631

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

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  • /29

    Starting at $1,404

    Total Monthly Price

    • 1 - 3 Beds

    3733 N Goldenrod Rd, Winter Park, FL 32792

    Welcome home to Atlas at Winter Park!

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
  • /20

    Starting at $1,328 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

    3250 Bishop Park Dr, Winter Park, FL 32792
  • /16

    $2,300 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
  • /19

    $2,245 Per Month

    • 3 Beds
    • 2 Baths
    • 1,359 Sq Ft
    • House for Rent

    7418 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 $2389.90. That covers your base rent, $2245.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7418 Antietam Ct E, Winter Park, FL 32792
  • /20

    $2,300 Per Month

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

    151 N Orlando Ave Unit 207, Winter Park, FL 32789

    Welcome to your future home in the heart of Winter Park, located in the desirable Maitland district! This charming property offers a comfortable and convenient lifestyle, with easy access to an array of amenities and attractions.Experience the ease of living with central heating and cooling, complemented by air conditioning and ceiling fans for your comfort throughout the year. This

    151 N Orlando Ave Unit 207, Winter Park, FL 32789
  • /19

    $1,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,060 Sq Ft
    • House for Rent

    2772 Prism Point, Winter Park, FL 32792

    Property Id: 2809706 Townhouse duplex for rent, very private culdesac. Two bedroom, 1 1/2 bath. All tiled except carpet on stairs… galley kitchen, stainless appliances, huge laundry room. Balcony off master bedroom Beautifully maintained all lawn care included. Sprinkler system…fence yard… cats ok Dogs ok must be under 25 pounds. Carport

    2772 Prism Point, Winter Park, FL 32792
  • /20

    $1,730 Per Month

    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft
    • Condo for Rent

    659 Montego Bay Ct, Winter Park, FL 32792

    WINTER PARK VILLAS — 2-BEDROOM CONDO | $1,000 MOVE-IN CREDIT + WATER INCLUDED!$1,730/month • 2 Bedrooms • 2 Full Bathrooms • 1,037 Sq. Ft. LIMITED-TIME MOVE-IN SPECIALReceive a $1,000 MOVE-IN CREDIT with an approved 12-month lease! WATER INCLUDED IN RENT!No separate monthly water bill — water is included in your rent.Welcome to this charming

    659 Montego Bay Ct, Winter Park, FL 32792
  • /20

    $2,300 Per Month

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

    151 N Orlando Ave Unit 207, Winter Park, FL 32789

    Welcome to your future home in the heart of Winter Park, located in the desirable Maitland district! This charming property offers a comfortable and convenient lifestyle, with easy access to an array of amenities and attractions.Experience the ease of living with central heating and cooling, complemented by air conditioning and ceiling fans for your comfort throughout the year. This

    151 N Orlando Ave Unit 207, Winter Park, FL 32789
  • /16

    $2,360 Per Month

    • 3 Beds
    • 2 Baths
    • 1,384 Sq Ft
    • House for Rent

    3016 Village Hill Place, 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 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    3016 Village Hill Place, Winter Park, FL 32792
  • /8

    $2,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    1250 S Denning Dr, Winter Park, FL 32789

    Property Id: 346094 Spacious living area, large master bedroom w/ private bathroom & linen closet. Wide Closets in each bedroom. Quiet neighborhood. Lots of sunlight enters the apartment. Shaded and screened patio faces a courtyard/garden w/ seating. Brand new sliding glass patio door. Incredible location short distance to Park Avenue, Trader Joes/Whole Foods/Publix, I4 exit, & shopping

    1250 S Denning Dr, Winter Park, FL 32789
  • /17

    $2,210 Per Month

    • 3 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • House for Rent

    1710 Puritan Ave, 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 $2354.90. That covers your base rent, $2210.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1710 Puritan Ave, Winter Park, FL 32792
  • /13

    $1,675 Per Month

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

    200 St Andrews Blvd Unit 316, Winter Park, FL 32792

    Property Id: 2751801 Beautiful 1-Bedroom Condo for Rent in Winter Park Available Now! Enjoy comfortable living in this beautiful 1-bedroom, 1-bathroom condo located in the highly desirable Four Seasons Condominium Community in Winter Park. Conveniently situated at 200 St. Andrews Blvd, Winter Park, FL 32792, this condo offers an unbeatable location just minutes from

    200 St Andrews Blvd Unit 316, Winter Park, FL 32792
  • /7

    $2,083 Per Month

    • 3 Beds
    • 2 Baths
    • 1,197 Sq Ft
    • House for Rent

    3321 Royal St, Winter Park, FL 32792

    Property Id: 2821609 Welcome to 3321 Royal Street in Winter Park! This beautifully updated 3-bedroom, 2-bathroom home offers approximately 1,197 sq. ft. of comfortable living space. Features include a spacious family room, durable tile and luxury vinyl flooring, central air conditioning, a 1-car attached garage with laundry area, and a large fully fenced backyard with a screened-in patio.

