168

Winter Park, FL Homes for Rent

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  • /20

    Starting at $1,383 Per Month

    • 1 - 2 Beds

    3250 Bishop Park Dr, Winter Park, FL 32792

    Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

    ARIUM Winter Park

    (321) 346-5593

    3250 Bishop Park Dr, Winter Park, FL 32792
  • /12

    Starting at $3,350 Per Month

    • 2 Beds

    1894 Demetree Dr, Winter Park, FL 32789

    Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter ParkWelcome home to this stylish, move-in-ready townhome located in the heart of Winter Park. Enjoy the perfect balance of convenience and comfort—just a short walk to Winter Park Dog Park and Baldwin Park, and minutes from Rollins College, Park Avenue, downtown Orlando, and major hospitals.This thoughtfully

    Waterbridge Subdivision

    (844) 871-1098

    1894 Demetree Dr, Winter Park, FL 32789
  • /20

    $2,698

    Total Monthly Price

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

    2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789

    The advertised rate of $2,699/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 22, 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

    (321) 265-3710

    2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789
  • /11

    $1,350 Per Month

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

    2942 Antique Oaks Cir Unit 82, Winter Park, FL 32792

    Property Id: 1010517Second Floor one bedroom unit in the highly desirable Parkview Condominium Complex across from Full Sail University. The rent includes water and sewer. All floors are laminate.

    (689) 210-4760

    2942 Antique Oaks Cir Unit 82, Winter Park, FL 32792
  • /11

    $1,350 Per Month

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

    5319 N Orange Ave, Winter Park, FL 32792

    Property Id: 2494175Great location for getting around the greater Orlando area and avoiding traffic. Close to many hospitals, easy access to both airports. Close to groceries, Sprouts, Publix, CVS, Walgreens, Costco, Walmart all within a mile plus countless great restaurants. Whole Foods and Trader Joe’s are about 6 miles away. Nice neighborhood. Friendly neighbors. New paint, new

    (425) 521-6919

    5319 N Orange Ave, Winter Park, FL 32792
  • /20

    $2,495 Per Month

    • 5 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    3628 Datura Ct, 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 $2639.90. That covers your base rent, $2495.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (321) 285-1423

    3628 Datura Ct, Winter Park, FL 32792
  • /10

    $3,300 Per Month

    • 3 Beds
    • 1 Bath
    • 820 Sq Ft
    • House for Rent

    853 W Lyman Ave, Winter Park, FL 32789

    Property Id: 1403118Our home is convenient for your extended friends and family, remote workers, traveling nurses, Rollins College parents and alum, snowbirds, conference attendees, or exploring travelers who prefer to stay in our home away from home.Three bedrooms (one queen and two double beds) accommodate three couples, Living room has large sectional and flat screen TV (bring

    (386) 267-8041

    853 W Lyman Ave, Winter Park, FL 32789
  • /16

    $2,675 Per Month

    • 3 Beds
    • 2 Baths
    • 1,525 Sq Ft
    • House for Rent

    1721 Shasta Ct, Winter Park, FL 32792

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    (407) 641-3217

    1721 Shasta Ct, Winter Park, FL 32792
  • /17

    $2,530 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • House for Rent

    3313 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.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    (689) 329-3269

    3313 Hamlet Loop, Winter Park, FL 32792
  • /15

    $2,175 Per Month

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

    3091 Crane Strand Dr, Winter Park, FL 32792

    We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

    (689) 399-2369

    3091 Crane Strand Dr, Winter Park, FL 32792
  • /3

    $2,300 Per Month

    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft
    • Condo for Rent

    2827 Riddle Dr, Winter Park, FL 32789

    Welcome to your new oasis in the charming city of Winter Park, FL! This beautiful property is perfect for those seeking comfort and convenience in a vibrant community. With nearby restaurants offering a delightful culinary experience, you'll always have something new to explore.This property features spacious accommodations designed for your relaxation. Enjoy a comfortable living

    (321) 381-3659

    2827 Riddle Dr, Winter Park, FL 32789
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    $1,950 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    520 Holt Ave, Winter Park, FL 32789

    Property Id: 578482One-bedroom / one-bathroom cottage style apartment located within a five-minute walk to Rollins College, Park Avenue, and Hannibal Square. Newly-renovated interior includes condominium grade appliances, upgraded bathroom, and in-unit washer dryer. Unit includes off-street parking and private entry porch. Available for lease beginning of June 2026. Rent includes

    (321) 304-2205

    520 Holt Ave, Winter Park, FL 32789
  • /20

    $2,385 Per Month

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • House for Rent

    2313 Dunbury Ct, 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 $2529.90. That covers your base rent, $2385.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (321) 205-9980

