
Deals & Discount Filters
Houses for Rent in Winter Park, FL
132 Rentals
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3 BEDS, 2 BATHS$3,040
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3 BEDS, 2 BATHS$3,450
1946 Strathaven Rd
1946 Strathaven Rd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,550
2831 Lion Heart Rd
2831 Lion Heart Rd, Winter Park, FL 32792 -
4 BEDS, 3 BATHS$4,000
1289 Heavenly Cove
1289 Heavenly Cove, Winter Park, FL 32792 -
4 BEDS, 2 BATHS$3,600
1846 Barker Dr
1846 Barker Dr, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,999
101 S Lakemont Ave
101 S Lakemont Ave, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$4,199
1681 Walnut Ave
1681 Walnut Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$5,000
2227 Howard Dr
2227 Howard Dr, Winter Park, FL 32789 -
1 BED, 1 BATH$1,200
2011 Cornell Ave
2011 Cornell Ave, Winter Park, FL 32789 -
4 BEDS, 2.5 BATHS$5,400
1580 Oakhurst Ave
1580 Oakhurst Ave, Winter Park, FL 32789 -
4 BEDS, 2 BATHS$2,950
5037 Lake Howell Rd
5037 Lake Howell Rd, Winter Park, FL 32792 -
4 BEDS, 3 BATHS$3,300
2680 Fitzhugh Rd
2680 Fitzhugh Rd, Winter Park, FL 32792 -
4 BEDS, 3 BATHS$5,050
2627 Verona Trail
2627 Verona Trail, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$2,500
689 Overspin Dr
689 Overspin Dr, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,500
7733 Fox Knoll Pl
7733 Fox Knoll Pl, Winter Park, FL 32792 -
4 BEDS, 2.5 BATHS$2,600
2886 Carew Ave
2886 Carew Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$2,500
1911 Canton St
1911 Canton St, Orlando, FL 32803 -
2 BEDS, 1 BATH$2,950
1504 Minnesota St
1504 Minnesota St, Orlando, FL 32803 -
2 BEDS, 1 BATH$2,000
12 W Hazel St
12 W Hazel St, Orlando, FL 32804 -
4 BEDS, 2 BATHS$3,250
2120 Deloraine Trail
2120 Deloraine Trail, Maitland, FL 32751 -
3 BEDS, 2 BATHS$2,950
1516 Dove Dr
1516 Dove Dr, Orlando, FL 32803 -
3 BEDS, 2 BATHS$4,750
201 Cedarwood Dr
201 Cedarwood Dr, Maitland, FL 32751 -
2 BEDS, 2 BATHS$2,600
808 Malone Dr
808 Malone Dr, Orlando, FL 32810 -
1 BED, 1 BATH$2,050
2835 Stanfield Ave
2835 Stanfield Ave, Orlando, FL 32814 -
3 BEDS, 2 BATHS$1,800
300 Campus View Dr
300 Campus View Dr, Orlando, FL 32810 -
3 BEDS, 2 BATHS$2,450
4506 Santee St
4506 Santee St, Orlando, FL 32804 -
3 BEDS, 1.5 BATHS$1,700
1112 Princewood Dr
1112 Princewood Dr, Orlando, FL 32810 -
3 BEDS, 2 BATHS$2,000
319 Eaton St
319 Eaton St, Maitland, FL 32751 -
3 BEDS, 2.5 BATHS$2,695
1502 Lawndale Cir
1502 Lawndale Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$2,000
1835 Biscayne Dr
1835 Biscayne Dr, Winter Park, FL 32789 -
4 BEDS, 2 BATHS$2,850
3300 Bennington Ct
3300 Bennington Ct, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,750
1280 Gladiolas Dr
1280 Gladiolas Dr, Winter Park, FL 32792 -
4 BEDS, 3.5 BATHS$7,495
1841 Harland Park Dr
1841 Harland Park Dr, Winter Park, FL 32789 -
1 BED, 1 BATH$950
Grdyn House
1855 Eastbrook Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,050
525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,250
1096 Azalea Ln
1096 Azalea Ln, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,800
5334 Lake Howell Rd
5334 Lake Howell Rd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,900
644 N Knowles Ave
644 N Knowles Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,250
1436 Tangerine Ct
1436 Tangerine Ct, Winter Park, FL 32792 -
4 BEDS, 2.5 BATHS$4,900
2952 De Brocy Way
2952 De Brocy Way, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$2,650
645 Huntington Ave
645 Huntington Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$1,995
7473 Belle River Ct
7473 Belle River Ct, Winter Park, FL 32792
Showing 42 of 130 results, Page 2 of 4
Winter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 538 Sq Ft $1,405 / mo
- 1 Bedroom 708 Sq Ft $1,496 / mo
- 2 Bedrooms 1,019 Sq Ft $1,768 / mo
- 3 Bedrooms 1,271 Sq Ft $2,019 / mo
- 4 Bedrooms 1,506 Sq Ft $1,526 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 767 Sq Ft $1,451/mo
- Eastbrook 720 Sq Ft $1,481/mo
- Cedarwood Village 642 Sq Ft $1,486/mo
- Winter Park Pines 707 Sq Ft $1,495/mo
- Four Seasons 640 Sq Ft $1,512/mo
- Winter Park Pines Merrie Oaks 640 Sq Ft $1,512/mo
- Albert Lee Ridge 768 Sq Ft $1,581/mo
- Lake Howell 726 Sq Ft $1,601/mo
- Winter Park Estates 692 Sq Ft $1,632/mo
- Windward Square 779 Sq Ft $1,648/mo
Getting Around Winter Park
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