69

Winter Park, FL Houses for Rent

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  • /68

    $8,650 per month

    • 5 Beds
    • 5 Baths
    • 4,953 Sq Ft
    • House for Rent

    2851 Dorell Ave Unit 10, Orlando, FL 32814

    NEWLY LISTED HOME IN BALDWIN PARK. Welcome home to this Gorgeous Courtyard Style floor Plan that boasts a beautiful pond view and just steps from the pool and pavilion at High Park. This 5-bedroom, 5-bath estate home offers a spacious open floorplan and a range of desirable features. As you enter home you will be greeted by a covered porch perfect for relaxing or unwinding after a day’s work.

    Agent Photo

    Bruce Kalin

    JC FLORIDA REALTY LLC

    (321) 384-9558

    2851 Dorell Ave Unit 10, Orlando, FL 32814
  • /15

    $2,950 per month

    • 3 Beds
    • 2 Baths
    • 1,118 Sq Ft
    • House for Rent

    779 W Lyman Ave, Winter Park, FL 32789

    Charming 3BR/2BA Home in the Heart of Winter Park – Walk to Park Ave & Hannibal Square!Rent: $2,950/monthAvailable: 8/1/2025Location: Winter Park, FL 32789Discover this cozy and well-maintained 3-bedroom, 2-bathroom home nestled in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue and Hannibal Square, you'll enjoy premier shopping,

    779 W Lyman 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

    Experience sophisticated living in the heart of prestigious Winter Park with this stunning 4-bedroom, 2-bath single-family home. Designed with both comfort and elegance in mind, every detail has been thoughtfully crafted to create an inviting, high-end retreat.From the moment you step inside, natural light floods the open-concept layout, illuminating sleek ceramic tile floors and a warm,

    Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

    1368 Hibiscus Ave, Winter Park, FL 32789
  • /10

    $2,275 per month

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • House for Rent

    7457 Blue Jacket Place E, 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 $2539.90. That covers your base rent, $2275.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7457 Blue Jacket Place E, Winter Park, FL 32792
  • /45

    $6,000 per month

    • 4 Beds
    • 3 Baths
    • 3,296 Sq Ft
    • House for Rent

    2330 Westminster Ct, Winter Park, FL 32789

    Welcome to 2330 Westminster Court, a stunning 5-bedroom, 3-bathroom residence nestled in the heart of Winter Park. This beautifully, fully updated home offers a perfect blend of modern elegance and classic charm, making it an ideal retreat for families and entertainers alike. Step inside to discover a spacious, light-filled interior featuring top-to-bottom renovations that include a stylish

    Brandon Geers COMPASS FLORIDA LLC

    2330 Westminster Ct, Winter Park, FL 32789
  • /2

    $2,749 per month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    881 Julian St, Winter Park, FL 32789

    This home is currently undergoing exciting renovations and will be ready for you soon. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon

    881 Julian St, Winter Park, FL 32789
  • /10

    $2,300 per month

    • 2 Beds
    • 1.5 Baths
    • 1,091 Sq Ft
    • House for Rent

    2011 Cornell Ave, Winter Park, FL 32789

    Charming 3-Bedroom Home for Rent in Winter ParkThis beautiful 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. Featuring spacious living areas and modern appliances, it offers a comfortable and convenient living environment. Located in a quiet, family-friendly neighborhood, it provides easy access to local shops, restaurants,

    Andres Ospina Rivera LPT REALTY, LLC

    2011 Cornell Ave, Winter Park, FL 32789
  • /16

    $800 per month

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

    1450 Cavendish Rd, Winter Park, FL 32789

    Property Id: 2051407Charming 1938 Deco influenced design - block home with cottage feel - in coveted Winter Park side of historic Orwin Manor - on a very quiet street. Newly renovated. New standing seam metal roof & galvanized rain gutters, new windows, new 2" white vinyl blinds, new front door, new closet doors, entire house is newly painted inside & out (including kitchen cabinets with

    1450 Cavendish Rd, Winter Park, FL 32789
  • /14

    $2,250 per month

    • 3 Beds
    • 2 Baths
    • 1,531 Sq Ft
    • House for Rent

    1436 Tangerine Ct, Winter Park, FL 32792

    This beautifully renovated 3-bedroom, 2-bathroom home is nestled in a quiet cul-de-sac in the heart of Winter Park. Featuring an open-concept layout, and abundant natural light, this home offers both comfort and style. The functional kitchen boasts granite countertops and seamlessly flows into the spacious living and dining areas, perfect for everyday living or entertaining guests. Step out back

