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Luxury Houses for Rent in Winter Park, FL

25 rentals

850 W Canton Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

850 W Canton Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Dishwasher

2 beds

2 baths

$2,600

House for rent

Top amenities
In-Unit Laundry
645 Huntington Ave #7 - Photo 1 of 1

1d ago

Luxury house for rent in Winter Park

645 Huntington Ave #7, Winter Park, FL 32789

Luxury | In-unit laundry | Assigned parking

2 beds

2 baths

$2,380

House for rent

Available Jun 30

Top amenities
Concierge Service
In-Unit Laundry
On-Site Management
645 Huntington Ave - Photo 1 of 1

1d ago

Luxury townhouse for rent in Winter Park

645 Huntington Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Outdoor space

2 beds

2 baths

$2,380

House for rent

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

4d 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
1919 Azalea Ave - Photo 1 of 1

4d ago

Luxury house for rent in Winter Park

1919 Azalea Ave, Winter Park, FL 32792

Luxury | In-unit laundry | On-site laundry

2 beds

1 bath

$2,275

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
7309 Daniel Webster Dr #A - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

Luxury | Outdoor space | Concierge service

Studio

1 bath

$995

House for rent

Available Sep 26

Nearby rental good for eco-living

$2,600

850 W Canton Ave

Nearby rental good for pet owners

Nearby rental good for social life

$3,330

Maitland

1807 N Park Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1807 N Park Ave, Winter Park, FL 32789

Luxury

3 beds

3 baths

$3,395

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 baths

$5,200

$4,950

Price drop

House for rent

Top amenities
Fireplace
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Laundry
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1661 Hillcrest Ave - Photo 1 of 1

5d+ ago

Luxury Virginia Heights house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1661 Hillcrest Ave, Winter Park, FL 32789

Luxury | Balcony | Walk-in closets

4 beds

3 baths

$11,000

$10,000

Price drop

House for rent

Top amenities
Ceiling Fan
High Ceilings
In-Unit Laundry
On-Site Laundry
Storage
Swimming Pool
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

$6,995

House for rent

Top amenities
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
Package Service
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.

$4,950

Winter Park

$2,180

Maitland

1860 Via Contessa #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

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

$19,500

House for rent

Available Aug 29

Top amenities
Air Conditioning
Fitness Center
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site 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

2431 E. Pine St. - Photo 1 of 1

3d ago

8.5

Very good

2431 E. Pine St.

2431 E Pine St, Orlando, FL 32803

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$2,795

House for rent

Top amenities
Garage Parking
In-Unit Laundry
2708 E Church St #1 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2708 E Church St #1, Orlando, FL 32803

Luxury | Balcony | In-unit laundry

3 beds

2 baths

$2,650

House for rent

Available Sep 15

Top amenities
Assigned Parking
In-Unit Laundry
On-Site Laundry
5309 Andrus Ave #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

5309 Andrus Ave #NA, Fairview Shores, FL 32810

Luxury | In-unit laundry | On-site laundry

2 beds

1 bath

$1,590

House for rent

Available Sep 8

Top amenities
In-Unit Laundry
On-Site Laundry
510 Iris Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

510 Iris Rd, Casselberry, FL 32707

Luxury | Balcony | Swimming pool

4 beds

3 baths

$2,600

House for rent

Top amenities
In-Unit Laundry
On-Site Management
7666 Glenmoor Ln - Photo 1 of 1

3d ago

Our team has verified this company

Verified

7666 Glenmoor Ln, Goldenrod, FL 32792

Luxury | Swimming pool | Outdoor space

3 beds

2 baths

$2,640

$2,480

Price drop

House for rent

Top amenities
On-Site Management
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6226 Dahlia Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6226 Dahlia Dr Orlando, FL 32807

6226 Dahlia Dr, Azalea Park, FL 32807

Luxury | Outdoor space

4 beds

2 baths

$2,249

House for rent

Available Sep 10

Listings within 10 miles
231 N Pine Ave - Photo 1 of 1

4d ago

Luxury house for rent in Oviedo

231 N Pine Ave, Oviedo, FL 32765

Luxury

4 beds

2 baths

$2,800

House for rent

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

$2,695

House for rent

8042 Tabby Ln #NA - Photo 1 of 1

4h ago

Our team has verified this company

Verified

$2,180-3 Bedroom 2 Bathroom House In Maitland With Great Amenities in Desirable Location

8042 Tabby Ln #NA, Maitland, FL 32751

Luxury | In-unit laundry | On-site laundry

3 beds

2 baths

$2,480

$2,180

Price drop

House for rent

Available Oct 1

Top amenities
Air Conditioning
Assigned Parking
Garage Parking
High Ceilings
In-Unit Laundry
Storage
10272 Willowemac Ct - Photo 1 of 1

2d ago

Our team has verified this company

Verified

10272 Willowemac Ct, Union Park, FL 32817

Luxury | Balcony | Swimming pool

4 beds

2 baths

$2,740

House for rent

Top amenities
On-Site Management
Swimming Pool
3300 Drake Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Coming HOME never felt so good!

3300 Drake Dr, Lockhart, FL 32810

Luxury

4 beds

3 baths

$2,460

House for rent

6905 Firebird Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6905 Firebird Dr Orlando, FL 32810

6905 Firebird Dr, Lockhart, FL 32810

Luxury | Outdoor space | Garage parking

3 beds

1 bath

$1,745

House for rent

Available Sep 15

Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent
Updated: September 21, 2025

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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