41

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

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  • /16

    $2,390 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,277 Sq Ft
    • House for Rent

    2866 Euston Rd, Winter Park, FL 32789

    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,

    2866 Euston Rd, Winter Park, FL 32789
  • /20

    $2,249 Per Month

    • 3 Beds
    • 2 Baths
    • 1,921 Sq Ft
    • House for Rent

    1546 Peruvian 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 $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

    1546 Peruvian Ln, Winter Park, FL 32792
  • /11

    $2,500 Per Month

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

    1840 Bachman Way, Winter Park, FL 32792

    Property Id: 502903Amazing 3 bedroom, 2.5 bathroom house in Winter Park. Freshly painted home with vaulted ceiling throughout! Tile floor on 1st floor and carpet on 2nd floor. Spacious living room area. Great neighborhood with A+ Seminole County schools. Great location and close to schools, shopping and restaurants. Easy access to 436 and major highways. Amenities included: central air,

    1840 Bachman Way, 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

    5319 N Orange Ave, Winter Park, FL 32792
  • /19

    $2,149 Per Month

    • 3 Beds
    • 2 Baths
    • 1,227 Sq Ft
    • House for Rent

    3451 Australian Cir, 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 $2293.90. That covers your base rent, $2149.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3451 Australian Cir, Winter Park, FL 32792
  • /20

    $2,430 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 lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.5-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    3313 Hamlet Loop, Winter Park, FL 32792
  • /12

    $2,000

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,519 Sq Ft
    • House for Rent

    2810 Sandwell Dr, Winter Park, FL 32792

    The home features gorgeous travertine flooring and a huge laundry room with extra storage. This exceptionally cared for home has character, charm and warmth. The fenced backyard and patio offer peaceful privacy. It's great outdoor space for entertaining or relaxing. The kitchen is bright and sunny with granite countertops and updated cabinets, along with a pass-through window to the patio. The

    2810 Sandwell Dr, Winter Park, FL 32792
  • /10

    $1,150

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    1901 Magnolia Ave, Winter Park, FL 32792

    It's 1150$ per month. WiFi, Utilities, Water, Trash, etc. is all included in the price - I won't ever charge you for those.It's a very quiet and very safe area.I have 2 dogs and 1 cat - so you MUST be okay living with animals.The dogs are both friendly, and they stay in their crate when I'm away from home (and at night)I'm renting 1 room. Single occupant only (no

    1901 Magnolia Ave, 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

    Bernardo Reynoso La Rosa Realty Llc

    2523 Alexa Ct, Winter Park, FL 32792
  • /16

    $1,399 Per Month

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

    2500 Lee Rd, Winter Park, FL 32789

    Serene scenes surround the Lakeside Manor, absolutely beautiful through all the seasons. Waterfront Complex on Lake Killarney. Found on the ground floor, the unit opens up to the living room and dining room. Tile is laid all throughout the property, easy to clean and maintain! The bedroom and bathroom are toward the back of the unit. The bedroom features two closets! The community amenities

    2500 Lee Rd, Winter Park, FL 32789
  • /26

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,158 Sq Ft
    • House for Rent

    301 S Capen Ave, Winter Park, FL 32789

    Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms with

    Jordan Heidrich CORCORAN PREMIER REALTY

    301 S Capen Ave, Winter Park, FL 32789
  • /12

    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • House for Rent

    851 Carver St, Winter Park, FL 32789

    Welcome home to this beautiful 3-bedroom, 2-bathroom residence located in the highly desirable Winter Park area. This inviting home offers a spacious and functional floor plan with comfortable living areas, a well-appointed kitchen, and generously sized bedrooms designed for everyday living.Enjoy the convenience of being close to shopping, dining, entertainment, major roadways, and

    851 Carver St, Winter Park, FL 32789
  • /17

    $2,129 Per Month

    • 3 Beds
    • 2 Baths
    • 1,266 Sq Ft
    • House for Rent

    Unlisted Address

    Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 1,266 car garage and approximately 1,266 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,

    Laidy Mataushek TAH FLORIDA LLC

    Unlisted Address
  • /42

    $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
  • /32

    $2,200 Per Month

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • House for Rent

    5212 N Indiana Ave, Winter Park, FL 32792

    Welcome to this beautifully remodeled 1,000-square-foot Mid-Century Modern home offering the perfect blend of timeless design and modern updates. This charming residence features 3 spacious bedrooms and 1.5 updated bathrooms, creating a comfortable and functional layout for everyday living. The heart of the home is the stunning new kitchen, showcasing crisp white shaker cabinets, elegant quartz

    Edward Diamond CREEGAN GROUP

    5212 N Indiana Ave, Winter Park, FL 32792
  • /26

    $2,350 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • Beautiful 3 bedroom 2.5 bath home with vaulted ceilings and 2 car garage

