Luxury Houses for Rent in Winter Park, FL

25 rentals available

22h ago

Verified

$3,450 - 3 Bedroom 2 Bathroom Updated House In Winter Park With Great Amenities $3,450 - 3 Bedroom 2 Bathroom House In Winter Park With Great Amenities

1817 Loch Berry Rd #NA, Winter Park, FL 32789

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$3,450

5d+ ago

Verified

2000 Galen Avenue, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

3 beds

2 baths

$4,500

21h ago

Luxury house for rent in Winter Park

6508 Centerwalk Dr #NA, Winter Park, FL 32792

Luxury | Balcony | Swimming pool

3 beds

3 baths

$7,990

1d ago

Luxury house for rent in Winter Park

2500 Lee Rd, Winter Park, FL 32789

Luxury

1 bed

1 bath

$1,099

1d ago

Luxury house for rent in Winter Park

Minnesota Ave 737 - A

737 Minnesota Ave #A, Winter Park, FL 32789

Luxury | In-unit laundry | Storage

3 beds

3 baths

$3,995

2d ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

800 W Canton Ave, Winter Park, FL 32789

Luxury | In-unit laundry | On-site laundry

2 beds

1 bath

$2,500

Nearby rental good for eco-living

$2,400

920 Aragon Ave

Nearby rental good for pet owners

$2,360

Orlando

2d ago

Luxury house for rent in Winter Park

PRICE DROP! The Michigan Avenue Muse | A Winter Park Retreat Reimagined for Modern Luxury Living! PRIVATE POOL! WASHER & DRYER INCLUDED WITH STANDBY GENERATOR!

1403 Michigan Ave, Winter Park, FL 32789

Luxury | In-unit laundry

4 beds

3.5 baths

$4,999

3d ago

Luxury house for rent in Winter Park

1100 Aragon Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Dishwasher

1 bed

1 bath

$1,895

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3d ago

Luxury house for rent in Winter Park

Furnished Private Room + Private Bath |Winter Park, FL | Utilities Included | Month-to-Month Leasing

741 Minnesota Ave, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

1 bed

1 bath

$1,663

3d ago

Luxury house for rent in Winter Park

Spacious 3-Bedroom House for Rent in Winter Park, FL - WiFi Included + Community Pool

737 Minnesota Ave, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

3 beds

3.5 baths

$3,995

Find sweet deals near Winter Park

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

$1,099

Winter Park

$1,099

Winter Park

$2,710

Winter Park

$2,445

Winter Park

3d ago

Luxury house for rent in Winter Park

Spacious 3-Bedroom House for Rent in Winter Park, FL - WiFi Included + Community Pool

735 Minnesota Ave, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

3 beds

3.5 baths

$3,995

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

2056 Wood Thrush Ln, Winter Park, FL 32792

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,500

7309 Daniel Webster Dr #D - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

7309 Daniel Webster Dr #D, Winter Park, FL 32792

Luxury | Air conditioning | Carpet

1 bed

1 bath

$1,099

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

1667 Mizell Ave, Winter Park, FL 32789

Luxury | Outdoor space | Ceiling fan

3 beds

3 baths

$3,500

5d+ ago

Luxury house for rent in Winter Park

904 Carvell Dr, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,400

5d+ ago

Luxury house for rent in Winter Park

759 Antonette Ave, Winter Park, FL 32789

Luxury

1 bed

1 bath

$1,800

5d+ ago

Luxury house for rent in Winter Park

1939 Gunn Rd, Winter Park, FL 32792

Luxury

3 beds

2 baths

$3,400

5d+ ago

Luxury townhouse for rent in Winter Park

920 Aragon Ave

920 Aragon Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Outdoor space

2 beds

2.5 baths

$2,400

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

1620 Palm Ave, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

6 beds

4.5 baths

$10,000

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

1368 Hibiscus Ave, Winter Park, FL 32789

Luxury | Balcony | Walk-in closets

4 beds

2.5 baths

$7,250

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

1442 Palm Ave, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

5 beds

6 baths

$9,900

5d+ ago

Verified

$4100 - 3 Bedroom 3.5 Bathroom Apartment In Baldwin Park With Great Amenities

1733 Prospect Ave #1733, Orlando, FL 32814

Luxury | Balcony | In-unit laundry

3 beds

3.5 baths

$3,950

1h ago

Verified

3028 Dikewood Ct, Winter Park, FL 32792

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$3,720

$2,710

Price drop

5d+ ago

Verified

1409 Bridlebrook Drive

1409 Bridlebrook Dr, Casselberry, FL 32707

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,255

$2,165

Price drop

Listings within 10 miles

1d ago

Verified

3762 Peaceful Pl, Lockhart, FL 32810

Luxury | Walk-in closets | On-site laundry

3 beds

2 baths

$2,990

$2,180

Price drop

Showing 1 - 25 of 25 results

Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent

Updated: September 26, 2026

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Luxury Houses for Rent in Winter Park, FL

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