Apartments and houses for rent in Winter Park, FL
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For Rent
For Sale39 listings
2251 Nairn Dr, Winter Park, FL 32792
$3,200
1978 sqft
4 beds
3 baths
July 03, 2026 - Source: realtor.com +1 more
New
2 days ago
2500 Lee Rd #244, Winter Park, FL 32789
$1,350
645 sqft
1 bed
1 bath
July 03, 2026 - Source: redfin.com
New
3 days ago
630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
$2,695
1428 sqft
2 beds
3 baths
July 02, 2026 - Source: realtor.com
New
4 days ago
150 Killarney Bay Ct Unit 5-5, Winter Park, FL 32789
$2,450
1140 sqft
2 beds
2 baths
July 01, 2026 - Source: realtor.com
New
4 days ago
Address Not Disclosed, Winter Park, FL 32789
$1,447
2252 sqft
4 beds
3 baths
July 01, 2026 - Source: trulia.com
New
4 days ago
150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
$2,450
1140 sqft
2 beds
2 baths
June 30, 2026 - Source: zillow.com +1 more
New
6 days ago
1695 Lee Rd Apt A101, Winter Park, FL 32789
$1,695
1149 sqft
3 beds
2 baths
June 30, 2026 - Source: realtor.com +1 more
New
6 days ago
520 N Orlando Ave, Winter Park, FL 32789
$1,575
668 sqft
1 bed
1 bath
June 29, 2026 - Source: redfin.com
New
6 days ago
Paseo at Winter Park Village, Winter Park, FL 32789
$1,930
758 sqft
1 bed
1 bath
June 28, 2026 - Source: trulia.com
New
8 days ago
1791 Spruce Ave, Winter Park, FL 32789
$4,900
1776 sqft
3 beds
2 baths
June 26, 2026 - Source: realtor.com +1 more
New
9 days ago
The Fisher Apartments, Winter Park | 12 Bedrooms Available-One Month Free On Select Homes, Winter Park, FL 32792
$1,699
656 sqft
1 bed
1 bath
June 26, 2026 - Source: trulia.com
New
10 days ago
301 S Capen Ave, Winter Park, FL 32789
$2,500
1158 sqft
3 beds
2 baths
June 25, 2026 - Source: redfin.com
New
11 days ago
1600 Drum St, Winter Park, FL 32789
$3,495
1374 sqft
3 beds
2 baths
June 23, 2026 - Source: realtor.com
New
13 days ago
2234 Howard Dr, Winter Park, FL 32789
$8,295
3295 sqft
4 beds
6 baths
June 22, 2026 - Source: zillow.com +3 more
New
13 days ago
301 S Capen Ave, Winter Park, FL 32789
No price
1158 sqft
3 beds
2 baths
June 22, 2026 - Source: zillow.com +1 more
New
13 days ago
The Taylor at Winter Park, Winter Park, FL 32792
$1,253
528 sqft
1 bed
1 bath
June 22, 2026 - Source: trulia.com
New
14 days ago
1046 Azalea Ln #B, Winter Park, FL 32789
$1,800
550 sqft
1 bed
1 bath
June 21, 2026 - Source: zillow.com +3 more
New
15 days ago
200 Saint Andrews Blvd, Winter Park, FL 32792
$1,850
1219 sqft
2 beds
2 baths
June 20, 2026 - Source: zillow.com +1 more
New
16 days ago
What's the average rent in Winter Park, FL?
Based on the last 30 days, the average rent in Winter Park, FL is $3,337.
This is 12.7% higher than the average rental price in Florida.
This is 12.7% higher than the average rental price in Florida.
How often do new rentals come on the market in Winter Park, FL?
On average, 1 rentals are put on the market in Winter Park, FL per day.
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