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Luxury Houses for Rent in Winter Park, FL

25 rentals available

2234 Howard Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

2234 Howard Dr, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

4 beds

5.5 baths

$8,295

House for rent

Top amenities
Dishwasher
In-Unit Laundry
Swimming Pool
616 Ellendale Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

SINGLE_FAMILY - WINTER PARK, FL

616 Ellendale Dr, Winter Park, FL 32792

Luxury | Swimming pool | Fitness center

4 beds

2 baths

$5,000

House for rent

Top amenities
Dishwasher
Fitness Center
Swimming Pool
1368 Hibiscus Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

SINGLE_FAMILY - WINTER PARK, FL

1368 Hibiscus Ave, Winter Park, FL 32789

Luxury | Balcony | Walk-in closets

4 beds

2.5 baths

$7,500

House for rent

Top amenities
Dishwasher
Garage Parking
High Ceilings
Swimming Pool
1403 Michigan Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1403 Michigan Ave, Winter Park, FL 32789

Luxury

4 beds

3.5 baths

$6,400

House for rent

1442 Palm Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

SINGLE_FAMILY - WINTER PARK, FL

1442 Palm Ave, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

5 beds

6 baths

$9,900

House for rent

Top amenities
Garage Parking
High Ceilings
In-Unit Laundry
630 Killarney Bay Ct #3 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

CONDOS - WINTER PARK, FL

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

Luxury | Walk-in closets | Swimming pool

2 beds

2.5 baths

$2,695

House for rent

Top amenities
Carpet
Ceiling Fan
Dishwasher
In-Unit Laundry

Nearby rental good for eco-living

$2,410

Winter Park

Nearby rental good for pet owners

$2,270

Casselberry

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

$3,795

House for rent

5117 Lake Howell Rd - Photo 1 of 1

18h ago

Luxury house for rent in Winter Park

5117 Lake Howell Rd, Winter Park, FL 32792

Luxury | Outdoor space | Dishwasher

3 beds

1 bath

$2,295

$2,195

Price drop

House for rent

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7033 Easter St #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

$3,100 - 4 Bedroom 3 Bathroom House In Winter Park With Great Amenities

7033 Easter St #NA, Winter Park, FL 32792

Luxury | Swimming pool | Outdoor space

4 beds

3 baths

$3,100

House for rent

Available Aug 1

Top amenities
Air Conditioning
Storage
1839 Blaine Ter - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1839 Blaine Ter, Winter Park, FL 32792

Luxury | Walk-in closets | Outdoor space

3 beds

2.5 baths

$2,410

House for rent

Available Jul 20

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Find sweet deals near Winter Park

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

$2,195

Winter Park

$2,410

Winter Park

$2,510

Winter Park

$2,275

Goldenrod

1409 Bridlebrook Dr - Photo 1 of 1

3d ago

Our team has verified this company

Verified

1409 Bridlebrook Drive

1409 Bridlebrook Dr, Casselberry, FL 32707

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,315

House for rent

Available Oct 12

Top amenities
Ceiling Fan
High Ceilings
7424 Azalea Cove Cir - Photo 1 of 1

4d ago

Our team has verified this company

Verified

7424 Azalea Cove Cir, Azalea Park, FL 32807

Luxury

3 beds

2 baths

$3,270

$2,385

Price drop

House for rent

Available Sep 11

3016 Village Hill Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3016 Village Hill Pl, Winter Park, FL 32792

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,510

House for rent

Available Aug 24

Top amenities
Ceiling Fan
456 Copperstone Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

456 Copperstone Cir, Casselberry, FL 32707

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,165

House for rent

Available Sep 29

Top amenities
Ceiling Fan
3362 Bougainvillea Dr - Photo 1 of 1

4d ago

Our team has verified this company

Verified

3362 Bougainvillea Dr Winter Park, FL 32792

3362 Bougainvillea Dr, Goldenrod, FL 32792

Luxury | Outdoor space | Garage parking

4 beds

2 baths

$2,275

House for rent

Available Aug 6

613 Brittany Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

613 Brittany Ct, Casselberry, FL 32707

Luxury | Swimming pool | On-site laundry

3 beds

2 baths

$2,505

House for rent

Available Oct 5

Top amenities
On-Site Laundry
On-Site Management
8140 Tumeric Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

8140 Tumeric Ct, Orlando, FL 32817

Luxury | Balcony | Swimming pool

3 beds

3 baths

$3,430

House for rent

Available Sep 14

Top amenities
On-Site Laundry
On-Site Management
Swimming Pool
7039 Pecan Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

7039 Pecan Ct, Goldenrod, FL 32792

Luxury | Balcony | Swimming pool

4 beds

2 baths

$3,305

House for rent

Available Sep 23

Top amenities
On-Site Laundry
On-Site Management
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3908 Woodglade Cv - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3908 Woodglade Cv Winter Park, FL 32792

3908 Woodglade Cv, Winter Park, FL 32792

Luxury | Outdoor space | Garage parking

3 beds

2 baths

$2,480

House for rent

Available Jul 29

561 Hibiscus Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

561 Hibiscus Rd, Casselberry, FL 32707

Luxury | Swimming pool | On-site laundry

4 beds

2 baths

$2,325

House for rent

Available Sep 1

Top amenities
On-Site Laundry
On-Site Management
2943 Mallorn Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2943 Mallorn Way, Casselberry, FL 32707

Luxury | Swimming pool | On-site laundry

3 beds

2 baths

$2,730

House for rent

Available Sep 1

Top amenities
On-Site Laundry
On-Site Management
Listings within 10 miles
3598 S Saint Lucie Dr - Photo 1 of 1

1d ago

Our team has verified this company

Verified

3598 S Saint Lucie Dr, Casselberry, FL 32707

Luxury | Walk-in closets | Outdoor space

3 beds

2.5 baths

$2,480

$2,270

Price drop

House for rent

Available Jul 15

Top amenities
Ceiling Fan
Fireplace
Garage Parking
7526 Bear Claw Run - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

7526 Bear Claw Run, Orlando, FL 32825

Luxury | Walk-in closets | On-site laundry

3 beds

2 baths

$2,425

House for rent

Available Sep 28

Top amenities
Ceiling Fan
Garage Parking
High Ceilings
On-Site Laundry
7930 Soft Pine Cir - Photo 1 of 1

4d ago

Our team has verified this company

Verified

7930 Soft Pine Cir, Orlando, FL 32825

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,430

House for rent

Available Oct 2

6702 Cocos Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6702 Cocos Dr, Azalea Park, FL 32807

Luxury | Swimming pool | On-site laundry

4 beds

2 baths

$2,680

House for rent

Available Sep 7

Top amenities
On-Site Laundry
On-Site Management
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent
Updated: August 12, 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