36

Winter Park, FL Houses for Rent under $2,500

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  • /15

    $2,275 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
  • /31

    $2,350 per month

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

    1571 Magnolia Ave, Winter Park, FL 32789

    Fantastic bungalow in sought-after Winter Park. Great location, close to Advent Hospital Winter Park, Park Avenue, 10 minutes to I4. Large, fenced-in backyard, original hardwood floors in living area & bedrooms. Stainless appliances, granite countertops in kitchen, one car garage. Tons of natural light, indoor laundry.

    Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

    1571 Magnolia Ave, Winter Park, FL 32789
  • /15

    $2,215 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
  • /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
  • /15

    $2,330 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
  • /8

    $2,195 per month

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • House for Rent

    5523 Cretan Way, Winter Park, FL 32792

    3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and

    Shawn Beard RE/MAX 200 REALTY

    5523 Cretan Way, Winter Park, FL 32792
  • /19

    $2,245 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
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    $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
  • /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
  • /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
  • /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
  • /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
  • /6

    $1,650 per month

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • 2 bedroom 2 bath condo in Parkview Village of Winter Park

    2936 Antique Oaks Cir, Winter Park, FL 32792

    Please call JML Realty Investments to view this 2 bedroom 2 bath condo Located on the 2nd floor of the Parkview Village Subdivision . The living room is spacious with vaulted ceilings and is in front of the kitchen . There is a formal dining area next to the kitchen as well. Down the hall there is a laundry room with full size WASHER AND DRYER INCLUDED IN THE RENT. There is ample storage in

    2936 Antique Oaks Cir, 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
  • /11

    $2,050 per month

    • 3 Beds
    • 2 Baths
    • 1,317 Sq Ft
    • Winter Park 3 Bedroom 2 Bath Renovated!

    5171 N Orange Ave, Winter Park, FL 32792

    You don't want to miss out on this Winter Park Beauty! This lovely, RENOVATED, 3/2 block home, is situated on a large, fenced in lot and has been recently renovated ! The house has a nice open floor plan, with a great room and family room. The great room even has a wood burning fireplace. Renovations include...laminate wood floors throughout, interior paint, almost new kitchen appliances,

    5171 N Orange Ave, Winter Park, FL 32792
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    $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
  • /4

    $1,050 per month

    • 1 Bed
    • 1 Bath
    • House for Rent

    525 S Lakemont Ave, Winter Park, FL 32792

    Room Rental Listing: Room 01 – Master Bedroom with Attached BathroomThis listing is for Room 01, the Master Bedroom with an attached bathroom, in a fully furnished 3-bedroom, 2-bathroom house.Location: SW Zone @ 525 S Lakemont Ave, Winter Park, FloridaProperty Features: Preliminary Information :Appliances Provided:Cooking range with

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

    $2,300 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
  • /3

    $2,195 per month

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • House for Rent

    3238 Black Pine Ave, Winter Park, FL 32792

    3 bed, 2 bath 1,625 sqft, Single Family Home, double garage, all kitchen appliances NO PETS!! Deposit is the same as the rent amount. CARPET floors and tile. Schools are Winter Park High School, Glenridge Middle School, and Aloma Elementary.Great neighborhood Available April 5. SHOWINGS BY APPOINTMENT ONLY contact Terri at The Property Management Specialist of Central FL Year Lease. Deposit

    3238 Black Pine Ave, Winter Park, FL 32792
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    $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
  • /3

    $2,095 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    5139 Oak Hill Dr, Winter Park, FL 32792

    3/2 home with updated kitchen, large yard & screen patio. 3/2 home with updated kitchen, large yard & screen patio. Lawn service included

    5139 Oak Hill Dr, 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
  • /12

    $1,900 per month

    • 2 Beds
    • 2.5 Baths
    • 960 Sq Ft
    • Gorgeous, Completely Remodeled 2/2.5 Condo in Sandlewood Creek- Winter Park!

    303 Sandlewood Trail, Winter Park, FL 32789

    Welcome home to this beautifully renovated two-story condo in desirable Sandlewood Trails. This 2-Bedroom, 2.5 Bath condo home is ideally located in Winter Park and is one of the few condo communities where residents are close enough to bike or walk to Dommerich Elementary and Maitland Middle School.As you enter, you are welcomed by a spacious Great Room and attractive gray-toned laminate

    303 Sandlewood Trail, Winter Park, FL 32789
  • /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
  • /15

    $2,195 per month

    • 3 Beds
    • 2 Baths
    • 1,324 Sq Ft
    • House for Rent

    704 Carnation Dr, Winter Park, FL 32792

    Welcome to 704 Carnation Drive in Winter Park! This amazing home is located on a quiet street in the Eastbrook subdivision off Aloma Ave and was just freshly painted inside and out. The single-story home features an open concept living room/dining room/kitchen floorplan with stainless steel appliances, granite countertops, ceiling fan and ceramic tile flooring throughout. There is plenty of

    704 Carnation Dr, 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
  • /9

    $2,100 per month

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Nice 3 bedroom, 2 bath single family home

    3036 Patel Dr, Winter Park, FL 32792

    Available May 1st! 3/2 with open-concept kitchen. Your new home has an open and airy living room/kitchen area with easy-to-maintain tile. A HUGE screened patio looks out to a private wooded backyard. Privacy fence and attached one-car garage make this the perfect place to call home! The home is nestled on a cul-de-sac minutes from Full Sail.All ERA Grizzard Real Estate residents are

    3036 Patel Dr, Winter Park, FL 32792
  • /21

    $1,200 per month

    • 1 Bed
    • 1 Bath
    • 537 Sq Ft
    • One bedroom apt 7 or 12 months furnish or unfurnished. Apartamento disponible amueblado o sin mue...