    3449 Allston Ln, Winter Park, FL 32792

    Come check out this gorgeous Winter Park home with a BRAND NEW ROOF! Home has 3 walk-in closets and vaulted ceilings throughout. Enjoy the large eat-in kitchen with plenty of cabinet space for all of your home cooked meals. The living room is spacious with room for a formal dining room or office. Home features the main floor master and laundry with two additional bedrooms upstairs. You will

    3449 Allston Ln, Winter Park, FL 32792
  • /19

    $1,750 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 table with 4 chairs - picnic in your own park

    Scott Banta BLACKFIN REALTY LLC

    1942 Conifer Ct, Winter Park, FL 32792
  • /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
  • /25

    $2,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,852 Sq Ft
    • House for Rent

    521 Ohio St, Winter Park, FL 32789

    WINTER PARK! 3 bedroom/2 bathroom single family home blocks from I-4. Newer luxury vinyl floors installed throughout home. Stainless steel refrigerator and range, new SS dishwasher, separate dining room, family room, living room, and 2 bonus rooms for offices or storage. 2-car carport with private drive. Big yard (1/3 acre lot) corner lot, rear patio. Inside laundry room with washer / dryer

    Kathleen Gallagher McIver RE/MAX CENTRAL REALTY

    521 Ohio St, Winter Park, FL 32789
  • /14

    $1,995 Per Month

    • 3 Beds
    • 1 Bath
    • 1,038 Sq Ft
    • House for Rent

    830 Carver St, Winter Park, FL 32789

    Fabulous Winter Park home with upgraded kitchen. Super adorable 3 bedroom 1 bath home in Winter Park with all tile flooring, screened patio, bonus room and close to Winter Park Village, Park Ave., Rollins College. Fenced yard and plenty of parking. Home available for move-in now. Please call to schedule an appointment to view this wonderful home. All applicants whether you have a pet or not will

    830 Carver St, Winter Park, FL 32789
  • /13

    $2,050 Per Month

    • 2 Beds
    • 1 Bath
    • 1,125 Sq Ft
    • House for Rent

    503 Kilshore Ln, Winter Park, FL 32789

    LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park , that just had a new roof put on.. At just a ten minute drive from Orlando, this home is in a very convenient location for anyone who wants to be in and out of the city whenever they'd like. Beautiful interior, with original wood flooring throughout.

    Vincent Paige, PA COLDWELL BANKER REALTY

    503 Kilshore Ln, Winter Park, FL 32789
  • /14

    $1,595 Per Month

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

    1941 Lanier Ct, Winter Park, FL 32792

    AVAILABLE NOW! Please call or text to schedule a showing. This first floor, 2 bedroom, 1 bathroom condo is located in the heart of Winter Park. Enjoy all Downtown Winter Park has to offer, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include an open main

    1941 Lanier Ct, Winter Park, FL 32792
  • /15

    $2,395 Per Month

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • House for Rent

    5117 Lake Howell Rd, Winter Park, FL 32792

    3/1, Carport, Single Family Home, Living Room, Dining Room, Eat in Kitchen, Stainless Steel Appliances Included: Stove, Microwave, Refrigerator, Dishwasher, Disposal, Inside Utility Room with Washer and Dryer Hookups, Laminate Wood Flooring & Ceramic Tile Throughout, Fenced Backyard, Pets Ok Upon Owner's Approval, NO SMOKING, Year Built: 1957/1300 Sqft.

    Tina Lopez LEGENDS REALTY

    5117 Lake Howell Rd, Winter Park, FL 32792
  • /3

    $2,000 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
  • /24

    $2,450 Per Month

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

    3121 Heartwood Ave, Winter Park, FL 32792

    Discover this beautifully updated 3-bedroom, 2-bathroom home located in a highly sought-after neighborhood in Winter Park, served by A-rated schools. This property features stunning ceramic tile flooring throughout, a modern kitchen equipped with stainless steel appliances and elegant quartz countertops, and luxurious upgraded bathrooms that offer both style and comfort. Relax on the inviting

    Haimdatt Sadoo DELUXE REALTY OF CENTRAL FLORIDA

    3121 Heartwood Ave, Winter Park, FL 32792
  • /26

    $2,350 Per Month

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

    1340 Paradise Ln, Winter Park, FL 32792

    Welcome to this charming and well-maintained home located in the heart of Winter Park at 1340 Paradise Lane. This beautiful property offers 3 spacious bedrooms and 2 full bathrooms with a comfortable and functional layout perfect for families or anyone looking for a cozy place to call home.The home features elegant tile flooring throughout the main living areas and stylish vinyl flooring

    1340 Paradise Ln, Winter Park, FL 32792
  • /30

    $2,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,106 Sq Ft
    • House for Rent

    7522 Laurel Springs Dr, Winter Park, FL 32792

    Located in the highly sought-after Winter Park High School district, this beautifully maintained 3-bedroom, 2-bath home in Laurel Springs provides comfort, space, and convenience. The bright and inviting living area features tile and an open, welcoming feel. Enjoy year-round indoor-outdoor living in the expansive 400+ sq. feet. enclosed patio overlooking a fully fenced backyard—perfect for

