Deals & Discount Filters
Apartments for Rent in Winter Park, FL with a Swimming Pool
1,518 Rentals
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1 BED$1,095+2 BEDS$1,631+ -
1 BED$1,475+2 BEDS$1,699+POSTE Winter Park
800 Semoran Park Dr, Winter Park, FL 32792 -
1 BED$1,295+2 BEDS$1,495+3 BEDS$1,720+
Signal Pointe
2500 Howell Branch Rd, Winter Park, FL 32792 -
1 BED$1,213+2 BEDS$1,567+3 BEDS$1,787+
Venue At Winter Park
5 Autumn Breeze Way, Winter Park, FL 32792 -
1 BED$1,346+2 BEDS$1,707+3 BEDS$1,676+
Atlas at Winter Park
3733 N Goldenrod Rd, Winter Park, FL 32792 -
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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 -
1 BED$1,236+2 BEDS$1,437+3 BEDS$2,399+
Village Park Senior
550 W Denning Dr, Winter Park, FL 32789 -
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$1,641+2 BEDS$2,166+3 BEDS$3,359+
Audubon Park
990 Warehouse Rd, Orlando, FL 32803 -
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3 BEDS, 2.5 BATHS$3,200
2963 Upper Park Rd
2963 Upper Park Rd, Orlando, FL 32814 -
1 BED$1,074+2 BEDS$1,174+3 BEDS$1,395+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 -
1 BED, 1 BATH$1,4752500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
4 BEDS, 3.5 BATHS$4,1501470 Lone Feather Trail
1470 Lone Feather Trail, Winter Park, FL 32792 -
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1 BED, 1 BATH$1,995
4438 Virginia Dr Unit Baldwin Park 1 bedroom
4438 Virginia Dr, Orlando, FL 32814 -
3 BEDS, 2 BATHS$2,9952809 Bower Rd
2809 Bower Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,7003057 Aaron Burr Ave Unit 1
3057 Aaron Burr Ave, Winter Park, FL 32792 -
STUDIO, 1 BATH$1,1007417 Daniel Webster Dr Unit 3
7417 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$2,600
640 N Park Ave Unit 26
640 N Park Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$3,400
690 Osceola Ave Unit 203
690 Osceola Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$2,950
338 Brassie Dr
338 Brassie Dr, Orlando, FL 32804 -
3 BEDS, 2 BATHS$3,2503707 Pelican Ln
3707 Pelican Ln, Orlando, FL 32803 -
3 BEDS, 2 BATHS$2,7502467 Sunderland Rd
2467 Sunderland Rd, Maitland, FL 32751 -
3 BEDS, 2 BATHS$3,4501594 Common Way Rd
1594 Common Way Rd, Orlando, FL 32814 -
3 BEDS, 2.5 BATHS$2,275824 Town Cir
824 Town Cir, Maitland, FL 32751 -
3 BEDS, 3 BATHS$2,200
1718 Gulfview Dr Unit 429 B
1718 Gulfview Dr, Maitland, FL 32751 -
1 BED$1,199+2 BEDS$1,599+Whisper Lake Apartments
3250 Whisper Lake Ln, Winter Park, FL 32792 -
1 BED$1,263+2 BEDS$1,484+Alvista Winter Park
3935 Sutton Place Blvd, Winter Park, FL 32792 -
1 BED$1,399
Indigo Winter Park
220 S Semoran Blvd, Winter Park, FL 32792 -
1 BED$1,299+2 BEDS$1,499+3 BEDS$1,999+
Sapphire Winter Park
1743 Semoran North Cir, Winter Park, FL 32792 -
1 BED$1,199+2 BEDS$1,899+
Serena Winter Park
2890 Red Lion Sq, Winter Park, FL 32792 -
Call for RentThe Fisher
2001 Glenridge Way, Winter Park, FL 32792
Showing 42 of 85 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 539 Sq Ft $1,375 / mo
- 1 Bedroom 707 Sq Ft $1,440 / mo
- 2 Bedrooms 1,019 Sq Ft $1,748 / mo
- 3 Bedrooms 1,273 Sq Ft $2,014 / mo
- 4 Bedrooms 1,506 Sq Ft $1,540 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Four Seasons 604 Sq Ft $1,368/mo
- Winter Park Pines Merrie Oaks 604 Sq Ft $1,368/mo
- Winter Park Woods 763 Sq Ft $1,375/mo
- Winter Park Pines 682 Sq Ft $1,409/mo
- Laurel Springs 741 Sq Ft $1,418/mo
- Eastbrook 747 Sq Ft $1,449/mo
- Lake Howell 747 Sq Ft $1,517/mo
- Villas of Casselberry 768 Sq Ft $1,532/mo
- Windward Square 783 Sq Ft $1,540/mo
- Glenmoor 713 Sq Ft $1,560/mo
Getting Around Winter Park
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About Our Deals
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Note: Based on community-supplied data and independent market research. Subject to change without notice.