694

Winter Park, FL Homes for Rent

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  • /15

    $3,305 Per Month

    • 4 Beds
    • 2 Baths
    • 2,218 Sq Ft
    • House for Rent

    7039 Pecan Ct, Winter Park, FL 32792

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple! This 4-bedroom, 2-bathroom rental home in Winter Park, FL, has a lot to offer; does it check all your boxes?

    7039 Pecan Ct, Winter Park, FL 32792
  • /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
  • /16

    $2,515 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 $2659.90. That covers your base rent, $2515.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7423 Antietam Ct E, Winter Park, FL 32792
  • /16

    $2,480 Per Month

    • 3 Beds
    • 2 Baths
    • 1,726 Sq Ft
    • House for Rent

    3908 Woodglade Cove, 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 $2624.90. That covers your base rent, $2480.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3908 Woodglade Cove, 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

    $1,995 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
  • /16

    $2,340 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

    $2,100 Per Month

    • 2 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Condo for Rent

    955 Aragon Ave Unit A, Winter Park, FL 32789

    Property Id: 1217869 Spacious 1,055 Sq Ft Duplex - Winter Park Move-In Date: August 1st! Rent: $2,100/month Message me to schedule an appointment or to request a full video walkthrough sent directly to your phone! Key Features Fully renovated 2-Bed / 2-Bath front duplex layout (Unit A) on a tree-lined brick street. Nearly 10-foot ceilings create a bright, airy

    955 Aragon Ave Unit A, Winter Park, FL 32789
  • /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
  • /20

    $2,410 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,397 Sq Ft
    • Townhouse for Rent

    1839 Blaine Terrace, 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, 2.5-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    1839 Blaine Terrace, Winter Park, FL 32792
  • /20

    $2,625 Per Month

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • House for Rent

    4040 Waterview Loop, 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

    4040 Waterview Loop, Winter Park, FL 32792
  • /13

    $2,499

    Total Monthly Price

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

    662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789

    The advertised rate of $2,500/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 6, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789
  • /2

    $2,510 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 holding fee agreement is signed and the holding fee is paid by the primary applicant.This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

    3016 Village Hill Place, 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

    Welcome to your dream condo in Winter Park! This charming **2-bedroom, 2-full bathrooms** home offers the perfect blend of comfort, convenience, and an unbeatable location, making it an ideal place to call home. With 1,037 square feet of well-designed living space, you'll enjoy modern conveniences, desirable community amenities, and easy access to everything you need for everyday

    659 Montego Bay Ct, Winter Park, FL 32792
  • /19

    $3,590 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,806 Sq Ft
    • Townhouse for Rent

    5489 Baldwin Park St, Orlando, FL 32814

    Property Id: 2714618 Stunning 2-story townhome located in the highly desirable Baldwin Park community in Orlando. This elegant property features 3 spacious bedrooms, 2.5 bathrooms, and approximately 1,800 sq ft of living space, offering a well-designed and functional layout. The first floor showcases an open-concept design with combined living and dining areas, perfect for entertaining,

    5489 Baldwin Park St, Orlando, FL 32814
  • /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
  • /6

    $1,100

    Total Monthly Price

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

    2333 E Winter Park Rd Unit Guest House, Winter Park, FL 32789

    Charming one-bedroom guest house located in a beautiful Winter Park neighborhood. Enjoy a peaceful setting just steps away from local shops, dining, and everyday conveniences. This inviting space offers both comfort and walkability in one of the area’s most desirable locations, along with the convenience of private parking.

    2333 E Winter Park Rd Unit Guest House, Winter Park, FL 32789
  • /53

    $2,000

    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 First-Floor Condo in Winter Park – Pool View, Water Included!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

    $2,450

    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
  • /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
  • /22

    $1,650

    Total Monthly Price

    • 2 Beds
    • 2.5 Baths
    • 1,061 Sq Ft
    • Townhouse for Rent

    3373 Cedar Springs Place, Winter Park, FL 32792

    GORGEOUS TOWN-HOME, 2 MASTER BEDROOM (with Mirrored Closets)2 1/2 BATHROOMS. HALF BATH LOCATED ON THE MAIN FLOOR FOR THE CONVENIENCE OF GUESTS. NEW LAMINATE FLOORS ON SECOND LEVEL. LAMINATE/TILE ON FIRST FLOOR. FENCED PATIO WITH STORAGE ROOM. PRIVATE GARBAGE SHED. WATER AND GARAGE PICKUP INCLUDED.2 DEDICATED PARKING SPACES!RESORT- STYLE COMMUNITY POOL. PLAYGROUNDHIDDEN