    3321 Royal St, Winter Park, FL 32792
  • /13

    $1,675 Per Month

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

    200 St Andrews Blvd Unit 316, Winter Park, FL 32792

    Property Id: 2751801 Beautiful 1-Bedroom Condo for Rent in Winter Park Available Now! Enjoy comfortable living in this beautiful 1-bedroom, 1-bathroom condo located in the highly desirable Four Seasons Condominium Community in Winter Park. Conveniently situated at 200 St. Andrews Blvd, Winter Park, FL 32792, this condo offers an unbeatable location just minutes from

    200 St Andrews Blvd Unit 316, Winter Park, FL 32792
  • /20

    $1,895 Per Month

    • 2 Beds
    • 2 Baths
    • 1,098 Sq Ft
    • Townhouse for Rent

    162 Moyses Rd, Winter Park, FL 32792

    Property Id: 2563758 Be the first to live in this beautifully renovated home that has been completely remodeled from top to bottom! Everything is brand new, giving you the feel of moving into a new home with modern finishes throughout. This home features 2 spacious bedrooms and 1 full bathroom upstairs, creating a private and comfortable living space. The first floor offers an open

    162 Moyses Rd, Winter Park, FL 32792
  • /6

    $1,950

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 989 Sq Ft
    • Townhouse for Rent

    2399 Antilles Dr, Winter Park, FL 32792

    Beautifully updated 2 bedroom / 1 bath townhome in Casselberry.? Updated kitchen? Freshly painted? Washer/Dryer? Large fenced backyard? 2 community pools? Pet friendly (under 50lbs)Minutes to Full Sail, AdventHealth Winter Park, UCF, shopping & restaurants.

    2399 Antilles Dr, Winter Park, FL 32792
  • /10

    $1,245

    Total Monthly Price

    • Studio - 1 Bed
    • 1 Bath
    • 615 Sq Ft
    • Condo for Rent

    2037 Linden Rd, Winter Park, FL 32792

    Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door

    2037 Linden Rd, Winter Park, FL 32792
  • /12

    $1,000

    Total Monthly Price

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

    5312 Poinsetta Ave 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 three rooms has its own electronic keypad lock for your privacy and security. The large common areas provide the perfect space for dining and living. A spacious laundry and kitchen provide you with plenty of space

    5312 Poinsetta Ave Unit 2, Winter Park, FL 32792
  • /24

    $1,800

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,236 Sq Ft
    • Condo for Rent

    1920 Woodcrest Dr Unit 13, Winter Park, FL 32792

    Unit 13 is a direct pool front unit. Large (1,236 sq. ft.), quiet first floor 2 bedroom 2 bathroom condo in smaller community with only 18 units in the City of Winter Park, Florida. The Floor plan has a double primary bedroom layout. Ceramic tile flooring in the foyer, living/dining area, kitchen, and both bathrooms. Both bedrooms have new easy-care luxury vinyl wood-look flooring. Primary bath

    1920 Woodcrest Dr Unit 13, Winter Park, FL 32792
  • /24

    $1,800

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,236 Sq Ft
    • Condo for Rent

    1920 Woodcrest Dr Unit 13, Winter Park, FL 32792

    Unit 13 is a direct pool front unit. Large (1,236 sq. ft.), quiet first floor 2 bedroom 2 bathroom condo in smaller community with only 18 units in the City of Winter Park, Florida. The Floor plan has a double primary bedroom layout. Ceramic tile flooring in the foyer, living/dining area, kitchen, and both bathrooms. Both bedrooms have new easy-care luxury vinyl wood-look flooring. Primary bath

    1920 Woodcrest Dr Unit 13, 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
  • /53

    $1,900

    Total Monthly Price

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

    1250 S Denning Dr Unit 127, Winter Park, FL 32789

    Updated 2BR/2BA Condo in Fabulous Winter Park – Water Included and Trash!1250 S. Denning Drive – Winter Park, FLEnjoy comfortable, low-maintenance living in this beautifully updated 2-bedroom, 2-bathroom condo located in one of Winter Park's most convenient neighborhoods.This 910-square-foot, first-floor unit features luxury vinyl plank flooring throughout, a modern

