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

1,247 Rentals
.
  3. 1 Month Free
    1 Month Free
    |
    STUDIO
    $2,282+
    1 BED
    $2,502+
    2 BEDS
    $3,071+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,229 - $4,343
    Required Monthly Fees$53
    Utilities & EssentialsVaries
    Total Monthly Price$2,282 - $4,396

    Gables Baldwin Park

    2050 Jake St, Orlando, FL 32814
    (470) 305-6691
  8. |
    1 BED
    $1,719+
    2 BEDS
    $1,932+
    3 BEDS
    $2,386+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,586 - $2,458
    Required Monthly Fees$133
    Utilities & EssentialsVaries
    Total Monthly Price$1,719 - $2,591

    Vintage Winter Park Apartments

    7490 Dwell Well Way, Winter Park, FL 32792
    (689) 220-1305
  11. Rent Special
    Rent Special
    1 BED
    $1,253+
    2 BEDS
    $1,509+

    Seabrook

    3114 Terry Brook Dr, Winter Park, FL 32792
    (689) 220-5925
  13. $566 Off
    Price Drop. $566 Off
    1 BED
    $1,960+
    2 BEDS
    $3,040+
    3 BEDS
    $3,886+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,883 - $5,058
    Required Monthly Fees$77
    Utilities & EssentialsVaries
    Total Monthly Price$1,960 - $5,135

    Baldwin Harbor

    1771-1887 Jake St, Orlando, FL 32814
    (689) 207-3563
  14. $165 Off
    Price Drop. $165 Off
    |
    1 BED
    $1,552+
    2 BEDS
    $1,853+
    3 BEDS
    $2,098+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,468 - $2,214
    Required Monthly Fees$84
    Utilities & EssentialsVaries
    Total Monthly Price$1,552 - $2,298

    Cortland Lake Howell

    1280 Vinings Ln, Casselberry, FL 32707
    (321) 710-4674
  17. Rent Special
    Rent Special
    |
    1 BED
    $1,727+
    2 BEDS
    $2,202+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,692 - $2,582
    Required Monthly Fees$35
    Utilities & EssentialsVaries
    Total Monthly Price$1,727 - $2,617

    The Village at Lake Lily

    925 S Orlando Ave, Maitland, FL 32751
    (689) 219-5267
  18. $265 Off
    Price Drop. $265 Off
    STUDIO
    $1,798+
    1 BED
    $2,274+
    2 BEDS
    $2,749+
    3 BEDS
    $3,373+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,699 - $3,475
    Required Monthly Fees$99
    Utilities & EssentialsVaries
    Total Monthly Price$1,798 - $3,574

    Enders Place at Baldwin Park

    4220 New Broad St, Orlando, FL 32814
    (689) 220-2141
  19. $473 Off
    Price Drop. $473 Off
    |
    1 BED
    $1,570+
    2 BEDS
    $2,016+
    3 BEDS
    $2,678+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,570 - $3,043
    Utilities & EssentialsVaries
    Total Monthly Price$1,570 - $3,043

    The Adeline

    304 Lake Ave, Maitland, FL 32751
    (689) 219-8866
  20. $285 Off
    Price Drop. $285 Off
    |
    1 BED
    $1,850+
    2 BEDS
    $2,323+
    3 BEDS
    $2,566+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,749 - $2,828
    Required Monthly Fees$101
    Utilities & EssentialsVaries
    Total Monthly Price$1,850 - $2,929

    Village at Baldwin Park

    2055 Lake Baldwin Ln, Orlando, FL 32814
    (352) 632-9622
  34. Good Value
    STUDIO
    $1,831+
    1 BED
    $1,719+
    2 BEDS
    $2,171+
    3 BEDS
    $2,691+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,644 - $3,178
    Required Monthly Fees$75
    Total Monthly Price$1,719 - $3,253

    Aurora on the Trail

    825 McCullough Ave, Orlando, FL 32803
    (689) 219-5368
  35. 2 BEDS
    $2,232+
    3 BEDS
    $2,637+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,190 - $2,595
    Required Monthly Fees$42
    Utilities & EssentialsVaries
    Total Monthly Price$2,232 - $2,637

    400 North

    400 N Orlando Ave, Maitland, FL 32751
    (689) 219-4863
  36. 1 Month Free
    1 Month Free
    STUDIO
    $1,800+
    1 BED
    $2,064+
    2 BEDS
    $2,695+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,712 - $2,751
    Required Monthly Fees$88
    Utilities & EssentialsVaries
    Total Monthly Price$1,800 - $2,839

    Vida at Health Village

    2680 N Orange Ave, Orlando, FL 32804
    (321) 621-2828
  38. $200 Off
    Price Drop. $200 Off
    1 BED
    $1,399+
    2 BEDS
    $1,299+

    Soraya

    1485 Ash Cir, Casselberry, FL 32707
    (689) 205-8365
  42. Good Value
    1 BED
    $1,275+
    2 BEDS
    $1,514+
    3 BEDS
    $2,002+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,250 - $1,977
    Required Monthly Fees$25
    Utilities & EssentialsVaries
    Total Monthly Price$1,275 - $2,002

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
    (689) 219-8770
Showing 42 of 108 results, Page 1 of 3

Winter Park at a Glance

Average Rent

$1,471
(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)
  • Neighborhoods Average Sq Ft Average Rent
  • Lake Howell 727 Sq Ft $1,531/mo
  • Fairview 743 Sq Ft $1,804/mo

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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