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

1,665 Rentals
.
  1. Building Photo - Solis at Winter Park
    $283 Off
    Price Drop. $283 Off
    1 BED
    $1,256+
    2 BEDS
    $1,764+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,138 - $1,811
    Required Monthly Fees$118
    Utilities & EssentialsVaries
    Total Monthly Price$1,256 - $1,929

    Solis at Winter Park

    7502 Sun Key Blvd, Winter Park, FL 32792
    (321) 366-6748
  5. $151 Off
    Price Drop. $151 Off
    1 BED
    $1,305+
    2 BEDS
    $1,647+
    3 BEDS
    $1,861+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,285 - $2,034
    Required Monthly Fees$20
    Utilities & EssentialsVaries
    Total Monthly Price$1,305 - $2,054

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
    (689) 219-8770
  10. $239 Off
    Price Drop. $239 Off
    1 BED
    $1,749+
    2 BEDS
    $2,168+
    3 BEDS
    $2,927+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,714 - $3,124
    Required Monthly Fees$30
    Total Monthly Price$1,749 - $3,154

    Audubon Park

    990 Warehouse Rd, Orlando, FL 32803
    (689) 219-8885
  11. 1 BED, 1 BATH
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    700 Melrose Ave

    700 Melrose Ave, Winter Park, FL 32789
    (978) 984-3360
  13. Building Photo - Sumerset Apartments
    1 BED
    $1,150+
    2 BEDS
    $1,200+
    3 BEDS
    $1,295+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,150 - $1,663
    Required Monthly FeesNone
    Total Monthly Price$1,150 - $1,663

    Sumerset Apartments

    1051 Lee Rd, Orlando, FL 32810
  14. Good Value
    STUDIO
    $900+
    1 BED
    $1,050+
    2 BEDS
    $1,200+
    3 BEDS
    $1,600+

    Kingswood Apartments

    1101 Lee Rd, Orlando, FL 32810
  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
  17. Building Photo - 7454 Wynnewood Square
    3 BEDS, 3 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    7454 Wynnewood Square

    7454 Wynnewood Square, Winter Park, FL 32792
  19. Building Photo - 7473 Belle River Ct
    3 BEDS, 3 BATHS
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    7473 Belle River Ct

    7473 Belle River Ct, Winter Park, FL 32792
  23. Building Photo - 1500 Gay Rd
    2 BEDS, 2 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    1500 Gay Rd Unit 9D

    1500 Gay Rd, Winter Park, FL 32789
    Apply
  24. Front of House - 281 Shell Pt E
    4 BEDS, 4.5 BATHS
    $20,000
    Total Monthly Price Total Monthly Price New
    Base Rent$20,000
    Required Monthly FeesNone
    Total Monthly Price$20,000

    281 Shell Pt E

    281 Shell Pt E, Maitland, FL 32751
    Apply
  26. Building Photo - 1500 Gay Rd
    1 BED, 1 BATH
    $1,522
    Total Monthly Price Total Monthly Price New
    Base Rent$1,522
    Required Monthly FeesNone
    Total Monthly Price$1,522

    1500 Gay Rd Unit 1D

    1500 Gay Rd, Winter Park, FL 32789
  27. Building Photo - 10 W Evans St
    3 BEDS, 1.5 BATHS
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    10 W Evans St

    10 W Evans St, Orlando, FL 32804
  28. 1 BED, 1 BATH
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    1140 S Orlando Ave Unit Exeter E2

    1140 S Orlando Ave, Maitland, FL 32751
  36. Building Photo - Park Apartments
    1 BED
    $1,250+
    2 BEDS
    $1,550+
    3 BEDS
    $1,800+

    Park Apartments

    7528 Park Promenade Dr, Winter Park, FL 32792
  38. 2 Months Free
    2 Months Free
    1 BED
    $1,229

    Indigo Winter Park

    220 S Semoran Blvd, Winter Park, FL 32792
  39. 2 Months Free
    2 Months Free
    1 BED
    $1,219+
    2 BEDS
    $1,449+
    3 BEDS
    $1,999+

    Sapphire Winter Park

    1743 Semoran North Cir, Winter Park, FL 32792
  41. Building Photo - The Fisher
    1 Month Free
    1 Month Free
    1 BED
    $1,799+
    2 BEDS
    $1,899+

    The Fisher

    2001 Glenridge Way, Winter Park, FL 32792
  42. Kitchen - Serena Winter Park
    2 Months Free
    2 Months Free
    1 BED
    $1,229+
    2 BEDS
    $1,799+

    Serena Winter Park

    2890 Red Lion Sq, Winter Park, FL 32792
Showing 42 of 84 results, Page 2 of 2

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Winter Park at a Glance

Average Rent

$1,454
(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 747 Sq Ft $1,535/mo
  • Fairview 750 Sq Ft $1,903/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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