2 BEDS, 2 BATHS
$1,700
Deals & Discount Filters
Apartments under $2,000 for Rent in Winter Park, FL
1,235 Rentals
-
-
3 BEDS, 2 BATHS$1,850685 Grenadine Ct
685 Grenadine Ct, Winter Park, FL 32792 -
1 BED, 1 BATH$1,4652500 Lee Rd Unit 244
2500 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,400
1000 S Semoran Blvd Unit 115
1000 S Semoran Blvd, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$1,8957473 Belle River Ct
7473 Belle River Ct, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,850200 St Andrews Blvd Unit 2903
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,525
1565 Michigan Ave
1565 Michigan Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,320
3011 George Mason Ave Unit 3
3011 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,270
2183 Crandon Ave
2183 Crandon Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$1,6951695 Lee Rd Unit C216
1695 Lee Rd, Winter Park, FL 32789 -
1 BED, 1 BATH$1,3501250 S Denning Dr Unit 208
1250 S Denning Dr, Winter Park, FL 32789 -
2 BEDS, 1.5 BATHS$1,600
2523 Alexa Ct
2523 Alexa Ct, Winter Park, FL 32792 -
1 BED, 1 BATH$1,475
1300 Indiana Ave
1300 Indiana Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,950
205 Lewfield Cir Unit 205
205 Lewfield Cir, Winter Park, FL 32792 -
1 BED, 1 BATH$1,450651 Trinidad Ct Unit S
651 Trinidad Ct, Winter Park, FL 32792 -
1 BED, 1 BATH$1,3702905 Antique Oaks Cir Unit 4
2905 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,600
1000 S Semoran Blvd Unit 116
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,500
1695 Lee Rd Unit B114
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,420
3651 N Goldenrod Rd Unit C204
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,4503651 N Goldenrod Rd Unit 110
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$2,0002011 Cornell Ave
2011 Cornell Ave, Winter Park, FL 32789 -
2 BEDS, 1 BATH$1,590
151 N Orlando Ave Unit 0226
151 N Orlando Ave, Winter Park, FL 32789 -
2 BEDS, 2.5 BATHS$1,975
5169 Lazy Oaks Dr
5169 Lazy Oaks Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,495
3651 N Goldenrod Rd Unit C205
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,4003212 Netherwood Dr
3212 Netherwood Dr, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,4951380 Indiana Ave Unit 3
1380 Indiana Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,400
1695 Lee Rd Unit C110
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,795
627 Grenadine Ct Unit S
627 Grenadine Ct, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,350
3651 N Goldenrod Rd Unit B#104
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,3003060 George Mason Ave Unit 10C
3060 George Mason Ave, Winter Park, FL 32792 -
1 BED, 1 BATH$925555 Flemming Way Unit 207
555 Flemming Way, Maitland, FL 32751 -
3 BEDS, 2 BATHS$2,000
319 Eaton St
319 Eaton St, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,575
4425 Fairview Ave
4425 Fairview Ave, Orlando, FL 32804 -
3 BEDS, 1.5 BATHS$1,995
776 Carew Ave
776 Carew Ave, Orlando, FL 32804 -
STUDIO, 1 BATH$1,7001420 Lake Baldwin Ln
1420 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,5201418 Beatrice Dr
1418 Beatrice Dr, Orlando, FL 32810 -
1 BED, 1 BATH$1,150
2075 Howell Branch Rd Unit 109
2075 Howell Branch Rd, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,700Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
1 BED, 1 BATH$1,050525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,850200 St Andrews Blvd Unit 2903
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$1,750
650 Trinidad Ct
650 Trinidad Ct, Winter Park, FL 32792
Showing 42 of 173 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 537 Sq Ft $1,385 / mo
- 1 Bedroom 707 Sq Ft $1,453 / mo
- 2 Bedrooms 1,020 Sq Ft $1,715 / mo
- 3 Bedrooms 1,273 Sq Ft $2,016 / 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 602 Sq Ft $1,262/mo
- Winter Park Pines Merrie Oaks 602 Sq Ft $1,262/mo
- Winter Park Woods 765 Sq Ft $1,392/mo
- Winter Park Pines 706 Sq Ft $1,440/mo
- Eastbrook 724 Sq Ft $1,453/mo
- Laurel Springs 741 Sq Ft $1,475/mo
- Lake Howell 745 Sq Ft $1,546/mo
- Winter Park Estates 679 Sq Ft $1,554/mo
- Windward Square 780 Sq Ft $1,566/mo
- Glenmoor 708 Sq Ft $1,567/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.