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

1,386 Rentals
.
  1. Building Photo - Gables Baldwin Park
    Rent Special
    Rent Special
    |
    STUDIO
    $2,381+
    1 BED
    $2,456+
    2 BEDS
    $3,146+
    3 BEDS
    $4,367+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,333 - $4,319
    Required Monthly Fees$48
    Utilities & EssentialsVaries
    Total Monthly Price$2,381 - $4,367

    Gables Baldwin Park

    2050 Jake St, Orlando, FL 32814
    (470) 305-6691
  7. |
    1 BED
    $1,838+
    2 BEDS
    $2,181+
    3 BEDS
    $2,729+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,705 - $2,643
    Required Monthly Fees$133
    Total Monthly Price$1,838 - $2,776

    Vintage Winter Park Apartments

    7490 Dwell Well Way, Winter Park, FL 32792
    (689) 220-1305
  8. $209 Off
    Price Drop. $209 Off
    1 BED
    $1,291+
    2 BEDS
    $1,224+

    Seabrook

    3114 Terry Brook Dr, Winter Park, FL 32792
    (689) 220-5925
  12. 1 Month Free
    1 Month Free
    STUDIO
    $1,903+
    1 BED
    $2,569+
    2 BEDS
    $2,749+
    3 BEDS
    $3,298+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,804 - $3,475
    Required Monthly Fees$99
    Utilities & EssentialsVaries
    Total Monthly Price$1,903 - $3,574

    Enders Place at Baldwin Park

    4220 New Broad St, Orlando, FL 32814
    (689) 220-2141
  13. 1 BED
    $2,324+
    2 BEDS
    $3,099+
    3 BEDS
    $4,858+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,247 - $4,781
    Required Monthly Fees$77
    Utilities & EssentialsVaries
    Total Monthly Price$2,324 - $4,858

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  14. $250 Off
    Price Drop. $250 Off
    |
    1 BED
    $1,612+
    2 BEDS
    $2,404+
    3 BEDS
    $2,852+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,577 - $4,898
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,612 - $4,933

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  16. |
    1 BED
    $1,688+
    2 BEDS
    $2,075+
    3 BEDS
    $2,259+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,604 - $2,205
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,688 - $2,289

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  19. $988 Off
    Price Drop. $988 Off
    |
    1 BED
    $1,684+
    2 BEDS
    $2,199+
    3 BEDS
    $3,311+

    The Adeline

    304 Lake Ave, Maitland, FL 32751
    (689) 219-8866
  33. 3 BEDS
    $2,879
    Total Monthly Price Total Monthly Price New
    Base Rent$2,837
    Required Monthly Fees$42
    Utilities & EssentialsVaries
    Total Monthly Price$2,879

    400 North

    400 N Orlando Ave, Maitland, FL 32751
    (689) 219-4863
  34. $194 Off
    Price Drop. $194 Off
    STUDIO
    $1,831+
    1 BED
    $1,582+
    2 BEDS
    $2,277+
    3 BEDS
    $2,873+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,507 - $3,266
    Required Monthly Fees$75
    Total Monthly Price$1,582 - $3,341

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  35. Rent Special
    Rent Special
    STUDIO
    $1,682+
    1 BED
    $1,997+
    2 BEDS
    $2,560+
    3 BEDS
    $3,398+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,594 - $4,965
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,682 - $5,053

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  37. $400 Off
    Price Drop. $400 Off
    1 BED
    $999+
    2 BEDS
    $1,299+

    Soraya

    1485 Ash Cir, Casselberry, FL 32707
    (689) 205-8365
  40. Building Photo - Stonecastle Apartment Homes
    1 BED
    $1,592+
    2 BEDS
    $1,957+
    3 BEDS
    $1,956+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,441 - $2,620
    Required Monthly Fees$151
    Utilities & EssentialsVaries
    Total Monthly Price$1,592 - $2,771

    Stonecastle Apartment Homes

    2015 New Stonecastle Ter, Winter Park, FL 32792
    (689) 219-5272
  41. $348 Off
    Price Drop. $348 Off
    1 BED
    $1,514+
    2 BEDS
    $1,836+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,396 - $1,900
    Required Monthly Fees$118
    Utilities & EssentialsVaries
    Total Monthly Price$1,514 - $2,018

    Solis at Winter Park

    7502 Sun Key Blvd, Winter Park, FL 32792
    (321) 366-6748
  42. STUDIO
    $1,355+
    1 BED
    $1,443+
    2 BEDS
    $1,545+
    3 BEDS
    $1,851+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,344 - $2,204
    Required Monthly Fees$11
    Utilities & EssentialsVaries
    Total Monthly Price$1,355 - $2,215

    Westmount at Winter Park

    1701 Lee Rd, Winter Park, FL 32789
    (689) 205-8291
Showing 42 of 86 results, Page 1 of 3

Winter Park at a Glance

Average Rent

$1,482
(All bedrooms and property types)
Learn more about
Average Rent in Winter Park
7

School Rating

out of 10 Rating
Learn more about
Schools in Winter Park

Winter Park, FL Apartments for Rent

Winter Park was founded as a resort community by northern business magnates in the late 19th century and has maintained its reputation as one of Central Florida's most desirable places to live. Those searching for apartments for rent in Winter Park will discover tree-lined brick streets, a chain of interconnected lakes, and the cultural centerpiece of Park Avenue, which features boutique shops, art galleries, and dining options. The city is also home to Rollins College and the Charles Hosmer Morse Museum of American Art, which houses the world's most comprehensive collection of Tiffany glass.

Renting in Winter Park provides convenient access to both local attractions and the broader Orlando metropolitan area. The city's apartment communities range from lakefront properties to garden-style residences near downtown, with options spanning studios to multi-bedroom layouts. Major highways including Interstate 4 are easily accessible for commuters heading to Orlando's business districts, theme parks, and employment centers. The 47.6-acre Mead Botanical Garden and the city's scenic canal system offer outdoor recreation, while Park Avenue's walkable downtown creates opportunities for shopping and entertainment without leaving the city limits.

Renting in Winter Park

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winter Park

(For 1 bedroom apartments)

Education

GreatSchools Rating
Winter Park High

Public High School

Public
Grades 9-12
3,369 Students
GreatSchools Rating
Winter Park High School

Public High School

Public
Grades 9-12
3,304 Students
GreatSchools Rating
Lake Howell High School

Public High School

Public
Grades 9-12
2,239 Students

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

Apartments for Rent Near Winter Park

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