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Condos for Rent in Winter Park, FL

The average rent for condos in Winter Park is down 2.94% compared to last month but up 6.16% year-over-year.

All rentals

204 Lewfield Cir - Photo 1 of 1
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4d ago

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204 Lewfield Cir, Winter Park, FL 32792

In-unit laundry | On-site laundry | Balcony

2 beds

2 baths

$1,700

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1000 S Semoran Blvd #715 - Photo 1 of 1

5d+ ago

Golfside condo for rent in Winter Park

Residential Lease, WINTER PARK, FL

1000 S Semoran Blvd #715, Winter Park, FL 32792

On-site laundry | Swimming pool | Ceiling fan

1 bed

1 bath

$1,150

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
700 Melrose Ave #A5 - Photo 1 of 1
Age restricted

12h ago

Condo for rent in Winter Park

2 beds

2 baths

$1,995

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
7429 Daniel Webster Dr #B - Photo 1 of 1

4d ago

Condo for rent in Winter Park

7429 Daniel Webster Dr #B, Winter Park, FL 32792

1 bed

1 bath

$1,095

Price dropped $155Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1695 Lee Rd #A103 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

1695 Lee Rd #A103, Winter Park, FL 32789

In-unit laundry | Assigned parking | Walk-in closets

2 beds

1 bath

$1,350

Price dropped $75Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
98 S Virginia Ave #111 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Residential Lease, WINTER PARK, FL

98 S Virginia Ave #111, Winter Park, FL 32789

In-unit laundry | Assigned parking | Walk-in closets

3 beds

3.5 baths

$5,700

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.

Nearby rental good for eco-living

$1,800

Lake Dot

Nearby rental good for pet owners

$1,550

Orlando

2924 Antique Oaks Cir #42 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

2924 Antique Oaks Cir #42, Winter Park, FL 32792

Swimming pool | Storage | On-site management

2 beds

2 baths

$1,595

Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
7453 Daniel Webster Dr #A5 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Residential Lease, WINTER PARK, FL

7453 Daniel Webster Dr #A5, Winter Park, FL 32792

In-unit laundry | Balcony | Walk-in closets

2 beds

2 baths

$1,500

Price dropped $100Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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1695 Lee Rd #E213 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

1695 Lee Rd #E213, Winter Park, FL 32789

In-unit laundry | Balcony | Ceiling fan

2 beds

1 bath

$1,600

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
659 Montego Bay Ct - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

659 Montego Bay Ct, Winter Park, FL 32792

In-unit laundry | Swimming pool | Fitness center

2 beds

2 baths

$1,695

Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
100 S Virginia Ave #320 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

3 beds

3 baths

$4,995

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.

Find sweet deals in Winter Park

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$1,095

7429 Daniel Webster Dr #B

$1,595

2924 Antique Oaks Cir #42

$1,500

7453 Daniel Webster Dr #A5

1695 Lee Rd #E103 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

1695 Lee Rd #E103, Winter Park, FL 32789

In-unit laundry | Walk-in closets | Ceiling fan

2 beds

1 bath

$1,600

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2404 Gallery View Dr - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

2404 Gallery View Dr, Winter Park, FL 32792

In-unit laundry | Swimming pool | On-site management

2 beds

2 baths

$1,575

Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
660 Osceola Ave - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

660 Osceola Ave, Winter Park, FL 32789

In-unit laundry | Dishwasher | Microwave

3 beds

3.5 baths

$8,500

Price dropped $400Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
7444 Woodburn Ct #29 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Residential Lease, WINTER PARK, FL

7444 Woodburn Ct #29, Winter Park, FL 32792

In-unit laundry | Air conditioning | Swimming pool

2 beds

2.5 baths

$1,585

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
690 Osceola Ave #407 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Residential Lease, WINTER PARK, FL

690 Osceola Ave #407, Winter Park, FL 32789

Balcony | Swimming pool | Fitness center

1 bed

1.5 baths

$2,200

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
7726 Country Pl - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

7726 Country Pl, Winter Park, FL 32792

2 beds

2 baths

$1,750

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2948 Antique Oaks Cir #96 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

In-unit laundry | Swimming pool | Dishwasher

1 bed

1 bath

$1,425

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2911 Antique Oaks Cir - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

2911 Antique Oaks Cir, Winter Park, FL 32792

2 beds

2 baths

$1,600

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1695 Lee Rd #A113 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

1695 Lee Rd #A113, Winter Park, FL 32789

In-unit laundry | On-site laundry | Swimming pool

2 beds

1 bath

$1,600

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
3651 N Goldenrod Rd #A103 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Residential Lease, WINTER PARK, FL

3651 N Goldenrod Rd #A103, Winter Park, FL 32792

In-unit laundry | Swimming pool | Ceiling fan

2 beds

2 baths

$1,575

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
151 N Orlando Ave #207 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

151 N Orlando Ave #207, Winter Park, FL 32789

In-unit laundry | Assigned parking | Swimming pool

2 beds

1 bath

$2,150

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2918 Antique Oaks Cir #25 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

2918 Antique Oaks Cir #25, Winter Park, FL 32792

In-unit laundry | Swimming pool | Dishwasher

2 beds

2 baths

$1,595

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
151 N Orlando Ave #118 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

151 N Orlando Ave #118, Winter Park, FL 32789

Swimming pool | Ceiling fan | Storage

2 beds

1 bath

$1,900

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1250 S Denning Dr - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Winter Park 2/2 condo - Rollins, Park Avenue - great location!

1250 S Denning Dr, Winter Park, FL 32789

On-site laundry | Swimming pool | Dishwasher

2 beds

2 baths

$1,900

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
612 Trinidad Ct #612 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Residential Lease, WINTER PARK, FL

612 Trinidad Ct #612, Winter Park, FL 32792

In-unit laundry | Swimming pool | Fitness center

2 beds

2 baths

$1,750

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1695 Lee Rd #C103 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

1695 Lee Rd #C103, Winter Park, FL 32789

In-unit laundry | On-site laundry | Walk-in closets

2 beds

1 bath

$1,600

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
Showing 1 - 27 of 27 results
Home > Condo Rentals in Winter Park
Updated: October 27, 2026

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