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257 rentals available
5d+ ago
Condo for rent in Winter Park
In-unit laundry | Air conditioning | On-site laundry
2 beds
2 baths
$2,450
Condo for rent
Available Jun 29
5d+ ago
Apartment for rent in Winter Park
In-unit laundry | Fitness center | Elevator
1 bed
1 bath
$1,875
Apartment for rent
Available Jun 29
5d+ ago
Condo for rent in Winter Park
1 bed
1 bath
$1,150
Condo for rent
Available Jun 5
5d+ ago
Condo for rent in Winter Park
1 bed
1 bath
$1,495
Condo for rent
Available Jun 26
5d+ ago
Apartment for rent in Winter Park
In-unit laundry | Balcony | Assigned parking
2 beds
1 bath
$1,550
Apartment for rent
Available Jun 26
5d+ ago
Condo for rent in Winter Park
2500 Lee Rd #244, Winter Park, FL 32789
In-unit laundry | Assigned parking | Swimming pool
1 bed
1 bath
$1,350
Condo for rent
5d+ ago
Townhouse for rent in Winter Park
3 beds
2.5 baths
$2,850
House for rent
Available Jun 25
5d+ ago
Townhouse for rent in Winter Park
1951 Canny Cv, Winter Park, FL 32792
In-unit laundry | Garage parking | Swimming pool
3 beds
2.5 baths
$2,700
House for rent
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5d+ ago
Condo for rent in Winter Park
In-unit laundry | Swimming pool | On-site management
1 bed
1 bath
$1,495
Condo for rent
Available Jun 25
5d+ ago
Condo for rent in Winter Park
Garage parking | Carpet | On-site management
3 beds
2 baths
$1,745
Condo for rent
Available Aug 15
5d+ ago
Condo for rent in Winter Park
151 N Orlando Ave #118, Winter Park, FL 32789
In-unit laundry | Swimming pool | Ceiling fan
3 beds
1 bath
$2,200
Condo for rent
5d+ ago
Condo for rent in Winter Park
3 beds
2 baths
$1,795
Condo for rent
Available Jun 1
5d+ ago
Condo for rent in Winter Park
7338 Swallow Run #7338, Winter Park, FL 32792
In-unit laundry | Swimming pool | Walk-in closets
2 beds
2 baths
$1,598
Condo for rent
5d+ ago
Townhouse for rent in Winter Park
3 beds
2.5 baths
$2,975
$2,875
Price drop
House for rent
5d+ ago
Apartment for rent in Winter Park
147 S Interlachen Ave #250, Winter Park, FL 32789
In-unit laundry | Air conditioning | Garage parking
3 beds
5 baths
$10,500
$9,500
Price drop
Apartment for rent
Available Jun 10
5d+ ago
House for rent in Winter Park
3 beds
2 baths
$2,350
House for rent
Available Jun 18
5d+ ago
Condo for rent in Winter Park
2 beds
2 baths
$1,495
Condo for rent
5d+ ago
Condo for rent in Winter Park
1941 Lanier Ct, Winter Park, FL 32792
On-site laundry | Outdoor space
2 beds
1 bath
$1,595
Condo for rent
5d+ ago
House for rent in Winter Park
2 beds
1 bath
$2,750
House for rent
5d+ ago
Townhouse for rent in Winter Park
5523 Cretan Way, Winter Park, FL 32792
In-unit laundry | Assigned parking | Central heat
3 beds
2 baths
$1,795
House for rent
5d+ ago
House for rent in Winter Park
1840 Bachman Way, Winter Park, FL 32792
In-unit laundry | Garage parking | Swimming pool
3 beds
3 baths
$2,500
House for rent
Available Jul 12
5d+ ago
House for rent in Winter Park
1840 Bachman Way #NA, Winter Park, FL 32792
In-unit laundry | Garage parking | Assigned parking
3 beds
2.5 baths
$2,500
House for rent
Available Jul 10
5d+ ago
Condo for rent in Winter Park
2 beds
2 baths
$1,650
Condo for rent
5d+ ago
Condo for rent in Winter Park
2304 Inagua Way #2304, Winter Park, FL 32792
In-unit laundry | Swimming pool | Walk-in closets
2 beds
1 bath
$1,750
Condo for rent
5d+ ago
Condo for rent in Winter Park
350 Carolina Ave #407, Winter Park, FL 32789
In-unit laundry | Garage parking | Assigned parking
2 beds
2 baths
$2,895
Condo for rent
5d+ ago
House for rent in Winter Park
418R Gilbert Rd, Winter Park, FL 32792
In-unit laundry | Air conditioning | Garage parking
3 beds
3 baths
$4,000
House for rent
5d+ ago
Townhouse for rent in Winter Park
2233 Shadowland Loop, Winter Park, FL 32792
In-unit laundry | Furnished | Air conditioning
3 beds
2.5 baths
$2,900
House for rent
5d+ ago
House for rent in Winter Park
648 W Swoope Ave, Winter Park, FL 32789
In-unit laundry | Outdoor space
3 beds
1 bath
$2,700
House for rent
5d+ ago
House for rent in Winter Park
853 W Lyman Ave, Winter Park, FL 32789
In-unit laundry | Furnished | On-site laundry
3 beds
1 bath
$3,300
House for rent
Available Jun 1
5d+ ago
House for rent in Winter Park
2730 Prince John Rd, Winter Park, FL 32792
In-unit laundry | Garage parking | Ceiling fan
4 beds
2 baths
$2,495
House for rent
5d+ ago
Condo for rent in Winter Park
2918 Antique Oaks Cir #26, Winter Park, FL 32792
In-unit laundry | Balcony | Swimming pool
2 beds
2 baths
$1,575
Condo for rent
5d+ ago
House for rent in Winter Park
