo offers a bedroom with King-sized bed and walk-in closet, a separate office, and a sunroom with floor to ceiling windows. Newly installed bathroom and central air system. Combo washer/dryer unit in kitchen or optional coin laundry in building. Sorry, no tenant pets allowed per complex rules. One reserved parking space plus ample visitor parking. Residents will enjoy the private lakefront park, picnic tables and Adirondack chairs, and waterfront swimming pool. Located adjacent to the Trader Joe's plaza and only one mile to Park Avenue.

Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)

Listing Agent: Robert Arnold, Jr (407-389-7318)

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: 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: 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)