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Houses for Rent in Winter Park, FL

The average rent for houses in Winter Park is up 4% compared to last month but down 3.85% year-over-year.

All rentals

3028 Dikewood Ct - Photo 1 of 1

5d+ ago

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Verified

3028 Dikewood Ct, Winter Park, FL 32792

Outdoor space | Garage parking | Walk-in closets

3 beds

2 baths

$2,740

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
630 N Lakemont Ave - Photo 1 of 1

10h ago

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Verified

630 N Lakemont Ave, Winter Park, FL 32792

On-site laundry | Outdoor space | Swimming pool

3 beds

2 baths

$2,881

Price dropped $105Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
2821 Buccaneer Dr - Photo 1 of 1

2d ago

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Verified

2821 Buccaneer Dr Winter Park, FL 32792

2821 Buccaneer Dr, Winter Park, FL 32792

Outdoor space | Garage parking

4 beds

2 baths

$2,625

Price dropped $130Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
3650 Jonquil Ln - Photo 1 of 1

5d+ ago

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Verified

3650 Jonquil Ln, Winter Park, FL 32792

On-site laundry | Swimming pool | Balcony

3 beds

2 baths

$2,786

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
2217 Sussex Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2217 Sussex Rd, Winter Park, FL 32792

In-unit laundry | Swimming pool | Dishwasher

4 beds

2 baths

$3,400

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.
301 S Capen Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

301 S Capen Ave, Winter Park, FL 32789

In-unit laundry | Dishwasher

3 beds

2 baths

$2,100

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

Nearby rental good for pet owners

408 London Rd - Photo 1 of 1

1m ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

408 London Rd, Winter Park, FL 32792

Outdoor space | Garage parking | Ceiling fan

3 beds

2 baths

$2,540

Price dropped $300Fees 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.
630 Killarney Bay Ct #3 - Photo 1 of 1

10h ago

Townhouse for rent in Winter Park

630 Killarney Bay Ct #3, Winter Park, FL 32789

In-unit laundry | Swimming pool | Carpet

2 beds

2.5 baths

$2,695

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.
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307 Sandlewood Trl - Photo 1 of 1

14h ago

Townhouse for rent in Winter Park

2 BR / 2.5 BA Townhome In Sandlewood Creek

307 Sandlewood Trl, Winter Park, FL 32789

On-site laundry | Outdoor space

2 beds

2.5 baths

$1,800

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.
3051 Autumn Ct - Photo 1 of 1

1d ago

House for rent in Winter Park

3051 Autumn Ct, Winter Park, FL 32792

In-unit laundry | On-site management | Package service

3 beds

2 baths

$2,000

Price dropped $200Additional 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.
1020 Minnesota Ave #1 - Photo 1 of 1

1d ago

Townhouse for rent in Winter Park

Residential Lease, WINTER PARK, FL

1020 Minnesota Ave #1, Winter Park, FL 32789

In-unit laundry | Garage parking | Ceiling fan

3 beds

2.5 baths

$3,800

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.

$2,740

3028 Dikewood Ct

$2,881

630 N Lakemont Ave

$2,786

3650 Jonquil Ln

$3,400

2217 Sussex Rd

624 London Rd - Photo 1 of 1

2d ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

624 London Rd, Winter Park, FL 32792

Outdoor space | Garage parking | Swimming pool

4 beds

2 baths

$3,250

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.
3036 Patel Dr - Photo 1 of 1

2d ago

House for rent in Winter Park

Your Own Private Corner of Winter Park

3036 Patel Dr, Winter Park, FL 32792

Outdoor space

3 beds

2 baths

$1,950

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.
3148 Crown Jewel Ct - Photo 1 of 1

2d ago

Townhouse for rent in Winter Park

3148 Crown Jewel Ct, Winter Park, FL 32792

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

3 beds

2.5 baths

$2,200

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.
850 N Phelps Ave - Photo 1 of 1