    1250 S Denning Dr Unit 127, Winter Park, FL 32789
  • /10

    $1,245

    Total Monthly Price

    • Studio - 1 Bed
    • 1 Bath
    • 615 Sq Ft
    • Condo for Rent

    2037 Linden Rd, Winter Park, FL 32792

    Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door

    2037 Linden Rd, Winter Park, FL 32792
  • /53

    $1,900

    Total Monthly Price

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

    1250 S Denning Dr Unit 127, Winter Park, FL 32789

    Updated 2BR/2BA Condo in Fabulous Winter Park – Water Included and Trash!1250 S. Denning Drive – Winter Park, FLEnjoy comfortable, low-maintenance living in this beautifully updated 2-bedroom, 2-bathroom condo located in one of Winter Park's most convenient neighborhoods.This 910-square-foot, first-floor unit features luxury vinyl plank flooring throughout, a modern

    1250 S Denning Dr Unit 127, Winter Park, FL 32789
  • /30

    $2,300

    Total Monthly Price

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

    151 N Orlando Ave Unit 262, Winter Park, FL 32789

    Modern furnished waterfront 1bdrm/1bath condo rental, move-in ready. Fully renovated, equipped kitchen with smooth stone countertops, stainless steel-appliances (Fridge/Stove/Dishwasher), a sleek under-mount sink, and minimalist cabinetry. In unit full-size stacked washer & dryer, walk-in closet. Remote control blinds throughout, including blackout one in the bedroom.Fresh, modern interior

    151 N Orlando Ave Unit 262, Winter Park, FL 32789
  • /12

    $1,000

    Total Monthly Price

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

    5312 Poinsetta Ave 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 three rooms has its own electronic keypad lock for your privacy and security. The large common areas provide the perfect space for dining and living. A spacious laundry and kitchen provide you with plenty of space

    5312 Poinsetta Ave Unit 2, Winter Park, FL 32792
  • /7

    $1,900

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,158 Sq Ft
    • Townhouse for Rent

    622 St Johns Ct, Winter Park, FL 32792

    BRAND NEW LAMINATE FLOORING, FIREPLACE, ACROSS TENNIS COURT, COMMUNITY POOL, PARKING IN FRONT, RANGE, DISPOSAL, REFRIGERATOR, DISHWASHER, MICROWAVE, NEW CENTRAL AC UNIT, WALK IN CLOSETS, DEN, WASHER/DRYER HOOKUPS

    622 St Johns Ct, Winter Park, FL 32792
  • /16

    $2,400

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • House for Rent

    530 Byron Rd, Winter Park, FL 32792

    Charming 3 bedroom, 2 bath, quiet neighborhood with nearby Wintee Park schools, Rollins college, Publix, Winter Park Hospital, YMCA. Freshly painted inside, new blinds, bathroom upgraded, fenced backyard, brand new washer and dryer

    530 Byron Rd, Winter Park, FL 32792
  • /25

    $2,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,612 Sq Ft
    • Condo for Rent

    2526 Tahoe Cir Unit 2526, Winter Park, FL 32792

    Must-See WINTER PARK CONDO, beautifully remodeled 2BR / 2BA + LOFT / potential office / 3rd BR or office. Formal Living Room w / wood-burning fireplace & Dining Room w/ wet-bar, beautiful open kitchen w/ island and stainless-steel appliances, laundry closet w/ washer & dryer, enclosed patio, bamboo & porcelain tile floors. Centrally located near SR 417 and 20 minutes from airport, zoned for great

    Elizabeth Beaudoin PR REAL ESTATE SERVICES

    2526 Tahoe Cir Unit 2526, Winter Park, FL 32792
  • /20

    $2,275 Per Month

    • 4 Beds
    • 2 Baths
    • 1,351 Sq Ft
    • House for Rent

    3362 Bougainvillea 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 $2419.90. That covers your base rent, $2275.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3362 Bougainvillea Dr, Winter Park, FL 32792
  • /14

