146

Winter Springs, FL Homes for Rent under $2,000

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  • /82

    Starting at $1,840 Per Month

    • 1 - 3 Beds

    500 Sugar Mill Rd, Oviedo, FL 32765

    Dwell Oviedo

    500 Sugar Mill Rd, Oviedo, FL 32765
  • /116

    Starting at $1,243 Per Month

    • 1 - 3 Beds

    1 Laurel Oaks Dr, Winter Springs, FL 32708

    Experience resort-style living at The Avenues at Winter Springs! Our pet-friendly community offers spacious 1, 2, and 3-bedroom apartment homes with modern finishes and everyday conveniences.Enjoy amenities like a resort-style pool with sundeck, 24-hour fitness and wellness center, tennis court, playground, and leash-free pet park. Stay connected with 400 Mbps internet, and take advantage

    The Avenues at Winter Springs

    1 Laurel Oaks Dr, Winter Springs, FL 32708
  • /31

    Starting at $1,395

    Total Monthly Price

    • 1 - 3 Beds

    440 Courtney Springs Cir, Winter Springs, FL 32708

    Legends Winter Springs effortlessly combines exceptional service with outstanding features to provide the ultimate living experience. Located near upscale shopping and entertainment, your home is minutes to Lake Jessup and the excitement of downtown Orlando. Enjoy the peaceful, relaxing atmosphere of Legends Winter Springs. Please call for an appointment today.

    Legends Winter Springs

    440 Courtney Springs Cir, Winter Springs, FL 32708
  • /55

    Starting at $1,580 Per Month

    • 1 - 3 Beds

    150 Bear Springs Dr, Winter Springs, FL 32708

    RiZE at Winter Springs is located in Winter Springs, Florida. We offer sixteen floor plans with one, two, and three bedroom apartment homes for rent. Apartment features include 9-foot ceilings, ceiling fans, central air and heating, a coat closet, vinyl plank flooring, walk-in closets, washer and dryer in home, an all-electric kitchen with a breakfast bar, a refrigerator, and a pantry.All

    RIZE at Winter Springs

    150 Bear Springs Dr, Winter Springs, FL 32708
  • /48

    Starting at $1,627 Per Month

    • 1 - 3 Beds

    990 English Town Ln, Winter Springs, FL 32708

    Indulge in the luxury of living where others vacation at The Eli Winter Springs! Our community offers resort-class amenities and exceptional service to pamper residents. With a rich array of amenities, picturesque landscapes featuring swaying palm trees and tranquil waters, you can enjoy a paradise lifestyle. Conveniently located with easy access to 417, the Oviedo Marketplace, and major

    The Eli Winter Springs

    990 English Town Ln, Winter Springs, FL 32708
  • /38

    Starting at $1,308 Per Month

    • 1 - 3 Beds

    300 Sheoah Blvd, Winter Springs, FL 32708

    Find the life of sophistication and style that awaits you at Seville on the Green. Our Winter Springs community is nestled in the Highland Residential Neighborhood, right off of 434 and 17-92. We are minutes from I-4 and SR-417 and are less than six miles from major shopping and dining. We proudly offer one, two, and three-bedroom apartments with multiple floor plans. Select homes feature

    Seville on the Green

    300 Sheoah Blvd, Winter Springs, FL 32708
  • /24

    Starting at $1,454

    Total Monthly Price

    • 1 - 3 Beds

    4545 Willa Creek Dr, Winter Springs, FL 32708

    We are now welcoming in-person, virtual and self-guided tours by appointment only. Please contact us today to schedule your appointment.Tuskawilla, Winter Springs, FL Apartments boast premier location great for both business and leisure. Located just minutes from SR417 and SR408, the Tuskawilla Apartments in Winter Springs are perfect for commuters all across Florida. Choose from a variety of

    Tuskawilla at Winter Springs

    4545 Willa Creek Dr, Winter Springs, FL 32708
  • /21

    Starting at $1,273 Per Month

    • 1 - 4 Beds

    170 N Gardenridge Ct, Winter Springs, FL 32708

    Experience the many benefits of this Winter Springs apartment community, where we bring affordability, comfort, and convenience to home. Moss Park Apartments is located off Moss Park Road and State Road 434, approximately two miles east of Highway 17-92.Moss Park Apartments is a mixed-income community that offers apartment homes for unrestricted and restricted-income residents. Located

