Winter Park Apartments for Rent - 77 rentals

Remarks: Beautifully Renovated 2-Bedroom Home in Desirable Winter Park! Welcome to this charming newly renovated 2-bedroom, 2-bath home located in the highly desirable Winter Park area. Featuring modern upgrades and a warm, inviting layout, this home offers the perfect blend of comfort and style. Enjoy ceramic tile flooring throughout the first floor, brand-new carpet in the upstairs bedroom, and a beautifully updated kitchen complete with new cabinets and appliances for a fresh contemporary feel. Step outside to your own private fenced yard—perfect for relaxing, entertaining, or enjoying peaceful outdoor living. Residents also have access to fantastic community amenities, including a swimming pool and tennis courts for recreation and leisure. Conveniently located near shopping, dining, parks, and everything Winter Park has to offer, this move-in-ready home is an opportunity you won’t want to miss. Schedule your showing today!

Listing is courtesy of: TRANSCEND REALTY (407-518-7653)

Listing Agent: Jacob Hara (407-933-5478)

Remarks: Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center, Basic tenant requirements: 650+ credit score, no BAD history, no BAD rental history, income 3 times monthly rent as a household. FIRST, LAST and SECURITY DEPOSIT MAY required.

Listing is courtesy of: CINO INTERNATIONAL INC (407-354-3318)

Listing Agent: Daniel Zheng (407-683-1881)

Remarks: Virtually Staged. Available for Rent in the Gated Community of Vistas at Lake Howell! **INTERIOR JUST REPAINTED!** Welcome home to this beautifully maintained 2-bedroom, 2.5-bath townhome in the desirable gated community of Vistas at Lake Howell in Winter Park. Featuring tile and luxury vinyl flooring throughout—no carpet—this home offers easy maintenance and a clean, modern feel. The open-concept floor plan creates an inviting space for everyday living and entertaining, with the living and dining areas flowing seamlessly to a private screened patio, perfect for enjoying your morning coffee or relaxing after a long day. Upstairs, you'll find two spacious bedroom suites, each offering large walk-in closets for abundant storage. Separating the bedrooms is a generous open loft, ideal for a home office, media room, study area, or fitness space. The primary suite features a walk-in closet complete with built-in organizer shelving to maximize storage and organization. Ideally located just minutes from shopping, dining, parks, and entertainment, this home also offers quick access to major roadways, making commuting a breeze. Convenient to UCF, Full Sail University, Winter Park, Downtown Orlando, and more, this location truly puts everything Central Florida has to offer within easy reach. Don't miss this opportunity to enjoy low-maintenance living in a sought-after Winter Park community!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Sharyon Neilen (407-810-2888)

Remarks: WINTER PARK 4BR/2BA, Single Story, Built in 2016. Located in the GATED COMMUNITY of Enclave At Aloma. Fantastic open floor plan. Plank wood-looking ceramic tile throughout the entire home. Loads of options. House was extended 4 feet to increase the size of dining room, great room, and master bedroom. 10' x 40' Covered Lanai in the rear. Center Island with Pendant Lighting in the Kitchen. Stainless Steel Appliances, Upgraded Cabinets, Crown Molding. Solid Surface Counters throughout the home. Volume Ceilings & Recessed Lighting. Master Bathroom has dual sinks, a huge walk in shower with a seat, and private toilet closet. Inside utility room with washer/dryer hook-ups. Easy access to the major highways 417, 426, 436, and a short commute to downtown Winter Park. First, Last & Security are required. No smoking or vaping. No pets

Listing is courtesy of: LAKEFRONT REALTY, INC. (407-592-6700)

Listing Agent: Bill Cook (407-592-6700)

Remarks: Unfurnished – No Pets. Beautiful modern 4-bedroom, 2.5-bath home located in one of Winter Park's most established and sought-after neighborhoods. This spacious home features wood and laminate flooring throughout, a downstairs bonus room, a separate utility room, a private second-floor sun deck/terrace perfect for relaxing or entertaining, and a first-floor concrete patio. The contemporary kitchen is equipped with 42-inch European-style cabinetry, granite countertops, and stainless steel appliances. Residents also enjoy access to attractive community green spaces.Ideally situated within walking distance of Winter Park Hospital and AdventHealth Winter Park, this home is also just minutes from Cady Way Park, Ward Park, shopping, dining, and entertainment along Aloma Avenue and Lakemont Avenue. Conveniently located near Rollins College, the University of Central Florida (UCF), and Full Sail University, making it an excellent choice for healthcare professionals, faculty, and other professionals. Landscaping and lawn care are included in the rent.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Alfredo Karam (407-476-5115)