    $1,995 Per Month

    • 2 Beds
    • 1 Bath
    • 1,604 Sq Ft
    • Townhouse for Rent

    1618 Indiana Ave, Winter Park, FL 32789

    et on a friendly street in the heart of Winter Park, this freshly remodeled duplex delivers easy, low-maintenance living in one of Central Florida's most sought-after zip codes. Inside, 805 square feet of thoughtfully refreshed space welcomes you with brand-new appliances, a crisp new A/C system, and a casual breakfast bar top perfect for quick meals or morning coffee. Two comfortable bedrooms

    Brock Stocksett HOMEVEST REALTY

    1618 Indiana Ave, Winter Park, FL 32789
  • /35

    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • House for Rent

    3043 Antique Oaks Cir, Winter Park, FL 32792

    Discover this spacious 2-bedroom, 2-bath condo in the heart of Winter Park. Perfectly located just steps from Full Sail University and minutes from UCF and Valencia, this home offers unmatched convenience to schools, restaurants, shopping, and major highways—making daily commutes simple and stress-free.This property offers reliable comfort with essential features already in

    3043 Antique Oaks Cir, Winter Park, FL 32792
  • /14

    $1,995 Per Month

    • 2 Beds
    • 1 Bath
    • 802 Sq Ft
    • Townhouse for Rent

    1618 Indiana Ave Unit 1616, Winter Park, FL 32789

    Freshly reimagined and ready for its next resident, this newly remodeled duplex in the heart of Winter Park pairs modern updates with an unbeatable central location. Offering two bedrooms, one bathroom, and 805 square feet of thoughtfully arranged living space, this half of a charming duplex feels both smart and welcoming from the moment you step inside. This duplex has been recently updated from

    Brock Stocksett HOMEVEST REALTY

    1618 Indiana Ave Unit 1616, Winter Park, FL 32789
  • /16

    $1,250 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
  • /5

    $1,350 Per Month

    • 1 Bed
    • 1 Bath
    • 620 Sq Ft
    • Townhouse for Rent

    1600 Indiana Ave, Winter Park, FL 32789

    This 1 bedroom, 1 bathroom home is located in the heart of Winter Park. Enjoy the best of Downtown Winter Park, 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 tile throughout the main living area, dining room, utility room with washer/dryer hookups, and a

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    1600 Indiana Ave, Winter Park, FL 32789
  • /11

    $1,375 Per Month

    • 2 Beds
    • 2 Baths
    • 1,045 Sq Ft
    • Condo for Rent

    1000 S Semoran Blvd Unit 806, Winter Park, FL 32792

    LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included! Apply Today!TO SCHEDULE A SHOWING YOU MUST EMAIL US WITH YOUR CONTACT INFORMATION AND THE PROPERTY YOU WISH TO SEE AT AND AN AGENT WILL RESPOND BACK WITH THE AVAILABLE SHOW TIMES.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process

    1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
  • /20

    $2,100 Per Month

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

    151 N Orlando Ave Unit 203, Winter Park, FL 32789

    FURNISHED 6-12 month executive rental available immediately in Lake Killarney Condominiums. Perfect for one or two residents, this condooffers a bedroom with King-sized bed and walk-in closet, a separate office, and a sunroom with floor to ceiling windows. Newly installedbathroom and central air system. Combo washer/dryer unit in kitchen or optional coin laundry in building. Sorry, no

    Robert Arnold SAND DOLLAR REALTY GROUP INC

    151 N Orlando Ave Unit 203, Winter Park, FL 32789
  • /14

    $1,200 Per Month

    • 1 Bed
    • 1 Bath
    • 590 Sq Ft
    • Townhouse for Rent

    7309 Daniel Webster Dr, Winter Park, FL 32792

    Discover this charming 1-bedroom, 1-bath condo nestled in the desirable Colonies Condo community. Boasting 610 sq. ft. of thoughtfully designed living space, this unit is perfect for young professionals, students, or anyone seeking affordable comfort in a prime location. The apartment features durable vinyl flooring throughout, eliminating worries about carpet maintenance, and a fully equipped

    7309 Daniel Webster Dr, Winter Park, FL 32792
  • /13

    $1,750 Per Month

    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft
    • Condo for Rent

    612 Trinidad Ct Unit 612, Winter Park, FL 32792

    Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area

    Carolina Barriento JEXOR LLC

    612 Trinidad Ct Unit 612, Winter Park, FL 32792
  • /16

    $1,600 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

    This charming 2-bedroom, 2-bath duplex is ready for immediate move-in, offering a warm and inviting atmosphere for comfortable living.Step inside to discover a thoughtfully designed space with tile flooring throughout, providing both durability and easy maintenance. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances and solid-surface countertops.

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

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