    Moss Park

    170 N Gardenridge Ct, Winter Springs, FL 32708
  • /16

    $1,915 Per Month

    • 3 Beds
    • 1 Bath
    • 1,123 Sq Ft
    • House for Rent

    500 George St, Winter Springs, FL 32708

    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,

    500 George St, Winter Springs, FL 32708
  • /19

    $1,800 Per Month

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

    1824 Lake St Unit 3, Oviedo, FL 32765

    Property Id: 1632126Welcome to Your Cozy Home Away from Home!Relax in your private bedroom, bathroom, living room, dining area, and fully equipped kitchen—everything you need for a comfortable and stress-free stay.Property DetailsThis charming unit is part of a quadruplex, with shared walls and ceilings, but it’s expertly insulated to ensure your peace and

    1824 Lake St Unit 3, Oviedo, FL 32765
  • /11

    $1,863

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    1882 Lake St Unit SI ID1094219P, Oviedo, FL 32765

    The advertised rate of $1,864/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 23, 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

    1882 Lake St Unit SI ID1094219P, Oviedo, FL 32765
  • /7

    $700 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    1824 Lake St, Oviedo, FL 32765

    Property Id: 2275043Make yourself at home in this comfy room for rent! Enjoy a cozy fireplace, fully equipped kitchen, fast Wi-Fi, and plenty of space to relax or work. Perfect for remote workers, solo travelers, or small groups. The bedroom includes a Twin-size bed. Just 30 mins from the airport and near Orlando’s top attractions.• Cleaning fee: $40/month• Common areas are

    1824 Lake St, Oviedo, FL 32765
  • /7

    $850 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    1824 Lake St, Oviedo, FL 32765

    Property Id: 2274885Make yourself at home in this comfortable room for rent in Oviedo! Enjoy access to a cozy fireplace, fully equipped kitchen, fast Wi-Fi, and plenty of space to relax or work. Perfect for remote workers, solo travelers, or small groups. Just 30 minutes from the airport and close to Orlando’s top attractions. Book your stay today and feel right at home.• Cleaning

    1824 Lake St, Oviedo, FL 32765
  • /11

    $1,800

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 896 Sq Ft
    • Townhouse for Rent

    130 Kristi Ann Ct, Winter Springs, FL 32708

    Welcome home to this 2 bed, 1.5 bath townhouse in the heart of Winter Springs. You will be just minutes away from the Winter Springs Town Center, Great Seminole County Schools, Coffee Shops, Premium Gyms, Center Winds Park, and multiple conveniences nearby. The living room and patio offer ample space for relaxation and entertainment. Each bedroom is designed for functionality, with ceiling fans

    130 Kristi Ann Ct, Winter Springs, FL 32708
  • /24

    $1,599 Per Month

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

    10 Sheoah Blvd Unit 8, Winter Springs, FL 32708

    Spacious and bright fully renovated 2-bedroom, 2-bathroom condo available for rent at The Highlands in Winter Springs. The entire interior has been freshly repainted and features tile flooring throughout. This inviting home offers a large family room with a cozy dining area and a split-bedroom floor plan for added privacy. The spacious primary bedroom includes sliding glass doors leading to the

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    10 Sheoah Blvd Unit 8, Winter Springs, FL 32708
  • /9

    $1,395 Per Month

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

    112 Cory Ln, Winter Springs, FL 32708

    Welcome to 112 Cory Lane, a bright and spacious 2-bedroom, 2-bathroom apartment that perfectly balances comfort and convenience. Step inside to find an open-concept living and dining area, designed for seamless entertaining and a relaxed Florida lifestyle. Both bedrooms are generously sized with ample closet space, providing a quiet retreat at the end of the day.Availability Note: Current

    112 Cory Ln, Winter Springs, FL 32708
  • /16

    $1,695 Per Month

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Townhouse for Rent

    208 Perth Ct Unit B, Winter Springs, FL 32708

    Highlights: 2 Car Garage | Spacious Backyard | Serene Patio | Community Pool | Nature Trails | BBQ Area Grills | Tennis Court | Community Playground | Picnic Area |Discover the vibrant charm of Winter Springs, nestled by the serene Lake Jesup and offering upscale living, diverse dining options, and a rich cultural scene. With pristine parks, top-notch schools, and annual festivities like