    3373 Cedar Springs Place, 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

    $1,245

    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
  • /21

    $2,100

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft
    • Condo for Rent

    2383 Sun Valley Cir Unit Winter Park, Winter Park, FL 32792

    Welcome to this charming and beautifully updated home in the serene Cedarwood Village community! Tucked away in a peaceful location, this unit offers a quiet retreat from traffic noise and features a private backyard with no rear neighbors perfect for enjoying the spacious, enclosed lanai. The modern kitchen features sleek granite countertops and matching cabinets, with the bathrooms and dining

    2383 Sun Valley Cir Unit Winter Park, Winter Park, FL 32792
  • /24

    $1,950

    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
  • /18

    $2,685 Per Month

    • 4 Beds
    • 2 Baths
    • 1,409 Sq Ft
    • House for Rent

    2366 Coldstream Dr, Winter Park, FL 32792

    Welcome to this beautiful 3-bed, 2-bath home featuring solid wood cabinets, crown molding, and ceramic tile flooring in the kitchen. Enjoy plenty of space for relaxing and entertaining with a spacious living and dining room combination accented by hardwood floors, a versatile bonus room just off the kitchen, and generously sized bedrooms, including a primary suite with dual closets and a large

    Summer Hornburg BELMONT REALTY

    2366 Coldstream Dr, Winter Park, FL 32792
  • /18

    $2,650 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    5119 Ferncrest Dr, Winter Park, FL 32792

    Stunning 3-Bedroom Home with Pool and Custom Features in Winter Park, FLDiscover your new oasis in the vibrant community of Winter Park! This exceptional 3-bedroom, 2-bathroom home is designed for comfort and luxury, offering an array of custom features that set it apart.Enjoy the warm Florida sunshine in your own backyard paradise, complete with a sparkling pool, artificial

    5119 Ferncrest Dr, Winter Park, FL 32792
  • /30

    $3,500 Per Month

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

    5354 Lanyard Ct, Winter Park, FL 32792

    Welcome to this spacious 5-bedroom, 3-bathroom home designed for comfort, functionality, and flexible living. One of the home’s standout features is a private area that includes two of the bedrooms and a full bathroom, offering added privacy and versatility. This thoughtfully designed layout creates the feel of two living spaces within one home, making it ideal for multi-generational living,

    Nancy Conde JUPITER PROPERTIES, INC

    5354 Lanyard Ct, Winter Park, FL 32792
  • /83

    $4,402

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 990 Sq Ft
    • Condo for Rent

    2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789

    The advertised rate of $4,403/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 4, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789
  • /11

    $2,950 Per Month

    • 4 Beds
    • 2 Baths
    • 2,003 Sq Ft
    • House for Rent

    8104 Pleasant Pine Cir, Winter Park, FL 32792

    WINTER PARK 4BR/2BA, Single Story, Built in 2016. Located in the GATED COMMUNITY of Enclave At Aloma. Fantastic open floor plan. Plank wood-looking ceramic tile throughout the entire home. Loads of options. House was extended 4 feet to increase the size of dining room, great room, and master bedroom. 10' x 40' Covered Lanai in the rear. Center Island with Pendant Lighting in the Kitchen.

    Bill Cook, II LAKEFRONT REALTY, INC.

    8104 Pleasant Pine Cir, Winter Park, FL 32792
  • /31

    $8,295 Per Month

    • 4 Beds
    • 5.5 Baths
    • 3,350 Sq Ft
    • House for Rent

    2234 Howard Dr, Winter Park, FL 32789

    Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park’s most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility.Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal

    2234 Howard Dr, Winter Park, FL 32789
  • /34

    $3,100 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,978 Sq Ft
    • Property for Rent

    2251 Nairn Dr, Winter Park, FL 32792

    Virtually Staged. Unfurnished – No Pets. Beautiful modern 4-bedroom, 2.5-bath home located in one of Winter Park's most established and sought-after neighborhoods. This spacious home features wood and laminate flooring throughout, a downstairs bonus room, a separate utility room, a private second-floor sun deck/terrace perfect for relaxing or entertaining, and a first-floor concrete patio. The

    Alfredo Karam COLDWELL BANKER REALTY

    2251 Nairn Dr, Winter Park, FL 32792
  • /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
  • /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
  • /5

    $1,665 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • House for Rent

    3372 Riverview Way, Winter Park, FL 32792

    Welcome home to this ADORABLE 3 bed 2.5 unit for rent in Winter Park, FL! You will feel right at home the moment you step in. LOVELY kitchen features an ample amount of cabinetry. Quiet neighborhood. SPACIOUS living area, great for entertaining family and friends. MUST SEE!!! Conveniently located minutes from local shops, restaurants, , and more. Zoned for Aloma Elementary School,

    3372 Riverview Way, Winter Park, FL 32792
  • /17

    $6,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Apartment for Rent

    301 W Comstock Ave, Winter Park, FL 32789

    Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

    Sydney Brownlee THE SYDGAN CORP

    301 W Comstock Ave, Winter Park, FL 32789

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