    3075 Aaron Burr Ave, Winter Park, FL 32792

    Centrally located in Winter Park near Full Sail University, and check out this cute move-in ready, 1 Bed/1 Bath second-floor condo with a rear balcony. All tiled flooring, new paint, new toilets and light fixtures, new dishwasher and range. The community features a large swimming pool and a coined laundry room inside a community multipurpose room. This location is zoned for A-rated schools and

    3075 Aaron Burr Ave, Winter Park, FL 32792
  • /11

    $1,995 per month

    • 3 Beds
    • 1.5 Baths
    • 1,024 Sq Ft
    • House for Rent

    731 W Comstock Ave, Winter Park, FL 32789

    Close to downtown Winter Park, Winter Park Village, and Park Avenue - Charming 3 bedroom 1.5 bath home, with single carport, fenced backyard, ceiling fans and blinds. Tile floors in main living areas and NEW carpet in bedrooms. Additional sun room located off the kitchen with entry to/from carport. This home is available for immediate move in. PETS NEGOTIABLE. Please call to schedule an

    731 W Comstock Ave, Winter Park, FL 32789
  • /5

    $1,950 per month

    • 2 Beds
    • 2 Baths
    • 1,058 Sq Ft
    • House for Rent

    4800 Tangerine Ave, Winter Park, FL 32792

    Beautiful & Spacious 2-Bedroom, 2-Bath Condo for Rent in Winter Park – $1,950/MonthDiscover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained condo located in the highly desirable Winter Park area. This home offers an exceptional layout with 2 spacious bedrooms and 2 full bathrooms, ideal for families, professionals, or roommates seeking a comfortable and

    4800 Tangerine Ave, Winter Park, FL 32792
  • /19

    $2,099 per month

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

    717 Denton Rd, Winter Park, FL 32792

    AVAILABLE: May 19, 2026Pets: OK (Dangerous Pets are not permitted, Pit Bulls, etc.)***EASY TO VIEW AT A CONVENIENT TIME******EASY TO APPLY*** Once ALL ADULTS have VIEWED this property, go here: SAVE MONEY ON THE APPLICATION FEES: We recommend that you not fill out an application if any of the following apply to you: Evictions, Unpaid balances due to landlords, a

    717 Denton Rd, Winter Park, FL 32792
  • /15

    $1,740 per month

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease!

    7429 Daniel Webster Dr, Winter Park, FL 32792

    Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease! Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all

    7429 Daniel Webster Dr, Winter Park, FL 32792
  • /37

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Affordable 3BR Home in Winter Park – Prime Location & Move-In Ready!

    151 N Orlando Ave, Winter Park, FL 32789

    Discover this affordable and well-located 3-bedroom, 2-bathroom home in the desirable Winter Park area, perfect for those seeking comfort, convenience, and long-term stability.This property offers a functional layout with comfortable living spaces, ideal for families or individuals looking for a practical and welcoming place to call home.

    151 N Orlando Ave, Winter Park, FL 32789
  • /11

    $2,395 per month

    • 3 Beds
    • 2 Baths
    • 1,609 Sq Ft
    • House for Rent

    3146 Dwarf Pine Ave, Winter Park, FL 32792

    Welcome to 3146 Dwarf Pine Ave in Winter Park, FL! This lovely 3-bedroom, 2-bath home offers a great location, a bright open floor plan, freshly painted interior, and a nice-sized kitchen perfect for everyday living. Enjoy the double car garage, covered back porch, fully fenced yard, and a screen-enclosed pool that is currently being refinished and will look like new soon. A wonderful place to

    3146 Dwarf Pine Ave, Winter Park, FL 32792
  • /19

    $1,400 per month

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

    1695 Lee Rd, Winter Park, FL 32789

    Don't miss out on this cozy 1-bedroom, 1-bathroom condo at Waterfall Cove. The unit has been newly painted throughout and features kitchen appliances, upgraded blinds, ceiling fans, and a full-size washer and dryer. You can also enjoy your morning coffee on the private patio. The community offers excellent amenities, including a pool, playground, and picnic area. Waterfall Cove is ideally located

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

    $1,500 per month

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

    2619 Marble Ave, Orlando, FL 32803

    Welcome to your charming 600 square foot home in Orlando, FL! This delightful house, built in 1955, offers a cozy and inviting living space with all the essential amenities. Step inside and discover a well-designed layout featuring 1 bedroom and 1 bathroom, perfect for those seeking a comfortable and manageable home.As you enter, you will be greeted by a spacious living-room with a

    2619 Marble Ave, Orlando, FL 32803

Rental Home Trends in Winter Park, FL

Rental Home Trends

Number of Houses for Rent
36
Median Single Family Home Rent
$2,668
Median 3 Bedroom Single Family Home Rent
$2,625
Median 4 Bedroom Single Family Home Rent
$3,548
Median 5 Bedroom Single Family Home Rent
$6,500
How to Rent a Home