    Liu Zhang JOY ESTATE ENTERPRISE INC

    7522 Laurel Springs Dr, Winter Park, FL 32792
  • /25

    $2,250 Per Month

    • 2 Beds
    • 1 Bath
    • 1,131 Sq Ft
    • House for Rent

    1671 Dale Ave, Winter Park, FL 32789

    SMALL PETS ACCEPTEDNestled in a quiet, established neighborhood, this beautifully maintained 2-bedroom, 1-bath home offers 1,131 square feet of comfortable living space with timeless charm and modern conveniences. The refinished original hardwood floors add warmth and character throughout, while abundant natural light enhances every room.A spacious bonus room provides the perfect

    1671 Dale Ave, Winter Park, FL 32789
  • /12

    $1,825 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
  • /27

    $2,450 Per Month

    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Killarney Bay Condo - 150-5 - Killarney Bay Condo - 150-5

    150 Killarney Bay Ct, Winter Park, FL 32789

    Welcome to this beautifully updated first-floor 2-bedroom, 2-bath condo in the highly desirable Killarney Bay community in Winter Park, offering a perfect blend of comfort, style, and lakefront living. Step inside to an inviting open-concept layout filled with natural light and designed for both everyday living and entertaining. The modern kitchen features upgraded cabinetry, sleek countertops,

    150 Killarney Bay Ct, Winter Park, FL 32789
  • /23

    $2,300 Per Month

    • 3 Beds
    • 2 Baths
    • 1,371 Sq Ft
    • House for Rent

    2441 Fifeshire Dr, Winter Park, FL 32792

    Welcome to this charming 3BR/2BA Single Family Home in Winter Park! This cozy home is located in the heart of Winter Park, FL, and boasts a range of amenities that make it a perfect place to call home. The house features three generously sized bedrooms and two full bathrooms, with stand-in showers. The living area is enhanced with a fireplace and ceiling fans for added comfort. The fully equipped

    2441 Fifeshire Dr, Winter Park, FL 32792
  • /11

    $1,350 Per Month

    • 2 Beds
    • 2 Baths
    • 850 Sq Ft
    • 2 bed 2 bath in winterpark!

    7328 Swallow Run, Winter Park, FL 32792

    2 bed 2 bath in winterpark!

    7328 Swallow Run, Winter Park, FL 32792
  • /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
  • /15

    $2,095 Per Month

    • 3 Beds
    • 2 Baths
    • 1,083 Sq Ft
    • 3 Bedroom 2 Bath Duplex in Winter Park For RENT!

    2700 Tortoise Cove, Winter Park, FL 32792

    * 3 Bedroom 2 bath with a 2 car garage, 1083 sq. ft.* Eat in kitchen, stove, fridge, dishwasher included* Kitchen newly remodeled* Blinds and Ceiling fans* Tile through out* Walk in closets* Rear yard privacy fence* All new paint, and fencing* Rear patio* Sliding glass doors off master to back yard* Pet Friendly* Washer dryer hookups in garage*

    2700 Tortoise Cove, Winter Park, FL 32792
  • /11

    $1,950 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
  • /20

    $2,499 Per Month

    • 3 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • House for Rent

    1947 Summerfield Rd, Winter Park, FL 32792

    Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act

    1947 Summerfield Rd, Winter Park, FL 32792
  • /15

    $2,495 Per Month

    • 4 Beds
    • 2 Baths
    • 1,669 Sq Ft
    • House for Rent

    2730 Prince John Rd, Winter Park, FL 32792

    Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *Bonus Amenity Included* -All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident

    2730 Prince John Rd, Winter Park, FL 32792
  • /7

    $1,350 Per Month

    • 1 Bed
    • 1 Bath
    • 759 Sq Ft
    • 1/1 @ Winter Park Villas

    667 Trinidad Ct, Winter Park, FL 32792

    1/1 condo at Winter Park Villas. Minutes from UCF,Full Sail University and downtown Winter Park. Winter Park Villas community have many amenities, including pool, tennis court,fitness room, car care center, and picnic area w/ grills.Appointment require to show the unitClose to bus line. Pets are subject of approval of owner/HOA. Security Deposit amount subject to credit/background

    667 Trinidad Ct, Winter Park, FL 32792
  • /7

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 967 Sq Ft
    • 1/2 Duplex in Winter Park

    3012 Patel Dr, Winter Park, FL 32792

    Nice two bedroom, two bath home with spacious kitchen and living area. House is tiled throughout. Driveway accommodates 2 cars. Fenced in backyard with small shed. Close to Target, Costco Publix, Aldi. Winter Park Schools.

    3012 Patel Dr, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 2

Rental Home Trends

Number of Houses for Rent
41
Median Single Family Home Rent
$2,550
Median 3 Bedroom Single Family Home Rent
$2,500
Median 4 Bedroom Single Family Home Rent
$3,800
Median 5 Bedroom Single Family Home Rent
$5,650
How to Rent a Home