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: Welcome to this beautifully updated first-floor 2-bedroom, 2-bath condo in the highly desirable Killarney Bay community in Winter Park, offering a perfect blend of comfort, style, and lakefront living. Step inside to an inviting open-concept layout filled with natural light and designed for both everyday living and entertaining. The modern kitchen features upgraded cabinetry, sleek countertops, and newer appliances, making it as functional as it is stylish. The spacious living and dining areas flow seamlessly, leading to a relaxing setting just steps from Lake Killarney, a fishing dock, and serene water views—perfect for enjoying Florida living at its best. The primary suite offers a private retreat with a custom-tiled walk-in shower, while both bedrooms feature cozy carpet flooring for added comfort. The main living areas are finished with durable vinyl flooring, combining style and easy maintenance. Additional highlights include a full-size washer and dryer in a dedicated laundry room, generous storage, and the convenience of first-floor access. Located just minutes from shopping, dining, and major roadways, and zoned for sought-after schools, this home offers both lifestyle and location. Residents can enjoy a community pool overlooking Lake Killarney, along with kayak and paddleboard storage for easy access to the water. Just minutes from Winter Park Village, Trader Joe’s, and a wide selection of dining and shopping, with quick access to I-4, this location truly stands out. Schedule your showing today! Top Rated Schools* Killarny Elementary School Collage Park Middle School Edgewater High School *Please verify schools with Orange County School District Criteria for approval: • $50 application fee •$150 HOA approval required • 580+ credit score (Low score thanks to medical or student loans? You may still qualify with a higher deposit. (Please refer to the flyer for specific information.) • Income must be 2.5x rent • No evictions or unpaid rent • Background checks are done on all adults. We are HUD compliant in our review process. For details refer to Qualification Criteria Flyer included in photos. Move-In Cost Breakdown: • $2450 Security Deposit (Due immediately! Home is only held for you after deposit has been paid!) • $2450 First month’s rent+ fees due (Due 10 days before move-in) Proration applies to month #2. • $125 Admin Fee - This fee will increase if you need to rush the move in. Monthly Fees (in addition to rent): • $65 Internet (1 Gig!) Discounted rate for Supercharged Spectrum WiFi courtesy of Rent Prosper perks( Optional) • $55 Resident Benefit Package - Includes the required renter’s insurance, as well as pest control, AC filters, and other magical adulting tools. • $2 Transaction Fee • Pet Rent (if applicable) — Pets must be approved through petscreening and Community association). ? All pet/ESA/no-pet declarations go through petscreening Total Monthly Charges: $2,622 Includes Rent, Electric Fee, Resident Benefit Package, Lawncare and Transaction Fee)

Listing is courtesy of: RP INVESTMENT REALTY LLC (407-283-7133)

Listing Agent: Giovanna D'Alessandro (609-840-7000)

Remarks: This Winter Park condo features two bedrooms and three bathrooms, with an attached garage for convenient parking. The entrance welcomes you with a charming foyer. At the heart of the spacious open great room is the kitchen—highlighted by custom cabinets, quartz countertops, and stainless-steel appliances, all thoughtfully arranged on the first floor. An oversized counter provides space for dining, and the combined dining and living area provide access through French doors to the enclosed rear porch. The living room is enhanced by a decorative built-in electric fireplace. Upstairs you'll find two bedrooms, each with en suite baths. The master bedroom stands out with custom closets, a large window that fills the space with natural light and raised ceilings that add dimension. Two-tone contrasting colors create a cozy and inviting atmosphere, and the master bath includes a double sink vanity, walk-in shower, and linen closet. The second bedroom also boasts raised ceilings, custom closets, and its own private bathroom. Lazy Oaks Condominium is a highly sought-after community in Winter Park, located off Old Howell Branch Road. Residents enjoy amenities such as monthly pest control, guest parking, curbside garbage collection, and private mailboxes.

Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)

Listing Agent: Joyce Gary (407-782-3276)

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: 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 landscaping an 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 home it'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: Come see this 4 bedroom 2 bath in the beautiful Winter Park neighborhood of Eastbrook. This home is completely move in ready with granite counter-tops and stainless steel appliances in the kitchen and new microwave. Large open kitchen/living room. Spacious bedrooms with lots of closets and storage space. Updated modern light fixtures and fans adorn the rooms throughout the home. Home is tiled and has new laminate throughout. Fenced backyard with huge screened in back porch.

Listing is courtesy of: ABSOLUTE REALTY GROUP, LLC (407-673-1400)

Listing Agent: Courtney Davis (407-493-8329)

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: ***New residents will receive three (3) complimentary months of the Resident Benefits Package (RBP). Take advantage of this exclusive offer and enjoy added benefits at no cost for your first three months!*** This property will not last long! Schedule a showing today! Winter Park Two Story 2/2.5 Townhome located in the Private - Gated Community of Vistas at Lake Howell. All Stainless Steel Kitchen Appliances Included (Dishwasher, Range, Refrigerator, and Microwave). Living & Dining Room Combo. All bedrooms are located on the second floor. Primary Bedroom has custom closet design and ensuite bathroom. Ceiling Fans in Many Rooms. Half Bathroom Downstairs. Screened in Private Back Patio/Porch. Attached One Car Garage. Convenient to SR-436 & I-4. Laundry Room is upstairs near bedrooms. Washer and Dryer Convenience Only. Separate HOA Application & Approval Required. Schedule a showing today! All our residents are enrolled in our Resident Benefits Package for $55.00 per month, charged as additional rent. This package includes Pest Assurance powered by Pest Share, access to an online resident portal, and availability of a dedicated 24/7 maintenance portal. Additionally, it offers monthly reporting of rental payments to Experian RentBureau, bi-monthly home delivery of replacement HVAC filters, and the use of resident-completed inspection technology. Residents are entitled to one late fee waiver during their residency and have access to concierge utility services

Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC (407-557-3164)

Listing Agent: Elizabeth Santiago Moyet (321-231-2105)

Remarks: This charming 2-bedroom, 2-bath duplex is ready for immediate move-in, offering a warm and inviting atmosphere for comfortable living. Step inside to discover a thoughtfully designed space with tile flooring throughout, providing both durability and easy maintenance. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances and solid-surface countertops. This kitchen effortlessly flows into the spacious living room, where a cozy wood-burning fireplace beckons for memorable gatherings and relaxing evenings. The large master bedroom is a true sanctuary, boasting an en-suite bath complete with dual vanities and a convenient walk-in closet. But the delights continue outdoors, as you'll be treated to a vast, fenced-in backyard adorned with plenty of shade – perfect for your family to savor outdoor moments and create lasting memories. 3254 Howell Branch Road enjoys an excellent location in desirable Winter Park, placing you close to everything you need. You'll find convenient access to SR436 shopping and dining, nearby hospitals, and the vibrant University of Central Florida campus. $1,600.00 Monthly Rent (MOVE IN BY JULY 31st) Pets Not Allowed! Tenant Liability Insurance **Required**

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Carissa Lawhun (407-207-2220)

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: 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: WINTER PARK RENOVATED -WHAT MORE CAN YOU ASK FOR Mid Century Modern-A+ NEIGHBORHOOD & SCHOOLS. Just 1 block to Baldwin Park & Audubon Park and minutes to Downtown Winter Park, College Park and Downtown Orlando. Gas Cooking, Marble countertops 3 bedroom/2 bath with TONS of NATURAL light and CHARM plus TONS of outdoor living space! This home has Luxury Vinyl Plank Floors, Ceiling Fans, Stainless Steel Appliances, Washer and Dryer TOO! SOLAR with battery backup! Set Flat Fee of $150 for electric. Lawncare and washer/dryer included in rent! Hurry, This home will rent fast!

Listing is courtesy of: REALTY PROS UNLIMITED INC (407-473-1526)

Listing Agent: Michelle Morrow (407-473-1526)

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: Virtually Staged. 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: Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *Bonus Amenity Included* -All residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application. Pet Friendly Home (with approval and a non-refundable pet fee).

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Mo Jabr (407-571-1441)