$1,900
2 beds2 baths1,000 sqftCondo
1250 S Denning Dr, Winter Park, FL, 32789
31 Results
$1,900
2 beds2 baths1,000 sqftCondo
1250 S Denning Dr, Winter Park, FL, 32789
$1,825
2 beds1 bath816 sqftCondo
1140 S Orlando Avenue Unit K-16, Maitland, FL, 32751
$1,590
2 beds1 bath1,193 sqftCondo
600 Huntington Ave, Winter Park, FL, 32789
$2,350
2 beds1 bath865 sqftHouse
521 W. Winter Park St., Orlando, FL, 32804
$2,095
2 beds2.5 baths1,550 sqftHouse
2577 Galliano Cir, Winter Park, FL, 32792
$1,425
2 beds1.5 bathsTownhome
1756 Memphis Ave, Orlando, FL, 32807
$1,499
2 beds1 bath838 sqftCondo
2001 Glenridge Way, Winter Park, FL, 32792
$1,499
2 beds1 bath838 sqftCondo
2001 Glenridge Way, Winter Park, FL, 32792
$1,545
2 beds1 bath860 sqftCondo
3524 Eagle Dr, Orlando, FL, 32804
$1,995
2 beds1.5 baths988 sqftHouse
937 Aragon Ave, Winter Park, FL, 32789
$1,600
2 beds1 bath765 sqftCondo
640 Robinhood Drive Unit C, Maitland, FL, 32751
$1,900
2 beds2 baths1,173 sqftApartment
2503 Tahoe Circle, Winter Park, FL, 32792
$2,000
2 beds2 baths1,095 sqftHouse
401 Balfour Drive, Winter Park, FL, 32792
$1,595
2 beds2 baths1,022 sqftApartment
2917 Antique Oaks Cir Unit 21, Winter Park, FL, 32792
$1,595
2 beds2 baths1,018 sqftCondo
2918 ANTIQUE OAKS CIRCLE # 25, WINTER PARK, FL, 32792
$1,799
2 beds1 bath838 sqftApartment
2001 Glenridge Way, Winter Park, FL, 32792
$1,799
2 beds1 bath838 sqftApartment
2001 Glenridge Way, Winter Park, FL, 32792
$1,799
2 beds1 bath838 sqftApartment
2001 Glenridge Way, Winter Park, FL, 32792
$1,799
2 beds1 bath838 sqftApartment
2001 Glenridge Way, Winter Park, FL, 32792
$1,799
2 beds1 bath838 sqftApartment
2001 Glenridge Way, Winter Park, FL, 32792
$1,799
2 beds1 bath838 sqftApartment
2001 Glenridge Way, Winter Park, FL, 32792
$1,899
2 beds1 bath838 sqftApartment
2001 Glenridge Way, Winter Park, FL, 32792
$1,799
2 beds1 bath838 sqftApartment
2001 Glenridge Way, Winter Park, FL, 32792
$2,550
2 beds1 bath1,104 sqftApartment
245 Orange Pl, Maitland, FL, 32751
Showing 24 of 31 results
Showing 24 of 31 results
Load moreTwo-bedroom apartments in Winter Park suit roommates, small families, and renters who need a dedicated guest room or home office without paying for a third bedroom. When comparing 2-bedrooms in Winter Park, check whether both bedrooms are reasonably sized, how closets are split, and whether the second bedroom has a window — some floor plans label a den without a legal window as a bedroom. Parking, in-unit laundry, and storage often matter more at this size because households accumulate more gear. In Winter Park, 2-bedrooms in walkable corridors can lease quickly when priced fairly relative to nearby 1-bedrooms.
In Winter Park, 2-bedrooms average $1,747/mo versus $1,241/mo for a 1-bedroom. For solo renters on a tight budget, compare both filters on Rentler before applying. If you work from home or spend significant time in your apartment, the extra separation of a larger unit may be worth the difference.
Pet policies on 2-bedroom apartments vary by landlord and building — there's no blanket rule. Use Rentler's pet-friendly filter to narrow your search, then confirm breed, weight, and deposit requirements directly with the landlord before applying.
Furnished 2-bedrooms are available in Winter Park but represent a smaller share of total inventory compared to unfurnished units. Use Rentler's furnished filter to surface move-in-ready options. Furnished units are most common in newer construction buildings and in complexes that cater to corporate or short-term renters.
Most landlords in Winter Park require gross monthly income of 2.5–3x the monthly rent. For a 2-bedroom at Winter Park's current average of $1,747/mo, that means demonstrating roughly 2.5–3x that amount in gross income. If you're below that threshold, a co-signer, larger security deposit, or prepaid rent may be accepted by some landlords — always worth asking.











