Winter Park Single Family Homes For Rent - 33 homes

Remarks: One or more photo(s) has been virtually staged. Beautifully mainted and move-in ready home available for rent in a convenient location. This property features a bright and inviting interior with functional layout, spacious living areas, and well-sized bed rooms. The home offers a clean feel with plenty of natural light throughout, creating a comfortable and welcoming environment. Enjoy a private outdoor space perfect for relaxing or entertaining. Conveniently located near major roadways, shopping, dining, and everyday amenities. Available for immediate occupancy! Schedule your showing today.

Listing is courtesy of: PRIMAC GROUP, INC (407-889-7075)

Listing Agent: Paula Wells (407-463-8792)

Remarks: Adorable mid century modern bungalow in Winter Park! This 3 bedroom, 1 bathroom home has been beautifully updated with new tile wood floors in the main living area. The kitchen features white appliances and tasteful white cabinetry. The updated bathroom features a new vanity and classic mosaic tile floor. Enjoy the spacious backyard with wooden deck! Washer, dryer and lawn care is included! This property is available May 2026.

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

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

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)

Remarks: Fully renovated with stylish charm, this four-bedroom, three-bath home is in one of the most desired neighborhoods in Winter Park, the Tree Streets. A brick drive and path welcome you into this open living plan on a large 75-foot by 150-foot lot with tons of room to grow. Warm wood floors throughout and this home enjoys an open kitchen family plan with spaces that are flexible for your needs. The kitchen has custom cabinetry, quartz countertops, subway glass tile, GE stainless appliances including natural gas range and loads of storage. French doors lead to spacious patio and generous backyard. The owner’s retreat was seamlessly added with 9-foot ceilings, large walk-in closet and beautiful primary bath retreat with dual vanities, separate soaking tub and water closet. The home has lovely natural light throughout. Other features include newer Trane air conditioning, electric panel in 2010, updated plumbing, level five dry wall finish, new paint inside and out, upgraded lighting package, all baths renovated, generous closets, updated garage door, updated windows and treatments, and mature landscaping. Just a short distance to the YMCA, Phelps Park, Lakemont Elementary School and zoned for Winter Park High School. Close to all the amenities Park Avenue offers and the perfect location.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home located in the heart of highly desirable Winter Park area. Offering a rare combination of space, comfort and prime location. This home offers a spacious and functional layout with multiple living areas, abundant natural light, and well-sized bedrooms. The flexible floor plan provides plenty of room for a variety of living arrangements, including space for a home office, guest room, or additional living area. Step outside to enjoy a spacious Patio, ideal for relaxing , entertaining or enjoying florida's year round sunshine. The home also features a 2 car garage and extended driveway offering plenty of parking and storage. Enjoy a prime location just minutes from: Park Avenue dining and shopping, Rollins College, AdventHealth Winter Park and Major roads, grocery stores, and everyday conveniences Property Highlights: 4 Bedrooms | 3 Bathrooms, Spacious interior layout, Large outdoor yard, 2-car garage + additional parking, Convenient access to shopping, dining, and major roadways This Home offers a unique opportunity to enjoy both space and convenience in one of Central Florida most sought-after areas. Schedule your private showing today- Homes in this location and condition lease quickly

Listing is courtesy of: SOUTHERN PRESTIGE REALTY INC (407-614-3873)

Listing Agent: Razan Mohamed (407-989-8084)

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: 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: A absolutely stunning 3 Bedroom 2 Bath single family home, with upgrades galore, this is not your typical rental home. The owners have totally transformed this very unique home into a stunning retreat. From the minute you pull up to this home, you are wowed by the great curb appeal, brick paver driveway and manicured garden. You are welcomed by gorgeous wooden double doors, leading into a reception area in the heart of the home. Which in turn leads into a formal living room, formal dining room and a stunning state of the art kitchen. This new kitchen has it all, beautiful stainless appliances, with built in oven and microwave, double door fridge, quartz counter tops, with eating space. All leading into the family room, with wood burning fireplace and French doors leading to a screened, Spanish tiled sunroom, which in turns leads to a large deck for entertaining and a meandering garden with such a calming surreal feel. Large Master bedroom with spa like bathroom, double sinks with quartz counters, one of a kind shower with seat. Two additional generous bedrooms and second upgraded bathroom with tub complete this unique home. Inside laundry room including washer & dryer, double garage with opener. Includes lawn care, pest control and alarm. This home is situated in the much sought after Brookshire school district, close to shopping, restaurants and major hwys. On a quiet low traffic street close to the Winter Park Pines Golf course. Home will be available for a June 1st move in.

Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)

Listing Agent: Sarah Gholami (352-346-7857)

Remarks: Lovely 4 bed, 2 bath one story home in desirable Winter Park! Attached 2 car garage, GRANITE countertops in kitchen, walk in closet in primary bedroom. Patio has ceramic tile flooring, overlooking the FENCED backyard! This home features a spacious layout! Location is PERFECT! Convenient to shopping, dining, highways & more!

Listing is courtesy of: STRONG FOUNDATION REALTY LLC (407-272-2067)

Listing Agent: Harry Kazarian (407-272-2067)

Remarks: This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The backyard also has a gazebo, is totally fenced in and has lots of room to roam. Conveniently located between Baldwin Park and Winter Parks Park Avenue. Winter Park School district. Sorry, no pets.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Jackie O'Leary (407-718-0887)

Remarks: Winter Park 4 Bedrm Home for Rent! Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application results. Pets: OK (Dangerous Pets are not permitted, Pit Bulls, etc.) Priced $2,099.00 for the first 4 months, $2,199.00 for the remaining 8 months (Average: $2,167.00/mo). AVAILABLE: May 19, 2026

Listing is courtesy of: ORLANDO REALTY & PROPERTY MGNT (407-641-5782)

Listing Agent: Jay Myers (407-641-5782)

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Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)

Listing Agent: Maggie Walas (407-701-0144)

Remarks: Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are welcomed by an abundance of natural light filling the entryway, dining room and formal living room. The inviting family room includes a stylish wood burning fireplace and French doors that lead out to the backyard. Cook and enjoy your favorite meals in the home’s gourmet kitchen and dinette area. Right off the large 2-car garage is a walk-in laundry room and a lovely half bathroom. Upstairs is the spacious master bedroom and master bathroom including a large soaker tub and walk-in shower. Experience gorgeous Florida outdoor living in the impressive second floor deck that can be accessed through the master bedroom or backyard. Enjoy the lime and pineapple trees in this well-maintained backyard. The home is conveniently located in close proximity to Winter Park’s Park Avenue restaurants and shops and incredible schools. Landscaping/Lawn Care will be provided by landlord.

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

Listing Agent: Lisa Gould (407-721-7612)