17

Winter Park, FL Houses for Rent with Garage

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  • /36

    $2,750 Per Month

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft
    • House for Rent

    1627 Orange Ave, Winter Park, FL 32789

    Charming 3-bedroom, 2-bath bungalow located in the highly desirable, well-established Orwin Manor neighborhood in the City of Winter Park. Ideally situated between Downtown Orlando and Park Avenue, this home is just minutes from AdventHealth Hospital, Rollins College, and offers convenient access to I-4. The spacious retreat is located just across the hall from a beautifully renovated bathroom.

    Agent Photo

    Peter Dang

    ALLIANCE RENTAL HOMES

    1627 Orange Ave, Winter Park, FL 32789
  • /11

    $1,600 Per Month

    • 2 Beds
    • 1.5 Baths
    • 825 Sq Ft
    • House for Rent

    2523 Alexa Ct, Winter Park, FL 32792

    Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

    Bernardo Reynoso La Rosa Realty Llc

    2523 Alexa Ct, Winter Park, FL 32792
  • /34

    $3,895 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,553 Sq Ft
    • House for Rent

    2348 Kestrel Perch Place, Winter Park, FL 32792

    A beautiful tile roof single-family house is available in Hawks Crest, the only gated community in Winter Park! UV sanitizing lights are installed in all bathrooms. A water filter system is installed in the kitchen sink. This 4-bed 3.5-bathroom plus an office and second-floor loft is ready to move in. When you enter the home, an open-concept floor plan leads you to the family room and the

    Yan Zuo EAST PEARL REALTY

    2348 Kestrel Perch Place, Winter Park, FL 32792
  • /37

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,027 Sq Ft
    • House for Rent

    1450 Cavendish Rd, Winter Park, FL 32789

    WINTER PARK - Located in the highly desirable ORWIN MANOR neighborhood, this charming one-story 2BR/1BA single-family home offers 1,027 sq.ft. of living space, thoughtfully blending its original character with modern updates. The living room provides a comfortable and cozy gathering space, while the adjoining dinette is filled with natural light, creating an inviting setting for casual meals or

    Margaret Steiner KELLER WILLIAMS REALTY AT THE PARKS

    1450 Cavendish Rd, Winter Park, FL 32789
  • /33

    $9,900 Per Month

    • 5 Beds
    • 6 Baths
    • 2,735 Sq Ft
    • House for Rent

    1442 Palm Ave, Winter Park, FL 32789

    Gorgeous 5-bedroom /6-bathroom Luxury Estate with Guest House & Pool in Winter ParkThis stunning two-story home offers the perfect blend of luxury and comfort right in the heart of Winter Park. At the center of the home is a beautiful open kitchen outfitted with high-end appliances, solid wood cabinets, and granite countertops . A true chef’s layout that flows into the living spaces. You'll

    Magdalena Cuprys KELLER WILLIAMS REALTY AT THE PARKS

    1442 Palm Ave, Winter Park, FL 32789
  • /46

    $7,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,394 Sq Ft
    • House for Rent

    1368 Hibiscus Ave, Winter Park, FL 32789

    Discover refined living in the heart of Winter Park in this beautifully appointed 4-bedroom, 2.5-bathroom single-family pool home. Immediately to the right of the entryway, a beautiful private office provides a convenient and quiet space for working from home or studying. Filled with natural light, the home features an inviting open layout, and a spacious living area centered around a cozy

    Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

    1368 Hibiscus Ave, Winter Park, FL 32789
  • /19

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1942 Conifer Ct, Winter Park, FL 32792

    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

    Scott Banta BLACKFIN REALTY LLC

    1942 Conifer Ct, Winter Park, FL 32792
  • /32

    $6,450 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,415 Sq Ft
    • House for Rent

    835 W Canton Ave, Winter Park, FL 32789

    Now available for lease in the highly desirable Gardens at Park West, this beautifully completed home offers luxury living in the heart of Winter Park. Ideally located within walking distance of Winter Park Village, Park Avenue's renowned dining and shopping, the Winter Park Farmers' Market, and more, this home combines convenience with an exceptional lifestyle. Designed with an open,

    Brian Hyser THE AGENCY FL

    835 W Canton Ave, Winter Park, FL 32789
  • /15

    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    1340 Paradise Ln, Winter Park, FL 32792

    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

    Robert Dion D & D PROPERTY MANAGEMENT SOLUTIONS LLC

    1340 Paradise Ln, Winter Park, FL 32792
  • /21

    $2,495 Per Month

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft
    • House for Rent

    3976 Waterview Loop, Winter Park, FL 32792

    3 bedrooms, 2 bathrooms and a two car garage offering 1,444 square feet. Open floor plan with neutral colors, high ceilings. This home has a nice and open kitchen with an over abundance of cabinets, granite counter tops and stainless steel appliances. Open to the kitchen you’ll find a large eat in nook and a family room/ dining room combination floor plan with sliding glass doors leading to a