2d ago

House for rent in Winter Park

850 N Phelps Ave, Winter Park, FL 32789

Outdoor space | Garage parking | On-site management

2 beds

2 baths

$2,908

Price dropped $100Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
3238 Crown Jewel Ct - Photo 1 of 1

3d ago

Townhouse for rent in Winter Park

3238 Crown Jewel Ct, Winter Park, FL 32792

3 beds

2.5 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.
3226 Crown Jewel Ct #1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

3226 Crown Jewel Ct #1, Winter Park, FL 32792

In-unit laundry | Garage parking | Air conditioning

3 beds

2.5 baths

$2,200

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.
1935 Canny Cv - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Residential Lease, WINTER PARK, FL

1935 Canny Cv, Winter Park, FL 32792

In-unit laundry | Storage | Garage parking

3 beds

2.5 baths

$2,800

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.
2940 Parkland Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

2940 Parkland Dr, Winter Park, FL 32789

In-unit laundry | Outdoor space | Dishwasher

3 beds

1 bath

$3,000

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.
1919 Azalea Avenue - Photo 1 of 1

5d+ ago

8.3

Very good

1919 Azalea Avenue

1919 Azalea Ave, Winter Park, FL 32792

In-unit laundry | Outdoor space | Storage

2 beds

1 bath

$1,875

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.
3416 Hamlet Loop - Photo 1 of 1

5d+ ago

House for rent in Winter Park

3416 Hamlet Loop, Winter Park, FL 32792

Assigned parking | Air conditioning | Central heat

3 beds

3 baths

$2,300

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.
957 Dupont Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

957 Dupont Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

3 beds

2.5 baths

$2,800

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.
424 Dunraven Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

424 Dunraven Dr, Winter Park, FL 32792

In-unit laundry | Hardwood floor | Ceiling fan

3 beds

2 baths

$3,100

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.
1401 Aster Ct - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1401 Aster Ct, Winter Park, FL 32792

Outdoor space | Garage parking | Air conditioning

4 beds

2 baths

$2,395

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.
173 Lewfield Cir #1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

173 Lewfield Cir #1, Winter Park, FL 32792

In-unit laundry | On-site management

1 bed

1 bath

$1,400

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.
343 Harris Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

343 Harris Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Furnished

3 beds

2 baths

$4,500

Price dropped $200Fees 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.
2006 Canny Cv - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Residential Lease, WINTER PARK, FL

2006 Canny Cv, Winter Park, FL 32792

In-unit laundry | Outdoor space | Storage

3 beds

2.5 baths

$2,700

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.
7512 Cranes Creek Ct #NA - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

7512 Cranes Creek Ct - N/A

7512 Cranes Creek Ct #NA, Winter Park, FL 32792

In-unit laundry | Air conditioning | Carpet

3 beds

2.5 baths

$2,250

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.
2417 Lafayette Ave - Photo 1 of 1
New construction

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

2417 Lafayette Ave, Winter Park, FL 32789

On-site laundry | Outdoor space | Garage parking

4 beds

3 baths

$10,000

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.
3991 Waterview Loop - Photo 1 of 1

5d+ ago

House for rent in Winter Park

3991 Waterview Loop, Winter Park, FL 32792

In-unit laundry | Assigned parking | Air conditioning

3 beds

2 baths

$2,400

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.
2181 Linden Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

2181 Linden Rd, Winter Park, FL 32792

In-unit laundry | Dishwasher

5 beds

3.5 baths

$2,600

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.
1981 Blue Ridge Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

1981 Blue Ridge Rd, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

5 beds

2 baths

$5,995

Price dropped $500Fees 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.
7487 Canford Ct #5 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Residential Lease, WINTER PARK, FL

7487 Canford Ct #5, Winter Park, FL 32792

In-unit laundry | Outdoor space | Storage

4 beds

3 baths

$2,150

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.
1415 Harmon Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

