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Apartments for Rent in Winter Garden, FL with a Swimming Pool

1,016 Rentals
.
  1. Building Photo - Elan Crown Point
    Rent Special
    Rent Special
    1 BED
    $1,826+
    2 BEDS
    $2,246+
    3 BEDS
    $3,121+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,705 - $3,435
    Required Monthly Fees$121
    Utilities & EssentialsVaries
    Total Monthly Price$1,826 - $3,556

    Elan Crown Point

    2285 Crown Vlg Rd, Ocoee, FL 34761
    (689) 407-6923
  2. Building Photo - Vida Winter Garden
    $191 Off
    Price Drop. $191 Off
    |
    STUDIO
    $1,496+
    1 BED
    $1,560+
    2 BEDS
    $2,236+
    3 BEDS
    $2,631+

    Vida Winter Garden

    1223 E Plant St, Winter Garden, FL 34787
    (689) 600-3438
  3. $220 Off
    Price Drop. $220 Off
    |
    1 BED
    $1,530+
    2 BEDS
    $1,751+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,395 - $1,896
    Required Monthly Fees$135
    Utilities & EssentialsVaries
    Total Monthly Price$1,530 - $2,031

    Prose Horizons Village

    16810 Easthampstead Rd, Winter Garden, FL 34787
    (689) 220-3728
  4. $171 Off
    Price Drop. $171 Off
    1 BED
    $1,444+
    2 BEDS
    $1,799+
    3 BEDS
    $2,346+

    Integra Avalon

    17825 Avalon Grove Loop, Winter Garden, FL 34787
    (689) 215-7867
  5. Rent Special
    Rent Special
    |
    STUDIO
    $1,841+
    1 BED
    $1,912+
    2 BEDS
    $2,412+
    3 BEDS
    $2,892+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,724 - $2,995
    Required Monthly Fees$117
    Total Monthly Price$1,841 - $3,112

    The Regency

    1601 Maguire Rd, Ocoee, FL 34761
    (689) 329-1873
  6. Rent Special
    Rent Special
    1 BED
    $1,730+
    2 BEDS
    $2,487+
    3 BEDS
    $3,376+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,595 - $3,511
    Required Monthly Fees$135
    Utilities & EssentialsVaries
    Total Monthly Price$1,730 - $3,646

    Homestead at Hamlin

    15100 Free Range Run, Winter Garden, FL 34787
    (689) 400-7126
  9. Good Value
    1 BED
    $1,836+
    2 BEDS
    $2,153+
    3 BEDS
    $2,455+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,757 - $2,416
    Required Monthly Fees$79
    Utilities & EssentialsVaries
    Total Monthly Price$1,836 - $2,495

    Cortland Independence

    14600 Avenue of the Groves Ave, Winter Garden, FL 34787
    (689) 407-7472
  10. Good Value
    |
    1 BED
    $1,429+
    2 BEDS
    $1,745+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,389 - $2,159
    Required Monthly Fees$40
    Utilities & EssentialsVaries
    Total Monthly Price$1,429 - $2,199

    Prose Avalon Pointe

    14505 Tristan Cir, Winter Garden, FL 34787
    (407) 934-0429
  11. $225 Off
    Price Drop. $225 Off
    1 BED
    $1,615+
    2 BEDS
    $1,820+
    3 BEDS
    $2,500+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,575 - $2,510
    Required Monthly Fees$40
    Utilities & EssentialsVaries
    Total Monthly Price$1,615 - $2,550

    IMT Sonoma Hills

    14619 Casita Ridge, Winter Garden, FL 34787
    (689) 407-8016
  12. |
    1 BED
    $1,961+
    2 BEDS
    $2,419+
    3 BEDS
    $2,630+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,831 - $2,635
    Required Monthly Fees$130 - $140
    Utilities & EssentialsVaries
    Total Monthly Price$1,961 - $2,775

    Windermere Cay

    8200 Jayme Dr, Winter Garden, FL 34787
    (689) 600-2212
  13. $683 Off
    Price Drop. $683 Off
    |
    STUDIO
    $1,468+
    1 BED
    $1,589+
    2 BEDS
    $2,141+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,359 - $2,158
    Required Monthly Fees$109
    Utilities & EssentialsVaries
    Total Monthly Price$1,468 - $2,267

    Apollo Apartments

    7000 Kiran Patel Dr, Winter Garden, FL 34787
    (689) 400-8498
  17. Kitchen - Garden City Apartments
    1 Month Free
    1 Month Free
    2 BEDS
    $1,499
    Total Monthly Price Total Monthly Price New
    Base Rent$1,499 - $1,749
    Required Monthly FeesNone
    Total Monthly Price$1,499 - $1,749

    Garden City Apartments

    521 S Park Ave, Winter Garden, FL 34787
    (689) 407-8861
  19. 2 Months Free
    2 Months Free
    1 BED
    $1,805+
    2 BEDS
    $2,335+
    3 BEDS
    $2,650+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750 - $2,783
    Required Monthly Fees$55
    Utilities & EssentialsVaries
    Total Monthly Price$1,805 - $2,838

    Corban Horizon West

    15000 Stratus Loop, Winter Garden, FL 34787
    (689) 407-2283
  21. 2 Months Free
    2 Months Free
    1 BED
    $1,865+
    2 BEDS
    $2,385+
    3 BEDS
    $2,900+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,834 - $3,359
    Required Monthly Fees$31
    Utilities & EssentialsVaries
    Total Monthly Price$1,865 - $3,390

