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Luxury Houses for Rent in Winter Park, FL

25 rentals

1671 Dale Ave #1 - Photo 1 of 1

6h ago

Luxury house for rent in Winter Park

1671 Dale Ave. - 1

1671 Dale Ave #1, Winter Park, FL 32789

Luxury | In-unit laundry | Controlled access

2 beds

1 bath

$2,250

House for rent

Available Jun 1

Top amenities
Cable
Garage Parking
Hardwood Floor
In-Unit Laundry
Microwave
1760 Legion Dr - Photo 1 of 1

23h ago

Luxury house for rent in Winter Park

1760 Legion Dr, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

4 beds

5.5 baths

$9,700

House for rent

Top amenities
Ceiling Fan
Dishwasher
Fireplace
High Ceilings
In-Unit Laundry
Swimming Pool
1850 Whitehall Dr - Photo 1 of 1

2d ago

Luxury house for rent in Winter Park

1850 Whitehall Dr, Winter Park, FL 32789

Luxury | Swimming pool | Furnished

3 beds

2 baths

$3,350

House for rent

1937 Strathaven Rd - Photo 1 of 1

3d ago

Luxury house for rent in Winter Park

Newly Renovated

1937 Strathaven Rd, Winter Park, FL 32792

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$3,395

House for rent

Top amenities
Garage Parking
In-Unit Laundry
438 Lakeview Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

438 Lakeview Ave, Winter Park, FL 32789

Luxury

2 beds

1 bath

$3,400

$3,200

Price drop

House for rent

1580 Oakhurst Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1580 Oakhurst Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

4 beds

2.5 baths

$4,600

House for rent

Top amenities
Dishwasher
Fireplace
Hardwood Floor
In-Unit Laundry
On-Site Laundry

Nearby rental good for eco-living

Nearby rental good for pet owners

$2,200

Orlando

1041 Tuscany Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1041 Tuscany Pl, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

4 beds

3.5 baths

$12,000

House for rent

Top amenities
Dishwasher
Garage Parking
High Ceilings
In-Unit Laundry
1026 S Lakemont Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1026 S Lakemont Ave, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$4,300

House for rent

Top amenities
Carpet
In-Unit Laundry
On-Site Laundry
Residents Lounge
Storage
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1776 Mondrian Cir - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1776 Mondrian Cir, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

3 beds

3.5 baths

$5,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
1508 Florentino Ln - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1508 Florentino Ln, Winter Park, FL 32792

Luxury | Walk-in closets | Fitness center

2 beds

2.5 baths

$2,350

House for rent

Top amenities
Ceiling Fan
Fitness Center
Garage Parking
High Ceilings
In-Unit Laundry
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Find sweet deals near Winter Park

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

$2,200

Orlando

$2,530

Winter Park

$2,385

Winter Park

$1,745

Azalea Park

1521 Chestnut Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1521 Chestnut Ave, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

4 beds

3 baths

$6,500

House for rent

Top amenities
Garage Parking
High Ceilings
1814 Barker Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1814 Barker Dr, Winter Park, FL 32789

Luxury | Swimming pool | Fitness center

5 beds

4 baths

$11,000

House for rent

Top amenities
Fitness Center
Garage Parking
High Ceilings
In-Unit Laundry
On-Site Laundry
Swimming Pool
1441 Oneco Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1441 Oneco Ave, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

4 beds

3.5 baths

$6,000

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
Storage
1667 Mizell Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1667 Mizell Ave, Winter Park, FL 32789

Luxury | Outdoor space | Dishwasher

3 beds

3 baths

$3,995

House for rent

1235 Via Estrella - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1235 Via Estrella, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$5,895

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
Storage
300 Killarney Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

300 Killarney Dr, Winter Park, FL 32789

Luxury | Walk-in closets | Fitness center

4 beds

3 baths

$7,900

House for rent

Top amenities
Fireplace
Fitness Center
Garage Parking
High Ceilings
In-Unit Laundry
1221 Richmond Rd - Photo 1 of 1
New construction

5d+ ago

Luxury Virginia Heights house for rent in Winter Park

House (Detached) - Winter Park, FL

1221 Richmond Rd, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

5 beds

5.5 baths

$19,000

House for rent

Top amenities
Carpet
In-Unit Laundry
Swimming Pool
722 Ellwood Ave - Photo 1 of 1

5d+ ago

Luxury College Park house for rent in Orlando

722 Ellwood Ave, Orlando, FL 32804

Luxury | Outdoor space | Dishwasher

5 beds

3 baths

$4,750

$4,350

Price drop

House for rent

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2525 Native Ct #NA - Photo 1 of 1

3d ago

Our team has verified this company

Verified

Fully remodeled- Dommerich School with Great Amenities

2525 Native Ct #NA, Maitland, FL 32751

Luxury | Swimming pool | In-unit laundry

4 beds

2.5 baths

$4,900

$4,700

Price drop

House for rent

Available Apr 20

Top amenities
Air Conditioning
Fireplace
Garage Parking
In-Unit Laundry
Swimming Pool
3313 Hamlet Loop - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3313 Hamlet Loop, Winter Park, FL 32792

Luxury | Walk-in closets | Swimming pool

3 beds

2.5 baths

$2,530

House for rent

Available Jul 3

Top amenities
Ceiling Fan
High Ceilings
Swimming Pool
372 Fairgreen Pl - Photo 1 of 1

3d ago

Our team has verified this company

Verified

372 Fairgreen Pl, Casselberry, FL 32707

Luxury | Swimming pool | On-site laundry

3 beds

2 baths

$3,065

House for rent

Available Jul 6

Top amenities
On-Site Laundry
On-Site Management
622 Ellsworth St - Photo 1 of 1

3d ago

Our team has verified this company

Verified

622 Ellsworth St, Altamonte Springs, FL 32701

Luxury | Swimming pool | On-site laundry

3 beds

2 baths

$2,765

House for rent

Available Jul 7

Top amenities
On-Site Laundry
On-Site Management
Listings within 10 miles
7032 Carna Ct #NA - Photo 1 of 1

3d ago

Our team has verified this company

Verified

$2,700 - 4 Bedroom 2 Bathroom House In Orlando With Pool, pavers backyard, and Solar Panels $2,700

7032 Carna Ct #NA, Azalea Park, FL 32807

Luxury | Swimming pool | In-unit laundry

4 beds

2 baths

$2,700

House for rent

Available Jul 6

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry
On-Site Laundry
Swimming Pool
7934 Winter Song Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

7934 Winter Song Dr, Orlando, FL 32825

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,355

$2,200

Price drop

House for rent

Available Apr 10

Top amenities
Garage Parking
High Ceilings
713 Fenwick Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

713 Fenwick Dr, Orlando, FL 32825

Luxury | Walk-in closets | Outdoor space

3 beds

2.5 baths

$2,460

$2,345

Price drop

House for rent

Available Apr 4

Top amenities
Garage Parking
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent
Updated: May 13, 2026

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Pet friendly houses in Winter Park, FL19 rentals

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Discover luxury Winter Park, FL houses for rent

🌇Available luxury house rentals25 houses
⭐Popular amenities, ,
🍽With dishwasher
❄️With air conditioning
🚗With garage parking
🍃With outdoor space
🏠With photos