    2313 Dunbury Ct, Winter Park, FL 32792
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    $2,645 Per Month

    • 4 Beds
    • 2 Baths
    • 1,646 Sq Ft
    • House for Rent

    2141 Ridge Dr, Winter Park, FL 32792

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    (689) 220-1676

    2141 Ridge Dr, Winter Park, FL 32792
  • /18

    $1,890 Per Month

    • 2 Beds
    • 3 Baths
    • 1,400 Sq Ft
    • Townhouse for Rent

    7290 Daniel Webster Dr, Winter Park, FL 32792

    Property Id: 2485692The house is large and comfortable.it has two garden and transport and college university and supermarket and discount

    (786) 396-6891

    7290 Daniel Webster Dr, Winter Park, FL 32792
  • /16

    $3,025 Per Month

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft
    • House for Rent

    504 St Dunstan Way, Winter Park, FL 32792

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    (321) 339-1052

    504 St Dunstan Way, Winter Park, FL 32792
  • /20

    $2,728

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    662 Callahan St Unit SI ID1308311P, Winter Park, FL 32789

    The advertised rate of $2,729/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 25, 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

    (321) 483-3204

    662 Callahan St Unit SI ID1308311P, Winter Park, FL 32789
  • /13

    $1,900 Per Month

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

    2687 Stanfield Ave, Orlando, FL 32814

    Property Id: 21487811bedroom and 1 bath apt with private entrace in baldwin park with 1 car garage. There is a Publix, restaurants and pharmacy in the neighborhood.

    (321) 424-6641

    2687 Stanfield Ave, Orlando, FL 32814
  • /47

    $2,675 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Townhouse for Rent

    2760 Bright Bird Ln, Winter Park, FL 32792

    Stunning 3 beds/2.5 bath/1car garage townhome ready to move-in June at Grayson Square, Winter park. RENT INCLUDES high-speed 1GB fiber optic internet & 75 streaming cable and music channels. The first floor is efficiently laid out with the kitchen, powder room, and spacious gathering room perfect for entertaining with a sliding glass door that opens to the covered lanai and patio that overlooks a

    Fabian Berastegui P & C PROPERTIES

    2760 Bright Bird Ln, Winter Park, FL 32792
  • /15

    $2,125 Per Month

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • House for Rent

    1407 Chilean Ln, Winter Park, FL 32792

    We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

    1407 Chilean Ln, Winter Park, FL 32792
  • /11

    $2,350 Per Month

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft
    • House for Rent

    1931 Staunton Ave, Winter Park, FL 32789

    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

    Zach Mitchell SAND DOLLAR REALTY GROUP INC

    1931 Staunton Ave, Winter Park, FL 32789
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    $2,525 Per Month

    • 4 Beds
    • 3 Baths
    • 1,856 Sq Ft
    • House for Rent

    2029 Taylor Ave, Winter Park, FL 32792

    Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently

    2029 Taylor Ave, Winter Park, FL 32792
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    $2,599 Per Month

    • 3 Beds
    • 2 Baths
    • 1,535 Sq Ft
    • House for Rent

    3465 Balsam Dr, Winter Park, FL 32792

    Welcome to this charming 3-bedroom, 2-bathroom home located in a well-established Winter Park neighborhood. This property offers a comfortable single-story layout with inviting living spaces, ideal for everyday living and entertaining. The home features a functional floor plan with a bright living area, an eat-in kitchen, and well-sized bedrooms, including a primary suite with a private bath.

    Steve Simpson 407 PROPERTIES

    3465 Balsam Dr, Winter Park, FL 32792
  • /13

    $1,522

    Total Monthly Price

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

    1500 Gay Rd Unit 1D, Winter Park, FL 32789

    EXCELLENT LOCATION within walking distance to retail stores, restaurants, and parks. This remodeled second-floor unit offers lake access, a pool, and includes water in the rent. Flexible deposit option available—can be split over the first three months.

    1500 Gay Rd Unit 1D, Winter Park, FL 32789
  • /12

    $2,550 Per Month

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

    110 Killarney Bay Ct Unit 1, Winter Park, FL 32789

    **MOVE IN SPECIAL $500 off first months rent** Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
  • /9

    $1,850

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft
    • Condo for Rent

    1500 Gay Rd Unit 9D, Winter Park, FL 32789

    Two-bedroom, two-bath walk-up condo off Lake Killarney in Winter Park, Florida. Spacious rooms, custom upgrades, quiet, and well maintained. Located in the Chateaux du Lac community at 1500 GayRoad. Within walking distance of Winter Park Village, Traders Joe's, restaurants and more. Minutes from AdventHealth Orlando, Park Avenue, Rollins College, and I-4.Pet free unit. Ideally seeking

    1500 Gay Rd Unit 9D, Winter Park, FL 32789
  • /12

    $6,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Apartment for Rent

    301 W Comstock Ave, Winter Park, FL 32789

    Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

    Sydney Brownlee THE SYDGAN CORP

    301 W Comstock Ave, Winter Park, FL 32789
  • /24

    $3,350

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,312 Sq Ft
    • Townhouse for Rent