    Summer Hornburg BELMONT REALTY

    1436 Tangerine Ct, Winter Park, FL 32792
  • /2

    $2,160 per month

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • House for Rent

    1061 Portsmouth Ln, 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

    1061 Portsmouth Ln, Winter Park, FL 32792
  • /45

    $4,199 per month

    • 3 Beds
    • 2 Baths
    • 1,499 Sq Ft
    • House for Rent

    1681 Walnut Ave, Winter Park, FL 32789

    Fully furnished with dishes and all ! Tastefully decorated !Can be rented unfurnished if needed .Also month to a year lease is ok !Two separate living quarters en suite with private entrance and small fridge and microwave /dining /living area ( or master )Fully renovated this adorable 3 bedroom, 2 bath bungalow home is a rare find in one of Winter Park's most sought-after neighborhoods.Fully

    Natalie Citarelli CITARELLI REALTY GROUP LLC

    1681 Walnut Ave, Winter Park, FL 32789
  • /15

    $2,480 per month

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • House for Rent

    1729 Puritan Ave, 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, nestled

    1729 Puritan Ave, Winter Park, FL 32792
  • /17

    $2,999 per month

    • 3 Beds
    • 2 Baths
    • 1,641 Sq Ft
    • House for Rent

    101 S Lakemont Ave, Winter Park, FL 32792

    Welcome to this beautifully renovated 3-bedroom, 2-bathroom single-family home, perfectly positioned just minutes away from shopping, dining, and all the charm of Winter Park. This home combines modern luxury with everyday convenience. As you step inside, you're greeted by the elegance of Calacatta Quartz countertops, sleek waterproof flooring, and top-of-the-line appliances that set the tone for

    Robert Isaac Rodriguez RE/MAX DOWNTOWN

    101 S Lakemont Ave, Winter Park, FL 32792
  • /13

    $2,175 per month

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft
    • House for Rent

    5351 Cypress 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 $2319.90. That covers your base rent, $2175.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    5351 Cypress Dr, Winter Park, FL 32792
  • /32

    $3,200 per month

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft
    • House for Rent

    1816 Mizell Ave, Winter Park, FL 32789

    Welcome to this charming 3-bedroom, 2-bath home in the heart of Winter Park, complete with a 1-car garage and unbeatable location. Just minutes from Park Avenue, Winter Park Hospital, top-rated shopping, and dining, convenience is at your doorstep. Start your mornings with peaceful strolls through the beautiful Windsong neighborhood and take in the serene views of Lake Mizell. Whether you're

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    1816 Mizell Ave, Winter Park, FL 32789
  • /9

    $2,630 per month

    • 4 Beds
    • 2 Baths
    • 2,288 Sq Ft
    • House for Rent

    3330 Coleus 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 $2894.90. That covers your base rent, $2630.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3330 Coleus Ct, Winter Park, FL 32792
  • /18

    $3,600 per month

    • 4 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • House for Rent

    1846 Barker Dr, Winter Park, FL 32789

    Welcome to 1846 Barker Dr- a charming and well maintained single family home located in one of Winter Park's most desirable neighborhoods. This inviting 4- bedrooms, -2 bath residence offers a perfect blend of comfort and convenience, just minutes from top-rated schools, beautiful parks, shopping, dining and all amenities of the sought-after Winter Park-Baldwin Park lifestyle. Enjoy a bright and

    Cliff Glansen FLATFEE.COM

    1846 Barker Dr, Winter Park, FL 32789
  • /16

    $2,875 per month

    • 4 Beds
    • 2 Baths
    • 1,970 Sq Ft
    • House for Rent

    2843 Riddle Dr, Winter Park, FL 32789

    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 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    2843 Riddle Dr, Winter Park, FL 32789
  • /16

    $2,380 per month

    • 3 Beds
    • 2 Baths
    • 1,909 Sq Ft
    • House for Rent

    2717 Amsden Rd, 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, nestled

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    2717 Amsden Rd, Winter Park, FL 32792
  • /15

    $2,015 per month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    5335 N Orange Ave, 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

