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Apartments for Rent in Winter Park, FL
1,895 Rentals
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2 BEDS, 2 BATHS$1,695 -
2 BEDS, 1 BATH$1,4951380 Indiana Ave Unit 3
1380 Indiana Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,3751812 Pineview Cir
1812 Pineview Cir, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$3,000
1278 Miller Ave
1278 Miller Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,400
1695 Lee Rd Unit C110
1695 Lee Rd, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$6,000
782 S Pennsylvania Ave Unit 1
782 S Pennsylvania Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,6002344 Flamingo Way
2344 Flamingo Way, Winter Park, FL 32792 -
4 BEDS, 2 BATHS$5,5001815 Barker Dr
1815 Barker Dr, Winter Park, FL 32789 -
2 BEDS, 1.5 BATHS$1,750
3355 Riverview Way Unit 42
3355 Riverview Way, Winter Park, FL 32792 -
3 BEDS, 3.5 BATHS$6,000
503 W Canton Ave
503 W Canton Ave, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$2,695
2800 Bright Bird Ln
2800 Bright Bird Ln, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,850612 Montego Bay Ct Unit 612
612 Montego Bay Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,850612 Trinidad Ct Unit 612
612 Trinidad Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$2,400
2411 Gallery View Dr Unit #5
2411 Gallery View Dr, Winter Park, FL 32792 -
5 BEDS, 5.5 BATHS$19,000
1221 Richmond Rd
1221 Richmond Rd, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$4,500
4461 Trapp Ln
4461 Trapp Ln, Orlando, FL 32814 -
3 BEDS, 2 BATHS$1,780
400 Banyon Tree Cir Unit 102
400 Banyon Tree Cir, Maitland, FL 32751 -
3 BEDS, 3.5 BATHS$3,700
1438 Chatfield Pl
1438 Chatfield Pl, Orlando, FL 32814 -
3 BEDS, 1 BATH$2,250
3511 Backspin Ln
3511 Backspin Ln, Orlando, FL 32804 -
3 BEDS, 2 BATHS$3,250
3707 Pelican Ln
3707 Pelican Ln, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,495
4425 Fairview Ave
4425 Fairview Ave, Orlando, FL 32804 -
3 BEDS, 1.5 BATHS$1,940
776 Carew Ave
776 Carew Ave, Orlando, FL 32804 -
4 BEDS, 3 BATHS$3,590
1511 E Horatio Ave
1511 E Horatio Ave, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,520
1418 Beatrice Dr
1418 Beatrice Dr, Orlando, FL 32810 -
3 BEDS, 2.5 BATHS$2,595
216 Harvard St
216 Harvard St, Orlando, FL 32804 -
1 BED, 1 BATH$1,125
2075 Howell Branch Rd Unit 109
2075 Howell Branch Rd, Maitland, FL 32751 -
STUDIO, 1 BATH$1,700
1420 Lake Baldwin Ln
1420 Lake Baldwin Ln, Orlando, FL 32814 -
4 BEDS, 2 BATHS$2,500
101 S College Ave
101 S College Ave, Eatonville, FL 32751 -
3 BEDS, 2 BATHS$2,245
1247 Kingston Ave
1247 Kingston Ave, Orlando, FL 32807 -
3 BEDS, 2 BATHS$2,000
319 Eaton St
319 Eaton St, Maitland, FL 32751 -
2 BEDS, 2 BATHS$3,250
206 Quayside Cir Unit 503
206 Quayside Cir, Maitland, FL 32751 -
2 BEDS, 1 BATH$2,100
19 W King St
19 W King St, Orlando, FL 32804 -
3 BEDS, 2.5 BATHS$2,500
2421 Laura Pl
2421 Laura Pl, Orlando, FL 32803 -
3 BEDS, 2 BATHS$2,240
852 Woodside Rd
852 Woodside Rd, Maitland, FL 32751 -
4 BEDS, 2 BATHS$2,495
2632 Talbot Rd
2632 Talbot Rd, Casselberry, FL 32730 -
3 BEDS, 2 BATHS$2,425
882 Prim Dr
882 Prim Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,225
2517 Caper Ln Unit 203
2517 Caper Ln, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,500
1159 Calle Del Norte Unit A
1159 Calle Del Norte, Casselberry, FL 32707 -
2 BEDS, 1.5 BATHS$1,925Cute 2/1.5 Quaint Bungalow with Single Garage in Winter Park right off Lee Road!
942 Gloriosa Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,690FIRST MONTH FREE - Cozy 2 bed 2 bath in Winter Park
211 Stefanik Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,325
Beautiful Remodeled 1/1 Condo x Rent @ Winter Park in front of Full Sail. Unit 146
3032 Antique Oaks Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,450
Beautiful 1/1 Wood Floor Condo for rent with Serene trees view from your screened balcony. Unit 96
2948 Antique Oaks Cir, Winter Park, FL 32792
Showing 42 of 279 results, Page 5 of 7
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
Average Rent in Nearby Cities
(For 1 bedroom apartments)- Cities Average Rent
- Winter Park $1,593/mo
- Maitland $1,747/mo
- Fern Park $1,282/mo
- Eatonville $850/mo
- Casselberry $1,734/mo
- Longwood $1,660/mo
- Altamonte Springs $1,552/mo
- Orlando $1,658/mo
- Pine Castle $1,206/mo
Getting Around Winter Park
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