Deals & Discount Filters
Apartments under $1,600 for Rent in Winter Park, FL
700 Rentals
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1 BED, 1 BATH$1,300 -
1 BED, 1 BATH$1,4752500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
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1 BED, 1 BATH$1,2002521 Caper Ln Unit 203
2521 Caper Ln, Maitland, FL 32751 -
1 BED, 1 BATH$1,299476 Banyon Tree Cir
476 Banyon Tree Cir, Maitland, FL 32751 -
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1 BED, 1 BATH$1,0005058 Seminole Ave Unit Seminole 2
5058 Seminole Ave, Winter Park, FL 32792 -
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2 BEDS, 1 BATH$1,2952183 Crandon Ave
2183 Crandon Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,3003060 George Mason Ave Unit 10C
3060 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,495
3651 N Goldenrod Rd Unit C204
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,550
316 Scottsdale Square Unit 316
316 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,595851 Miles Ave Unit 21
851 Miles Ave, Winter Park, FL 32789 -
STUDIO, 1 BATH$1,1007417 Daniel Webster Dr Unit 3
7417 Daniel Webster Dr, Winter Park, FL 32792 -
1 BED, 1 BATH$1,475
2500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,450
1000 S Semoran Blvd Unit 115
1000 S Semoran Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,350
200 St Andrews Blvd Unit 606
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,5001695 Lee Rd Unit B114
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,3503651 N Goldenrod Rd Unit B#104
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,350
4860 Tangerine Ave Unit 4860
4860 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,299
1436 Minnesota Ave
1436 Minnesota Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,575
1565 Michigan Ave
1565 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,6004418 Eli St
4418 Eli St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,5651418 Beatrice Dr
1418 Beatrice Dr, Orlando, FL 32810 -
2 BEDS, 1 BATH$1,400
496 Banyon Tree Cir Unit 104
496 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,400
550 Flemming Way Unit 200
550 Flemming Way, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,290
64 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
2 BEDS, 1 BATH$1,6005314 Andrus Ave
5314 Andrus Ave, Orlando, FL 32810 -
1 BED, 1 BATH$1,2002521 Caper Ln Unit 203
2521 Caper Ln, Maitland, FL 32751 -
1 BED, 1 BATH$1,450
2512 Musselwhite Ave Unit 3
2512 Musselwhite Ave, Orlando, FL 32804 -
2 BEDS, 2 BATHS$1,600
5532 Charleston St
5532 Charleston St, Orlando, FL 32807 -
1 BED, 1 BATH$1,000
421 E KENNEDY Blvd
421 E KENNEDY Blvd, EATONVILLE, FL 32751 -
1 BED, 1 BATH$1,2002517 Caper Ln Unit 205
2517 Caper Ln, Maitland, FL 32751 -
1 BED, 1 BATH$1,500Charming Condo Retreat in Winter Park - Spacious 727 sq. ft. Home with lots of Community Features! Unit 601
200 St Andrews Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,300Stylish Remodeled 1BR Condo with Pool & Low HOA – Ideal Winter Park Investment Unit N-10C
3060 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,495
3651 N Goldenrod Rd Unit C204
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,550
2651 Cayman Way
2651 Cayman Way, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,1293651 N Goldenrod Rd
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,2952183 Crandon Ave Unit 1
2183 Crandon Ave, Winter Park, FL 32789
Showing 42 of 120 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 $1,358 / mo
- 1 Bedroom 707 Sq Ft $1,455 / mo
- 2 Bedrooms 1,019 Sq Ft $1,733 / mo
- 3 Bedrooms 1,273 Sq Ft $2,030 / 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
- Winter Park Woods 761 Sq Ft $1,378/mo
- Four Seasons 606 Sq Ft $1,391/mo
- Winter Park Pines Merrie Oaks 606 Sq Ft $1,391/mo
- Laurel Springs 743 Sq Ft $1,392/mo
- Winter Park Pines 674 Sq Ft $1,431/mo
- Eastbrook 744 Sq Ft $1,442/mo
- Lake Howell 747 Sq Ft $1,511/mo
- Villas of Casselberry 759 Sq Ft $1,511/mo
- Cedarwood Village 653 Sq Ft $1,530/mo
- Windward Square 779 Sq Ft $1,538/mo
Getting Around Winter Park
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About Our Deals
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"Best value" units are located in buildings rated three stars or higher. We label apartment rentals that are priced significantly less than similar high-quality units nearby.
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Note: Based on community-supplied data and independent market research. Subject to change without notice.