157

Winter Park, FL Homes for Rent

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  • /12

    $1,525 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Townhouse for Rent

    1565 Michigan Ave, Winter Park, FL 32789

    Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

    Troy Hensley BHHS FLORIDA REALTY

    1565 Michigan Ave, Winter Park, FL 32789
  • /42

    $3,149 per month

    • 3 Beds
    • 2 Baths
    • 1,747 Sq Ft
    • House for Rent

    1807 N Park Ave, Winter Park, FL 32789

    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

    Jason Hamilton THE REALTY MEDICS

    1807 N Park Ave, Winter Park, FL 32789
  • /17

    $1,600 per month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Condo for Rent

    3651 N Goldenrod Rd Unit F208, Winter Park, FL 32792

    Amazing 2 bedroom, 2 bathroom condo in Winter Park and move in ready. Amenities included: central air, central heat, dishwasher, pool, stainless steel appliances, updated kitchen, and washer/dryer combo. Utilities included: heat, air conditioning and water. Is pet friendly. An ideal location adds to this gem's overall appeal with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail,

    3651 N Goldenrod Rd Unit F208, Winter Park, FL 32792
  • /18

    $1,899 per month

    • 3 Beds
    • 2 Baths
    • 1,136 Sq Ft
    • House for Rent

    Unlisted Address

    Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 1 car garage and approximately 1,136 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

    Cathy Behe TAH FLORIDA LLC

    Unlisted Address
  • /20

    $1,850 per month

    • 2 Beds
    • 1.5 Baths
    • 1,219 Sq Ft
    • Condo for Rent

    200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792

    *Move-In Special*$100 OFF FIRST MONTH RENT if lease is signed by February 10th. Experience the best of Winter Park living in this highly sought-after 2-bedroom, 1.5-bathroom 2-story condo located in the Four Seasons community! This beautiful unit features modern light fixtures, stainless steel appliances, and upgraded flooring throughout. Enjoy the convenience of an included washer and dryer.

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792
  • /20

    $4,150 per month

    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft
    • House for Rent

    1470 Lone Feather Trail, Winter Park, FL 32792

    Welcome to this inviting rental opportunity in the charming district of Winter Park, FL. Nestled in a vibrant area, this property offers a delightful experience for those looking to enjoy a serene lifestyle while still being close to modern conveniences.Key property features include spacious bedrooms and well-appointed bathrooms, all designed with comfort in mind. With ample square

    1470 Lone Feather Trail, Winter Park, FL 32792
  • /27

    $1,400 per month

    • 2 Beds
    • 1 Bath
    • 851 Sq Ft
    • Condo for Rent

    2500 Lee Rd Unit 212, Winter Park, FL 32789

    Welcome to Lakeside Manor on beautiful Lake Killarney! This charming 2 bedroom, 1 bathroom second-floor condo offers tranquil living in one of Central Florida’s most desirable areas. Enjoy a serene, park-like setting right outside your door and access to breathtaking sunset views from the private community dock.Just minutes from Park Ave, Rollins College, Mills District, top dining,

    2500 Lee Rd Unit 212, Winter Park, FL 32789
  • /19

    $1,000 per month

    • 1 Bed
    • 1 Bath
    • 408 Sq Ft
    • House for Rent

    5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792

    Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the 4 rooms has its own electronic keypad lock for your privacy and security. The extra large common areas provide the perfect space for dining and living. Spacious laundry and kitchen provide you with plenty of space

    5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792
  • /22

    $1,350 per month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Condo for Rent

    3651 N Goldenrod Rd Unit 104, Winter Park, FL 32792

    Great location in Winter Park! This 2-bedroom, 2-bath apartment offers comfortable living with easy access to everything you need. Open Parking in front and located close to Full Sail University, UCF, Valencia College, and major roads like University Blvd and SR-436 (Semoran Blvd). Enjoy being just minutes from shopping centers, grocery stores, coffee shops, and restaurants, including Publix,

    Julio Lopez JCL REALTY INC

    3651 N Goldenrod Rd Unit 104, Winter Park, FL 32792
  • /18

    $2,250 per month

    • 3 Beds
    • 2 Baths
    • 1,282 Sq Ft
    • House for Rent

    1148 Park Green Place, Winter Park, FL 32789

    Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments

    Linda Baez DON ASHER & ASSOCIATES, INC.

