Winter Park Apartments for Rent - 84 rentals

Remarks: Available for rent! Tucked onto a desirable corner lot just steps from Lake Killarney, this beautifully updated 3 bedroom, 2 bath single-family home puts you in one of the area's most sought-after spots. Walkable, quiet, and moments from the water. Inside, the home is move-in ready with a full suite of brand-new appliances (dishwasher, range, and refrigerator) plus washer/dryer hookups ready for your setup. Three comfortable bedrooms, two full baths, and bright, livable spaces make it easy to settle in from day one. Easy parking thanks to a covered carport and private driveway. Pets welcome on a case-by-case basis. Available now. Security deposit equal to one month's rent; move-in total is first month + security deposit. Tenant responsible for all utilities and minor maintenance (bulbs, filters); landlord handles major repairs and pest control.

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

Listing Agent: Zach Mitchell (407-920-6440)

Remarks: Beautifully Remodeled 2 Bed / 2 Bath Condo – Second Floor | Prime Location Charming and fully remodeled second-floor condo located just steps from the pool. Perfect for those seeking a low-maintenance lifestyle. This bright and inviting unit features fresh paint, new wood and ceramic tile flooring, and updated bathrooms and kitchen with granite countertops and new appliances, including a washer and dryer. The layout offers a comfortable living room, dining area, and a screened-in patio to relax and enjoy the outdoors. Community amenities include: Pool Sauna Clubhouse Ideally located within walking distance to Full Sail University and just minutes from UCF, Rollins College, and Valencia College, as well as shopping, dining, and major roadways. Note: Some images may be virtually staged.

Listing is courtesy of: CLARA HERRERA REALTY (407-921-1200)

Listing Agent: Clara Herrera (407-921-1200)

Remarks: Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from Interlachen Country Club and Winter Park Racquet Club, and is zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. Inside, natural light pours through windows in every room, giving the home a bright, airy feel throughout. The main living areas feature classic plantation shutters, while all bedrooms are fitted with blinds, a thoughtful touch that makes every space feel finished and move-in ready. Warm engineered hardwood floors, recessed lighting, and a flowing open layout connect the living room, dining area, and family room with ease. The chef's kitchen is the heart of the home, featuring granite countertops, a large center island, rich wood cabinetry, stainless steel appliances, and a professional-grade range hood, all opening into the spacious family room with its slate tile floors, wood-burning fireplace, built-in shelving, and French doors to the backyard. The primary suite overlooks the pool and rear yard, offering a serene and private feel. Its spa-inspired en suite bath features a dual-sink vanity, a walk-in tiled shower, and a private access directly to the backyard and pool, making it ideal for those who love to start or end the day outdoors. The second bedroom enjoys its own en suite bath. A third full bath serves the remaining bedrooms, beautifully updated with designer gold fixtures, modern vanity, and stylish lighting. The split bedroom layout offers privacy and flexibility for families, guests, or a dedicated home office. Out back, your private oasis awaits with a sparkling pool, concrete deck, lush lawn, and towering mature oaks creating that quintessential Winter Park canopy. Pool and lawn maintenance are included in rent, so you can simply enjoy. The attached 2-car garage includes laundry. No pets. No exceptions.

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

Listing Agent: Drew Henner (407-406-0662)

Remarks: 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: Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The home truly shines outdoors, offering an abundance of entertaining space. Enjoy a screened-in pool, covered patio, and multiple seating areas including a tiled lounge space with a firepit, all set within a large, fenced backyard with both lush grass and low-maintenance turf. Whether hosting guests or enjoying a quiet evening, this home provides the perfect setting. Inside, the light-filled dining room overlooks the backyard from three sides, while the primary suite features a spacious closet and private en-suite bath. All bedrooms include newer carpet, and a generous utility room off the carport offers ample space for laundry and storage. Located in a highly rated school zone and just minutes from Rollins College, parks, shopping, dining, and everything Winter Park has to offer, this home delivers both lifestyle and convenience in one exceptional rental opportunity.

Listing is courtesy of: SOTERA LIVING (407-725-9660)

Listing Agent: Lianna Dangelo (321-446-3509)

Remarks: 3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and lawn service included. *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.

