Deals & Discount Filters
Apartments for Rent in Winter Park, FL with a Swimming Pool
1,505 Rentals
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1 BED$1,426+2 BEDS$1,480+ -
1 BED$1,260+2 BEDS$1,480+3 BEDS$1,845+Signal Pointe
2500 Howell Branch Rd, Winter Park, FL 32792 -
1 BED$1,339+2 BEDS$1,558+3 BEDS$1,777+
Venue At Winter Park
5 Autumn Breeze Way, Winter Park, FL 32792 -
1 BED$1,375+2 BEDS$1,455+3 BEDS$1,805+
Stonecastle Apartment Homes
2015 New Stonecastle Ter, Winter Park, FL 32792 -
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1 BED$1,524+2 BEDS$1,649+
POSTE Winter Park
800 Semoran Park Dr, Winter Park, FL 32792 -
1 BED$1,236+2 BEDS$1,437+3 BEDS$2,399+
Village Park Senior
550 W Denning Dr, Winter Park, FL 32789 -
1 BED$1,300+2 BEDS$1,400+3 BEDS$1,600+
La Aloma
3040 Aloma Ave, Winter Park, FL 32792 -
1 BED$1,250+2 BEDS$1,550+3 BEDS$1,800+
Park Apartments
7528 Park Promenade Dr, Winter Park, FL 32792 -
STUDIO$991+1 BED$1,191+2 BEDS$1,322+3 BEDS$1,493+
Carlton Arms of Winter Park
300 Jamestown Dr, Winter Park, FL 32792 -
1 BED$1,583+2 BEDS$1,906+3 BEDS$2,746+
Audubon Park
990 Warehouse Rd, Orlando, FL 32803 -
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1 BED$1,269+2 BEDS$1,575+ARIUM Winter Park
3250 Bishop Park Dr, Winter Park, FL 32792 -
1 BED$1,074+2 BEDS$1,200+3 BEDS$1,300+Sumerset Apartments
1051 Lee Rd, Orlando, FL 32810 -
STUDIO$900+1 BED$1,050+2 BEDS$1,200+3 BEDS$1,600+
Kingswood Apartments
1101 Lee Rd, Orlando, FL 32810 -
4 BEDS, 3.5 BATHS$4,1501470 Lone Feather Trail
1470 Lone Feather Trail, Winter Park, FL 32792 -
1 BED, 1 BATH$1,4652500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,6003044 Antique Oaks Cir Unit 177
3044 Antique Oaks Cir, Winter Park, FL 32792 -
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1 BED, 1 BATH$1,380
2942 Antique Oaks Cir Unit 82
2942 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,050448 Banyon Tree Cir Unit 102
448 Banyon Tree Cir, Maitland, FL 32751 -
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2 BEDS, 2 BATHS$1,850
2918 Antique Oaks Cir Unit #31
2918 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
3651 N Goldenrod Rd Unit F208
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,3002520 Caper Ln Unit 102
2520 Caper Ln, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,6005460 decatur st
5460 decatur st, Orlando, FL 32807 -
4 BEDS, 4.5 BATHS$6,750132 Burks Cir
132 Burks Cir, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,6001000 S Semoran Blvd Unit 116
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,950
205 Lewfield Cir Unit 205
205 Lewfield Cir, Winter Park, FL 32792 -
4 BEDS, 5 BATHS$17,0001742 Temple Dr
1742 Temple Dr, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,4003383 Hamlet Loop
3383 Hamlet Loop, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,250
3707 Pelican Ln
3707 Pelican Ln, Orlando, FL 32803 -
5 BEDS, 3 BATHS$4,000Newly Renovated Pool Home
2920 Abbey Ct, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,275824 Town Cir
824 Town Cir, Maitland, FL 32751 -
1 BED, 1 BATH$1,1002517 Caper Ln Unit 207
2517 Caper Ln, Maitland, FL 32751 -
1 BED$1,350+2 BEDS$1,490+Whisper Lake Apartments
3250 Whisper Lake Ln, Winter Park, FL 32792 -
1 BED$1,349+2 BEDS$1,749+
Serena Winter Park
2890 Red Lion Sq, Winter Park, FL 32792 -
2 BEDS$1,799
The Fisher
2001 Glenridge Way, Winter Park, FL 32792 -
1 BED$1,449
Indigo Winter Park
220 S Semoran Blvd, Winter Park, FL 32792
Showing 42 of 86 results, Page 2 of 3
Winter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 537 Sq Ft $1,384 / mo
- 1 Bedroom 706 Sq Ft $1,442 / mo
- 2 Bedrooms 1,020 Sq Ft $1,707 / mo
- 3 Bedrooms 1,273 Sq Ft $2,003 / mo
- 4 Bedrooms 1,506 Sq Ft $1,544 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Four Seasons 582 Sq Ft $1,251/mo
- Winter Park Pines Merrie Oaks 582 Sq Ft $1,251/mo
- Laurel Springs 736 Sq Ft $1,392/mo
- Winter Park Woods 765 Sq Ft $1,414/mo
- Winter Park Pines 708 Sq Ft $1,458/mo
- Eastbrook 742 Sq Ft $1,471/mo
- Cedarwood Village 668 Sq Ft $1,525/mo
- Lake Howell 750 Sq Ft $1,533/mo
- Windward Square 780 Sq Ft $1,560/mo
- Villas of Casselberry 757 Sq Ft $1,562/mo
Getting Around Winter Park
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Note: Based on community-supplied data and independent market research. Subject to change without notice.