    Amy Johnston BELMONT REALTY

    208 Perth Ct Unit B, Winter Springs, FL 32708
  • /14

    $1,495 Per Month

    • 2 Beds
    • 1.5 Baths
    • 900 Sq Ft
    • 2/1.5 Winter Springs Townhome with screened patio-MOVE IN SPECIAL: $500 OFF FIRST MONTH'S RENT

    133 Garden Dr, Winter Springs, FL 32708

    MOVE IN SPECIAL: $500 OFF FIRST MONTH'S RENT. This renovated 2 bedroom and 1.5 bath Winter Springs townhome, features a large living area upon entry. There is a half bath downstairs for guests. The newly updated kitchen provides plenty of room for cooking, while the bedrooms offer peaceful retreats with ample natural light. Step outside to enjoy a private screen enclosed patio space, perfect for

    133 Garden Dr, Winter Springs, FL 32708
  • /6

    $1,450 Per Month

    • 2 Beds
    • 1.5 Baths
    • 930 Sq Ft
    • Townhouse for Rent

    Unlisted Address

    Spacious 2-Bedroom, 1.5-Bath Townhome in a Prime Location! Conveniently located near major highways, shopping, dining, and schools, this well-maintained townhome offers both comfort and convenience. The home features two spacious bedrooms, 1.5 bathrooms, a bright and open great room, a functional kitchen, a private patio perfect for relaxing, and a dedicated parking space. Enjoy easy access to

    maria vega THE EXPERTS TEAM REALTY INC

    Unlisted Address
  • /15

    $1,515 Per Month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • 2/1.5 Winter Springs Townhome with screen patio-MOVE IN SPECIAL: $500 OFF FIRST MONTH'S RENT

    137 Garden Dr, Winter Springs, FL 32708

    MOVE IN SPECIAL: $500 OFF FIRST MONTH'S RENT. This renovated 2 bedroom and 1.5 bath Winter Springs townhome, features a large living area upon entry. There is a half bath downstairs for guests. The newly updated kitchen provides plenty of room for cooking, while the bedrooms offer peaceful retreats with ample natural light. Step outside to enjoy a private screen enclosed patio space, perfect for

    137 Garden Dr, Winter Springs, FL 32708
  • /19

    $1,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft
    • Townhouse for Rent

    407 Sheoah Blvd Unit 9, Winter Springs, FL 32708

    This 3 bedroom, 2.5 bath condo is located in one of Winter Springs most desireable communities, THE HIGHLANDS! This unit features a large living and dining area, first floor guest half bath with a washer & dryer alcove, and large storage room. Back of property has private views with no rear neighbors. The community amenities offer miles of walking trails, playground, park, tennis court and

    Helen Marshall BENSON MARSHALL LLC

    407 Sheoah Blvd Unit 9, Winter Springs, FL 32708
  • /20

    $1,950 Per Month

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Condo for Rent

    411 Sheoah Blvd, Winter Springs, FL 32708

    Discover your dream 3-bed, 2.5-bath corner condo in Sheoah, Winter Springs. Enjoy a spacious open layout connecting living, dining, and a modern kitchen with ceramic tiles, wood cabinets, and a mosaic backsplash. Newly repainted with Luxury Vinyl Flooring throughout.Downstairs, find a stylish powder room and discreet laundry. Upstairs, sunlit bedrooms await. The master features an ensuite with a

    411 Sheoah Blvd, Winter Springs, FL 32708
  • /29

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft
    • Townhouse for Rent

    498 Club Dr, Winter Springs, FL 32708

    Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. New shingle roofing installed within the past months. Freshly painted and new luxury vinyl flooring throughout the unit. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    498 Club Dr, Winter Springs, FL 32708
  • /19

    $2,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,518 Sq Ft
    • Winter Springs: 3/2.5 in Heritage Park!! AVAILABLE AUGUST 17th!

