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

1,386 Rentals
.
  2. Building Photo - Solis at Winter Park
    $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
  3. $340 Off
    Price Drop. $340 Off
    1 BED
    $1,200+
    2 BEDS
    $1,455+
    3 BEDS
    $1,775+

    Signal Pointe

    2500 Howell Branch Rd, Winter Park, FL 32792
    (689) 220-5609
  4. 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
  9. $554 Off
    Price Drop. $554 Off
    1 BED
    $1,670+
    2 BEDS
    $2,103+
    3 BEDS
    $2,585+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,580 - $3,477
    Required Monthly Fees$90
    Total Monthly Price$1,670 - $3,567

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  12. Building Photo - Kingswood Apartments
    Exceptional Value
    STUDIO
    $900+
    1 BED
    $1,050+
    2 BEDS
    $1,200+
    3 BEDS
    $1,600+

    Kingswood Apartments

    1101 Lee Rd, Orlando, FL 32810
  13. Good Value
    1 BED
    $1,074+
    2 BEDS
    $1,274+
    3 BEDS
    $1,295+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,074 - $1,495
    Required Monthly FeesNone
    Total Monthly Price$1,074 - $1,495

    Sumerset Apartments

    1051 Lee Rd, Orlando, FL 32810
  14. Building Photo - 2500 Lee Rd
    1 BED, 1 BATH
    $1,350
    Total Monthly Price Total Monthly Price New
    Base Rent$1,350
    Required Monthly FeesNone
    Total Monthly Price$1,350

    2500 Lee Rd Unit 244

    2500 Lee Rd, Winter Park, FL 32789
  17. Building Photo - 551 Flemming Way
    1 BED, 1 BATH
    $1,150
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150
    Required Monthly FeesNone
    Total Monthly Price$1,150

    551 Flemming Way Unit 201

    551 Flemming Way, Maitland, FL 32751
  21. Building Photo - 1250 S Denning Dr
    2 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    1250 S Denning Dr Unit 127

    1250 S Denning Dr, Winter Park, FL 32789
    Apply
  22. Building Photo - 2924 Antique Oaks Cir
    2 BEDS, 2.5 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    2924 Antique Oaks Cir Unit 48

    2924 Antique Oaks Cir, Winter Park, FL 32792
    Apply
  23. 2 BEDS, 2 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    622 St Johns Ct

    622 St Johns Ct, Winter Park, FL 32792
    Apply
  24. Building Photo - 151 N Orlando Ave
    1 BED, 1 BATH
    $2,450
    Total Monthly Price Total Monthly Price New
    Base Rent$2,450
    Required Monthly FeesNone
    Total Monthly Price$2,450

    151 N Orlando Ave Unit 262

    151 N Orlando Ave, Winter Park, FL 32789
    Apply
  25. Pool #1 on the Lake - 2912 Plaza Terrace Dr
    2 BEDS, 2 BATHS
    $2,275
    Total Monthly Price Total Monthly Price New
    Base Rent$2,275
    Required Monthly FeesNone
    Total Monthly Price$2,275

    2912 Plaza Terrace Dr

    2912 Plaza Terrace Dr, Orlando, FL 32803
    Apply
  26. 2 BEDS, 2 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    1920 Woodcrest Dr Unit 13

    1920 Woodcrest Dr, Winter Park, FL 32792
  27. Discounts
    Discounts
    1 BED, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    468 Banyon Tree Cir Unit 202

    468 Banyon Tree Cir, Maitland, FL 32751
  28. 3 BEDS, 3.5 BATHS
    $4,100
    Total Monthly Price Total Monthly Price New
    Base Rent$4,100
    Required Monthly FeesNone
    Total Monthly Price$4,100

    1733 Prospect Ave

    1733 Prospect Ave, Orlando, FL 32814
  31. 5 BEDS, 6 BATHS
    $9,900

    1442 Palm Ave

    1442 Palm Ave, Winter Park, FL 32789
  39. Building Photo - Venue At Winter Park
    Rent Special
    Rent Special
    1 BED
    $1,224+
    2 BEDS
    $1,508+
    3 BEDS
    $1,847+

    Venue At Winter Park

    5 Autumn Breeze Way, Winter Park, FL 32792
  41. 2 Months Free
    2 Months Free
    1 BED
    $1,249

    Indigo Winter Park

    220 S Semoran Blvd, Winter Park, FL 32792
  42. 2 Months Free
    2 Months Free
    1 BED
    $1,049+
    2 BEDS
    $1,499+

    Serena Winter Park

    2890 Red Lion Sq, Winter Park, FL 32792
Showing 42 of 86 results, Page 2 of 3

Winter Park at a Glance

Average Rent

$1,481
(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)

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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