Winter Park, FL Apartments for rent under $2,000

707 rentals available

211 Holt Ave #5, Winter Park, FL 32789
$1,750
Studio · 1 bath
211 Holt Ave #5Winter Park, FL 32789
Call(321) 406-7307
2037 Linden Rd #A, Winter Park, FL 32792
$1,248
1 bed · 1 bath · 615 sq ft
2037 Linden Rd #AWinter Park, FL 32792
Call(321) 414-4341
3243 Forest Oaks Ct #117, Winter Park, FL 32792
$1,600
2 beds · 1.5 baths · 990 sq ft
3243 Forest Oaks Ct #117Winter Park, FL 32792
Call(407) 559-8409
2434 Barbados Dr, Winter Park, FL 32792
$2,000
3 beds · 2 baths · 1,284 sq ft
2434 Barbados DrWinter Park, FL 32792
Featured
Call(559) 337-6768
4946 N Palm Ave #GUEST HOUSE, Winter Park, FL 32792
$1,200
1 bed · 1 bath
4946 N Palm Ave #GUEST HOUSEWinter Park, FL 32792
Cambridge Blvd, Winter Park, FL 32789
$1,175
1 bed · 1 bath · 550 sq ft
Winter Park, FLWinter Park, FL 32789
Laurel Springs Dr, Winter Park, FL 32792
$1,139
4 beds · 2 baths · 1,182 sq ft
Laurel Springs DrWinter Park, FL 32792
Featured
Euston Rd, Winter Park, FL 32789
$1,061
4 beds · 2 baths · 2,000 sq ft
Euston RdWinter Park, FL 32789
Featured
624 Trinidad Ct #624, Winter Park, FL 32792
$1,700
2 beds · 2 baths
624 Trinidad Ct #624Winter Park, FL 32792
Featured
7309 Daniel Webster Dr #D, Winter Park, FL 32792
$1,200
1 bed · 1 bath · 590 sq ft
7309 Daniel Webster Dr #DWinter Park, FL 32792
Featured
5462 Bracken Ct, Winter Park, FL 32792
$1,695
2 beds · 2.5 baths · 1,200 sq ft
5462 Bracken CtWinter Park, FL 32792
659 Montego Bay Ct, Winter Park, FL 32792
$1,730
2 beds · 2 baths · 1,037 sq ft
659 Montego Bay CtWinter Park, FL 32792
Featured
NCEN130, Winter Park, FL 32789
$1,750
1 bed · 1 units available
NCEN130Winter Park, FL 32789
Price Drop
3053 George Mason Ave #A, Winter Park, FL 32792
$1,250
1 bed · 1 bath · 809 sq ft
3053 George Mason Ave #AWinter Park, FL 32792
Featured
Parkview Village, Winter Park, FL 32792
$1,295
1 bed · 1 units available
Parkview VillageWinter Park, FL 32792
Featured
3043 Antique Oaks Cir #170, Winter Park, FL 32792
$1,500
2 beds · 2 baths · 1,018 sq ft
3043 Antique Oaks Cir #170Winter Park, FL 32792
Special Offer
2500 Lee Rd #145, Winter Park, FL 32789
$1,250
1 bed · 1 bath · 645 sq ft
2500 Lee Rd #145Winter Park, FL 32789
Featured
1618 Indiana Ave, Winter Park, FL 32789
$1,995
2 beds · 1 bath · 805 sq ft
1618 Indiana AveWinter Park, FL 32789
Price Drop
937 Aragon Ave, Winter Park, FL 32789
$1,995
2 beds · 1.5 baths · 988 sq ft
937 Aragon AveWinter Park, FL 32789
Featured
3372 River View Way #49, Winter Park, FL 32792
$1,665
3 beds · 2.5 baths · 1,151 sq ft
3372 River View Way #49Winter Park, FL 32792
Featured
825 Driver Ave, Winter Park, FL 32789
$1,990
2 beds · 1.5 baths · 1,100 sq ft
825 Driver AveWinter Park, FL 32789
Featured
7421 Daniel Webster Dr #A, Winter Park, FL 32792
$950
1 bed · 1 bath · 809 sq ft
7421 Daniel Webster Dr #AWinter Park, FL 32792
Featured
3059 Autumn Ct, Winter Park, FL 32792
$1,745
3 beds · 2 baths · 1,266 sq ft
3059 Autumn CtWinter Park, FL 32792
Featured
830 Carver St, Winter Park, FL 32789
$1,795
3 beds · 1 bath · 1,038 sq ft
830 Carver StWinter Park, FL 32789
Featured
731 W Comstock Ave, Winter Park, FL 32789
$1,795
3 beds · 1.5 baths · 1,024 sq ft
731 W Comstock AveWinter Park, FL 32789
Featured
960 Aragon Ave, Winter Park, FL 32789
$1,800
1 bed · 1 bath · 1,647 sq ft
960 Aragon AveWinter Park, FL 32789
Special Offer
2317 Sun Valley Cir, Winter Park, FL 32792
$1,950
2 beds · 2 baths · 1,295 sq ft
2317 Sun Valley CirWinter Park, FL 32792
1695 Lee Rd #E115, Winter Park, FL 32789
$1,750
3 beds · 2 baths · 1,149 sq ft
1695 Lee Rd #E115Winter Park, FL 32789View units
Lewfield Cir, Winter Park, FL 32792
$1,450
1 bed · 1 bath · 680 sq ft
Lewfield CirWinter Park, FL 32792
3370 Cedar Springs Pl, Winter Park, FL 32792
$1,625
2 beds · 2.5 baths · 1,031 sq ft
3370 Cedar Springs PlWinter Park, FL 32792
2772 Prism Point, Winter Park, FL 32792
$1,800
2 beds · 1.5 baths · 1,060 sq ft
2772 Prism PointWinter Park, FL 32792
2383 Sun Valley Cir, Winter Park, FL 32792
$1,900
2 beds · 2 baths · 1,295 sq ft
2383 Sun Valley CirWinter Park, FL 32792
2437 Eastbrook Blvd, Winter Park, FL 32792
$750
4 beds · 2 baths · 1,521 sq ft
2437 Eastbrook BlvdWinter Park, FL 32792
205 Lewfield Cir #205, Winter Park, FL 32792
$1,700
2 beds · 2 baths · 927 sq ft
205 Lewfield Cir #205Winter Park, FL 32792
Winter Green Blvd, Winter Park, FL 32792
$950
3 beds · 2 baths · 1,187 sq ft
Winter Green BlvdWinter Park, FL 32792
Stanfield Ave, Orlando, FL 32814
$1,700
1 bed · 1 bath · 660 sq ft
Stanfield AveOrlando, FL 32814
1484 Broad Wing Ln, Winter Park, FL 32792
$1,500
3 beds · 2.5 baths · 1,700 sq ft
1484 Broad Wing LnWinter Park, FL 32792
1695 Lee Road E214, Winter Park, FL 32789
$1,450
2 beds · 1 bath · 881 sq ft
1695 Lee Road E214Winter Park, FL 32789
622 Saint Johns Ct, Winter Park, FL 32792
$1,900
2 beds · 2 baths · 1,158 sq ft
622 Saint Johns CtWinter Park, FL 32792
1102 Washington Ave, Winter Park, FL 32789
$800
4 beds · 3 baths · 1,584 sq ft
1102 Washington AveWinter Park, FL 32789