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

Listing Agent: Shawn Beard (407-739-7722)

Remarks: Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step outside to your own private oasis — a fully fenced backyard with a sparkling private pool, perfect for relaxing or entertaining year-round. The property also includes an attached 2½-car garage and 4 additional driveway parking spaces, providing plenty of room for vehicles. Located in a prime Winter Park neighborhood, this home is close to parks, shopping, dining, and top-rated schools. Pets are welcome, making this a perfect home for the whole family. Don’t miss this opportunity to enjoy privacy, space, and convenience in one of Central Florida’s most sought-after areas.

Listing is courtesy of: THE REALTY MEDICS (321-947-7653)

Listing Agent: Jason Hamilton (321-947-7653)

Remarks: Welcome to 3038 Antique Oaks Circle #165, a well-maintained and inviting 2-bedroom apartment located in the desirable Winter Park area. This charming residence features a functional layout with abundant natural light, tile flooring throughout, and a warm, welcoming atmosphere. The unit offers a spacious living and dining area, along with a well-appointed kitchen equipped with newer appliances, including a refrigerator, washer, and dryer for your convenience. The comfortable-sized primary bedroom includes a private, recently renovated bathroom, providing both privacy and modern appeal. A second bedroom offers flexibility for guests, a home office, or additional living space. Residents can enjoy community amenities such as a sparkling pool and relaxing spa, perfect for unwinding and enjoying Florida living year-round. Ideally located directly across the street from Full Sail University and just minutes from University of Central Florida, as well as major roadways, shopping, dining, and entertainment options. Experience comfort, convenience, and a prime location—schedule your private showing today.

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

Listing Agent: Edwin Rivera (407-394-7811)

Remarks: Two master bedrooms upstairs, one half bathroom and laundry room downstairs. one fenced patio on the back. Water is included. Two parking spaces belong to this property.

Listing is courtesy of: U S GLORY REALTY (407-222-7801)

Listing Agent: He Gao (407-955-0138)

Remarks: FOR RENT in Winter Park! Experience comfortable living in this beautiful 3-bedroom, 2.5-bathroom townhome located in the gated community of Grayson Square. Rent includes high-speed internet and cable, offering great value and convenience. The home features a bright open floor plan with abundant natural light, a modern kitchen with quartz countertops and stainless steel appliances, and sliding glass doors leading to a covered patio. Enjoy peaceful views with water, fountain features, and no rear neighbors, creating a relaxing and private outdoor setting that can be enjoyed from the living room, kitchen, and primary bedroom. Upstairs, you will find the spacious primary suite with a walk-in closet and an en-suite bathroom with dual vanities and a glass-enclosed shower. Two additional bedrooms share a full bathroom on the second floor.  A washer and dryer are included for added convenience. Residents of Grayson Square enjoy access to the community pool and playground. The property is conveniently located off Howell Branch Road, minutes away from downtown Winter Park, with easy access to major highways, shopping, dining, and entertainment.

Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)

Listing Agent: Vildan Nigro (352-988-3824)

Remarks: newly updated 3 bedroom 2 bath with flex room for home office. new appliances and ready for move-in.

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

Listing Agent: Mike Wang (631-748-6708)

Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath home located in the heart of Winter Park. Filled with abundant natural light throughout and thoughtful upgrades, this home offers a warm and inviting atmosphere that would be perfect for your family. Highlights: -Primary suite featuring a walk-in closet and private ensuite bathroom -Classic terrazzo flooring -Recently remodeled kitchen with brand-new appliances -Solid wood cabinetry -Fully fenced backyard -2-car parking space -Washer and dryer included -Lawn Service Included Enjoy living in a prime Winter Park location close to shopping, dining, parks, and top-rated schools. This home blends modern updates with timeless charm, definitely a must-see! 12-month Minimum Lease $85 Non-Refundable Application Fee (18+) All Belmont Management Group residents are enrolled in the Resident Benefits Package (RBP) for $50.00/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. Please note, that we require all applicants to have - a combined monthly, net household income of 3X the monthly rent, - good standing credit - minimum score of 650, No accounts in collections - and no prior evictions or collections from any apartment complexes Along with your application, please include a copy of your photo ID as well as two consecutive months of your most recent pay stubs or other proof of income. We will not accept W2s as proof of income. The application includes full background, credit check as well as eviction judgments Pets are allowed on a case-by-case basis via the owner's instructions.

