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

1,554 Rentals
.
  1. Building Photo - Signal Pointe
    $265 Off
    Price Drop. $265 Off
    1 BED
    $1,275+
    2 BEDS
    $1,370+
    3 BEDS
    $1,690+

    Signal Pointe

    2500 Howell Branch Rd, Winter Park, FL 32792
    (689) 220-5609
  3. $220 Off
    Price Drop. $220 Off
    1 BED
    $1,432+
    2 BEDS
    $1,731+
    3 BEDS
    $1,868+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,412 - $2,034
    Required Monthly Fees$20
    Utilities & EssentialsVaries
    Total Monthly Price$1,432 - $2,054

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
    (689) 219-8770
  8. $408 Off
    Price Drop. $408 Off
    1 BED
    $1,762+
    2 BEDS
    $2,046+
    3 BEDS
    $3,111+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,732 - $3,255
    Required Monthly Fees$30
    Total Monthly Price$1,762 - $3,285

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  10. Building Photo - Sumerset Apartments
    1 BED
    $1,074+
    2 BEDS
    $1,195+
    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
  11. Good Value
    STUDIO
    $900+
    1 BED
    $1,050+
    2 BEDS
    $1,200+
    3 BEDS
    $1,600+

    Kingswood Apartments

    1101 Lee Rd, Orlando, FL 32810
  12. Building Photo - 625 Trinidad Ct
    2 BEDS, 2 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    625 Trinidad Ct Unit 625

    625 Trinidad Ct, Winter Park, FL 32792
  16. Building Photo - 2500 Lee Rd
    1 BED, 1 BATH
    $1,465
    Total Monthly Price Total Monthly Price New
    Base Rent$1,465
    Required Monthly FeesNone
    Total Monthly Price$1,465

    2500 Lee Rd Unit 244

    2500 Lee Rd, Winter Park, FL 32789
  19. 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
  24. 2 BEDS, 2 BATHS
    $2,695
    Total Monthly Price Total Monthly Price New
    Base Rent$2,695
    Required Monthly FeesNone
    Total Monthly Price$2,695

    2912 Plaza Terrace Dr

    2912 Plaza Terrace Dr, Orlando, FL 32803
    Apply
  25. 3 BEDS, 2.5 BATHS
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500

    1840 Bachman Way

    1840 Bachman Way, Winter Park, FL 32792
  26. 3 BEDS, 3.5 BATHS
    $2,950
    Total Monthly Price Total Monthly Price New
    Base Rent$2,950
    Required Monthly FeesNone
    Total Monthly Price$2,950

    223 Sandlewood Trl

    223 Sandlewood Trl, Winter Park, FL 32789
  27. Building Photo - 200 Saint Andrews Blvd
    3 BEDS, 2 BATHS
    $1,150
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150
    Required Monthly FeesNone
    Total Monthly Price$1,150

    200 Saint Andrews Blvd Unit 2402

    200 Saint Andrews Blvd, Winter Park, FL 32792
  36. 1 BED
    $1,344+
    2 BEDS
    $1,586+
    3 BEDS
    $2,399+

    Village Park Senior

    550 W Denning Dr, Winter Park, FL 32789
  38. Building Photo - Venue At Winter Park
    Rent Special
    Rent Special
    1 BED
    $1,206+
    2 BEDS
    $1,520+
    3 BEDS
    $1,785+

    Venue At Winter Park

    5 Autumn Breeze Way, Winter Park, FL 32792
  39. 1 Month Free
    1 Month Free
    1 BED
    $1,699+
    2 BEDS
    $1,899+

    The Fisher

    2001 Glenridge Way, Winter Park, FL 32792
  41. 2 Months Free
    2 Months Free
    1 BED
    $1,369+
    2 BEDS
    $1,349+
    3 BEDS
    $1,899+

    Sapphire Winter Park

    1743 Semoran North Cir, Winter Park, FL 32792
  42. Kitchen - Serena Winter Park
    2 Months Free
    2 Months Free
    1 BED
    $1,099+
    2 BEDS
    $1,519+

    Serena Winter Park

    2890 Red Lion Sq, Winter Park, FL 32792
Showing 42 of 85 results, Page 2 of 3

Winter Park at a Glance

Average Rent

$1,468
(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 740 Sq Ft $1,571/mo
  • Fairview 732 Sq Ft $1,866/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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