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Luxury Houses for Rent in Winter Park, FL

25 rentals

1817 Loch Berry Rd #NA - Photo 1 of 1

5d+ ago

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Verified

$3,600 - 3 Bedroom 2 Bathroom Updated 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

$3,600

House for rent

Available Dec 13

Top amenities
Air Conditioning
Assigned Parking
Ceiling Fan
Dishwasher
Hardwood Floor
In-Unit Laundry
1860 Via Contessa #NA - Photo 1 of 1

5d+ ago

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Verified

Newly Renovated - 8 Bedroom 6 Bathroom House In Winter Park

1860 Via Contessa #NA, Winter Park, FL 32789

Luxury | Balcony | Walk-in closets

8 beds

6 baths

$16,550

House for rent

Available Sep 1

Top amenities
Air Conditioning
Assigned Parking
Dishwasher
Fireplace
On-Site Laundry
Swimming Pool
1681 Woodland Ave #NA - Photo 1 of 1

5d+ ago

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Verified

1681 Woodland Ave #NA, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

3 beds

2 baths

$4,100

House for rent

Available Oct 16

Top amenities
Air Conditioning
Dishwasher
Fireplace
Garage Parking
In-Unit Laundry
Swimming Pool
7309 Daniel Webster Dr #A - Photo 1 of 1

9h ago

Luxury townhouse for rent in Winter Park

Luxury | Outdoor space | Concierge service

Studio

1 bath

$925

House for rent

Available Sep 25

960 Georgia Ave - Photo 1 of 1

4d ago

Luxury house for rent in Winter Park

House for rent

1205 Mayfield Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1205 Mayfield Ave, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

4 beds

5 baths

$6,045

House for rent

Top amenities
Concierge Service
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Management

Nearby rental good for eco-living

$2,500

Casselberry

Nearby rental good for pet owners

$2,270

Azalea Park

236 Rippling Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Luxury | In-unit laundry | Dishwasher

3 beds

2 baths

$4,200

$4,000

Price drop

House for rent

Top amenities
In-Unit Laundry
216 Rippling Ln #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

216 Rippling Ln #NA, Winter Park, FL 32789

Luxury | In-unit laundry | On-site laundry

3 beds

2 baths

$3,500

House for rent

Available Nov 10

Top amenities
Assigned Parking
Central Heat
In-Unit Laundry
On-Site Laundry
Wi-Fi
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1120 Aragon Ave - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1120 Aragon Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

2 beds

2 baths

$3,100

House for rent

Top amenities
Carpet
Dishwasher
Garage Parking
Hardwood Floor
High Ceilings
In-Unit Laundry
1701 Palmer Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1701 Palmer Ave, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,400

House for rent

Top amenities
Carpet
Dishwasher
Fireplace
In-Unit Laundry
Swimming Pool
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Find sweet deals near Winter Park

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

$1,395

Colonialtown South

$2,395

Lake Davis-Greenwood

$1,725

Altamonte Springs

1641 Chestnut Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1641 Chestnut Ave, Winter Park, FL 32789

Luxury | Hardwood floor | Outdoor space

3 beds

3 baths

$3,495

House for rent

1166 Palmer Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1166 Palmer Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

3 beds

3 baths

$4,695

House for rent

Top amenities
Carpet
Fireplace
Garage Parking
In-Unit Laundry
Storage
2712 Goldenrod Dr #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

2712 Goldenrod Dr #NA, Winter Park, FL 32792

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$4,450

House for rent

Available Oct 15

Top amenities
Air Conditioning
Assigned Parking
Fireplace
Garage Parking
In-Unit Laundry
1681 Walnut Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1681 Walnut Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$3,750

House for rent

Top amenities
Fireplace
In-Unit Laundry
939 Aragon Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Luxury | In-unit laundry | Outdoor space

2 beds

2 baths

$2,725

House for rent

Top amenities
In-Unit Laundry
2020 Venetian Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

2020 Venetian Way, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$8,990

House for rent

Top amenities
Carpet
Fireplace
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
987 Cherokee Ave - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

987 Cherokee Ave, Winter Park, FL 32789

Luxury

Studio

0 baths

$1,500

House for rent

1835 Edwin Blvd - Photo 1 of 1

19h ago

Luxury house for rent in Winter Park

1835 Edwin Blvd, Winter Park, FL 32789

Luxury | In-unit laundry | On-site laundry

3 beds

2 baths

$3,450

$3,345

Price drop

House for rent

Top amenities
Dishwasher
Hardwood Floor
In-Unit Laundry
On-Site Laundry
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1230 1/2 E Concord St - Photo 1 of 1

5d+ ago

Luxury Colonialtown South house for rent in Orlando

1230 1/2 E Concord St, Orlando, FL 32803

Luxury

1 bed

1 bath

$1,450

$1,395

Price drop

House for rent

2510 Lauder Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Maitland

2510 Lauder Dr, Maitland, FL 32751

Luxury | Dishwasher

4 beds

3 baths

$4,995

House for rent

1100 Maury Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1100 Maury Rd, Orlando, FL 32804

Luxury | In-unit laundry | Outdoor space

2 beds

2 baths

$2,700

House for rent

Available Oct 15

Top amenities
Air Conditioning
In-Unit Laundry
Listings within 10 miles
1095 Elmwood St - Photo 1 of 1

2d ago

Luxury Lake Davis-Greenwood townhouse for rent in Orlando

1095 Elmwood St, Orlando, FL 32801

Luxury

3 beds

2 baths

$2,595

$2,395

Price drop

House for rent

824 Camargo Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Altamonte Springs

824 Camargo Way, Altamonte Springs, FL 32714

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$1,725

House for rent

Top amenities
In-Unit Laundry
137 Peppertree Dr #NA - Photo 1 of 1

3d ago

Our team has verified this company

Verified

Beautiful House at Rio Pinar

137 Peppertree Dr #NA, Orlando, FL 32825

Luxury | Outdoor space | Garage parking

3 beds

2 baths

$2,390

House for rent

Available Nov 1

861 Blackgum Ct #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

$2,500 - 3 Bedroom 2 Bathroom House In East Orlando, Waterford Lakes, UCF

861 Blackgum Ct #NA, Orlando, FL 32825

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,500

$2,400

Price drop

House for rent

Available Jun 30

Top amenities
Assigned Parking
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Management
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent
Updated: November 5, 2025

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Discover luxury Winter Park, FL houses for rent

🌇Available luxury house rentals25 houses
⭐Popular amenities, ,
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