    1148 Park Green Place, Winter Park, FL 32789
  • /28

    $2,350 per month

    • 3 Beds
    • 2 Baths
    • 1,334 Sq Ft
    • House for Rent

    1005 Bradford Dr, Winter Park, FL 32792

    Welcome to your new home in the desirable Winter Park, FL! This 3-bedroom single-family home is a perfect blend of comfort and convenience. The open floor plan is complemented by tile and wood floors, creating a warm and inviting atmosphere. Each bedroom is oversized, offering ample space for relaxation, and features walk-in closets for all your storage needs. The updated bathrooms, including a

    Justin Recca INNOVATIVE REALTY, LLC

    1005 Bradford Dr, Winter Park, FL 32792
  • /33

    $2,500 per month

    • 3 Beds
    • 1.5 Baths
    • 1,351 Sq Ft
    • House for Rent

    1622 Arbor Park Dr, Winter Park, FL 32789

    Offering a $500 move-in incentive if moved in by the end of February! Come view this 3 bed/1.5 bath home in Winter Park! With easy access to Lake Howell Rd and Lakemont Ave, it's close to several restaurants, surrounded by schools, parks, and lakes, Interlachen Country Club, AdventHealth, and Kraft Azalea Garden. Aloma and Old Winter Park are also nearby. Inside, you'll find a large living room

    Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

    1622 Arbor Park Dr, Winter Park, FL 32789
  • /21

    $1,795 per month

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • Townhouse for Rent

    7473 Belle River Ct Unit 16, Winter Park, FL 32792

    Spacious 3 Bed / 2.5 Bath Townhome-Style Condo in Hidden Oaks, Winter Park Welcome to this beautiful 3-bedroom, 2.5-bath townhome-style condo featuring modern finishes and a serene setting. Enjoy cooking in the kitchen with elegant granite countertops, durable tile flooring downstairs, and stylish luxury vinyl plank flooring upstairs. Step outside to your fenced patio with peaceful conservation

    Michael Barr PREMIUM PROPERTIES R.E SERVICE

    7473 Belle River Ct Unit 16, Winter Park, FL 32792
  • /90

    $15,500 per month

    • 8 Beds
    • 6 Baths
    • 7,000 Sq Ft
    • House for Rent

    1860 Via Contessa, Winter Park, FL 32789

    Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Viasneighborhood,offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcomingatmosphere.Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

    Sylvester Harding SIERRA REALTY GROUP LLC

    1860 Via Contessa, Winter Park, FL 32789
  • /25

    $8,500 per month

    • 4 Beds
    • 3.5 Baths
    • 3,341 Sq Ft
    • House for Rent

    1530 Via Tuscany, Winter Park, FL 32789

    Newly Remodeled Pool home located on premier street in Winter Park. This 4 bedroom home has just been totally updated with very tasteful upgrades. Notable items include: new paint in and out, new flooring in foyer, kitchen, baths. All baths remodeled, new light fixtures, new pavers on rear patio and pool, new landscaping package. The kitchen features new stone counters and backsplash. Also there

    Dan Haber CORCORAN PREMIER REALTY

    1530 Via Tuscany, Winter Park, FL 32789
  • /26

    $1,465 per month

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft
    • Condo for Rent

    2500 Lee Rd Unit 244, Winter Park, FL 32789

    Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

    Agent Photo

    Rustina Gibson

    RE/MAX VANTAGE

    (321) 336-5615

    2500 Lee Rd Unit 244, Winter Park, FL 32789
  • /17

    $1,300 - $1,855 per month

    La Aloma

    1 - 3 Beds

    3040 Aloma Ave, Winter Park, FL 32792

    La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

    3040 Aloma Ave, Winter Park, FL 32792
  • /15

    $1,850 per month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Apartment for Rent

    1500 Gay Rd Unit 3B, Winter Park, FL 32789

    Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

    Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

    1500 Gay Rd Unit 3B, Winter Park, FL 32789
  • /35

    $1,750 - $2,750 per month

    Hannibal Square

    2 Beds

    433 W New England Ave, Winter Park, FL 32789

    We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

    433 W New England Ave, Winter Park, FL 32789
  • /27

    $1,236 - $2,425 per month

    Village Park Senior

    1 - 3 Beds

    550 W Denning Dr, Winter Park, FL 32789

    WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

    550 W Denning Dr, Winter Park, FL 32789
  • /15

    $2,000 per month

    • 3 Beds
    • 1 Bath
    • 1,091 Sq Ft
    • House for Rent

    2011 Cornell Ave, Winter Park, FL 32789

    Charming 3-Bedroom Home for Rent in Winter Park This charming 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. The main home offers a functional and comfortable layout, ideal for everyday living. The property also includes a separate efficiency unit and a rear unit, both currently rented and featuring independent entrances, providing

    Andres Ospina Rivera LPT REALTY, LLC

    2011 Cornell Ave, Winter Park, FL 32789
  • /20

    $2,962 per month

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Condo for Rent

    1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

    The advertised rate of $2,962/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 19, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
  • /12