Listing is courtesy of: BELMONT REALTY (407-745-0696)

Listing Agent: Summer Hornburg (407-495-8134)

Remarks: Charming 2-bedroom, 1.5-bath townhouse located in the highly desirable Hidden Oaks community. This two-story home offers 990 sq ft of comfortable living space. The main floor features a spacious living area that flows into the dining area and kitchen, along with a convenient half bath for guests. Upstairs, you’ll find the primary bedroom with a spacious bathroom, as well as an additional comfortable bedroom. Enjoy a cozy private patio, perfect for relaxing or entertaining, and a low-maintenance. Two reserved parking spaces are conveniently located directly in front of the unit. Community amenities include a pool, sidewalks, and guest parking. Ideally located just minutes from FL-408 and FL-417, offering easy access to Orlando International Airport and Downtown Orlando. Close to shopping, dining, and excellent schools in the Winter Park area. A great opportunity to enjoy comfort, convenience, and community living—schedule your showing today!

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

Listing Agent: Moira Villavicencio (407-301-8030)

Remarks: Exceptional Lease Opportunity | The Vias, Winter Park $13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available Now Rarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched combination of scale, sophistication, and livability across three thoughtfully designed levels. Rich hardwood floors anchor the main living areas, setting a tone of warmth and understated elegance throughout. The open-concept floor plan transitions effortlessly between spaces, equally suited to quiet evenings at home and large-scale entertaining. At the center of it all is a chef's kitchen appointed with 42-inch cabinetry, quartz countertops, a professional gas range, and double ovens. An oversized eat-in bar and adjacent dining area connect seamlessly to the family room, ensuring the cook is always part of the conversation. The home offers two expansive primary suites, each a serene private retreat. The main floor — along with the second level — encompasses 4,500 SF and five bedrooms with four baths. The main suite is a true sanctuary, complete with a spa-caliber bath and a custom walk-in closet. A gas fireplace anchors the family room, while French doors open to the covered rear patio and pool deck. Upstairs, four additional bedrooms are served by two Jack-and-Jill baths, a generous laundry room, and a versatile studio or playroom. Custom loft stairs climb to a third-floor bonus space, ideal for creative pursuits or kids' play. The lower level is an exceptional offering in its own right — a fully appointed 2,500 SF in-law suite with a private living area, kitchenette and breakfast bar, a spacious primary bedroom with ensuite bath, two secondary bedrooms, a full hallway bath, gym, workshop, and a game room with pool table. Generous window wells flood the space with natural light, and direct access to the back patio and pool deck makes the transition between levels completely seamless. Zoned for the highly regarded Dommerich/Maitland/Winter Park High School district, and just minutes from the shops and dining of Park Avenue and a short stroll to the Winter Park Racquet Club — this is Winter Park living at its finest. All measurements and dimensions should be independently verified.

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

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

Remarks: Rare opportunity to lease a spacious 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence sits just a short stroll from the prestigious Winter Park Racquet Club. Flooded with natural light, the open-concept living spaces feature beautiful bamboo wood floors, a well-appointed kitchen with white cabinetry and a large island, and a sunken family room with walls of windows overlooking the pool and backyard. The primary suite enjoys its own private bath, while three guest bedrooms share a hall bath. A full pool bath with walk-in shower off the family room adds everyday convenience. An attached 2-car garage offers additional parking or storage. Step outside to your private backyard oasis, where a sparkling pool, heated spa, and generous yard space are ideal for effortless Florida living. Situated on a nicely sized lot, this home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School. Lawn care and pool care are included. Available May 1, 2026. 4 bedrooms, 3 bathrooms, 2,207 SF at $5,895 per month. Security deposit of $7,500 required. Renters insurance is required. Pets are considered on a case-by-case basis, subject to owner approval.

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

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

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 and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community. This unit offers the perfect combination of comfort, space, and convenience — ideal for families or professionals looking for a clean and functional home ready for immediate move-in. PROPERTY HIGHLIGHTS: 2 Bedrooms / 1 Full Bathroom - Second-floor unit (added privacy) - 881 sq ft of living space - Open floor plan with high ceilings - Walk-in closet(s) COMFORT & FEATURES: Central Air Conditioning & Heating - Ceiling fans throughout - Bright and open living areas KITCHEN & APPLIANCES INCLUDED: Refrigerator - Range - Microwave - Dishwasher - Garbage Disposal - Washer & Dryer included COMMUNITY FEATURES: Swimming pool - Playground - Quiet and well-maintained community ENJOY EASY ACCESS TO EVERYTHING YOU NEED: Shopping centers and grocery stores - Restaurants and cafés - Parks and recreational areas - Hospitals and clinics - Easy access to major roads MOVE-IN READY: This unit is available now and ready for immediate occupancy. MOVE-IN SPECIAL Lower upfront move-in options available — apply today to see how you may qualify for current specials. REQUIREMENTS: Proof of income (3x rent) - Background screening - No evictions CONTACT: Call or Text to schedule your showing today.

