37

Winter Park, FL Houses for Rent under $3,000

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  • /15

    $2,970 per month

    • 3 Beds
    • 2 Baths
    • 1,195 Sq Ft
    • House for Rent

    1891 Oglesby Ave, Winter Park, FL 32789

    Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus

    Agent Photo

    Paul Jimenez

    URBANISTA BROKERS

    (321) 977-5674

    1891 Oglesby Ave, Winter Park, FL 32789
  • /16

    $2,495 per month

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • House for Rent

    2316 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 $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

    2316 Dunbury Ct, Winter Park, FL 32792
  • /60

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,676 Sq Ft
    • House for Rent

    7508 Glenmoor Ln, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Welcome to this beautifully refreshed 3-bedroom, 2-bath home nestled in a highly desirable Winter Park location — offering comfort, style, and convenience with no HOA restrictions. With 1,676 square feet of thoughtfully designed living space, this home is the perfect blend of modern updates and timeless character.Step inside to discover

    Jenny Chien Lin AMERICAN DREAM HOMES INC

    7508 Glenmoor Ln, Winter Park, FL 32792
  • /15

    $2,565 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
  • /9

    $1,975 per month

    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft
    • House for Rent

    1803 Pineview Cir, Winter Park, FL 32792

    This beautiful 2 bed / 1 bath 1,029 square foot home in Winter Park is totally refurbished and available for immediate occupancy. Newer kitchen cabinets. Newer bathroom. With a single car carport. This property features wood floors throughout, tile floors in the kitchen, dining room and bathroom, large open yard. Washer/dryer, shed & lawn care included! Application Fee: $50 each adult

    Kenneth Warren PREMIER MANAGEMENT GROUP INC

    1803 Pineview Cir, Winter Park, FL 32792
  • /16

    $2,725 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.

    1721 Shasta Ct, Winter Park, FL 32792
  • /10

    $2,350 per month

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

    1589 Viburnum Ln, Winter Park, FL 32792

    newly updated 3 bedroom 2 bath with flex room for home office. new appliances and ready for move-in

    Mike Wang LOKATION

    1589 Viburnum Ln, Winter Park, FL 32792
  • /15

    $2,470 per month

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

    3021 Dikewood Ct, 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

    3021 Dikewood Ct, Winter Park, FL 32792
  • /13

    $2,695 per month

    • 2 Beds
    • 1.5 Baths
    • 1,149 Sq Ft
    • House for Rent

    1137 Oaks Blvd, Winter Park, FL 32789

    Rarely available neighborhood for rentals, this 2 bedroom 1 and a half bath house is surrounded by multi-million dollar homes. Large back yard is totally fenced for kids or pets. Zoned for Winter Park's finest schools and located just off Park Avenue for easy access to shopping and restaurants. Shorter term lease is negotiable. All appliances are in place, including washer/dryer. Don't miss this

    Jake Johnson SHORES REAL ESTATE

    1137 Oaks Blvd, Winter Park, FL 32789
  • /15

    $2,265 per month

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

    1407 Chilean Ln, 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

    1407 Chilean Ln, Winter Park, FL 32792
  • /35

    $3,000 per month

    • 4 Beds
    • 2 Baths
    • 2,268 Sq Ft
    • House for Rent

    4033 Yacht Ct, Winter Park, FL 32792

    Experience the rare luxury of a high-performance, meticulously updated 3-bedroom sanctuary in a quiet Winter Park cul-de-sac, offering the perfect blend of modern utility and suburban serenity. Zoned for Winter Park High School, this versatile floor plan features both a dedicated private office for the remote professional and an expansive game room for premier entertaining. Every major system has

    Brenden Rando NEXTHOME NEIGHBORHOOD REALTY

    4033 Yacht Ct, Winter Park, FL 32792
  • /15

    $2,249 per month

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

    1453 Hyde Park 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

    1453 Hyde Park Dr, Winter Park, FL 32792
  • /19

    $1,995 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 talbe with 4 chairs - picnic in your own park

    Scott Banta BLACKFIN REALTY LLC

    1942 Conifer Ct, Winter Park, FL 32792
  • /15

    $2,440 per month

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

    3091 Crane Strand Dr, 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

    3091 Crane Strand Dr, 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

    $2,670 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.

    2141 Ridge Dr, Winter Park, FL 32792
  • /33

    $2,890 per month

    • 4 Beds
    • 3 Baths
    • 1,469 Sq Ft
    • House for Rent

    524 Byron Rd, Winter Park, FL 32792

    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

    Razan Mohamed SOUTHERN PRESTIGE REALTY INC

    524 Byron Rd, Winter Park, FL 32792
  • /13

    $2,220 per month

    • 3 Beds
    • 2 Baths
    • 1,479 Sq Ft
    • House for Rent

    1185 Village Forest Place, 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 $2364.90. That covers your base rent, $2220.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1185 Village Forest Place, Winter Park, FL 32792
  • /30

    $2,350 per month

    • 3 Beds
    • 1.5 Baths
    • 1,279 Sq Ft
    • House for Rent

    2846 Euston Rd, Winter Park, FL 32789

    Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and

    Vanessa Laboy 365 REALTY, INC.