    $1,400 per month

    • 2 Beds
    • 2 Baths
    • 1,003 Sq Ft
    • Condo for Rent

    1000 S Semoran Blvd Unit 115, Winter Park, FL 32792

    Welcome to Golfside Villas. This community is nestled near Downtown Orlando, Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando International Airport. This condominium features an open floor plan that consist of 2 bedrooms, 2 bathrooms, and a screened in patio. Over 1000 sqft of living space awaits you with a few upgrades. This neighborhood features a laundry

    Damon Mayers MAYERS REAL ESTATE LLC

    1000 S Semoran Blvd Unit 115, Winter Park, FL 32792
  • /39

    $910 - $1,544 per month

    San Jose Apartments

    1 - 3 Beds

    2353 Winter Woods Blvd, Winter Park, FL 32792

    Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

    2353 Winter Woods Blvd, Winter Park, FL 32792
  • /17

    $2,365 per month

    • 3 Beds
    • 2.5 Baths
    • 1,397 Sq Ft
    • House for Rent

    3363 Hamlet Loop, Winter Park, FL 32792

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    3363 Hamlet Loop, Winter Park, FL 32792
  • /50

    $1,150 - $2,848 per month

    Sovereignty at Winter Park Apartments

    1 - 2 Beds

    7745 Brandywood Cir, Winter Park, FL 32792

    We offer 1 and 2 bedroom apartment homes with fully equipped kitchens, garden tubs, vaulted ceilings, ornamental chair rails, and so much more. Our community has a designer clubhouse, state-of-the-art fitness center, a sparkling pool, planned social activities, a high-speed internet business center, and 24 hour emergency maintenance. Winter Park location convenient to Full Sail, UCF, Valencia,

    7745 Brandywood Cir, Winter Park, FL 32792
  • /9

    $702,000 per month

    • Property for Rent

    7839 University Garden Dr, Winter Park, FL 32792

    Build your dream home on 4.93 acres in Winter Park. No HOA, lot dimensions 665ft x 323ft, zoning A-2/FARMLAND RURAL, land use vacant residential. The sale price included 2 parcels 11 22 30 0000 00 125 & 11 22 30 0000 00 042 with a factory home 3/2, 1344 sf. heated, built in 1976, and a mobile home. Convenient to SR-551/ Goldenrod Rd, SR-426/Aloma Rd, SR-50/Colonial Dr, University Blvd, FL-417,

    Shettle Huynh FLORIDA REALTY INVESTMENTS

    7839 University Garden Dr, Winter Park, FL 32792
  • /23

    $1,500 per month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit B114, Winter Park, FL 32789

    The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo brand new refrigerator , and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit B114, Winter Park, FL 32789
  • /20

    $3,174 per month

    • 3 Beds
    • 2 Baths
    • 990 Sq Ft
    • Condo for Rent

    2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789

    The advertised rate of $3,175/month is the lowest available price, based on a 30 day(s) stay with a move-in date of May 17, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789
  • /16

    $2,325 per month

    • 3 Beds
    • 2 Baths
    • 1,896 Sq Ft
    • House for Rent

    5133 Oak Hill Dr, Winter Park, FL 32792

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    5133 Oak Hill Dr, Winter Park, FL 32792
  • /12

    $2,245 per month

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • House for Rent

    5206 Ardmore Dr, Winter Park, FL 32792

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2389.90. That covers your base rent, $2245.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    5206 Ardmore Dr, Winter Park, FL 32792
  • /50

    $1,000 - $1,825 per month

    District On Baldwin Park

    Studio - 3 Beds

    5590 Baldwin Park St, Orlando, FL 32807

    Join us at District on Baldwin Park in Orlando, where you'll revel in luxurious apartment living and resort-style amenities minutes from shopping, entertainment, restaurants and recreation. Lounge by one of our three sparkling pools, sip a cup of coffee and surf the net in our Internet cafe?? or chat with neighbors over cards in our clubhouse. At District on Baldwin Park, you get the resort

    5590 Baldwin Park St, Orlando, FL 32807
  • /17

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,149 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit E115, Winter Park, FL 32789

    Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit E115, Winter Park, FL 32789
  • /14

    $1,250 - $1,800 per month

    Park Apartments

    1 - 3 Beds

    7528 Park Promenade Dr, Winter Park, FL 32792

    WELCOME TO THE PARK APARTMENTS (NEWLY RENOVATED!) Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two

    7528 Park Promenade Dr, Winter Park, FL 32792
  • /35

    $991 - $1,737 per month

    Carlton Arms of Winter Park

    Studio - 3 Beds

    300 Jamestown Dr, Winter Park, FL 32792

    *Call or email for today’s availabilityCarlton Arms of Winter Park, a well-established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff, offers an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

    300 Jamestown Dr, Winter Park, FL 32792

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