1415 Harmon Ave, Winter Park, FL 32789

Garage parking | Air conditioning | Carpet

3 beds

2.5 baths

$3,400

Price dropped $200Fees 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.
1029 Wading Waters Cir #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Park

$6,300 - 5 Bedroom 4.5 Bathroom House In Winter Park With Great Amenities

1029 Wading Waters Cir #NA, Winter Park, FL 32792

In-unit laundry | Outdoor space | Storage

5 beds

4.5 baths

$6,000

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.
2421 Passamonte Dr #C - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Via Lago Unit #C, Furnished Room w/Shared Bath

2421 Passamonte Dr #C, Winter Park, FL 32792

In-unit laundry | Outdoor space | Garage parking

1 bed

1 bath

$1,000

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.
3027 Aaron Burr Ave #L1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Residential Lease, WINTER PARK, FL

3027 Aaron Burr Ave #L1, Winter Park, FL 32792

In-unit laundry | Outdoor space | Swimming pool

2 beds

2.5 baths

$1,795

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.
3328 Hamlet Loop - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

3328 Hamlet Loop, Winter Park, FL 32792

Outdoor space | Garage parking | Swimming pool

3 beds

2.5 baths

$2,500

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.
1381 Orchid Ave - Photo 1 of 1

5d+ ago

Garden Acres townhouse for rent in Winter Park

1381 Orchid Ave, Winter Park, FL 32789

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

3 beds

2.5 baths

$2,995

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.
1751 Westchester Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

1751 Westchester Ave, Winter Park, FL 32789

On-site laundry | Outdoor space | Dishwasher

3 beds

2 baths

$2,100

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.
7328 Forest Hill Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

7328 Forest Hill Ct, Winter Park, FL 32792

2 beds

2.5 baths

$1,597

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.
2712 Goldenrod Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

2712 Goldenrod Dr, Winter Park, FL 32792

Outdoor space | Garage parking | Air conditioning

3 beds

2 baths

$4,500

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.
1666 Tremont Ln - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

1666 Tremont Ln, Winter Park, FL 32792

In-unit laundry | Outdoor space | Ceiling fan

3 beds

2 baths

$2,240

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.
1603 Winter Green Blvd - Photo 1 of 1
3D tour

5d+ ago

House for rent in Winter Park

1603 Winter Green Blvd, Winter Park, FL 32792

Outdoor space | Swimming pool | Carpet

3 beds

2 baths

$2,068

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
450 W Canton Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

450 W Canton Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$3,000

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.
7101 Swallow Run - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

7101 Swallow Run, Winter Park, FL 32792

In-unit laundry | Garage parking | Dishwasher

3 beds

2.5 baths

$1,895

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.
7033 Easter St - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

7033 Easter St, Winter Park, FL 32792

On-site laundry | Outdoor space | Storage

4 beds

3 baths

$2,850

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.
741 Minnesota Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Spacious 3-Bedroom, 4-Bath Home for Rent in Winter Park, FL | WiFi Included + Private Community Pool

741 Minnesota Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

3 beds

3.5 baths

$3,995

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.
800 W Canton Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Residential Lease, WINTER PARK, FL

800 W Canton Ave, Winter Park, FL 32789

In-unit laundry | Outdoor space | Dishwasher

2 beds

1 bath

$2,500

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.
2545 Madeline Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

2545 Madeline Ave, Winter Park, FL 32789

Outdoor space | Storage | Garage parking

3 beds

2 baths

$2,962

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
Showing 1 - 50 of 56 results
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Home > House Rentals in Winter Park
Updated: November 12, 2026

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Pet friendly houses in Winter Park, FL18 rentals

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Discover houses for rent in Winter Park, FL

🌇Available house rentals56 houses
💰Best rent deal2421 Passamonte Dr #C
🍃With outdoor space
⭐Popular amenities, ,
👚With laundry facilities
🍽With dishwasher
🚗With garage parking
❄️With air conditioning
🏠With photos