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

1,261 Rentals
.
  1. Building Photo - Elan Crown Point
    Rent Special
    Rent Special
    1 BED
    $1,627+
    2 BEDS
    $2,117+
    3 BEDS
    $2,842+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,620 - $3,435
    Required Monthly Fees$7
    Utilities & EssentialsVaries
    Total Monthly Price$1,627 - $3,442

    Elan Crown Point

    2285 Crown Vlg Rd, Ocoee, FL 34761
    (689) 407-6923
  2. Building Photo - Prose Horizons Village
    $238 Off
    Price Drop. $238 Off
    |
    1 BED
    $1,729+
    2 BEDS
    $2,029+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,599 - $2,095
    Required Monthly Fees$130
    Utilities & EssentialsVaries
    Total Monthly Price$1,729 - $2,225

    Prose Horizons Village

    16810 Easthampstead Rd, Winter Garden, FL 34787
    (689) 220-3728
  6. $489 Off
    Price Drop. $489 Off
    |
    1 BED
    $1,624+
    2 BEDS
    $1,827+
    3 BEDS
    $2,552+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,480 - $2,562
    Required Monthly Fees$130 - $140
    Utilities & EssentialsVaries
    Total Monthly Price$1,624 - $2,702

    Windermere Cay

    8200 Jayme Dr, Winter Garden, FL 34787
    (689) 600-2212
  7. $365 Off
    Price Drop. $365 Off
    1 BED
    $1,760+
    2 BEDS
    $1,910+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600 - $1,905
    Required Monthly Fees$40
    Utilities & EssentialsVaries
    Total Monthly Price$1,760 - $1,945

    IMT Sonoma Hills

    14619 Casita Ridge, Winter Garden, FL 34787
    (689) 407-8016
  9. $296 Off
    Price Drop. $296 Off
    |
    1 BED
    $1,634+
    2 BEDS
    $2,100+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,599 - $2,100
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,634 - $2,135

    Prose Avalon Pointe

    14505 Tristan Cir, Winter Garden, FL 34787
    (407) 934-0429
  11. 1 Month Free
    1 Month Free
    |
    1 BED
    $1,848+
    2 BEDS
    $2,350+
    3 BEDS
    $2,650+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,793 - $3,243
    Required Monthly Fees$55
    Utilities & EssentialsVaries
    Total Monthly Price$1,848 - $2,682

    Corban Horizon West

    15000 Stratus Loop, Winter Garden, FL 34787
    (689) 407-2283
  12. $505 Off
    Price Drop. $505 Off
    1 BED
    $1,677+
    2 BEDS
    $2,270+
    3 BEDS
    $2,842+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,557 - $3,925
    Required Monthly Fees$120
    Utilities & EssentialsVaries
    Total Monthly Price$1,677 - $3,136

    Homestead at Hamlin

    15100 Free Range Run, Winter Garden, FL 34787
    (689) 400-7126
  15. $499 Off
    Price Drop. $499 Off
    |
    STUDIO
    $1,578+
    1 BED
    $1,761+
    2 BEDS
    $2,015+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,469 - $2,200
    Required Monthly Fees$109
    Utilities & EssentialsVaries
    Total Monthly Price$1,578 - $2,309

    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
  18. Building Photo - The Lodge at Hamlin
    $400 Off
    Price Drop. $400 Off
    1 BED
    $1,700+
    2 BEDS
    $2,210+
    3 BEDS
    $2,660+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,669 - $3,064
    Required Monthly Fees$31
    Utilities & EssentialsVaries
    Total Monthly Price$1,700 - $3,095

    The Lodge at Hamlin

    6151 Lake Lodge Dr, Winter Garden, FL 34787
    (689) 400-7090
  20. STUDIO
    $1,836+
    1 BED
    $2,062+
    2 BEDS
    $2,662+
    3 BEDS
    $3,107+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,724 - $3,100
    Required Monthly Fees$112
    Total Monthly Price$1,836 - $3,212

    Regency

    1601 Maguire Rd, Ocoee, FL 34761
    (689) 329-1873
  21. Exceptional Value
    1 BED
    $1,785+
    2 BEDS
    $2,050+
    3 BEDS
    $2,468+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,616 - $2,324
    Required Monthly Fees$169
    Total Monthly Price$1,785 - $2,493

    Casa Mirella

    101 Casa Mirella Way, Windermere, FL 34786
    (689) 407-8243
  24. 1 BED
    $1,449+
    2 BEDS
    $1,629+
    3 BEDS
    $1,979+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,449 - $1,979
    Utilities & EssentialsVaries
    Total Monthly Price$1,449 - $1,979

    Country Gardens

    15122 W Colonial Dr, Winter Garden, FL 34787
    (689) 407-2059
  29. Building Photo - 16350 Hamlin Vw St
    3 BEDS, 3 BATHS
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    16350 Hamlin Vw St

    16350 Hamlin Vw St, Winter Garden, FL 34787
  31. Building Photo - 122 Windtree Ln
    2 BEDS, 2 BATHS
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    122 Windtree Ln Unit 122 - O

    122 Windtree Ln, Winter Garden, FL 34787
  34. Building Photo - 17877 C R 378
    3 BEDS, 2 BATHS
    $4,299

    17877 C R 378

    17877 C R 378, Winter Garden, FL 34787
  37. 4 BEDS, 3.5 BATHS
    $3,400

    1447 Roxy Ln

    1447 Roxy Ln, Winter Garden, FL 34787
Showing 42 of 50 results, Page 1 of 2

Winter Garden at a Glance

Average Rent

$1,700
(All bedrooms and property types)
Learn more about
Average Rent in Winter Garden
8

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
West Orange High School

Public High School

Public
Grades 9-12
2,804 Students
GreatSchools Rating
Horizon High School

Public High School

Public
Grades 9-12
3,046 Students
GreatSchools Rating
Orange Technical College Westside Campus

Public High School

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

Public Middle School

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

Public Middle School

Public
Grades 6-8
1,210 Students
GreatSchools Rating
Bridgewater Middle School

Public Middle School

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

Public Middle School

Public
Grades 6-8
1,178 Students
GreatSchools Rating
SunRidge Middle School

Public Middle School

Public
Grades 6-8
1,115 Students
GreatSchools Rating
Hamlin Elementary School

Public Elementary School

Public
Grades K-5
725 Students
GreatSchools Rating
Atwater Bay Elementary School

Public Elementary School

Public
Grades K-5
835 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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