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

1,588 Rentals
.
  1. Building Photo - Village Park Senior
    1 BED
    $1,344+
    2 BEDS
    $1,586+
    3 BEDS
    $2,399+

    Village Park Senior

    550 W Denning Dr, Winter Park, FL 32789
  2. Kitchen - Indigo Winter Park
    2 Months Free
    2 Months Free
    1 BED
    $1,149

    Indigo Winter Park

    220 S Semoran Blvd, Winter Park, FL 32792
  3. 2 Months Free
    2 Months Free
    1 BED
    $1,349+
    2 BEDS
    $1,349+
    3 BEDS
    $1,999+

    Sapphire Winter Park

    1743 Semoran North Cir, Winter Park, FL 32792
  4. 2 Months Free
    2 Months Free
    1 BED
    $1,099+
    2 BEDS
    $1,599+

    Serena Winter Park

    2890 Red Lion Sq, Winter Park, FL 32792
  5. Building Photo - Venue At Winter Park
    Rent Special
    Rent Special
    1 BED
    $1,239+
    2 BEDS
    $1,486+
    3 BEDS
    $1,837+

    Venue At Winter Park

    5 Autumn Breeze Way, Winter Park, FL 32792
  6. Building Photo - The Fisher
    1 Month Free
    1 Month Free
    1 BED
    $1,699

    The Fisher

    2001 Glenridge Way, Winter Park, FL 32792
Showing 42 of 91 results, Page 3 of 3

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Winter Park at a Glance

Average Rent

$1,458
(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

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 745 Sq Ft $1,542/mo
  • Fairview 736 Sq Ft $1,920/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.

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