3 beds
2.5 baths
$2,350
House for rent
5d+ ago
Condo for rent in Winter Park
614 Saint Johns Ct #614, Winter Park, FL 32792
In-unit laundry | Swimming pool | Fitness center
2 beds
2 baths
$1,750
Condo for rent
5d+ ago
Townhouse for rent in Winter Park
2 beds
2.5 baths
$2,250
House for rent
Available May 18
5d+ ago
Townhouse for rent in Winter Park
784 S Pennsylvania Ave, Winter Park, FL 32789
In-unit laundry | Garage parking | Swimming pool
3 beds
2.5 baths
$5,500
House for rent
5d+ ago
House for rent in Winter Park
1843 Shadyhill Ter, Winter Park, FL 32792
In-unit laundry | Garage parking | On-site laundry
4 beds
2.5 baths
$3,300
House for rent
5d+ ago
House for rent in Winter Park
1814 Barker Dr, Winter Park, FL 32789
In-unit laundry | Garage parking | On-site laundry
5 beds
4 baths
$10,000
House for rent
5d+ ago
House for rent in Winter Park
1671 Dale Ave #1, Winter Park, FL 32789
In-unit laundry | Air conditioning | Garage parking
2 beds
1 bath
$2,250
House for rent
Available Jun 1
5d+ ago
House for rent in Winter Park
2 beds
2 baths
$1,695
House for rent
5d+ ago
Condo for rent in Winter Park
625 Trinidad Ct #625, Winter Park, FL 32792
In-unit laundry | Ceiling fan | Carpet
2 beds
2 baths
$1,650
Condo for rent
5d+ ago
House for rent in Winter Park
2 beds
1 bath
$3,200
House for rent
5d+ ago
Condo for rent in Winter Park
7340 Swallow Run #7340, Winter Park, FL 32792
In-unit laundry | Hardwood floor | Walk-in closets
2 beds
2 baths
$1,500
Condo for rent
5d+ ago
House for rent in Winter Park
2 beds
2 baths
$1,600
House for rent
5d+ ago
House for rent in Winter Park
3 beds
2 baths
$2,100
House for rent
5d+ ago
Apartment for rent in Winter Park
3 beds
2 baths
$2,015
Apartment for rent
Available Apr 27
5d+ ago
Condo for rent in Winter Park
782 S Pennsylvania Ave #1, Winter Park, FL 32789
In-unit laundry | Garage parking | Ceiling fan
3 beds
2.5 baths
$5,490
Condo for rent
5d+ ago
Condo for rent in Winter Park
205 Lewfield Cir #205, Winter Park, FL 32792
In-unit laundry | Swimming pool | Fitness center
2 beds
2 baths
$1,800
Condo for rent
5d+ ago
Condo for rent in Winter Park
Leeward Way #C110, Winter Park, FL 32792
In-unit laundry | Walk-in closets | Ceiling fan
1 bed
1 bath
$1,400
Condo for rent
5d+ ago
Townhouse for rent in Winter Park
3 beds
2.5 baths
$2,690
House for rent
5d+ ago
Condo for rent in Winter Park
1695 Lee Rd #B114, Winter Park, FL 32789
In-unit laundry | Swimming pool | Walk-in closets
2 beds
1 bath
$1,500
Condo for rent
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Winter Park, FL, offers a blend of beautiful parks and lakes, making it a pleasant place for outdoor activities like jogging and biking. Residents appreciate the vibrant local arts scene, with frequent events and galleries to explore. The area is noted for its excellent schools, which is a significant draw for families. However, some locals mention frustrations with traffic and parking, especially around the popular Park Avenue shopping district, where congestion can be a hassle during peak times.
Winter Park's 2025 rental market shows one-bedroom apartments averaging around $1,400 per month, while two-bedroom units average around $1,700 monthly. Both apartment types experienced year-over-year decreases, with one-bedrooms declining 6.1% and two-bedrooms dropping 4.4% from 2024 levels.
October stands out as the optimal month for apartment hunting in Winter Park, offering both the lowest seasonal rents and reduced competition among renters. The city sees an 8% difference between peak July pricing and October's off-peak rates, making fall timing particularly advantageous for budget-conscious searches.
Winter Park offers solid options for pet owners, with 48% of rental listings welcoming pets. This represents a substantial portion of the city's average 258 monthly apartment listings, providing pet owners with multiple housing choices across different property types.
Utilities are rarely included in Winter Park rental agreements, appearing in less than 1% of total listings. Among the limited options, one-bedroom apartments show the highest rate at 0.08% of listings, while studios currently show no utility-included options available.
Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.
Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.
Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.
| 🔑Available apartment rentals | 257 |
|---|---|
| 💰Best rent deal | 7421 Daniel Webster Dr #A |
| ✨Popular amenities | , , |
| 🧦In-unit laundry | |
| 🍽With dishwasher | |
| 🏠With photos |