2 BEDS, 2.5 BATHS
$1,545
Deals & Discount Filters
Apartments under $1,900 for Rent in Winter Park, FL
1,147 Rentals
-
-
2 BEDS, 1.5 BATHS$1,600316 Scottsdale Square Unit 316
316 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
3019 Casselwood St
3019 Casselwood St, Winter Park, FL 32792 -
1 BED, 1 BATH$1,399
1000 S Semoran Blvd Unit 703
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,6003267 Forest Oaks Ct Unit 111
3267 Forest Oaks Ct, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,8402510 Roxbury Rd
2510 Roxbury Rd, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,705
851 Miles Ave Unit 8
851 Miles Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$1,885
2111 Conifer Ave
2111 Conifer Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
1250 S Denning Dr Unit 232
1250 S Denning Dr, Winter Park, FL 32789 -
6 BEDS, 2.5 BATHS$80014 Bel Air St
14 Bel Air St, Maitland, FL 32751 -
1 BED, 1 BATH$1,2002525 Caper Ln Unit 205
2525 Caper Ln, Maitland, FL 32751 -
2 BEDS, 1.5 BATHS$1,900
2822 Plaza Terrace Dr Unit 2822
2822 Plaza Terrace Dr, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,290
64 Taylor Ave
64 Taylor Ave, Eatonville, FL 32751 -
2 BEDS, 1 BATH$1,600
825 N Primrose Dr Unit 113
825 N Primrose Dr, Orlando, FL 32803 -
1 BED, 1 BATH$1,6504499 Twinview Ln
4499 Twinview Ln, Orlando, FL 32814 -
1 BED, 1 BATH$1,500540 Cascade Cir Unit 104
540 Cascade Cir, Casselberry, FL 32707 -
1 BED, 1 BATH$1,700
1483 Lake Baldwin Ln Unit C
1483 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,700
5314 Andrus Ave
5314 Andrus Ave, Orlando, FL 32810 -
1 BED, 1 BATH$1,000
421 E Kennedy Blvd
421 E Kennedy Blvd, Eatonville, FL 32751 -
3 BEDS, 2 BATHS$1,8001150 Carmel Cir Unit 308
1150 Carmel Cir, Casselberry, FL 32707 -
2 BEDS, 2 BATHS$1,550550 Flemming Way Unit 200
550 Flemming Way, Maitland, FL 32751 -
2 BEDS, 1.5 BATHS$1,690
222 E Yale St Unit 222
222 E Yale St, Orlando, FL 32804 -
2 BEDS, 2 BATHS$1,500
496 Banyon Tree Cir Unit 204
496 Banyon Tree Cir, Maitland, FL 32751 -
3 BEDS, 1.5 BATHS$1,475
1112 Princewood Dr
1112 Princewood Dr, Orlando, FL 32810 -
2 BEDS, 2 BATHS$1,4501166 Paseo De Las Flores Unit C
1166 Paseo De Las Flores, Casselberry, FL 32707 -
2 BEDS, 1 BATH$1,4951919 Canton St
1919 Canton St, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,395
113 E Smith St Unit 6
113 E Smith St, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,400
825 N Primrose Dr Unit 106
825 N Primrose Dr, Orlando, FL 32803 -
2 BEDS, 2 BATHS$1,799Well maintained 2 bedroom property with lo...
7781 Fernbrook Way, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,895Townhome in Winter Park
200 Sandlewood Trail, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,6003651 N Goldenrod Rd
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,650
FOR RENT! Gorgeous First Floor Remodeled 2... Unit 163
3038 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,675
Winter Park 2/2 Condo in Charming Parkview... Unit 79
2941 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,499
1500 Michigan Ave
1500 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,700Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,5502-story townhome - Private Patio - Pool - ... Unit 130
3271 Oak Lake Pl, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,699
Beautiful Remodeled First Floor 2/2 Condo ... Unit 17
2917 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
Charming 2-Bedroom Condo in Scenic Winter ... Unit 204
1250 S Denning Dr, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$1,895
Cute 3/2 Townhome in Winter Park - close t...
758 Warrenton Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,350Beautiful 1/1 Remodeled Condo for Rent in ... Unit 52
2929 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,840Fully Furnished 2/2 Condo!
7429 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,550
2/2 first floor unit Lancelot of Winter Park Unit E109
3651 N Goldenrod Rd, Winter Park, FL 32792
Showing 42 of 172 results, Page 3 of 5
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 $1,365 / mo
- 1 Bedroom 709 Sq Ft $1,460 / mo
- 2 Bedrooms 1,020 Sq Ft $1,696 / mo
- 3 Bedrooms 1,273 Sq Ft $2,013 / mo
- 4 Bedrooms 1,506 Sq Ft $1,535 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 760 Sq Ft $1,415/mo
- Winter Park Pines 668 Sq Ft $1,420/mo
- Eastbrook 737 Sq Ft $1,438/mo
- Four Seasons 622 Sq Ft $1,450/mo
- Winter Park Pines Merrie Oaks 622 Sq Ft $1,450/mo
- Laurel Springs 742 Sq Ft $1,473/mo
- Albert Lee Ridge 743 Sq Ft $1,493/mo
- Cedarwood Village 657 Sq Ft $1,537/mo
- Villas of Casselberry 775 Sq Ft $1,561/mo
- Georgetown Estates 735 Sq Ft $1,573/mo
Getting Around Winter Park
Education
Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
tooltips
Submitting Request
Thank You
About Our Deals
Apartment Finder utilizes the industry's largest and most complete database of real-time rents and availabilities to help you find an amazing deal on your next rental.
Price Drop
Apartment communities change their rental rates often - sometimes multiple times a day. We track the changes and keep you up to date when a rental rate decreases.
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.
Rent Specials
Apartment communities regularly advertise deals for new residents. Whether it's a move-in special or a free tv, we locate the rentals that offer a little something extra when you sign your lease.
Note: Based on community-supplied data and independent market research. Subject to change without notice.