    2846 Euston Rd, Winter Park, FL 32789
  • /15

    $2,560 per month

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

    1790 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 $2824.90. That covers your base rent, $2560.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1790 Viburnum Ln, Winter Park, FL 32792
  • /18

    $2,167 per month

    • 4 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • House for Rent

    717 Denton Rd, Winter Park, FL 32792

    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

    Jay Myers ORLANDO REALTY & PROPERTY MGNT

    717 Denton Rd, Winter Park, FL 32792
  • /19

    $2,395 per month

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

    3221 Thistle Hill Dr, Winter Park, FL 32792

    This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee (subject to approval).

    3221 Thistle Hill Dr, Winter Park, FL 32792
  • /13

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft
    • House for Rent

    2743 Sanbina St, Winter Park, FL 32789

    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

    Summer Hornburg BELMONT REALTY

    2743 Sanbina St, Winter Park, FL 32789
  • /17

    $2,625 per month

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • House for Rent

    6877 Jackman Blvd, 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 $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    6877 Jackman Blvd, Winter Park, FL 32792
  • /15

    $2,650 per month

    • 4 Beds
    • 2 Baths
    • 1,858 Sq Ft
    • House for Rent

    1813 E Cheryl Dr, Winter Park, FL 32792

    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!

    Harry Kazarian STRONG FOUNDATION REALTY LLC

    1813 E Cheryl Dr, Winter Park, FL 32792
  • /20

    $1,650 per month

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

    1550 Michigan Ave, Winter Park, FL 32789

    Welcome to your future home in the charming district of Winter Park, FL! This inviting property offers a warm atmosphere perfect for relaxation and convenience, surrounded by a vibrant community.This residence boasts spacious living equipped with essential comforts. With ample bedrooms and bathrooms, it accommodates various lifestyles. You'll appreciate the central heating and cooling

    1550 Michigan Ave, Winter Park, FL 32789
  • /15

    $2,095 per month

    • 3 Beds
    • 2 Baths
    • 1,613 Sq Ft
    • House for Rent

    1724 Peruvian Ln, Winter Park, FL 32792

    Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled

    Mo Jabr RE/MAX 200 REALTY

    1724 Peruvian Ln, Winter Park, FL 32792
  • /19

    $2,285 per month

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • House for Rent

    5484 Park Vale Blvd, 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

    5484 Park Vale Blvd, Winter Park, FL 32792
  • /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

    Joseph LaRosa La Rosa Realty Llc

    2523 Alexa Ct, Winter Park, FL 32792
  • /20

    $2,535 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 $2679.90. That covers your base rent, $2535.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3628 Datura Ct, Winter Park, FL 32792
  • /19

    $2,150 per month

    • 3 Beds
    • 2 Baths
    • 1,113 Sq Ft
    • House for Rent

    1931 Carrigan Ave, Winter Park, FL 32792

    An excellent place to call home. This newly renovated 3 bedroom 2 bath house offers a lot of entertainment options; it is sitting on an oversize lot which features ample backyard space which is completely fenced. This home has brand new AC, Plumbing and Electric and offers washer/dryer hookups. Close to A+ schools and is approximately 7 minutes from Park Ave shopping and dining. This will not

    Amanda Beckman RED DOOR INVESTMENT GRP LLC

    1931 Carrigan Ave, Winter Park, FL 32792
  • /16

    $2,640 per month

    • 3 Beds
    • 2 Baths
    • 1,653 Sq Ft
    • House for Rent

    1891 Aster Dr, Winter Park, FL 32792

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    1891 Aster Dr, Winter Park, FL 32792
  • /42

    $2,950 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
  • /19

    $1,000 total monthly price

    • 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
  • /33

    $2,435 per month

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

    1622 Arbor Park Dr, Winter Park, FL 32789

    Free 1/2 month's rent move in incentive! 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 with plenty of natural light

    Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

    1622 Arbor Park Dr, Winter Park, FL 32789
  • /15

    $2,900 total monthly price

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

    5417 Ferrol Dr, Winter Park, FL 32792

    Beautifully Remodeled 3 Bed, 2 Bath Home Energy Efficient & Prime Location!Welcome to your dream rental! This stunning newly remodeled 3-bedroom, 2-bath home offers modern comfort with a touch of elegance. Featuring an open floor concept, the spacious living area is perfect for entertaining, complete with a cozy fireplace and abundant natural light from double-glazed windows.The

    5417 Ferrol Dr, Winter Park, FL 32792
  • /20

    $2,120 per month

    • 2 Beds
    • 1 Bath
    • 1,146 Sq Ft
    • House for Rent

    1730 Ridgewood Ave, Maitland, FL 32751

    Property Id: 1799893LOCATION, LOCATION, LOCATION! Fabulous cottage in the heart of Winter Park / Maitland. This charming 1,146sf, 2-bedroom, 1-bath home is just off N Park Ave, it's close to Orlando Ave, Whole Foods, Publix, and in walking distance to The Enzian. The home sits with an expansive back yard with beautiful mature trees and a barbeque patio. It includes a detached garage with

    1730 Ridgewood Ave, Maitland, FL 32751
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