    The Lodge at Hamlin

    6151 Lake Lodge Dr, Winter Garden, FL 34787
    (689) 400-7090
  22. Discounts
    Discounts
    1 BED
    $1,349+
    2 BEDS
    $1,599+
    3 BEDS
    $1,959+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,349 - $1,959
    Utilities & EssentialsVaries
    Total Monthly Price$1,349 - $1,959

    Country Gardens

    15122 W Colonial Dr, Winter Garden, FL 34787
    (689) 407-2059
  23. 1 BED
    $1,653+
    2 BEDS
    $2,060+
    3 BEDS
    $2,622+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,484 - $2,478
    Required Monthly Fees$169
    Total Monthly Price$1,653 - $2,647

    Casa Mirella

    101 Casa Mirella Way, Windermere, FL 34786
    (689) 407-8243
  26. Building Photo - 17013 Haggerty Hollow Dr
    3 BEDS, 3 BATHS
    $2,950
    Total Monthly Price Total Monthly Price New
    Base Rent$2,950
    Required Monthly FeesNone
    Total Monthly Price$2,950

    17013 Haggerty Hollow Dr

    17013 Haggerty Hollow Dr, Winter Garden, FL 34787
  27. Building Photo - 17025 Haggerty Hollow Dr
    3 BEDS, 3 BATHS
    $2,850
    Total Monthly Price Total Monthly Price New
    Base Rent$2,850
    Required Monthly FeesNone
    Total Monthly Price$2,850

    17025 Haggerty Hollow Dr

    17025 Haggerty Hollow Dr, Winter Garden, FL 34787
  28. 4 BEDS, 2 BATHS
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800

    542 Groves End Ln

    542 Groves End Ln, Winter Garden, FL 34787
  29. 3 BEDS, 3 BATHS
    $2,750
    Total Monthly Price Total Monthly Price New
    Base Rent$2,750
    Required Monthly FeesNone
    Total Monthly Price$2,750

    15352 Burgtheater Dr

    15352 Burgtheater Dr, Winter Garden, FL 34787
  32. Building Photo - 142 Southern Pecan Cir
    3 BEDS, 2 BATHS
    $2,150
    Total Monthly Price Total Monthly Price New
    Base Rent$2,150
    Required Monthly FeesNone
    Total Monthly Price$2,150

    142 Southern Pecan Cir Unit 204

    142 Southern Pecan Cir, Winter Garden, FL 34787
  33. Building Photo - 17736 Porter Rd
    3 BEDS, 3 BATHS
    $3,100
    Total Monthly Price Total Monthly Price New
    Base Rent$3,100
    Required Monthly FeesNone
    Total Monthly Price$3,100

    17736 Porter Rd

    17736 Porter Rd, Winter Garden, FL 34787
Showing 42 of 58 results, Page 1 of 2

Winter Garden at a Glance

Average Rent

$1,670
(All bedrooms and property types)
Learn more about
Average Rent in Winter Garden
7

School Rating

out of 10 Rating
Learn more about
Schools in Winter Garden

Winter Garden, FL Apartments for Rent

Winter Garden is a city in western Orange County located about 14 miles west of Downtown Orlando, known for its restored historic downtown district with brick-lined streets and the popular West Orange Trail that winds through the heart of the city. Those looking for apartments for rent in Winter Garden will find a range of housing options, from modern apartment communities near Winter Garden Village to rentals in established neighborhoods like Stoneybrook West and Wintermere Pointe, with average one-bedroom rents around $1,736 per month.

Renting in Winter Garden offers convenient access to both local amenities and the greater Orlando metropolitan area. The downtown area features local shops, dining options, and the Garden Theatre for entertainment, while the weekend farmers market has become a community tradition. The West Orange Trail provides miles of paved paths for outdoor activities, and Lake Apopka offers additional recreation opportunities nearby. Residents benefit from the city's location along State Road 50 and the Florida Turnpike, making commutes to Orlando and surrounding areas straightforward, while still enjoying the city's distinctive downtown character and community atmosphere.

Renting in Winter Garden

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winter Garden

(For 1 bedroom apartments)

Education

GreatSchools Rating
West Orange High

Public High School

Public
Grades 9-12
2,816 Students
GreatSchools Rating
Horizon High School

Public High School

Public
Grades 9-12
3,046 Students
GreatSchools Rating
West Orange High School

Public High School

Public
Grades 9-12
2,804 Students
GreatSchools Rating
Water Spring Middle School-0482

Public Middle School

Public
Grades 6-8
1,274 Students
GreatSchools Rating
Bridgewater Middle School

Public Middle School

Public
Grades 6-8
1,098 Students
GreatSchools Rating
Hamlin Middle School

Public Middle School

Public
Grades 6-8
1,034 Students
GreatSchools Rating
SunRidge Middle School

Public Middle School

Public
Grades 6-8
1,115 Students
GreatSchools Rating
Lakeview Middle

Public Middle School

Public
Grades 6-8
843 Students
GreatSchools Rating
Hamlin Elementary School

Public Elementary School

Public
Grades K-5
725 Students
GreatSchools Rating
Independence Elementary

Public Elementary School

Public
Grades K-5
829 Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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