2 BEDS, 2 BATHS
$1,400
Deals & Discount Filters
Apartments under $1,900 for Rent in Winter Park, FL
1,150 Rentals
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1 BED, 1 BATH$1,4503060 George Mason Ave Unit 10C
3060 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
2535 Zelina Point
2535 Zelina Point, Winter Park, FL 32792 -
1 BED, 1 BATH$1,299
3044 Antique Oaks Cir Unit 184
3044 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,599
2917 Antique Oaks Cir Unit 17
2917 Antique Oaks Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,5004860 Tangerine Ave Unit 4860
4860 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,795918 Gloriosa Ave
918 Gloriosa Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,800
3057 Aaron Burr Ave Unit 1
3057 Aaron Burr Ave, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,695
115 Stefanik Rd
115 Stefanik Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,475
1000 S Semoran Blvd Unit 115
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,600316 Scottsdale Square Unit 316
316 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,8957337 Cedar Creek Ct
7337 Cedar Creek Ct, Winter Park, FL 32792 -
1 BED, 1 BATH$1,299
1000 S Semoran Blvd Unit 703
1000 S Semoran Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,200
484 Banyon Tree Cir Unit 204
484 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,850
2822 Plaza Terrace Dr Unit 2822
2822 Plaza Terrace Dr, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,6005314 Andrus Ave
5314 Andrus Ave, Orlando, FL 32810 -
2 BEDS, 2 BATHS$1,6005532 Charleston St
5532 Charleston St, Orlando, FL 32807 -
2 BEDS, 1 BATH$1,800
12 W Hazel St
12 W Hazel St, Orlando, FL 32804 -
1 BED, 1 BATH$1,000
421 E KENNEDY Blvd
421 E KENNEDY Blvd, EATONVILLE, FL 32751 -
1 BED, 1 BATH$1,450
2512 Musselwhite Ave Unit 3
2512 Musselwhite Ave, Orlando, FL 32804 -
1 BED, 1 BATH$1,2802521 Caper Ln Unit 203
2521 Caper Ln, Maitland, FL 32751 -
3 BEDS, 2 BATHS$1,8001150 Carmel Cir Unit 308
1150 Carmel Cir, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,290
64 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
2 BEDS, 2 BATHS$1,500
550 Flemming Way Unit 200
550 Flemming Way, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,399
496 Banyon Tree Cir Unit 204
496 Banyon Tree Cir, Maitland, FL 32751 -
1 BED, 1 BATH$1,7991384 Lake Baldwin Ln Unit C
1384 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,6501425 Virginia Dr
1425 Virginia Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,200
2517 Caper Ln Unit 205
2517 Caper Ln, Maitland, FL 32751 -
1 BED, 1 BATH$1,600
1483 Lake Baldwin Ln Unit C
1483 Lake Baldwin Ln, Orlando, FL 32814 -
1 BED, 1 BATH$1,350200 St Andrews Blvd Unit 200 St. Andrews Blvd 606
200 St Andrews Blvd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,3993044 Antique Oaks Cir Unit 178
3044 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,8952606 Aloma Ave
2606 Aloma Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
2651 Cayman Way
2651 Cayman Way, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,700
Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
1 BED, 1 BATH$1,050
525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,4503007 George Mason Ave Unit H
3007 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,740Rent Special: Receive $100 in rent credit ...
7429 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,875
232 Sandlewood Trail
232 Sandlewood Trail, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,600
3651 N Goldenrod Rd
3651 N Goldenrod Rd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,595
6805 Bonavista Ct
6805 Bonavista Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,900250 Carolina Ave Unit 250
250 Carolina Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,3493651 N Goldenrod Rd Unit B109
3651 N Goldenrod Rd, Winter Park, FL 32792
Showing 42 of 166 results, Page 3 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 539 Sq Ft $1,399 / mo
- 1 Bedroom 708 Sq Ft $1,442 / mo
- 2 Bedrooms 1,020 Sq Ft $1,720 / mo
- 3 Bedrooms 1,270 Sq Ft $2,008 / mo
- 4 Bedrooms 1,506 Sq Ft $1,536 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 760 Sq Ft $1,328/mo
- Four Seasons 599 Sq Ft $1,386/mo
- Winter Park Pines Merrie Oaks 599 Sq Ft $1,386/mo
- Whisperwood 739 Sq Ft $1,417/mo
- Winter Park Pines 670 Sq Ft $1,424/mo
- Eastbrook 720 Sq Ft $1,425/mo
- Cedarwood Village 639 Sq Ft $1,491/mo
- Laurel Springs 727 Sq Ft $1,510/mo
- Villas of Casselberry 762 Sq Ft $1,525/mo
- Windward Square 778 Sq Ft $1,530/mo
Getting Around Winter Park
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About Our Deals
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Best Value
"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.