    1886 Demetree Dr, Winter Park, FL 32789

    Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter Park Welcome home to this stylish, move-in-ready townhome located in the heart of Winter Park. Enjoy the perfect balance of convenience and comfort—just a short walk to Winter Park Dog Park and Baldwin Park, and minutes from Rollins College, Park Avenue, downtown Orlando, and major hospitals. This thoughtfully

    1886 Demetree Dr, Winter Park, FL 32789
  • /62

    $3,900 Per Month

    • 4 Beds
    • 3 Baths
    • 2,130 Sq Ft
    • House for Rent

    1542 Sugarwood Cir, Winter Park, FL 32792

    Spacious, fully remodeled 4-bedroom, 2.5-bath single-family home located in the desirable Amberwood community in Winter Park. This one-story property offers approximately 2,130 sq ft of living space, featuring vaulted ceilings, a functional layout, and a bright living and dining area. The home showcases luxury finishes throughout, a brand-new roof, central A/C, and a 2-car attached garage. Enjoy

    Dayana Perez Moreno AROD PARTNERS REALTY

    1542 Sugarwood Cir, Winter Park, FL 32792
  • /6

    $1,850

    Total Monthly Price

    • 2 Beds
    • 2.5 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792

    Close to Park Avenue Winter Park Restaurants and shopping near UCF and Full sail University also Rollins Colllege, Great Public schools. Close to the Orlando Airport and 30 minutes from Disney World and Universal Studios.

    2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792
  • /17

    $1,400 Per Month

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

    1695 Lee Rd Unit D213, Winter Park, FL 32789

    Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

    Rachel DeCamp RLL Real Estate Group

    1695 Lee Rd Unit D213, Winter Park, FL 32789
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    $1,000

    Total Monthly Price

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

    5058 Seminole Ave Unit Seminole Unit 1, 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 1, Winter Park, FL 32792
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    $1,725 Per Month

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

    3283 Oak Lake Place Unit 127, Winter Park, FL 32792

    Beautiful freshly painted and cleaned property in Winter park. This is a townhouse style condo (no neighbors above and only on one side)- end unit with rear patio and storage closet. The first floor is a large living space, kitchen, a half bath and laundry with a dining nook. While there are 3 bedrooms upstairs with 2 full baths. The first floor is fully tiled and the upstairs bedrooms have

    Kyle Petteway EXIT REAL ESTATE RESULTS

    3283 Oak Lake Place Unit 127, Winter Park, FL 32792
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    $3,150

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Townhouse for Rent

    1351 Merrydale Way, Winter Park, FL 32792

    Modern townhome in a gated community in Winter Park. This energy star-certified home features 3 BED/2.5 BATH, large two car garage and private driveway, tile floors all throughout the first floor, granite countertops in the kitchen and bathroom, and all stainless steel appliances. The downstairs is an airy open concept with views of the lake. There's a 1/2 bath downstairs so you are never

    1351 Merrydale Way, Winter Park, FL 32792
  • /40

    $3,895 Per Month

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

    1409 Lone Feather Trail, Winter Park, FL 32792

    Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! Landscape/Lawn Care and Reclaimed Water Bill are paid by landlord. UV sanitizing lights installed in all bathrooms. Water filter system installed in kitchen sink. This 4 bed 3.5 bathrooms plus an office and second floor loft is ready to move-in . When you enter

    Yan Zuo EAST PEARL REALTY

    1409 Lone Feather Trail, Winter Park, FL 32792
  • /50

    $2,100

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 1,360 Sq Ft
    • Condo for Rent

    600 Waverly Ln Unit 600 Waverly Lane, Maitland, FL 32751

    600 Waverly Lane offers the perfect blend of comfort, convenience, and classic Florida living.This inviting residence features a spacious layout with abundant natural light, creating a warm and welcoming atmosphere throughout. The home includes generously sized bedrooms, well appointed bathrooms, and a functional kitchen ideal for both everyday living and entertaining.Step outside

    600 Waverly Ln Unit 600 Waverly Lane, Maitland, FL 32751
  • /16

    $1,400 Per Month

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

    1695 Lee Rd Unit C110, Winter Park, FL 32789

    Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit C110, Winter Park, FL 32789
  • /14

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 854 Sq Ft
    • House for Rent

    2304 Inagua Way, Winter Park, FL 32792

    Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the

    2304 Inagua Way, Winter Park, FL 32792
  • /21

    $2,900 Per Month

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • House for Rent

    540 W Comstock Ave, Winter Park, FL 32789

    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

    Fredrick Jacobs KELLER WILLIAMS GAINESVILLE REALTY PARTNERS

    540 W Comstock Ave, Winter Park, FL 32789
  • /16

    $1,775 Per Month

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

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792

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