    5335 N Orange Ave, Winter Park, FL 32792
  • /16

    $2,815 per month

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft
    • House for Rent

    7431 Portside Ct, 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, nestled

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    7431 Portside Ct, Winter Park, FL 32792
  • /15

    $1,930 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
  • /20

    $3,100 per month

    • 3 Beds
    • 2 Baths
    • 1,329 Sq Ft
    • House for Rent

    424 Dunraven Dr, Winter Park, FL 32792

    Location! Schools! Community! Convenience! Corner lot! Don't miss this great Winter Park home

    Julia Magnani LOKATION

    424 Dunraven Dr, Winter Park, FL 32792
  • /15

    $1,985 per month

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • House for Rent

    1381 Viburnum 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

    1381 Viburnum Ln, Winter Park, FL 32792
  • /43

    $9,995 per month

    • 4 Beds
    • 3.5 Baths
    • 4,188 Sq Ft
    • House for Rent

    2020 Venetian Way, Winter Park, FL 32789

    This RARE LAKEFRONT retreat is located on a quiet, tree-lined street in the highly sought-after Vias of Winter Park. Custom-built and elevated on a prime lot with 90 feet of frontage on Lake Maitland, this one-of-a-kind mid-century home offers sweeping views of Lake Maitland and the Isle of Sicily. It combines timeless design, complete privacy, and a premier location just minutes from Park Avenue

    Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

    2020 Venetian Way, Winter Park, FL 32789
  • /7

    $2,000 per month

    • 2 Beds
    • 1 Bath
    • House for Rent

    1399 Miller Ave, Winter Park, FL 32789

    Property Id: 1795045Charming 1926 bungalow. 2 bedroom/1 bathroom house in prime location of Winter Park. Wood floors throughout the home, cast iron bathtub, hexagon tile in bathroom. Short drive to I-4, Park Ave, Rollins College, shopping, restaurants, downtown Orlando, hospitals, and more. Extra large front porch, fireplace, full kitchen, and washer and dryer.Renter responsible

    1399 Miller Ave, Winter Park, FL 32789
  • /13

    $2,500 per month

    • 2 Beds
    • 2 Baths
    • 1,286 Sq Ft
    • House for Rent

    689 Overspin Dr, Winter Park, FL 32789

    Welcome to 689 Overspin Rd – a beautifully maintained 2-bedroom, 2-bathroom home in the heart of Winter Park! This inviting residence features stunning hardwood floors throughout, creating a warm and stylish ambiance from the moment you walk in. Enjoy cooking and entertaining in the large open kitchen, complete with stainless steel appliances, ample counter space, and plenty of storage. Cozy up

    Megan Teal MAINFRAME REAL ESTATE

    689 Overspin Dr, Winter Park, FL 32789
  • /12

    $2,349 per month

    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft
    • House for Rent

    324 Lake Fair Ln, Winter Park, FL 32789

    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 $2493.90. That covers your base rent, $2349.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    324 Lake Fair Ln, Winter Park, FL 32789
  • /23

    $2,850 per month

    • 4 Beds
    • 2 Baths
    • 2,234 Sq Ft
    • House for Rent

    3300 Bennington Ct, Winter Park, FL 32792

    Winter Park Rental Home in Bennington Estates. Home offers 4 Bedrooms, 2 Baths, Split plan, Large Eat-in Kitchen w/Island, 2 Car Garage, 2234 Sqft under air, Tile & Laminate Wood flooring throughout home, Formal Dining Room & Formal Living Room with Bay Window. Enclosed Rear Patio that can be cooled, Large Backyard. The formal living area makes a great Den or Office space. Location offers

    Emily Lemieux RE/MAX TOWN & COUNTRY REALTY

    3300 Bennington Ct, Winter Park, FL 32792
  • /18

    $2,840 per month

    • 4 Beds
    • 2 Baths
    • 2,088 Sq Ft
    • House for Rent

    7145 Timber 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 $3104.90. That covers your base rent, $2840.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7145 Timber Dr, Winter Park, FL 32792
  • /30

    $6,200 per month

    • 4 Beds
    • 4 Baths
    • 3,654 Sq Ft
    • House for Rent

    960 Georgia Ave, Winter Park, FL 32789

    Quintessential Winter Park Stunner. This well appointed home is situated on a half acre corner lot just two blocks away from Winter Park's shopping and dining district, Park Avenue. Surrounded by majestic oak trees you find this classic 4 bedroom, 4 bath home with 3600sq ft of living space. An abundance of natural light welcomes you in the homes central hub, the Family Room. Anchored by one of