Listing is courtesy of: ROSS RENTALS LLC (727-687-5455)

Listing Agent: Yein Ross (844-476-7722)

Remarks: One or more photo(s) has been virtually staged. Welcome to Lake Killarney Townhomes, a modern luxury and new construction waterfront community. Nestled in the heart of Winter Park, just north of downtown Orlando, these exclusive townhomes offer a unique blend of urban contemporary design and comfort. This home features a private terrace perfect for relaxing in style with slight views of Lake Killarney. Bright, open interiors with expansive storefront-style windows and soaring 10'6" ceilings create an atmosphere of elegance and comfort. This home is a two-story concrete block construction complemented by woodgrain composite siding. The layout offers three spacious bedrooms on the second floor and three-and-a-half luxurious bathrooms. The modern kitchen includes sleek cabinetry, premium Samsung appliances with a natural gas cooktop and built-in wall oven, expansive quartz countertops, and a generous walk-in pantry. The bathrooms each showcase unique porcelain tile, modern backlit mirrors, frameless glass shower enclosures, undermount sinks, and custom-built closet systems. Step outside to your expansive outdoor patio, designed with glass railings and pre-plumbed for a future summer or cocktail kitchen, perfect for hosting gatherings or simply enjoying the outdoors. An inviting back patio is great for dining alfresco or enjoying the amazing central Florida weather this time of year. Every detail has been thoughtfully curated to ensure ultimate comfort and style. Enjoy the serene beauty of Lake Killarney from your side patio, or relax at the inviting lakefront pavilion. The location offers unparalleled convenience, being close to downtown Winter Park, Park Avenue, I-4, and just a short drive to neighboring towns like College Park and Maitland. The community also provides kayak, canoe, and paddle-board racks for a leisurely day on the water. Enjoy the perfect blend of luxury and convenience. This home is available for rent immediately.

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

Listing Agent: Kris Kennedy (813-947-3509)

Remarks: Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this space. Just off the dining room you will find the kitchen and eat in kitchen area.few stainless steel appliances and tons of storage. The eat in kitchen space is highlighted with a decorative wall and sliders leading to your fully fenced private backyard space. Upstairs you will find hardwood flooring, three bedrooms and master bathroom with a single vanity . Hidden Oaks community features on-site security, community pool & fenced playground area. Near Full Sail, UCF, Valencia & Rollins College, with easy access to shopping, Winter Park schools, Medical Facilities, Downtown Orlando, Downtown Winter Park, FL-408, FL-417 and the airport. This wonderful unit has it all...the only thing missing is YOU!

Listing is courtesy of: APPLE REALTY (407-647-6766)

Listing Agent: Manoj Patel (407-451-5872)

Remarks: Gorgeous single-family home in the "tree streets" of Winter Park now available for rent or purchase. Private pool, two car garage, fabulous location and newer construction! Don't wait! Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept main floor features a beautifully appointed kitchen, a spacious dining area, and a light-filled living room complete with a designer fireplace and custom built-in shelving. The stunning kitchen boasts quartz counters, spacious cabinetry, KitchenAid appliances, and designer lighting. A fourth bedroom (currently used as a study) is also located on the main level. From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an in-ground pool, a fully fenced yard, tongue-in-groove wood ceiling, and pre-plumbing in place for your dream summer kitchen—ideal for entertaining year-round. Upstairs, the luxurious primary suite provides a peaceful retreat with an oversized balcony overlooking the pool and rear yard. Two additional bedrooms are also featured on the second level, along with a second full bath. The first-floor office doubles as a fourth bedroom, with an adjacent full bath for guests or multi-generational living. This home boasts well-thought-out upgrades, including beautiful wood inlays in niches, open shelving, quartz countertops, slat wall features, and stunning light fixtures throughout. The work has been done for you in this like-new home! Located just steps from Phelps Park and minutes from the shops and dining of Park Avenue and the Winter Park Chain of Lakes, this home offers the perfect blend of modern design, comfort, and convenience. Don't miss your chance to rent or own this exceptional home in the heart of Winter Park!

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Sue Silberbusch (407-252-3157)