    Courtney Davis ABSOLUTE REALTY GROUP, LLC

    3976 Waterview Loop, Winter Park, FL 32792
  • /40

    $3,950 Per Month

    • 4 Beds
    • 2 Baths
    • 1,660 Sq Ft
    • House for Rent

    Unlisted Address

    Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having

    Melissa Johnson EXP REALTY LLC

    Unlisted Address
  • /27

    $4,400 Per Month

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • House for Rent

    648 Fitzwalter Dr, Winter Park, FL 32792

    Nestled beside Cady Way Park & Trail, this charming home offers an unbeatable location in a quiet, established neighborhood on a peaceful tree-lined cul-de-sac. Enjoy easy access to top-rated Winter Park schools, Winter Pines Golf Club, Showalter Field, AdventHealth Winter Park, Baldwin Park, Downtown Winter Park, and a wide variety of shopping, dining, and entertainment. Inside, you’ll find

    Paul Chisholm LOVEJOY PROFESSIONAL REALTY, INC

    648 Fitzwalter Dr, Winter Park, FL 32792
  • /43

    $4,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,345 Sq Ft
    • House for Rent

    344 Starling Rd, Winter Park, FL 32789

    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

    Kelly Price KELLY PRICE & COMPANY LLC

    344 Starling Rd, Winter Park, FL 32789
  • /12

    $3,200 Per Month

    • 4 Beds
    • 3 Baths
    • 2,319 Sq Ft
    • House for Rent

    7903 Pleasant Pine Cir, Winter Park, FL 32792

    WINTER PARK 4 BR / 3BA + BONUS ROOM, built in 2014. Located in the GATED COMMUNITY of Enclave At Aloma. All bedrooms are on the FIRST FLOOR, including the master bedroom with space for a king size bed and a HUGE WALK-IN CLOSET. The family room opens to the kitchen with 42" wood cabinets, white QUARTZ counter tops, STAINLESS STEEL appliances, KITCHEN ISLAND with breakfast bar seating and a large

    Elizabeth Beaudoin PR REAL ESTATE SERVICES

    7903 Pleasant Pine Cir, Winter Park, FL 32792
  • /22

    $2,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft
    • House for Rent

    912 Carvell Dr, Winter Park, FL 32792

    Nestled in the sought-after Winter Park Estates neighborhood, this beautifully maintained 3-bedroom, 2-bathroom pool home offers the perfect blend of classic charm and modern updates. Step through the front door into a warm, welcoming living room that flows effortlessly into a dining area featuring updated kitchen finishes and quality appliances.The spacious family room offers flexible living

    Grace Feng INTOP REALTY LLC

    912 Carvell Dr, Winter Park, FL 32792
  • /46

    $4,495 Per Month

    • 4 Beds
    • 3 Baths
    • 2,134 Sq Ft
    • House for Rent

    1625 Tioga Trail, Winter Park, FL 32789

    A RARE FIND IN WINTER PARK!! 4 BEDROOMS, 3 BATHROOMS, POOL, AND FENCED BACKYARD.Welcome home to this beautifully updated 4-bedroom, 3-bath pool home nestled on a quiet cul-de-sac in Winter Park Hills. Surrounded by million-dollar homes and zoned for excellent Winter Park schools (Dommerich Elementary, Maitland Middle and Winter Park High), this exceptional rental offers the perfect

    Nicholas Musashe SUN PROPERTIES, INC.

    1625 Tioga Trail, Winter Park, FL 32789
  • /18

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,812 Sq Ft
    • House for Rent

    622 Green Meadow Ave, Maitland, FL 32751

    NOW AVAILABLE! Wonderful Seminole County 3/2/2 block home in a favorite established Maitland neighborhood with underground utilities and sidewalks. LAWN CARE INCLUDED TOO! Ranch style home with nicely covered front patio and court yard perfect for potted paints and outdoor furniture. Huge open concept floor plan with the kitchen, dining room and great room wide open with 2 sets of french doors

    Sheryl Webster VENTURE HOME REALTY

    622 Green Meadow Ave, Maitland, FL 32751

Rental Home Trends

Number of Houses for Rent
17
Median Single Family Home Rent
$2,599
Median 3 Bedroom Single Family Home Rent
$2,498
Median 4 Bedroom Single Family Home Rent
$3,850
Median 5 Bedroom Single Family Home Rent
$6,000
How to Rent a Home