    Alison Ashby CORCORAN PREMIER REALTY

    960 Georgia Ave, Winter Park, FL 32789
  • /16

    $2,285 per month

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft
    • House for Rent

    7423 Antietam Ct E, 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 $2429.90. That covers your base rent, $2285.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7423 Antietam Ct E, Winter Park, FL 32792
  • /30

    $4,000 per month

    • 4 Beds
    • 3 Baths
    • 2,818 Sq Ft
    • House for Rent

    1289 Heavenly Cove, Winter Park, FL 32792

    Welcome to this move in ready 4-bedroom, 3-bath, 3-car garage pool home located in the exclusive gated community of Eden Point, a desirable Winter Park address! From the moment you arrive, you'll be impressed by the gorgeous elevation, paver driveway, and inviting front porch. This home offers a thoughtful split floor plan, tray ceilings, and rich Bamboo floors, creating a sense of space and

    Shahrin Alam COLDWELL BANKER RESIDENTIAL RE

    1289 Heavenly Cove, Winter Park, FL 32792
  • /2

    $2,780 per month

    • 3 Beds
    • 2 Baths
    • 1,553 Sq Ft
    • House for Rent

    630 N Lakemont Ave, 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

    630 N Lakemont Ave, Winter Park, FL 32792
  • /14

    $2,350 per month

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft
    • House for Rent

    5323 Poinsetta Ave, Winter Park, FL 32792

    Winter Park and NO HOA!! Newly remodeled 3/2 1,500 sqft $2,350/mo. Just a 1 minute car ride or 5-7 minute walk to Eastbrook Elementary. Remodeled kitchen with all the bells and whistles (new cabinets, countertops, backsplash, faucet, lights, and appliances - you get the idea, it's fancy!). Remodeled bathrooms with subway tiles, new tub, new vanities, new countertops, new toilets, new lighting &

    Ginnie England MAGNOLIA PROPERTY SALES

    5323 Poinsetta Ave, Winter Park, FL 32792
  • /10

    $2,190 per month

    • 3 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • House for Rent

    1305 Viburnum Ln, 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 $2334.90. That covers your base rent, $2190.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1305 Viburnum Ln, Winter Park, FL 32792
  • /67

    $5,050 per month

    • 4 Beds
    • 3 Baths
    • 2,422 Sq Ft
    • House for Rent

    2627 Verona Trail, Winter Park, FL 32789

    Beautiful 4 bedroom/ 3 bath Pool home for rent in Winter Park Range, D/W, Disposal, Central Heat and A/C.

    Rick Sein REALSOURCE PROPERTY MANGNT LLC

    2627 Verona Trail, Winter Park, FL 32789
  • /4

    $1,450 per month

    • 2 Beds
    • 2 Baths
    • 1,042 Sq Ft
    • House for Rent

    3054 George Mason Ave, Winter Park, FL 32792

    *ESTIMATED TOTAL MONTHLY LEASING PRICE: $1,499.95Base Rent: $1,450.00Filter Delivery: $5.00Renters Insurance: $10.95$1M Identify Protection, Credit Building, Resident Rewards, Move-In Concierge: $34.00 *The estimated total monthly leasing price does not include utilities or optional/conditional fees, such as: pet, utility service, and security deposit waiver fees. Our

    3054 George Mason Ave, Winter Park, FL 32792
  • /30

    $2,650 per month

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • House for Rent

    2831 Lion Heart Rd Unit 1, Winter Park, FL 32792

    " A " Winter Park School District. The well-kept 3-bedroom, 2-bath home features an open floor plan and a spacious bonus storage room. The upgraded gourmet kitchen flows seamlessly into the living room, which opens to a bright and cheerful Florida room—perfect for relaxing or entertaining. Enjoy added privacy with a fully fenced yard.

    Liu Zhang JOY ESTATE ENTERPRISE INC

    2831 Lion Heart Rd Unit 1, Winter Park, FL 32792
  • /20

    $2,249 per month

    • 3 Beds
    • 2 Baths
    • 1,549 Sq Ft
    • House for Rent

    1752 W Cheryl 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 $2393.90. That covers your base rent, $2249.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1752 W Cheryl Dr, Winter Park, FL 32792

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How to Rent a Home