    176 Constitution Way, Winter Springs, FL 32708

    Welcome home to this 2 story townhome with 3 bedrooms, 2.5 baths and a 1 car garage! The kitchen features all appliances, a breakfast bar and is open to the living room/dining area for optimal entertaining! Heritage Park is a gated community in the heart of Winter Springs. It is located in the Town Center area and is close to schools, shopping and walking trails. The outdoor pool is equipped

    176 Constitution Way, Winter Springs, FL 32708
  • /71

    $1,595 Per Month

    • 2 Beds
    • 1.5 Baths
    • 907 Sq Ft
    • Apartment for Rent

    10 N Fairfax Ave, Winter Springs, FL 32708

    LOCATION, LOCATION, LOCATION FULLY RENOVATED Condos in desirable Winter Springs. NO HOA!! BLOCK BUILDING! Unit offers 2 bedrooms, 1 full bath, 1 half bath, COMPLETELY FENCED BACKYARD!! Which provides you with Privacy and Security, a screened PRIVATE PORCH with storage, and NEWER SAMSUNG WASHER/DRYER IN EACH UNIT! Upgraded with STAINLESS STEEL appliances, GRANITE countertops, and engineered WOOD

    Jose Saba ALL SEASONS REALTY

    10 N Fairfax Ave, Winter Springs, FL 32708
  • /14

    $1,495 Per Month

    • 2 Beds
    • 1.5 Baths
    • 900 Sq Ft
    • Condo for Rent

    133 Garden Dr Unit 1, Winter Springs, FL 32708

    133 Garden Dr Unit 1, Winter Springs, FL 32708
  • /16

    $1,795 Per Month

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • House for Rent

    506 San Gabriel Ct, Winter Springs, FL 32708

    Move In Special! Receive $250 OFF your first month of rent if approved and moving in by February 23rd!Welcome home to 506 San Gabriel Court, a charming 3 bedroom, 2 bath home featuring 1,187 square feet of living space. As you enter the home, you are welcomed into the main living area, featuring vaulted ceilings and plenty of natural light through the numerous windows and sliding glass

    Justin Recca INNOVATIVE REALTY, LLC

    506 San Gabriel Ct, Winter Springs, FL 32708
  • /24

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 972 Sq Ft
    • The Highlands in Winter Springs

    10 Sheoah Blvd, Winter Springs, FL 32708

    Spacious and bright fully renovated 2-bedroom, 2-bathroom condo available for rent at The Highlands in Winter Springs. The entire interior has been freshly repainted and features tile flooring throughout. This inviting home offers a large family room with a cozy dining area and a split-bedroom floor plan for added privacy. The spacious primary bedroom includes sliding glass doors leading to the

    10 Sheoah Blvd, Winter Springs, FL 32708
  • /11

    $1,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,089 Sq Ft
    • House for Rent

    404 San Gabriel St, Winter Springs, FL 32708

    Welcome home to this beautifully maintained 3-bedroom, 2-bath residence offering comfort, convenience, and a fantastic location. Freshly updated with new paint in entire home, open living space, this home is ready for immediate occupancy. The kitchen features ample cabinet space and flows seamlessly into the living and dining areas, creating an inviting layout for everyday living. Step outside to

    Francisco Medina RODRIGUEZ PROPERTY MANAGEMENT

    404 San Gabriel St, Winter Springs, FL 32708
  • /8

    $1,300 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    1218 La Mesa Ave, Winter Springs, FL 32708

    Including utilities and internet, 1/1 garage apt, newly renovated, own entry, shared laundry room. Good income and credit, no pets.

    1218 La Mesa Ave, Winter Springs, FL 32708
  • /14

    $1,400 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    70 Moree Loop Unit 63, Winter Springs, FL 32708

    Two story condominium in Winter Springs. The two bedroom, 1 and 1/2 bath unit is located in the Highlands community. Tile and laminate flooring, spacious layout, kitchen has a pass thru window to the dining area. Combo living/dining with sliding glass doors which offers natural sunlight and opens to an exterior patio. Two bedrooms, master full bath and laundry utility on the second floor.

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    70 Moree Loop Unit 63, Winter Springs, FL 32708
  • /24

    $1,450 Per Month

    • 2 Beds
    • 2 Baths
    • 938 Sq Ft
    • Apartment for Rent

    101 Cory Ln, Winter Springs, FL 32708

    Make your new home in this spacious ground-floor apartment in Winter Springs, directly across from beautiful Torcaso Park with easy access to walking trails, green space, and recreation just outside the door. This two-bedroom, two-bathroom apartment features a practical layout with a galley kitchen open to a combined living and dining space that leads to a screen-enclosed covered patio, perfect

    Donna Vogler FLORIDA ONE REAL ESTATE LLC

    101 Cory Ln, Winter Springs, FL 32708

Rental Home Trends

Number of Homes for Rent
32
Median Rent
$2,265
Median Single Family Home Rent
$2,200
Median Townhouse Rent
$2,248
Median Condo Rent
$1,495
How to Rent a Home